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    Synopsis

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    Chemistry

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    Also known as: (-)-rapamycin, 53123-88-9, Ay 22989, Ay-22989, I 2190a, I-2190a
    Molecular Formula
    C51H79NO13
    Molecular Weight
    914.2  g/mol
    InChI Key
    QFJCIRLUMZQUOT-HPLJOQBZSA-N
    FDA UNII
    W36ZG6FT64
    Sirolimus
    A macrolide compound obtained from Streptomyces hygroscopicus that acts by selectively blocking the transcriptional activation of cytokines thereby inhibiting cytokine production. It is bioactive only when bound to IMMUNOPHILINS. Sirolimus is a potent immunosuppressant and possesses both antifungal and antineoplastic properties.
    Sirolimus is a mTOR Inhibitor Immunosuppressant and Kinase Inhibitor. The mechanism of action of sirolimus is as a mTOR Inhibitor and Protein Kinase Inhibitor. The physiologic effect of sirolimus is by means of Decreased Immunologic Activity.
    1 2D Structure

    Sirolimus

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-1,18-dihydroxy-12-[(2R)-1-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]propan-2-yl]-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo[30.3.1.04,9]hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentone
    2.1.2 InChI
    InChI=1S/C51H79NO13/c1-30-16-12-11-13-17-31(2)42(61-8)28-38-21-19-36(7)51(60,65-38)48(57)49(58)52-23-15-14-18-39(52)50(59)64-43(33(4)26-37-20-22-40(53)44(27-37)62-9)29-41(54)32(3)25-35(6)46(56)47(63-10)45(55)34(5)24-30/h11-13,16-17,25,30,32-34,36-40,42-44,46-47,53,56,60H,14-15,18-24,26-29H2,1-10H3/b13-11+,16-12+,31-17+,35-25+/t30-,32-,33-,34-,36-,37+,38+,39+,40-,42+,43+,44-,46-,47+,51-/m1/s1
    2.1.3 InChI Key
    QFJCIRLUMZQUOT-HPLJOQBZSA-N
    2.1.4 Canonical SMILES
    CC1CCC2CC(C(=CC=CC=CC(CC(C(=O)C(C(C(=CC(C(=O)CC(OC(=O)C3CCCCN3C(=O)C(=O)C1(O2)O)C(C)CC4CCC(C(C4)OC)O)C)C)O)OC)C)C)C)OC
    2.1.5 Isomeric SMILES
    C[C@@H]1CC[C@H]2C[C@@H](/C(=C/C=C/C=C/[C@H](C[C@H](C(=O)[C@@H]([C@@H](/C(=C/[C@H](C(=O)C[C@H](OC(=O)[C@@H]3CCCCN3C(=O)C(=O)[C@@]1(O2)O)[C@H](C)C[C@@H]4CC[C@H]([C@@H](C4)OC)O)C)/C)O)OC)C)C)/C)OC
    2.2 Other Identifiers
    2.2.1 UNII
    W36ZG6FT64
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Ay 22 989

    2. Ay 22-989

    3. Ay 22989

    4. I 2190a

    5. I-2190a

    6. I2190a

    7. Rapamune

    8. Rapamycin

    2.3.2 Depositor-Supplied Synonyms

    1. (-)-rapamycin

    2. 53123-88-9

    3. Ay 22989

    4. Ay-22989

    5. I 2190a

    6. I-2190a

    7. I2190a

    8. Nsc 226080

    9. Rapa

    10. Rapammune

    11. Rapamune

    12. Rapamycin

    13. Siia 9268a

    14. Wy 090217

    15. Rapamycin (sirolimus)

    16. Rapalimus

    17. Wy-090217

    18. L04aa10

    19. Npc-12g

    20. Antibiotic Ay 22989

    21. Chebi:9168

    22. W36zg6ft64

    23. Sm-88 Component Sirolimus

    24. De-109

    25. Mfcd00867594

    26. Nsc-226080

    27. Ncgc00021305-05

    28. Dsstox_cid_3582

    29. Sirolimusum

    30. Dsstox_rid_77091

    31. Dsstox_gsid_23582

    32. (3s,6r,7e,9r,10r,12r,14s,15e,17e,19e,21s,23s,26r,27r,34as)-9,27-dihydroxy-3-{(2r)-1-[(1s,3r,4r)-4-hydroxy-3-methoxycyclohexyl]propan-2-yl}-10,21-dimethoxy-6,8,12,14,20,26-hexamethyl-9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-hexadecahydro-3h-23,27-epoxypyrido[2,1-c][1,4]oxazacyclohentriacontine-1,5,11,28,29(4h,6h,31h)-pentone

    33. Sila 9268a

    34. Supralimus

    35. Rapamycin/sirolimus

    36. (1r,9s,12s,15r,16e,18r,19r,21r,23s,24e,26e,28e,30s,32s,35r)-1,18-dihydroxy-12-{(2s)-1-[(1s,3r,4r)-4-hydroxy-3-methoxycyclohexyl]propan-2-yl}-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo[30.3.1.0(4,9)]hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentone

    37. Cas-53123-88-9

    38. Perceiva

    39. Cypher

    40. Ccris 9024

    41. Nsc226080

    42. Hsdb 7284

    43. 1fkb

    44. 1pbk

    45. Ncgc00181146-01

    46. Lcp-siro

    47. (3s,6r,7e,9r,10r,12r,14s,15e,17e,19e,21s,23s,26r,27r,34as)-9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-hexadecahydro-9,27-dihydroxy-3-((1r)-2-((1s,3r,4r)-4-hydroxy-3-methoxycyclohexyl)-1-methylethyl)-10,21-dimethoxy-6,8,12,14,20,26-hexamethyl-23,27-epoxy-3h-pyrido(2,1-c)(1,4)oxaazacyclohentriacontine-1,5,11,28,29(4h,6h,31h)-pentone

    48. (3s,6r,7e,9r,10r,12r,14s,15e,17e,19e,21s,23s,26r,27r,34as)-9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-hexadecahydro-9,27-dihydroxy-3-[(1r)-2-[(1s,3r,4r)-4-hydroxy-3-methoxycyclohexyl]-1-methylethyl]-10,21-dimethoxy-6,8,12,14,20,26-hexamethyl-23,27-epoxy-3h-pyrido[2,1-c][1,4]oxaazacyclohentriacontine-1,5,11,28,29(4h,6h,31h)-pentone

    49. (3s,6r,7e,9r,10r,12r,14s,15e,17e,19e,21s,23s,26r,27r,34as)-9,27-dihydroxy-3-{(1r)-2-[(1s,3r,4r)-4-hydroxy-3-(methyloxy)cyclohexyl]-1-methylethyl}-6,8,12,14,20,26-hexamethyl-10,21-bis(methyloxy)-9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-hexadecahydro-3h-23,27-epoxypyrido[2,1-c][1,4]oxazacyclohentriacontine-1,5,11,28,29(6h,31h)-pentone

    50. Rap

    51. Fyarro

    52. Hyftor

    53. S1039

    54. Sirolimus [inn]

    55. Sirolimus [jan]

    56. Rapamycin [mi]

    57. Sirolimus [hsdb]

    58. Sirolimus [usan]

    59. Sirolimus [vandf]

    60. Biomolki2_000084

    61. Sirolimus [mart.]

    62. Rapamycin C-7, Analog 4

    63. Schembl3463

    64. Sirolimus [usp-rs]

    65. Sirolimus [who-dd]

    66. Rapamycin,sirolimus,rapamune

    67. Unii-w36zg6ft64

    68. Bidd:pxr0165

    69. Sirolimus [ema Epar]

    70. Mls006010168

    71. Sirolimus [usan:inn:ban]

    72. Gtpl6031

    73. Sirolimus [orange Book]

    74. Dtxsid5023582

    75. Bdbm36609

    76. Ms-r001

    77. Rapa, Rapamune, Sirolimus, Rpm

    78. Hms2089a21

    79. Hms3403f11

    80. Hms3884c03

    81. Ex-a1044

    82. Rpm

    83. Tox21_110870

    84. Tox21_112750

    85. Ac-722

    86. Bdbm50064359

    87. Stl570275

    88. Akos015850976

    89. Akos015961618

    90. Zinc169289388

    91. Ccg-100684

    92. Cs-0063

    93. Db00877

    94. Nab-rapamycin Component Rapamycin

    95. Nsc-2260804

    96. Ncgc00021305-06

    97. Ncgc00021305-07

    98. Rapamycin From Streptomyces Hygroscopicus

    99. As-11687

    100. Hy-10219

    101. Smr004701276

    102. Fyarro (sirolimus Albumin-bound Particles)

    103. Everolimus Impurity A [ep Impurity]

    104. Unm-0000358684

    105. A-275

    106. R0097

    107. Rapamycin, Vetranal(tm), Analytical Standard

    108. Ec 610-965-5

    109. M02444

    110. Q32089

    111. 123r889

    112. Q-201659

    113. Brd-k84937637-001-04-0

    114. Brd-k84937637-001-06-5

    115. Brd-k89626439-001-01-0

    116. 24,25,26,27,32,33,34,34a-hexadecahydro-3h-23,27-epoxypy

    117. Rapamycin From Streptomyces Hygroscopicus, >=95% (hplc), Powder

    118. Rapamycin From Streptomyces Hygroscopicus, Vetec(tm) Reagent Grade, >=95%

    119. Sirolimus Solution, 1.0 Mg/ml In Acetonitrile, Ampule Of 1 Ml, Certified Reference Material

    120. (1r,9s,12s,15r,16e,18r,19r,21r,23s,24e,26e,28e,30s,32s,35r)-1,18-dihydroxy-12-{(2s)-1-[(1s,3r,4r)-4-hydroxy-3-methoxycyclohexyl]propan-2-yl}-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo[30.3.1.04,9]hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentone

    121. (3s,6r,7e,9r,10r,12r,14s,15e,17e,19e,21s,23s,26r,27r,34 As)-9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-hex Adecahydro-9,27-dihydroxy-3-[(1r)-2-[(1s,3r,4r)-4-hydro Xy-3-methoxycyclohexyl]-1-methylethyl]-10,21-dimethoxy- 6,8,12,14,20,26-hexamethyl-23,27-ep

    122. (3s,6r,7e,9r,10r,12r,14s,15e,17e,19e,21s,23s,26r,27r,34as)-4,9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-heptadecahydro-9,27-dihydroxy-3-[(1r)-2-[(1s,3,4r)-4-hydroxy-3-methoxycyclohexyl]-1-methylethyl]-10,21-dimethoxy-6,8,12,14,20,26-hexamethyl-223,27-epoxy-3h-pyrido[2,1-c][1,4]oxaazacyclohentriacontine-1,5,11,28,29(6h,31h)-pentone

    123. (3s,6r,7e,9r,10r,12r,14s,15e,17e,19e,21s,23s,26r,27r,34as)-9,27-dihydroxy-3-{(1r)-2-[(1s,3r,4r)-4-hydroxy-3-(methyloxy)cyclohexyl]-1-methylethyl}-6,8,12,14,20,26-hexamethyl-10,21-bis(methyloxy)-9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-hexadecahydro

    124. (3s,6r,7e,9r,10r,12r,14s,15e,17e,19e,21s,23s,26r,27r,34as)-9,27-dihydroxy-3-{(1r)-2-[(1s,3r,4r)-4-hydroxy-3-methoxycyclohexyl]-1-methylethyl}-10,21-dimethoxy-6,8,12,14,20,26-hexamethyl-9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-hexadecahydro-3h-23,27-epoxypyrido[2,1-c][1,4]oxazacyclohentriacontine-1,5,11,28,29(4h,6h,31h)-pentone

    125. (3s,6r,7e,9r,10r,12r,14s,15e,17e,19e,21s,23s,26r,27r,34as)-9,27-dihydroxy-3-{1-[(1s,3r,4r)-4-hydroxy-3-methoxycyclohexyl]propan-2-yl}-10,21-dimethoxy-6,8,12,14,20,26-hexamethyl-9,10,12,13,14,21,22,23,

    126. 1,18-dihydroxy-12-[2-(4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-ethyl]-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-aza-tricyclo[30.3.1.0*4,9*]hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentaone (rapamycin)

    2.3.3 Other Synonyms

    1. (rs)-rapamycin

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 914.2 g/mol
    Molecular Formula C51H79NO13
    XLogP36
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count13
    Rotatable Bond Count6
    Exact Mass913.55514157 g/mol
    Monoisotopic Mass913.55514157 g/mol
    Topological Polar Surface Area195 Ų
    Heavy Atom Count65
    Formal Charge0
    Complexity1760
    Isotope Atom Count0
    Defined Atom Stereocenter Count15
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count4
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameRapamune
    PubMed HealthSirolimus (By mouth)
    Drug ClassesImmune Suppressant
    Drug LabelRapamune (sirolimus) is an immunosuppressive agent. Sirolimus is a macrocyclic lactone produced by Streptomyces hygroscopicus. The chemical name of sirolimus (also known as rapamycin) is (3S,6R,7E,9R,10R,12R,14S,15E,17E,19E,21S,23S,26R,27R,34aS)-9,10...
    Active IngredientSirolimus
    Dosage FormTablet; Solution
    RouteOral
    Strength1mg/ml; 0.5mg; 1mg; 2mg
    Market StatusPrescription
    CompanyPf Prism Cv

    2 of 4  
    Drug NameSirolimus
    PubMed HealthSirolimus (By mouth)
    Drug ClassesImmune Suppressant
    Drug LabelRapamune (sirolimus) is an immunosuppressive agent. Sirolimus is a macrocyclic lactone produced by Streptomyces hygroscopicus. The chemical name of sirolimus (also known as rapamycin) is (3S,6R,7E,9R,10R,12R,14S,15E,17E,19E,21S,23S,26R,27R,34aS)-9,10...
    Active IngredientSirolimus
    Dosage FormTablet
    Routeoral; Oral
    Strength0.5mg; 1mg; 2mg
    Market StatusTentative Approval; Prescription
    CompanyZydus Pharms Usa; Dr Reddys Labs

    3 of 4  
    Drug NameRapamune
    PubMed HealthSirolimus (By mouth)
    Drug ClassesImmune Suppressant
    Drug LabelRapamune (sirolimus) is an immunosuppressive agent. Sirolimus is a macrocyclic lactone produced by Streptomyces hygroscopicus. The chemical name of sirolimus (also known as rapamycin) is (3S,6R,7E,9R,10R,12R,14S,15E,17E,19E,21S,23S,26R,27R,34aS)-9,10...
    Active IngredientSirolimus
    Dosage FormTablet; Solution
    RouteOral
    Strength1mg/ml; 0.5mg; 1mg; 2mg
    Market StatusPrescription
    CompanyPf Prism Cv

    4 of 4  
    Drug NameSirolimus
    PubMed HealthSirolimus (By mouth)
    Drug ClassesImmune Suppressant
    Drug LabelRapamune (sirolimus) is an immunosuppressive agent. Sirolimus is a macrocyclic lactone produced by Streptomyces hygroscopicus. The chemical name of sirolimus (also known as rapamycin) is (3S,6R,7E,9R,10R,12R,14S,15E,17E,19E,21S,23S,26R,27R,34aS)-9,10...
    Active IngredientSirolimus
    Dosage FormTablet
    Routeoral; Oral
    Strength0.5mg; 1mg; 2mg
    Market StatusTentative Approval; Prescription
    CompanyZydus Pharms Usa; Dr Reddys Labs

    4.2 Therapeutic Uses

    Sirolimus is indicated for the prevention of rejection of transplanted kidney allografts. It is recommended that sirolimus be used in a regimen with cyclosporine and corticosteroids. /Included in US product labeling/

    Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 2546

    Long-term results after percutaneous coronary intervention in the treatment of chronic total coronary occlusions is hindered by a significant rate of restenosis and reocclusion. In the treatment of relatively simple nonocclusive lesions, sirolimus-eluting stents have shown dramatically reduced restenosis rates compared with bare metal stents, but whether these results are more widely applicable is unknown. ... The use of sirolimus-eluting stents in the treatment of chronic total coronary occlusions is associated with a reduction in the rate of major adverse cardiac events and restenosis compared with bare metal stents.

    PMID:15172397 Hoye A et al; J Am Coll Cardiol 43 (11): 1954-8 (2004)

    Chronic renal failure triggered by calcineurin inhibitor (CNI)-based immunosuppression is a common complication after cardiac transplantation. Sirolimus and mycophenolate mofetil (MMF) are 2 newer immunosuppressive agents with no documented nephrotoxic side effects. This case report describes a patient with ongoing chronic renal failure 10 months after cardiac transplantation on cyclosporine-based immunosuppressive therapy. Conversion of the immunosuppressive regimen from cyclosporine to sirolimus and MMF resulted in freedom from acute rejection, excellent cardiac graft function and consistently improved renal function. This case illustrates the beneficial potential of sirolimus and MMF as CNI-free and safe long-term immunosuppression in a patient with chronic renal failure after heart transplantation.

    PMID:15366440 Groetzner J et al; J Heart Lung Transplant 23 (6): 770-3 (2004)

    4.3 Drug Warning

    /BOXED WARNING/ IMMUNOSUPPRESSION, USE IS NOT RECOMMENDED IN LIVER OR LUNG TRANSPLANT PATIENTS. Increased susceptibility to infection and the possible development of lymphoma and other malignancies may result from immunosuppression Increased susceptibility to infection and the possible development of lymphoma may result from immunosuppression. Only physicians experienced in immunosuppressive therapy and management of renal transplant patients should use Rapamune. Patients receiving the drug should be managed in facilities equipped and staffed with adequate laboratory and supportive medical resources. The physician responsible for maintenance therapy should have complete information requisite for the follow-up of the patient. The safety and efficacy of Rapamune (sirolimus) as immunosuppressive therapy have not been established in liver or lung transplant patients, and therefore, such use is not recommended. Liver Transplantation - Excess Mortality, Graft Loss, and Hepatic Artery Thrombosis (HAT): The use of Rapamune in combination with tacrolimus was associated with excess mortality and graft loss in a study in de novo liver transplant patients. Many of these patients had evidence of infection at or near the time of death. In this and another study in de novo liver transplant patients, the use of Rapamune in combination with cyclosporine or tacrolimus was associated with an increase in HAT; most cases of HAT occurred within 30 days post-transplantation and most led to graft loss or death. Lung Transplantation - Bronchial Anastomotic Dehiscence: Cases of bronchial anastomotic dehiscence, most fatal, have been reported in de novo lung transplant patients when Rapamune has been used as part of an immunosuppressive regimen.

    US Natl Inst Health; DailyMed. Current Medication Information for Rapamune (sirolimus) solution; Rapamune (sirolimus) tablet, sugar coated (Updated: March 2015). Available from, as of April 23, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3275b824-3f82-4151-2ab2-0036a9ba0acc

    Grapefruit juice may inhibit CYP 3A4 enzymes, leading to decreased metabolism of sirolimus; must not be taken with or used to dilute sirolimus.

    Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 2547

    Cases of bronchial anastomotic dehiscence, most of which were fatal, have been reported in de novo lung transplant patients who received sirolimus in combination with other immunosuppressants. Because safety and efficacy of sirolimus as immunosuppressive therapy in lung transplant patients have not been established, such use in not recommended by the manufacturer.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2004. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2004 (Plus Supplements)., p. 3645

    Use of sirolimus in combination with other immunosuppressants (i.e., cyclosporine, tacrolimus) has been associated with an increased risk on hepatic artery thrombosis, graft loss, and death in de novo liver transplant recipients. Because safety and efficacy of sirolimus as immunosuppressive therapy in liver transplant patients have not been established, such use is not recommended by the manufacturer.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2004. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2004 (Plus Supplements)., p. 3646

    For more Drug Warnings (Complete) data for SIROLIMUS (27 total), please visit the HSDB record page.

    4.4 Drug Indication

    Sirolimus is indicated for the prophylaxis of organ rejection in patients aged 13 years or older receiving renal transplants. In patients at low-to moderate-immunologic risk, it is recommended that sirolimus be used initially in a regimen with [cyclosporine] and corticosteroids; cyclosporine should be withdrawn two to four months after transplantation. In patients at high-immunologic risk (defined as Black recipients and/or repeat renal transplant recipients who lost a previous allograft for immunologic reason and/or patients with high panel-reactive antibodies [PRA; peak PRA level > 80%]), it is recommended that sirolimus be used in combination with cyclosporine and corticosteroids for the first year following transplantation. It is also used to treat lymphangioleiomyomatosis. In the US, albumin-bound sirolimus for intravenous injection is indicated for the treatment of adult patients with locally advanced unresectable or metastatic malignant perivascular epithelioid cell tumour (PEComa). In Europe, it is recommended that sirolimus for the prophylaxis of organ rejection in renal transplants is used in combination with cyclosporin microemulsion and corticosteroids for two to three months. Sirolimus may be continued as maintenance therapy with corticosteroids only if cyclosporin microemulsion can be progressively discontinued.

    FDA Label

    Rapamune is indicated for the prophylaxis of organ rejection in adult patients at low to moderate immunological risk receiving a renal transplant. It is recommended that Rapamune be used initially in combination with ciclosporin microemulsion and corticosteroids for 2 to 3 months. Rapamune may be continued as maintenance therapy with corticosteroids only if ciclosporin microemulsion can be progressively discontinued.

    Rapamune is indicated for the treatment of patients with sporadic lymphangioleiomyomatosis with moderate lung disease or declining lung function.

    Prevention of arteriovenous access dysfunction

    Treatment of chronic non-infectious uveitis

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Sirolimus is an immunosuppressant drug with antifungal and antitumour effects. In animal models, sirolimus prolonged allograft survival following various organ transplants and reversed an acute rejection of heart and kidney allografts in rats. Upon oral administration of 2 mg/day and 5 mg/day, sirolimus significantly reduced the incidence of organ rejection in low- to moderate-immunologic risk renal transplant patients at six months following transplantation compared with either azathioprine or placebo. In some studies, the immunosuppressive effect of sirolimus lasted up to six months after discontinuation of therapy: this tolerization effect is alloantigen-specific. Sirolimus potently inhibits antigen-induced proliferation of T cells, B cells, and antibody production. In rodent models of autoimmune disease, sirolimus suppressed immune-mediated events associated with systemic lupus erythematosus, collagen-induced arthritis, autoimmune type I diabetes, autoimmune myocarditis, experimental allergic encephalomyelitis, graft-versus-host disease, and autoimmune uveoretinitis.

    5.2 MeSH Pharmacological Classification

    Antibiotics, Antineoplastic

    Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. (See all compounds classified as Antibiotics, Antineoplastic.)

    Antifungal Agents

    Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)

    Immunosuppressive Agents

    Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging. (See all compounds classified as Immunosuppressive Agents.)

    Anti-Bacterial Agents

    Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    SIROLIMUS
    5.3.2 FDA UNII
    W36ZG6FT64
    5.3.3 Pharmacological Classes
    Kinase Inhibitor [EPC]; Protein Kinase Inhibitors [MoA]; mTOR Inhibitor Immunosuppressant [EPC]; mTOR Inhibitors [MoA]; Decreased Immunologic Activity [PE]
    5.4 ATC Code

    L04AA10

    L04AA10

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    L - Antineoplastic and immunomodulating agents

    L04 - Immunosuppressants

    L04A - Immunosuppressants

    L04AA - Selective immunosuppressants

    L04AA10 - Sirolimus

    S - Sensory organs

    S01 - Ophthalmologicals

    S01X - Other ophthalmologicals

    S01XA - Other ophthalmologicals

    S01XA23 - Sirolimus

    5.5 Absorption, Distribution and Excretion

    Absorption

    In adult renal transplant patients with low- to moderate-immunologic risk, oral administration of 2 mg sirolimus led to a Cmax of 14.4 5.3 ng/mL for oral solution and 15.0 4.9 ng/mL for oral tablets. The tmax was 2.1 0.8 hours for oral solution and 3.5 2.4 hours for oral tablets. In healthy subjects, the tmax is one hour. In a multi-dose study, steady-state was reached six days following repeated twice-daily administration without an initial loading dose, with the average trough concentration of sirolimus increased approximately 2- to 3-fold. It is suspected that a loading dose of three times the maintenance dose will provide near steady-state concentrations within one day in most patients. The systemic availability of sirolimus is approximately 14%. In healthy subjects, the mean bioavailability of sirolimus after administration of the tablet is approximately 27% higher relative to the solution. Sirolimus tablets are not bioequivalent to the solution; however, clinical equivalence has been demonstrated at the 2 mg dose level. Sirolimus concentrations, following the administration of Rapamune Oral Solution to stable renal transplant patients, are dose-proportional between 3 and 12 mg/m2.

    Route of Elimination

    Following oral administration of [14C] sirolimus in healthy subjects, about 91% of the radioactivity was recovered from feces and only 2.2% of the radioactivity was detected in urine. Some of the metabolites of sirolimus are also detectable in feces and urine.

    Volume of Distribution

    The mean ( SD) blood-to-plasma ratio of sirolimus was 36 18 L in stable renal allograft patients, indicating that sirolimus is extensively partitioned into formed blood elements. The mean volume of distribution (Vss/F) of sirolimus is 12 8 L/kg.

    Clearance

    In adult renal transplant patients with low- to moderate-immunologic risk, oral administration of 2 mg sirolimus led to oral clearance of 173 50 mL/h/kg for oral solution and 139 63 mL/h/kg for oral tablets.

    Following administration of /Sirolimus/ Oral Solution, sirolimus is rapidly absorbed, with a mean time-to-peak concentration (t max ) of approximately 1 hour after a single dose in healthy subjects and approximately 2 hours after multiple oral doses in renal transplant recipients. The systemic availability of sirolimus was estimated to be approximately 14% after the administration of /Sirolimus/ Oral Solution. The mean bioavailability of sirolimus after administration of the tablet is about 27% higher relative to the oral solution.

    Physicians Desk Reference. 58th ed. Thomson PDR. Montvale, NJ 2004., p. 3483

    In 22 healthy volunteers receiving Rapamune Oral Solution, a high-fat meal altered the bioavailability characteristics of sirolimus. Compared with fasting, a 34% decrease in the peak blood sirolimus concentration (C max ), a 3.5-fold increase in the time-to-peak concentration (t max ), and a 35% increase in total exposure (AUC) was observed. After administration of Rapamune Tablets and a high-fat meal in 24 healthy volunteers, C max , t max , and AUC showed increases of 65%, 32%, and 23%, respectively.

    Physicians Desk Reference. 58th ed. Thomson PDR. Montvale, NJ 2004., p. 3483

    Absorption: Rapid, from the gastrointestinal tract. Bioavailability is approximately 14%. Rate of absorption is decreased in the presence of a high-fat diet. The rate and extent of absorption is reduced in black patients.

    Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 2546

    The mean (+/- SD) blood-to-plasma ratio of sirolimus was 36 +/- 17.9 in stable renal allograft recipients, indicating that sirolimus is extensively partitioned into formed blood elements. The mean volume of distribution of sirolimus is 12 +/- 7.52 L/kg. Sirolimus is extensively bound (approximately 92%) to human plasma proteins. In man, the binding of sirolimus was shown mainly to be associated with serum albumin (97%), (alpha) 1 -acid glycoprotein, and lipoproteins.

    Physicians Desk Reference. 58th ed. Thomson PDR. Montvale, NJ 2004., p. 3483

    For more Absorption, Distribution and Excretion (Complete) data for SIROLIMUS (7 total), please visit the HSDB record page.

    5.6 Metabolism/Metabolites

    Sirolimus undergoes extensive metabolism in the intestinal wall and liver. Sirolimus is primarily metabolized by O-demethylation and/or hydroxylation via CYP3A4 to form seven major metabolites, including hydroxy, demethyl, and hydroxydemethyl metabolites, which are pharmacologically inactive. Sirolimus also undergoes counter-transport from enterocytes of the small intestine into the gut lumen.

    Sirolimus is a substrate for both cytochrome P450 IIIA4 (CYP3A4) and P-glycoprotein. Sirolimus is extensively metabolized by O-demethylation and/or hydroxylation. Seven major metabolites, including hydroxy, demethyl, and hydroxydemethyl, are identifiable in whole blood. Some of these metabolites are also detectable in plasma, fecal, and urine samples. Glucuronide and sulfate conjugates are not present in any of the biologic matrices.

    Physicians Desk Reference. 58th ed. Thomson PDR. Montvale, NJ 2004., p. 3484

    Biotransformation: Hepatic, extensive, by cytochrome p450 3A enzymes. Major metabolites include hydroxysirolimus, demethylsirolimus, and hydroxydemethyl-sirolimus.

    Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 2546

    ... After incubation of sirolimus with human and pig small intestinal microsomes, five metabolites were detected using high performance liquid chromatography/electrospray-mass spectrometry: hydroxy, dihydroxy, trihydroxy, desmethyl and didesmethyl sirolimus. The same metabolites were generated by human liver microsomes and pig small intestinal mucosa in the Ussing chamber. Anti-CYP3A antibodies, as well as the specific CYP3A inhibitors troleandomycin and erythromycin, inhibited small intestinal metabolism of sirolimus, confirming that, as in the liver, CYP3A enzymes are responsible for sirolimus metabolism in the small intestine. ...

    PMID:9618413 Lampen A et al; J Pharmacol Exp Ther 285 (3): 1104-12 (1998)

    Sirolimus has known human metabolites that include 11-Hydroxy-sirolimus, 12-Hydroxy-sirolimus, 16-O-Desmethylsirolimus, 24-Hydroxy-sirolimus, 25-Hydroxy-sirolimus, 39-O-Desmethylsirolimus, and 46-Hydroxy-sirolimus.

    S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

    5.7 Biological Half-Life

    The mean SD terminal elimination half-life (t) of sirolimus after multiple dosing in stable renal transplant patients was estimated to be about 62 16 hours.

    The drug has an elimination half life of 57-63 hours in kidney transplant recipients.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2004. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2004 (Plus Supplements)., p. 3647

    5.8 Mechanism of Action

    Sirolimus works by inhibiting T-lymphocyte activation and proliferation stimulated by antigens and cytokines such as interleukin (IL)-2, IL-4, and IL-15. In target cells, sirolimus binds to the cytoplasmic receptor FK506-binding protein-12 (FKBP12), an immunophilin, to form an immunosuppressive complex. FKBP12-sirolimus complex binds to and inhibits the activation of the mammalian target of rapamycin (mTOR), which is a serine/threonine-specific protein kinase that regulates cell growth, proliferation, survival, mobility, and angiogenesis. mTOR regulates the downstream signalling pathways involved in cell survival, such as the phosphatidylinositol-3 kinase (PI3K)/Akt signalling pathway. Inhibition of mTOR leads to the suppression of cytokine-driven T-cell proliferation, thus the progression from the G1 to the S phase of the cell cycle is inhibited. Sirolimus also inhibits antibody production. _In vitro_, sirolimus and other mTOR inhibitors inhibit the production of certain growth factors that may affect angiogenesis, fibroblast proliferation, and vascular permeability. Lymphangioleiomyomatosis is a disorder that primarily affects the lungs. It is characterized by lung tissue infiltration, unregulated alveolar smooth muscle proliferation, and cystic destruction of parenchyma. Although infrequent, it occurs as a symptomatic pulmonary complication in tuberous sclerosis complex (TSC), which is an inherited disorder caused by mutations in TSC genes. Loss of functional TSC gene leads to the aberrant activation of the mTOR signalling pathway, resulting in cellular proliferation and release of lymphangiogenic growth factors. Sirolimus inhibits the activated mTOR pathway and proliferation of alveolar smooth muscle cell proliferation.

    Sirolimus inhibits cytokine (Interleukin (IL)-2, IL-4, and IL-15) -- stimulated T lymphocyte activation and proliferation; it also inhibits antibody production. This may occur through formation of an immunosuppressive complex with FK Binding Protein-12 (FKBP-12). Although the sirolimus-(FKBP-12) complex is inactive against calcineurin activity, the complex binds to and inhibits activation of a key regulatory kinase, mammalian Target of Rapamycin (mTOR). This is believed to suppress cytokine-driven T-cell proliferation, inhibiting cell cycle progression from the G, to S phase.

    Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 2546

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    SIROLIMUS

    NDC Package Code : 52076-6216

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    NDC Package Code : 65727-013

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    NDC Package Code : 55486-1592

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    NDC Package Code : 55486-1571

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    NDC Package Code : 71052-202

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    NDC Package Code : 59573-0004

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    NDC Package Code : 42513-0013

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    NDC Package Code : 49187-0801

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    NDC Package Code : 84517-032

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    05-Jan-2021
    27-Sep-2024
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    Drugs in Development

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    Virtual BoothAurigene is a global leader in accelerating drug innovation through discovery, development & manufacturing.

    Beroni Initiates Manufacture of its Novel, Potential Anti-Cancer Drug PENAO

    Details:

    This next-generation adenine nucleotide translocase (ANT) inhibitor, PENAO, was shown to be safe and well-tolerated in a phase I clinical trial conducted in Australia where encouraging efficacy data was observed.


    Lead Product(s): PENAO,Sirolimus

    Therapeutic Area: Oncology Brand Name: PENAO

    Study Phase: Phase I/ Phase IIProduct Type: Small molecule

    Sponsor: PENAO Pty Ltd

    Deal Size: Undisclosed Upfront Cash: Undisclosed

    Deal Type: Agreement August 18, 2021

    Aurigene

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    Aurigene Pharmaceutical Services

    India
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    AES 2024
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    Lead Product(s) : PENAO,Sirolimus

    Therapeutic Area : Oncology

    Highest Development Status : Phase I/ Phase II

    Partner/Sponsor/Collaborator : PENAO Pty Ltd

    Deal Size : Undisclosed

    Deal Type : Agreement

    DEALS_DEV arrow-down

    Beroni Initiates Manufacture of its Novel, Potential Anti-Cancer Drug PENAO

    Details : This next-generation adenine nucleotide translocase (ANT) inhibitor, PENAO, was shown to be safe and well-tolerated in a phase I clinical trial conducted in Australia where encouraging efficacy data was observed.

    Brand Name : PENAO

    Molecule Type : Small molecule

    Upfront Cash : Undisclosed

    August 18, 2021

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    Palvella Therapeutics Doses First Patient in SELVA Trial for Lymphatic Malformations

    Details:

    Qtorin (rapamycin) is a macrocyclic lactone antibiotic produced by bacteria Streptomyces hygroscopicus. It is being evaluated for the treatment of microcystic lymphatic malformations.


    Lead Product(s): Sirolimus

    Therapeutic Area: Rare Diseases and Disorders Brand Name: Qtorin

    Study Phase: Phase IIIProduct Type: Small molecule

    Sponsor: Not Applicable

    Deal Size: Not Applicable Upfront Cash: Not Applicable

    Deal Type: Not Applicable November 07, 2024

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    02

    Palvella Therapeutics

    U.S.A
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    AES 2024
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    Palvella Therapeutics

    U.S.A
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    AES 2024
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    Lead Product(s) : Sirolimus

    Therapeutic Area : Rare Diseases and Disorders

    Highest Development Status : Phase III

    Partner/Sponsor/Collaborator : Not Applicable

    Deal Size : Not Applicable

    Deal Type : Not Applicable

    DEALS_DEV arrow-down

    Palvella Therapeutics Doses First Patient in SELVA Trial for Lymphatic Malformations

    Details : Qtorin (rapamycin) is a macrocyclic lactone antibiotic produced by bacteria Streptomyces hygroscopicus. It is being evaluated for the treatment of microcystic lymphatic malformations.

    Brand Name : Qtorin

    Molecule Type : Small molecule

    Upfront Cash : Not Applicable

    November 07, 2024

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    AgelessRx’s PEARL Trial Links Rapamycin Use to Healthspan Improvement

    Details:

    Sirolimus (rapamycin) is an mTOR inhibitor, small molecule drug candidate, which is currently being evaluated for the treatment of aging.


    Lead Product(s): Sirolimus

    Therapeutic Area: Musculoskeletal Brand Name: Sirolimus

    Study Phase: Phase IIProduct Type: Small molecule

    Sponsor: Not Applicable

    Deal Size: Not Applicable Upfront Cash: Not Applicable

    Deal Type: Not Applicable October 10, 2024

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    03

    AgelessRx

    U.S.A
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    AES 2024
    Not Confirmed

    AgelessRx

    U.S.A
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    Not Confirmed
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    Lead Product(s) : Sirolimus

    Therapeutic Area : Musculoskeletal

    Highest Development Status : Phase II

    Partner/Sponsor/Collaborator : Not Applicable

    Deal Size : Not Applicable

    Deal Type : Not Applicable

    DEALS_DEV arrow-down

    AgelessRx’s PEARL Trial Links Rapamycin Use to Healthspan Improvement

    Details : Sirolimus (rapamycin) is an mTOR inhibitor, small molecule drug candidate, which is currently being evaluated for the treatment of aging.

    Brand Name : Sirolimus

    Molecule Type : Small molecule

    Upfront Cash : Not Applicable

    October 10, 2024

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    Palvella Wins $2.6M FDA Grant for Phase 3 Trial in Microcystic Lymphatic Malformations

    Details:

    The proceeds will support the ongoing Phase 3 of QTORIN rapamycin anhydrous gel for the treatment of microcystic lymphatic malformations (microcystic LMs).


    Lead Product(s): Sirolimus

    Therapeutic Area: Rare Diseases and Disorders Brand Name: Qtorin

    Study Phase: Phase IIIProduct Type: Small molecule

    Sponsor: FDA

    Deal Size: $2.6 million Upfront Cash: Undisclosed

    Deal Type: Funding October 03, 2024

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    04

    Palvella Therapeutics

    U.S.A
    arrow
    AES 2024
    Not Confirmed

    Palvella Therapeutics

    U.S.A
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    Not Confirmed
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    Lead Product(s) : Sirolimus

    Therapeutic Area : Rare Diseases and Disorders

    Highest Development Status : Phase III

    Partner/Sponsor/Collaborator : FDA

    Deal Size : $2.6 million

    Deal Type : Funding

    DEALS_DEV arrow-down

    Palvella Wins $2.6M FDA Grant for Phase 3 Trial in Microcystic Lymphatic Malformations

    Details : The proceeds will support the ongoing Phase 3 of QTORIN rapamycin anhydrous gel for the treatment of microcystic lymphatic malformations (microcystic LMs).

    Brand Name : Qtorin

    Molecule Type : Small molecule

    Upfront Cash : Undisclosed

    October 03, 2024

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    Company Pays $3M Final Match For $17M CPRIT Grant Access

    Details:

    The proceeds will be used to fund company's upcoming Phase 3 registrational study of eRapa, a proprietary oral tablet formulation of rapamycin, in Familial Adenomatous Polyposis.


    Lead Product(s): Sirolimus

    Therapeutic Area: Genetic Disease Brand Name: eRapa

    Study Phase: Phase IIProduct Type: Small molecule

    Sponsor: CPRIT

    Deal Size: $17.0 million Upfront Cash: Undisclosed

    Deal Type: Funding September 16, 2024

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    05

    Biodexa Pharmaceuticals

    United Kingdom
    arrow
    AES 2024
    Not Confirmed

    Biodexa Pharmaceuticals

    United Kingdom
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    Not Confirmed
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    Lead Product(s) : Sirolimus

    Therapeutic Area : Genetic Disease

    Highest Development Status : Phase II

    Partner/Sponsor/Collaborator : CPRIT

    Deal Size : $17.0 million

    Deal Type : Funding

    DEALS_DEV arrow-down

    Company Pays $3M Final Match For $17M CPRIT Grant Access

    Details : The proceeds will be used to fund company's upcoming Phase 3 registrational study of eRapa, a proprietary oral tablet formulation of rapamycin, in Familial Adenomatous Polyposis.

    Brand Name : eRapa

    Molecule Type : Small molecule

    Upfront Cash : Undisclosed

    September 16, 2024

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    Vascular Therapies Completes Enrollment in Phase III ACCESS 2 Sirolimus Study

    Details:

    Sirogen (sirolimus) for the surgical creation of arteriovenous (AV) fistula in patients requiring hemodialysis vascular access is being evaluated for Chronic Kidney Disease.


    Lead Product(s): Sirolimus

    Therapeutic Area: Nephrology Brand Name: Sirogen

    Study Phase: Phase IIIProduct Type: Small molecule

    Sponsor: Not Applicable

    Deal Size: Not Applicable Upfront Cash: Not Applicable

    Deal Type: Not Applicable August 05, 2024

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    06

    Vascular Therapies

    U.S.A
    arrow
    AES 2024
    Not Confirmed

    Vascular Therapies

    U.S.A
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    Not Confirmed
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    Lead Product(s) : Sirolimus

    Therapeutic Area : Nephrology

    Highest Development Status : Phase III

    Partner/Sponsor/Collaborator : Not Applicable

    Deal Size : Not Applicable

    Deal Type : Not Applicable

    DEALS_DEV arrow-down

    Vascular Therapies Completes Enrollment in Phase III ACCESS 2 Sirolimus Study

    Details : Sirogen (sirolimus) for the surgical creation of arteriovenous (AV) fistula in patients requiring hemodialysis vascular access is being evaluated for Chronic Kidney Disease.

    Brand Name : Sirogen

    Molecule Type : Small molecule

    Upfront Cash : Not Applicable

    August 05, 2024

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    Announces Pricing of $5M Registered Direct Offering and Concurrent Private Placement

    Details:

    The net proceeds will be used to advance the clinical development of eRapa (rapamycin), also known as sirolimus. It is being evaluated for treating Familial Adenomatous Polyposis.


    Lead Product(s): Sirolimus

    Therapeutic Area: Genetic Disease Brand Name: eRapa

    Study Phase: Phase IIProduct Type: Small molecule

    Sponsor: Ladenburg Thalmann & Co

    Deal Size: $5.0 million Upfront Cash: Undisclosed

    Deal Type: Public Offering July 19, 2024

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    07

    Biodexa Pharmaceuticals

    United Kingdom
    arrow
    AES 2024
    Not Confirmed

    Biodexa Pharmaceuticals

    United Kingdom
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    Not Confirmed
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    Lead Product(s) : Sirolimus

    Therapeutic Area : Genetic Disease

    Highest Development Status : Phase II

    Partner/Sponsor/Collaborator : Ladenburg Thalmann & Co

    Deal Size : $5.0 million

    Deal Type : Public Offering

    DEALS_DEV arrow-down

    Announces Pricing of $5M Registered Direct Offering and Concurrent Private Placement

    Details : The net proceeds will be used to advance the clinical development of eRapa (rapamycin), also known as sirolimus. It is being evaluated for treating Familial Adenomatous Polyposis.

    Brand Name : eRapa

    Molecule Type : Small molecule

    Upfront Cash : Undisclosed

    July 19, 2024

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    Biodexa Reports 12-Month Data from Phase 2 eRapa Trial for GI Tract Polyps

    Details:

    eRapa is a proprietary oral capsule formulation of rapamycin (mTOR inhibitor), also known as sirolimus. It is being developed for treating Familial Adenomatous Polyposis.


    Lead Product(s): Sirolimus

    Therapeutic Area: Genetic Disease Brand Name: eRapa

    Study Phase: Phase IIProduct Type: Small molecule

    Sponsor: Not Applicable

    Deal Size: Not Applicable Upfront Cash: Not Applicable

    Deal Type: Not Applicable July 11, 2024

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    08

    Biodexa Pharmaceuticals

    United Kingdom
    arrow
    AES 2024
    Not Confirmed

    Biodexa Pharmaceuticals

    United Kingdom
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    AES 2024
    Not Confirmed
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    Lead Product(s) : Sirolimus

    Therapeutic Area : Genetic Disease

    Highest Development Status : Phase II

    Partner/Sponsor/Collaborator : Not Applicable

    Deal Size : Not Applicable

    Deal Type : Not Applicable

    DEALS_DEV arrow-down

    Biodexa Reports 12-Month Data from Phase 2 eRapa Trial for GI Tract Polyps

    Details : eRapa is a proprietary oral capsule formulation of rapamycin (mTOR inhibitor), also known as sirolimus. It is being developed for treating Familial Adenomatous Polyposis.

    Brand Name : eRapa

    Molecule Type : Small molecule

    Upfront Cash : Not Applicable

    July 11, 2024

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    Biodexa Reports Positive Phase 2 Results of eRapa™ in Familial Adenomatous Polyposis

    Details:

    eRapa is a proprietary oral capsule formulation of rapamycin (mTOR inhibitor), also known as sirolimus. It is being developed for treating Familial Adenomatous Polyposis.


    Lead Product(s): Sirolimus

    Therapeutic Area: Genetic Disease Brand Name: eRapa

    Study Phase: Phase IIProduct Type: Small molecule

    Sponsor: Not Applicable

    Deal Size: Not Applicable Upfront Cash: Not Applicable

    Deal Type: Not Applicable June 24, 2024

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    09

    Biodexa Pharmaceuticals

    United Kingdom
    arrow
    AES 2024
    Not Confirmed

    Biodexa Pharmaceuticals

    United Kingdom
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    AES 2024
    Not Confirmed
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    Lead Product(s) : Sirolimus

    Therapeutic Area : Genetic Disease

    Highest Development Status : Phase II

    Partner/Sponsor/Collaborator : Not Applicable

    Deal Size : Not Applicable

    Deal Type : Not Applicable

    DEALS_DEV arrow-down

    Biodexa Reports Positive Phase 2 Results of eRapa™ in Familial Adenomatous Polyposis

    Details : eRapa is a proprietary oral capsule formulation of rapamycin (mTOR inhibitor), also known as sirolimus. It is being developed for treating Familial Adenomatous Polyposis.

    Brand Name : eRapa

    Molecule Type : Small molecule

    Upfront Cash : Not Applicable

    June 24, 2024

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    Quoin Signs Research Agreement With University College Cork, Ireland

    Details:

    Agreement will focus on the development of novel topical rapamycin (sirolimus) formulations as potential treatments for a number of rare and orphan diseases.


    Lead Product(s): Sirolimus

    Therapeutic Area: Rare Diseases and Disorders Brand Name: Sirolimus

    Study Phase: PreclinicalProduct Type: Small molecule

    Sponsor: University College Cork

    Deal Size: Undisclosed Upfront Cash: Undisclosed

    Deal Type: Agreement June 12, 2024

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    10

    Quoin Pharmaceuticals

    U.S.A
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    AES 2024
    Not Confirmed

    Quoin Pharmaceuticals

    U.S.A
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    Not Confirmed
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    Lead Product(s) : Sirolimus

    Therapeutic Area : Rare Diseases and Disorders

    Highest Development Status : Preclinical

    Partner/Sponsor/Collaborator : University College Cork

    Deal Size : Undisclosed

    Deal Type : Agreement

    DEALS_DEV arrow-down

    Quoin Signs Research Agreement With University College Cork, Ireland

    Details : Agreement will focus on the development of novel topical rapamycin (sirolimus) formulations as potential treatments for a number of rare and orphan diseases.

    Brand Name : Sirolimus

    Molecule Type : Small molecule

    Upfront Cash : Undisclosed

    June 12, 2024

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    INTERMEDIATES SUPPLIERS

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    01

    Hangzhou Longshine Bio-Tech Co.,LTD

    China
    DDL Conference
    Not Confirmed
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    Hangzhou Longshine Bio-Tech Co.,LTD

    China
    DDL Conference
    Not Confirmed
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    (S)-1-(3-Ethoxy-4-Methoxyphenyl)-2-(Methylsulfonyl...

    CAS Number : 608141-42-0

    End Use API : Sirolimus

    About The Company : Established in 2011 and situated in Hangzhou, Zhejiang, China, Hangzhou Longshine Bio-Tech CO., Ltd is dedicated to providing services for pharmaceutical and ch...

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    02

    Hangzhou Longshine Bio-Tech Co.,LTD

    China
    DDL Conference
    Not Confirmed
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    Hangzhou Longshine Bio-Tech Co.,LTD

    China
    DDL Conference
    Not Confirmed
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    3-Acetamidophthalic anhydride

    CAS Number : 6296-53-3

    End Use API : Sirolimus

    About The Company : Established in 2011 and situated in Hangzhou, Zhejiang, China, Hangzhou Longshine Bio-Tech CO., Ltd is dedicated to providing services for pharmaceutical and ch...

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    03

    Hangzhou Longshine Bio-Tech Co.,LTD

    China
    DDL Conference
    Not Confirmed
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    Hangzhou Longshine Bio-Tech Co.,LTD

    China
    DDL Conference
    Not Confirmed
    arrow
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    3- Ethoxy-4-methoxybenzonitrile

    CAS Number : 60758-86-3

    End Use API : Sirolimus

    About The Company : Established in 2011 and situated in Hangzhou, Zhejiang, China, Hangzhou Longshine Bio-Tech CO., Ltd is dedicated to providing services for pharmaceutical and ch...

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    FDF Dossiers

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    01

    Dr. Reddy's Laboratories

    India
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    DDL Conference
    Not Confirmed
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    Virtual BoothDRL offers a portfolio of products & services, including APIs, CMO services, generics, biosimilars & differentiated formulations.

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    Flag India
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    Regulatory Info : RX

    Registration Country : USA

    SIROLIMUS

    Brand Name : SIROLIMUS

    Dosage Form : TABLET;ORAL

    Dosage Strength : 1MG

    Packaging :

    Approval Date : 2014-10-27

    Application Number : 201578

    Regulatory Info : RX

    Registration Country : USA

    Dr Reddy Company Banner

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    02

    Dr. Reddy's Laboratories

    India
    arrow
    DDL Conference
    Not Confirmed
    • fda
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    • WHO-GMP

    Virtual BoothDRL offers a portfolio of products & services, including APIs, CMO services, generics, biosimilars & differentiated formulations.

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    Flag India
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    Regulatory Info : RX

    Registration Country : USA

    SIROLIMUS

    Brand Name : SIROLIMUS

    Dosage Form : TABLET;ORAL

    Dosage Strength : 2MG

    Packaging :

    Approval Date : 2014-10-27

    Application Number : 201578

    Regulatory Info : RX

    Registration Country : USA

    Dr Reddy Company Banner

    Portfolio PDF

    Product Web Link

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    Corporate PDF

    03

    Dr. Reddy's Laboratories

    India
    arrow
    DDL Conference
    Not Confirmed
    • fda
    • EDQM
    • WHO-GMP

    Virtual BoothDRL offers a portfolio of products & services, including APIs, CMO services, generics, biosimilars & differentiated formulations.

    Contact Supplier Contact Supplier
    Flag India
    Virtual Booth Virtual Booth
    Digital Content Digital Content

    Regulatory Info : Lead Market Dossiers- Filed

    Registration Country : India

    Sirolimus

    Brand Name :

    Dosage Form : Oral Solid Dosage Form

    Dosage Strength : 1MG

    Packaging :

    Approval Date :

    Application Number :

    Regulatory Info : Lead Market Dossiers- Filed

    Registration Country : India

    Dr Reddy Company Banner

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    04

    Dr. Reddy's Laboratories

    India
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    DDL Conference
    Not Confirmed
    • fda
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    Virtual BoothDRL offers a portfolio of products & services, including APIs, CMO services, generics, biosimilars & differentiated formulations.

    Contact Supplier Contact Supplier
    Flag India
    Virtual Booth Virtual Booth
    Digital Content Digital Content

    Regulatory Info : Lead Market Dossiers- Filed

    Registration Country : India

    Sirolimus

    Brand Name :

    Dosage Form : Oral Solid Dosage Form

    Dosage Strength : 2MG

    Packaging :

    Approval Date :

    Application Number :

    Regulatory Info : Lead Market Dossiers- Filed

    Registration Country : India

    Dr Reddy Company Banner

    Portfolio PDF

    Product Web Link

    Virtual Booth

    Digital Content

    Website

    Corporate PDF

    05

    Dr. Reddy's Laboratories

    India
    arrow
    DDL Conference
    Not Confirmed
    • fda
    • EDQM
    • WHO-GMP

    Virtual BoothDRL offers a portfolio of products & services, including APIs, CMO services, generics, biosimilars & differentiated formulations.

    Contact Supplier Contact Supplier
    Flag India
    Virtual Booth Virtual Booth
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    Regulatory Info : Lead Market Dossiers- Approved in US

    Registration Country : India

    Sirolimus

    Brand Name :

    Dosage Form : Tablet

    Dosage Strength : 1MG

    Packaging :

    Approval Date :

    Application Number :

    Regulatory Info : Lead Market Dossiers- Approved in US

    Registration Country : India

    Dr Reddy Company Banner

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    06

    Dr. Reddy's Laboratories

    India
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    DDL Conference
    Not Confirmed
    • fda
    • EDQM
    • WHO-GMP

    Virtual BoothDRL offers a portfolio of products & services, including APIs, CMO services, generics, biosimilars & differentiated formulations.

    Contact Supplier Contact Supplier
    Flag India
    Virtual Booth Virtual Booth
    Digital Content Digital Content

    Regulatory Info : Lead Market Dossiers- Approved in US

    Registration Country : India

    Sirolimus

    Brand Name :

    Dosage Form : Tablet

    Dosage Strength : 2MG

    Packaging :

    Approval Date :

    Application Number :

    Regulatory Info : Lead Market Dossiers- Approved in US

    Registration Country : India

    Dr Reddy Company Banner

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    07

    Glenmark Pharmaceuticals

    India
    DDL Conference
    Not Confirmed
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    Glenmark Pharmaceuticals

    India
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    Regulatory Info : RX

    Registration Country : USA

    SIROLIMUS

    Brand Name : SIROLIMUS

    Dosage Form : TABLET;ORAL

    Dosage Strength : 0.5MG

    Packaging :

    Approval Date : 2020-10-16

    Application Number : 208691

    Regulatory Info : RX

    Registration Country : USA

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    08

    ORIFARM GROUP AS

    Denmark
    DDL Conference
    Not Confirmed
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    ORIFARM GROUP AS

    Denmark
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    DDL Conference
    Not Confirmed
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    Regulatory Info :

    Registration Country : Norway

    Sirolimus

    Brand Name : Rapamune

    Dosage Form : Antic-calc Tablet, drasjert

    Dosage Strength : 2 mg

    Packaging : Blister

    Approval Date :

    Application Number :

    Regulatory Info :

    Registration Country : Norway

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    09

    Pfizer Consumer Healthcare

    Canada
    DDL Conference
    Not Confirmed
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    Pfizer Consumer Healthcare

    Canada
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    Regulatory Info :

    Registration Country : Australia

    sirolimus

    Brand Name : Rapamune

    Dosage Form : tablet

    Dosage Strength : 2 mg

    Packaging : 100

    Approval Date :

    Application Number :

    Regulatory Info :

    Registration Country : Australia

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    10

    Pfizer Inc

    U.S.A
    DDL Conference
    Not Confirmed
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    Pfizer Inc

    U.S.A
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    Regulatory Info : RX

    Registration Country : USA

    SIROLIMUS

    Brand Name : RAPAMUNE

    Dosage Form : SOLUTION;ORAL

    Dosage Strength : 1MG/ML

    Packaging :

    Approval Date : 1999-09-15

    Application Number : 21083

    Regulatory Info : RX

    Registration Country : USA

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    DOSAGE - TABLET;ORAL - 0.5MG

    USFDA APPLICATION NUMBER - 21110

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    DOSAGE - TABLET;ORAL - 1MG

    USFDA APPLICATION NUMBER - 21110

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    DOSAGE - TABLET;ORAL - 2MG

    USFDA APPLICATION NUMBER - 21110

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    DOSAGE - TABLET;ORAL - 5MG **Federal Register...DOSAGE - TABLET;ORAL - 5MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 21110

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    APIs

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    United_States_of_America.png
    USP Grade Rapamycin API needed in the U.S.A [ENA20971]
    A compounding pharmacy specializing in the preparation of various health and nutrition finished formulations is looking for suppliers of USP Grade Rapamycin API for commercial purposes. The suppliers must support this enquiry with USDMF & CoA.
    28 Oct 2024

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    28 Oct 2024

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    28 Oct 2024

    india-flag.png
    Rapamycin (100 g) API needed in India [ENA20308]
    A research based organization that focuses on providing services to pharmaceutical industry, API Manufacturers, bulk drug suppliers and clinical CROs is looking for suppliers of Rapamycin (100 g) API for development purposes. The suppliers must support this enquiry with CoA.
    20 Aug 2024

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    20 Aug 2024

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    20 Aug 2024

    Brazil.png
    Sirolimus API needed in Brazil [ENA19048]
    A company that focuses on manufacturing, development and distribution of various cardiovascular medical devices is looking for suppliers of Sirolimus API for development purposes. The required quantity is MOQ. The suppliers must support this enquiry with GMP & CoA.
    15 Feb 2024

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    15 Feb 2024

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    15 Feb 2024

    india-flag.png
    Istradefylline & Sirolimus APIs needed in India [ENA16692]
    A company that focuses on the research, development and manufacturing of OSDs, solutions, suspensions, creams, ointments, lotions, solutions and injectables for human & veterinary use is looking for suppliers of Istradefylline & Sirolimus APIs for development purposes. The suppliers must support this enquiry with USDMF & CoA.
    23 Mar 2023

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    23 Mar 2023

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    23 Mar 2023

    United_States_of_America.png
    Injectable Grade Sirolimus (100 g - 500 g) API needed in the United States [ENA16554]
    A clinical stage T cell immunotherapy company that focuses on the development of injectables to treat and prevent cancer and infectious diseases is looking for suppliers of Injectable Grade Sirolimus (100 g - 500 g) API for development purposes. The suppliers must support this enquiry with cGMP & CoA.
    08 Mar 2023

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    08 Mar 2023

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    08 Mar 2023

    United_States_of_America.png
    Rapamycin (MOQ) API needed in the United States [ENA16175]
    A company that deals in import, export, trading and also provides consulting services to the pharmaceutical industry is looking for suppliers of Rapamycin (MOQ) API for development purposes. The suppliers must support this enquiry with CoA.
    21 Jan 2023

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    21 Jan 2023

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    21 Jan 2023

    China.png
    Sirolimus (MOQ) API needed in China [ENA15995]
    A company that focuses on research, development and manufacturing of medical devices is looking for suppliers of Sirolimus (MOQ) API for development purposes. The suppliers must support this enquiry with CoA.
    04 Jan 2023

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    04 Jan 2023

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    04 Jan 2023

    Israel.png
    Sirolimus (5 g) API needed in Israel [ENA11733]
    A company that deals in the research and development of innovative skin-related technologies is looking for suppliers of Sirolimus (5 g) API for development purpose.
    25 Oct 2021

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    25 Oct 2021

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    25 Oct 2021

    Iran.png
    Sirolimus (20 g) API needed in Iran [ENA10840]
    A pharmacy store that provides medical supplies, medicines and pharmaceutical supplements is looking for suppliers of Sirolimus (20 g) API to be used in the formulation of gel for research on Tuberous sclerosis in cooperation with a dermatological clinic.
    12 Jul 2021

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    12 Jul 2021

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    12 Jul 2021

    Israel.png
    Sirolimus (500 g, 1 kg and 2 kg) API needed in Israel [ENA10627]
    A company that is dedicated to the science of cardiovascular intervention is looking for suppliers of Sirolimus (500 g, 1 kg and 2 kg) API for development purposes. The suppliers must support this enquiry with USDMF and/ or EUDMF.
    12 Jun 2021

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    12 Jun 2021

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    12 Jun 2021

    Only 10 entries up to this point, click to access all click full view read-more
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    Patents & EXCLUSIVITIES

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    Health Canada Patents

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    01

    Pfizer Canada Inc.

    Sirolimus
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    DDL Conference
    Not Confirmed

    Pfizer Canada Inc.

    U.S.A
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    DDL Conference
    Not Confirmed

    Patent Expiration Date : 2018-03-02

    Date Granted : 2010-08-03

    Sirolimus

    Brand Name : RAPAMUNE

    Patent Number : 2230748

    Filing Date : 1998-03-02

    Strength per Unit : 2 mg

    Dosage Form : Tablet

    Human Or VET : Human

    Route of Administration : Oral

    Patent Expiration Date : 2018-03-02

    Date Granted : 2010-08-03

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    02

    Pfizer Canada Inc.

    Sirolimus
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    DDL Conference
    Not Confirmed

    Pfizer Canada Inc.

    U.S.A
    arrow
    DDL Conference
    Not Confirmed

    Patent Expiration Date : 2018-03-02

    Date Granted : 2010-08-03

    Sirolimus

    Brand Name : RAPAMUNE

    Patent Number : 2230748

    Filing Date : 1998-03-02

    Strength per Unit : 5 mg

    Dosage Form : Tablet

    Human Or VET : Human

    Route of Administration : Oral

    Patent Expiration Date : 2018-03-02

    Date Granted : 2010-08-03

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    03

    Pfizer Canada Inc.

    Sirolimus
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    DDL Conference
    Not Confirmed

    Pfizer Canada Inc.

    U.S.A
    arrow
    DDL Conference
    Not Confirmed

    Patent Expiration Date : 2018-03-02

    Date Granted : 2010-08-03

    Sirolimus

    Brand Name : RAPAMUNE

    Patent Number : 2230748

    Filing Date : 1998-03-02

    Strength per Unit : 1mg

    Dosage Form : Tablet

    Human Or VET : Human

    Route of Administration : Oral

    Patent Expiration Date : 2018-03-02

    Date Granted : 2010-08-03

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    04

    Pfizer Canada Inc.

    Sirolimus
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    Not Confirmed

    Pfizer Canada Inc.

    U.S.A
    arrow
    DDL Conference
    Not Confirmed

    Patent Expiration Date : 2013-01-04

    Date Granted : 2004-06-15

    Sirolimus

    Brand Name : RAPAMUNE

    Patent Number : 2086642

    Filing Date : 1993-01-04

    Strength per Unit : 1.0 mg / ml

    Dosage Form : Oral Solution

    Human Or VET : Human

    Route of Administration : Oral

    Patent Expiration Date : 2013-01-04

    Date Granted : 2004-06-15

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    05

    Pfizer Canada Inc.

    Sirolimus
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    DDL Conference
    Not Confirmed

    Pfizer Canada Inc.

    U.S.A
    arrow
    DDL Conference
    Not Confirmed

    Patent Expiration Date : 2014-09-28

    Date Granted : 2004-08-17

    Sirolimus

    Brand Name : RAPAMUNE

    Patent Number : 2133175

    Filing Date : 1994-09-28

    Strength per Unit : 1.0 mg / ml

    Dosage Form : Oral Solution

    Human Or VET : Human

    Route of Administration : Oral

    Patent Expiration Date : 2014-09-28

    Date Granted : 2004-08-17

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    06

    Pfizer Canada Inc.

    Sirolimus
    arrow
    DDL Conference
    Not Confirmed

    Pfizer Canada Inc.

    U.S.A
    arrow
    DDL Conference
    Not Confirmed

    Patent Expiration Date : 2014-09-28

    Date Granted : 2004-08-17

    Sirolimus

    Brand Name : RAPAMUNE

    Patent Number : 2133177

    Filing Date : 1994-09-28

    Strength per Unit : 1.0 mg / ml

    Dosage Form : Oral Solution

    Human Or VET : Human

    Route of Administration : Oral

    Patent Expiration Date : 2014-09-28

    Date Granted : 2004-08-17

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    07

    Pfizer Canada Inc.

    Sirolimus
    arrow
    DDL Conference
    Not Confirmed

    Pfizer Canada Inc.

    U.S.A
    arrow
    DDL Conference
    Not Confirmed

    Patent Expiration Date : 2018-06-11

    Date Granted : 2006-07-11

    Sirolimus

    Brand Name : RAPAMUNE

    Patent Number : 2293793

    Filing Date : 1998-06-11

    Strength per Unit : 2 mg

    Dosage Form : Tablet

    Human Or VET : Human

    Route of Administration : Oral

    Patent Expiration Date : 2018-06-11

    Date Granted : 2006-07-11

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    08

    Pfizer Canada Inc.

    Sirolimus
    arrow
    DDL Conference
    Not Confirmed

    Pfizer Canada Inc.

    U.S.A
    arrow
    DDL Conference
    Not Confirmed

    Patent Expiration Date : 2013-01-04

    Date Granted : 2006-06-15

    Sirolimus

    Brand Name : RAPAMUNE

    Patent Number : 2086642

    Filing Date : 1993-01-04

    Strength per Unit : 2 mg

    Dosage Form : Tablet

    Human Or VET : Human

    Route of Administration : Oral

    Patent Expiration Date : 2013-01-04

    Date Granted : 2006-06-15

    blank

    Portfolio PDF

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    09

    Pfizer Canada Inc.

    Sirolimus
    arrow
    DDL Conference
    Not Confirmed

    Pfizer Canada Inc.

    U.S.A
    arrow
    DDL Conference
    Not Confirmed

    Patent Expiration Date : 2018-06-11

    Date Granted : 2006-07-11

    Sirolimus

    Brand Name : RAPAMUNE

    Patent Number : 2293793

    Filing Date : 1998-06-11

    Strength per Unit : 5 mg

    Dosage Form : Tablet

    Human Or VET : Human

    Route of Administration : Oral

    Patent Expiration Date : 2018-06-11

    Date Granted : 2006-07-11

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    Portfolio PDF

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    Corporate PDF

    10

    Pfizer Canada Inc.

    Sirolimus
    arrow
    DDL Conference
    Not Confirmed

    Pfizer Canada Inc.

    U.S.A
    arrow
    DDL Conference
    Not Confirmed

    Patent Expiration Date : 2013-01-04

    Date Granted : 2004-06-15

    Sirolimus

    Brand Name : RAPAMUNE

    Patent Number : 2086642

    Filing Date : 1993-01-04

    Strength per Unit : 5 mg

    Dosage Form : Tablet

    Human Or VET : Human

    Route of Administration : Oral

    Patent Expiration Date : 2013-01-04

    Date Granted : 2004-06-15

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    REF. STANDARDS & IMPURITIES

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    Others

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    01

    USP

    U.S.A
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    Not Confirmed

    USP

    U.S.A
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    Not Confirmed

    Sirolimus (50 mg)

    CAS Number : 53123-88-9

    Quantity Per Vial : 50

    Sale Unit : mg

    Price : $245.00

    Details : Material Origin- Fermentation; USMCA- No; KOR...

    Monograph :

    Storage :

    Code/Batch No : Catalog #1612765 / F074Y0

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