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    Chemistry

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    Also known as: Elidel, 137071-32-0, Sdz-asm 981, Sdz-asm-981, Sdz asm 981, 33-epi-chloro-33-desoxyascomycin
    Molecular Formula
    C43H68ClNO11
    Molecular Weight
    810.4  g/mol
    InChI Key
    KASDHRXLYQOAKZ-XDSKOBMDSA-N
    FDA UNII
    7KYV510875
    Pimecrolimus
    Pimecrolimus is a 33-epi-chloro-derivative of the ascomycin macrolactam with immunosuppressant property. Pimecrolimus binds to the receptor macrophilin-12 (FKBP-12) forming a complex that blocks the calcium-dependent signal transduction cascade mediated by calcineurin. Via dephosphorylation, calcineurin is the enzyme responsible for activating nuclear factor of activated T-cells (NF-AT), a T cell transcriptional regulatory factor. As a consequence, the synthesis and release of Th1- (T helper 1) and Th2- (T helper 2) type cytokines, and other inflammatory mediators from T-cells and mast cells are blocked and the expression of signals essential for the activation of inflammatory T-lymphocytes is inhibited. However, pimecrolimus mode of action is cell-selective and does not affect Langerhans' cells/dendritic cells and primary fibroblasts.
    Pimecrolimus is a Calcineurin Inhibitor Immunosuppressant. The mechanism of action of pimecrolimus is as a Calcineurin Inhibitor.
    1 2D Structure

    Pimecrolimus

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-12-[(E)-1-[(1R,3R,4S)-4-chloro-3-methoxycyclohexyl]prop-1-en-2-yl]-17-ethyl-1,14-dihydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetrone
    2.1.2 InChI
    InChI=1S/C43H68ClNO11/c1-10-30-18-24(2)17-25(3)19-36(53-8)39-37(54-9)21-27(5)43(51,56-39)40(48)41(49)45-16-12-11-13-32(45)42(50)55-38(28(6)33(46)23-34(30)47)26(4)20-29-14-15-31(44)35(22-29)52-7/h18,20,25,27-33,35-39,46,51H,10-17,19,21-23H2,1-9H3/b24-18+,26-20+/t25-,27+,28+,29-,30+,31-,32-,33-,35+,36-,37-,38+,39+,43+/m0/s1
    2.1.3 InChI Key
    KASDHRXLYQOAKZ-XDSKOBMDSA-N
    2.1.4 Canonical SMILES
    CCC1C=C(CC(CC(C2C(CC(C(O2)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C(CC1=O)O)C)C(=CC4CCC(C(C4)OC)Cl)C)O)C)OC)OC)C)C
    2.1.5 Isomeric SMILES
    CC[C@@H]1/C=C(/C[C@@H](C[C@@H]([C@@H]2[C@H](C[C@H]([C@@](O2)(C(=O)C(=O)N3CCCC[C@H]3C(=O)O[C@@H]([C@@H]([C@H](CC1=O)O)C)/C(=C/[C@@H]4CC[C@@H]([C@@H](C4)OC)Cl)/C)O)C)OC)OC)C)\C
    2.2 Other Identifiers
    2.2.1 UNII
    7KYV510875
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 33-epi-chloro-33-desoxyascomycin

    2. Asm 981

    3. Elidel

    4. Sdz Asm 981

    5. Sdz-asm-981

    2.3.2 Depositor-Supplied Synonyms

    1. Elidel

    2. 137071-32-0

    3. Sdz-asm 981

    4. Sdz-asm-981

    5. Sdz Asm 981

    6. 33-epi-chloro-33-desoxyascomycin

    7. Asm 981

    8. 7kyv510875

    9. Elidel (tn)

    10. Pimecrolimus [usan:inn:ban]

    11. 1000802-56-1

    12. 33-epichloro-33-desoxyascomycin

    13. Pimecrolimus (jan/usan/inn)

    14. Unii-7kyv510875

    15. Asm-981

    16. Asm-998

    17. Ncgc00167506-01

    18. Pimecrolimus (elidel)

    19. Pimecrolimus [mi]

    20. (-)-pimecrolimus

    21. Pimecrolimus [inn]

    22. Pimecrolimus [jan]

    23. Pimecrolimus [usan]

    24. Pimecrolimus [vandf]

    25. Pimecrolimus [mart.]

    26. Pimecrolimus [who-dd]

    27. Schembl438880

    28. Sdz Asm-981

    29. Gtpl6783

    30. Schembl3000675

    31. Chembl1200686

    32. Pimecrolimus, >=97% (hplc)

    33. Chebi:135888

    34. Pimecrolimus [orange Book]

    35. Ex-a2138

    36. Bdbm50248356

    37. Mfcd00901792

    38. S5004

    39. Zinc85536990

    40. Akos015895946

    41. Ccg-270502

    42. Db00337

    43. Ncgc00167506-04

    44. Hy-13723

    45. B1817

    46. D05480

    47. Ab01566841_01

    48. 071p320

    49. Q417489

    50. Q-201579

    51. Brd-k92107055-001-01-9

    52. (1r,9s,12s,13r,14s,17r,18e,21s,23s,24r,25s,27r)-12-[(1e)-1-[(1r,3r,4s)-4-chloro-3-methoxycyclohexyl]prop-1-en-2-yl]-17-ethyl-1,14-dihydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.0?,?]octacos-18-ene-2,3,10,16-tetrone

    53. (3s,4r,5s,8r,9e,12s,14s,15r,16s,18r,19r,26as)-3-((e)-2-((1r,3r,4s)-4-chloro-3-methoxycyclohexyl)-1-methylvinyl)-8-ethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,26,26a-hexadecahydro-5,19-epoxy-3h-pyrido(2,1-c)(1,4)oxaazacyclotricosine-1,17,20,21(4h,23h)-tetrone

    54. 15,19-epoxy-3h-pyrido(2,1-c)(1,4)oxaazacyclotricosine-1,7,20,21(4h,23h)-tetrone, 3-((1e)-2-((1r,3r,4s)-4-chloro-3-methoxycyclohexyl)-1-methylethenyl)-8-ethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-14,16-dimethoxy-4,10,12,18-tetramethyl-, (3s,4r,5s,8r,9e,12s,14s,15r,16s,18r,19r,26as)-

    55. 15,19-epoxy-3h-pyrido(2,1-c)(1,4)oxaazacyclotricosine-1,7,20,21(4h,23h)-tetrone, 3-(2-(4-chloro-3-methoxycyclohexyl)-1-methylethenyl)-8-ethyl-, 5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-14,16-dimethoxy-4,10,12,18-tetramethyl-, (3s-(3r*(e(1s*,3s*,4r*)),4s*,5r*,8s*,9e,12r*,14r*,15s*,16r*,18s*,19s*,26ar*))-

    2.4 Create Date
    2006-05-02
    3 Chemical and Physical Properties
    Molecular Weight 810.4 g/mol
    Molecular Formula C43H68ClNO11
    XLogP33.8
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count11
    Rotatable Bond Count6
    Exact Mass809.4480897 g/mol
    Monoisotopic Mass809.4480897 g/mol
    Topological Polar Surface Area158 Ų
    Heavy Atom Count56
    Formal Charge0
    Complexity1440
    Isotope Atom Count0
    Defined Atom Stereocenter Count14
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count2
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameElidel
    PubMed HealthPimecrolimus (On the skin)
    Drug ClassesDermatological Agent
    Drug LabelELIDEL (pimecrolimus) Cream 1% contains the compound pimecrolimus, the immunosuppressant 33-epi-chloro-derivative of the macrolactam ascomycin.Chemically, pimecrolimus is (1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-12-[(1E)-2-{(1R,3R,4S)-4-chl...
    Active IngredientPimecrolimus
    Dosage FormCream
    RouteTopical
    Strength1%
    Market StatusPrescription
    CompanyValeant Bermuda

    2 of 2  
    Drug NameElidel
    PubMed HealthPimecrolimus (On the skin)
    Drug ClassesDermatological Agent
    Drug LabelELIDEL (pimecrolimus) Cream 1% contains the compound pimecrolimus, the immunosuppressant 33-epi-chloro-derivative of the macrolactam ascomycin.Chemically, pimecrolimus is (1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-12-[(1E)-2-{(1R,3R,4S)-4-chl...
    Active IngredientPimecrolimus
    Dosage FormCream
    RouteTopical
    Strength1%
    Market StatusPrescription
    CompanyValeant Bermuda

    4.2 Drug Indication

    For treatment of mild to moderate atopic dermatitis.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Pimecrolimus is a chemical that is used to treat atopic dermatitis (eczema). Atopic dermatitis is a skin condition characterized by redness, itching, scaling and inflammation of the skin. The cause of atopic dermatitis is not known; however, scientists believe that it may be due to activation of the immune system by various environmental or emotional triggers. Scientists do not know exactly how pimecrolimus reduces the manifestations of atopic dermatitis, but pimecrolimus reduces the action of T-cells and mast cells which are part of the immune system and contribute to responses of the immune system. Pimecrolimus prevents the activation of T-cells by blocking the effects of chemicals (cytokines) released by the body that stimulate T-cells. Pimecrolimus also reduces the ability of mast cells to release chemicals that promote inflammation.

    5.2 MeSH Pharmacological Classification

    Anti-Inflammatory Agents, Non-Steroidal

    Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)

    Calcineurin Inhibitors

    Compounds that inhibit or block the PHOSPHATASE activity of CALCINEURIN. (See all compounds classified as Calcineurin Inhibitors.)

    Dermatologic Agents

    Drugs used to treat or prevent skin disorders or for the routine care of skin. (See all compounds classified as Dermatologic 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.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    PIMECROLIMUS
    5.3.2 FDA UNII
    7KYV510875
    5.3.3 Pharmacological Classes
    Calcineurin Inhibitors [MoA]; Calcineurin Inhibitor Immunosuppressant [EPC]
    5.4 ATC Code

    D - Dermatologicals

    D11 - Other dermatological preparations

    D11A - Other dermatological preparations

    D11AH - Agents for dermatitis, excluding corticosteroids

    D11AH02 - Pimecrolimus

    5.5 Absorption, Distribution and Excretion

    Absorption

    Because of the low systemic absorption of pimecrolimus following topical application the calculation of standard pharmacokinetic measures such as AUC, Cmax, half-life, etc. cannot be reliably done.

    Route of Elimination

    80% of the drug is excreted in the feces.

    5.6 Metabolism/Metabolites

    No drug metabolism was observed in human skin in vitro. Oral administration yielded metabolites produced from O-demethylation and oxygenation reactions.

    5.7 Mechanism of Action

    Pimecrolimus binds with high affinity to macrophilin-12 (FKBP-12) and inhibits the calcium-dependent phosphatase, calcineurin. As a consequence, it inhibits T cell activation by blocking the transcription of early cytokines. In particular, pimecrolimus inhibits at nanomolar concentrations Interleukin-2 and interferon gamma (Th1-type) and Interleukin-4 and Interleukin-10 (Th2-type) cytokine synthesis in human T cells. Also, pimecrolimus prevents the release of inflammatory cytokines and mediators from mast cells in vitro after stimulation by antigen/lgE.

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    20-Jan-2021
    12-Aug-2024
    KGS
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    Average Price (USD/KGS)

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    Quantity (KGS) & Unit rate (USD/KGS) over time

    API Imports and Exports

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    (KGS)    		 Average Price
    (USD/KGS)    		 Number of Transactions

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