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    Irinotecan

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    2D Structure
    Also known as: 100286-90-6, Irinotecan hcl, Topotecin, Campto, Camptothecin 11 hydrochloride, Camptosar
    Molecular Formula
    C33H39ClN4O6
    Molecular Weight
    623.1  g/mol
    InChI Key
    GURKHSYORGJETM-WAQYZQTGSA-N
    FDA UNII
    06X131E4OE
    A semisynthetic camptothecin derivative that inhibits DNA TOPOISOMERASE I to prevent nucleic acid synthesis during S PHASE. It is used as an antineoplastic agent for the treatment of COLORECTAL NEOPLASMS and PANCREATIC NEOPLASMS.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [(19S)-10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaen-7-yl] 4-piperidin-1-ylpiperidine-1-carboxylate;hydrochloride
    2.1.2 InChI
    InChI=1S/C33H38N4O6.ClH/c1-3-22-23-16-21(43-32(40)36-14-10-20(11-15-36)35-12-6-5-7-13-35)8-9-27(23)34-29-24(22)18-37-28(29)17-26-25(30(37)38)19-42-31(39)33(26,41)4-2;/h8-9,16-17,20,41H,3-7,10-15,18-19H2,1-2H3;1H/t33-;/m0./s1
    2.1.3 InChI Key
    GURKHSYORGJETM-WAQYZQTGSA-N
    2.1.4 Canonical SMILES
    CCC1=C2CN3C(=CC4=C(C3=O)COC(=O)C4(CC)O)C2=NC5=C1C=C(C=C5)OC(=O)N6CCC(CC6)N7CCCCC7.Cl
    2.1.5 Isomeric SMILES
    CCC1=C2CN3C(=CC4=C(C3=O)COC(=O)[C@@]4(CC)O)C2=NC5=C1C=C(C=C5)OC(=O)N6CCC(CC6)N7CCCCC7.Cl
    2.2 Other Identifiers
    2.2.1 UNII
    06X131E4OE
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 7 Ethyl 10 Hydroxycamptothecin

    2. 7-ethyl-10-hydroxycamptothecin

    3. Camptosar

    4. Camptothecin 11

    5. Camptothecin-11

    6. Cpt 11

    7. Cpt-11

    8. Cpt11

    9. Irinotecan

    10. Irrinotecan

    11. Nk012 Compound

    12. Sn 38

    13. Sn 38 11

    14. Sn-38

    15. Sn-38-11

    16. Sn3811

    2.3.2 Depositor-Supplied Synonyms

    1. 100286-90-6

    2. Irinotecan Hcl

    3. Topotecin

    4. Campto

    5. Camptothecin 11 Hydrochloride

    6. Camptosar

    7. Cpt 11

    8. Cpt-11

    9. Irinotecan (hydrochloride)

    10. Camptothecin 11

    11. U 101440e

    12. Chebi:5971

    13. (s)-4,11-diethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl [1,4'-bipiperidine]-1'-carboxylate Hydrochloride

    14. Camptothecin Analog

    15. 06x131e4oe

    16. 7-ethyl-10-(4-(1-piperidino)-1-piperidino)carbonyloxy Camptothecin Hydrochloride

    17. Nsc616348

    18. Nsc-616348

    19. Ncgc00095190-01

    20. Dsstox_cid_25953

    21. Dsstox_rid_81249

    22. Dsstox_gsid_45953

    23. [(19s)-10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaen-7-yl] 4-piperidin-1-ylpiperidine-1-carboxylate;hydrochloride

    24. Irinotecan Hydrochloride Anhydrous

    25. Cas-100286-90-6

    26. U-101440e

    27. Unii-06x131e4oe

    28. Irinotecan Hydrochloride [usan:jan]

    29. Mfcd01862255

    30. Irinotecanhydrochloride

    31. Cpt-11 Hydrochloride

    32. Irinotecan Monohydrochloride

    33. Schembl4033

    34. Camptosar (tn) (pharmacia)

    35. (s)-[1,4'-bipiperidine]-1'-carboxylic Acid, 4,11-diethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl Ester Hydrochloride

    36. Spectrum1505821

    37. Chembl541887

    38. Dtxsid6045953

    39. Hms1922j04

    40. Pharmakon1600-01505821

    41. Amy24895

    42. Bcp17234

    43. Irinotecan Hydrochloride (anhydrous)

    44. Tox21_111479

    45. Hy-16562a

    46. Nsc759878

    47. S5026

    48. Akos015901921

    49. Tox21_111479_1

    50. Ccg-213561

    51. Irinotecan Hydrochloride [who-dd]

    52. Ncgc00095190-02

    53. Ncgc00178697-04

    54. (1,4'-bipiperidine)-1'-carboxylic Acid, (4s)-4,11-diethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-1h-pyrano(3',4':6,7)indolizino(1,2-b)quinolin-9-yl Ester, Monohydrochloride

    55. (1,4'-bipiperidine)-1'-carboxylic Acid, 3,4,12,14-tetrahydro-4,11-diethyl-4-hydroxy-3,4-dioxo-1h-pyrano(3',4':6,7)indolizino(1,2-b)quinolin-9-yl Ester, Monohydrochloride, (s)-

    56. Ac-28335

    57. As-13304

    58. I0714

    59. Irinotecan Hydrochloride Anhydrous [mi]

    60. Irinotecan Hydrochloride, Topoisomerase Inhibitor

    61. 286i906

    62. A897508

    63. Sr-01000763864

    64. Q-100016

    65. Sr-01000763864-3

    66. Q27106952

    67. Z1550648758

    68. (+)-7-ethyl-10-hydroxycamptothecine 10-(1,4'-bipiperidine)-1'-carboxylate, Monohydrochloride

    69. (1,4'-bipiperidine)-1'-carboxylic Acid, (4s)-4,11-diethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-1h-pyrano(3',4':6,7)indolizino(1,2-b)quinolin-9-yl Ester, Hydrochloride (1:1)

    70. (19s)-10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaen-7-yl [1,4'-bipiperidine]-1'-carboxylate Hydrochloride

    71. (4s)-4,11-diethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl [1,4'-bipiperidine]-1'-carboxylic Acid Ester Hydrochloride

    72. (4s)-4,11-diethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl [1,4'-bipiperidine]-1'-carboxylate Hydrochloride

    73. (s)-4,11-diethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl[1,4'-bipiperidine]-1'-carboxylatehydrochloride

    74. [(19s)-10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaen-7-yl] 4-piperidin-1-ylpiperidine-1-carboxylate Hydrochloride

    75. [1, 4,11-diethyl-3,4,12, 14-tetrahydro-4-hydroxy-3,14-dioxo-1h-pyrano[3',4':6,7] Indolizino[1,2-b]quinolin-9-yl Ester, Monohydrochloride (s)-

    76. [1,4'-bipiperidine]-1'-carboxylic Acid,(4s)-4,11-diethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl Ester, Monohydrochloride

    77. 1-[1-({[(4s)-4,11-diethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl]oxy}carbonyl)piperidin-4-yl]piperidin-1-ium Chloride

    2.3.3 Other Synonyms

    1. Camptosar

    2. Campto

    3. Irinotecan

    4. Hy-16562

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 623.1 g/mol
    Molecular Formula C33H39ClN4O6
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count8
    Rotatable Bond Count5
    Exact Mass622.2558127 g/mol
    Monoisotopic Mass622.2558127 g/mol
    Topological Polar Surface Area113 Ų
    Heavy Atom Count44
    Formal Charge0
    Complexity1200
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameIrinotecan hydrochloride
    Drug LabelIrinotecan hydrochloride injection is an antineoplastic agent of the topoisomerase I inhibitor class. Irinotecan hydrochloride was clinically investigated as CPT-11. Irinotecan hydrochloride injection is supplied as a sterile, pale yellow, clear, aqu...
    Active IngredientIrinotecan hydrochloride
    Dosage FormInjectable
    Routeinjection; Injection
    Strength20mg/ml; 100mg/5ml (20mg/ml); 500mg/25ml (20mg/ml); 100mg/5ml; 40mg/2ml (20mg/ml)
    Market StatusPrescription
    CompanyPliva Lachema; Hospira; Teva Parenteral; Fresenius Kabi Oncol; Accord Hlthcare; Jiangsu Hengrui Med; Hikma Farmaceutica; Teva Pharms Usa; Cipla; Hisun Pharm Hangzhou; Sun Pharma Global; Actavis Elizabeth; Emcure Pharms; Mustafa Nevzat Ilac; Fresenius Kabi

    2 of 2  
    Drug NameIrinotecan hydrochloride
    Drug LabelIrinotecan hydrochloride injection is an antineoplastic agent of the topoisomerase I inhibitor class. Irinotecan hydrochloride was clinically investigated as CPT-11. Irinotecan hydrochloride injection is supplied as a sterile, pale yellow, clear, aqu...
    Active IngredientIrinotecan hydrochloride
    Dosage FormInjectable
    Routeinjection; Injection
    Strength20mg/ml; 100mg/5ml (20mg/ml); 500mg/25ml (20mg/ml); 100mg/5ml; 40mg/2ml (20mg/ml)
    Market StatusPrescription
    CompanyPliva Lachema; Hospira; Teva Parenteral; Fresenius Kabi Oncol; Accord Hlthcare; Jiangsu Hengrui Med; Hikma Farmaceutica; Teva Pharms Usa; Cipla; Hisun Pharm Hangzhou; Sun Pharma Global; Actavis Elizabeth; Emcure Pharms; Mustafa Nevzat Ilac; Fresenius Kabi

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Topoisomerase I Inhibitors

    Compounds that inhibit the activity of DNA TOPOISOMERASE I. (See all compounds classified as Topoisomerase I Inhibitors.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Topoisomerase Inhibitors [MoA]; Topoisomerase Inhibitor [EPC]