(-)-Pimecrolimus
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(-)-Pimecrolimus
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CAS No:
137071-32-0
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Formula:
C43H68ClNO11
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Chemical Name:
(-)-Pimecrolimus
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Synonyms:
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)-;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*]]-;(3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-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-15,19-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone;33-epi-Chloro-33-desoxyascomycin;SDZ-ASM 981;Pimecrolimus;Elidel;ASM 981;33-Epichloro-33-desoxyascomycin;Picrolimus;(-)-Pimecrolimus
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CAS No:
Description
Pimecrolimus is an immunophilin ligand, which binds specifically to the cytosolic receptor, immunophilin macrophilin-12.Target: OthersPimecrolimus blocks T-lymphocyte activation pathway by inhibiting calcineurin function [1]. Pimecrolimus prevents the release of cytokines and pro-inflammatory mediators from mast cells. Pimecrolimus binds to macrophilin-12, the pimecrolimusmacrophilin complex then binds to the cytosolic enzyme calcineurin phosphatase. The pimecrolimus-macrophilin complex
Characteristics
158.13000
5.65730
white crystalline powder
1.2±0.1 g/cm3
135-136 °C
866.1°C at 760 mmHg
477.6±37.1 °C
1.543
-20°C Freezer
5.44E-35mmHg at 25°C
Safety Information
NONH for all modes of transport
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P312, P304+P340, P308+P313, P312, P314, P322, P330, P363, P405, and P501|Aggregated GHS information provided by 3 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Drug Information
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.)|Compounds that inhibit or block the PHOSPHATASE activity of CALCINEURIN. (See all compounds classified as Calcineurin Inhibitors.)|Drugs used to treat or prevent skin disorders or for the routine care of skin. (See all compounds classified as Dermatologic 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.)
33-epi-chloro-33-desoxyascomycin
(-)-Pimecrolimus Use and Manufacturing
Pimecrolimus caused a strong and dose-dependent inhibition of anti-IgE–induced release of histamine from mast cells and basophils (maximally 73% and 82%, respectively, at 500 nmol/L pimecrolimus) and of mast cell tryptase (maximally 75%) and a less pronou
Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients
Computed Properties
Molecular Weight:810.4
XLogP3:3.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:11
Rotatable Bond Count:6
Exact Mass:809.4480897
Monoisotopic Mass:809.4480897
Topological Polar Surface Area:158
Heavy Atom Count:56
Complexity:1440
Defined Atom Stereocenter Count:14
Defined Bond Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
Pimecrolimus is a lipophilic anti-inflammatory derivative of ascomycin macrolactam that selectively inhibits the production and release of pro-inflammatory cytokines and mediators by pro-T cells and macrophages. Pimecrolimus has a high affinity for macrophilin-12 and inhibits calcineurin. Therefore, pimecrolimus inhibits T cell proliferation and blocks the transcription of helper T cells 1 (TH1) and helper T cells 2 (TH2), thereby inhibiting the release of inflammatory cytokines, such as interleukin-2, interferon-γ, interleukin-4, interleukin-5, interleukin-10, tumor necrosis factor-α, and granulocyte-macrophage colony factor. In vitro studies of helper T cells isolated from the skin of patients with atopic dermatitis showed that pimecrolimus and tacrolimus were equally effective in inhibiting memory antigen responses. Pimecrolimus also inhibited the release of cytokines and inflammatory mediators by mast cells activated by IgE. Pimecrolimus had no effect on the growth of keratinocytes, fibroblasts, or endothelial cells. Unlike glucocorticoids, pimecrolimus does not affect the differentiation, maturation, function and proliferation of Langerhans cells and human dendritic monocytes, thus having cell-selective effects.
Registered Holders
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CURIA Italy SRL
Active
United States
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BrightGene Pharmaceutical Co., Ltd.
Active
China
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CHENGDU YACHT BIOTECHNOLOGY CO LTD
Active
United States
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