기본 정보
- CAS
137071-32-0- 표준 SMILES
CC[C@@H]1/C=C(\C)C[C@H](C)C[C@H](OC)[C@H]2O[C@@](O)(C(=O)C(=O)N3CCCC[C@H]3C(=O)O[C@H](/C(C)=C/[C@@H]3CC[C@H](Cl)[C@H](OC)C3)[C@H](C)[C@@H](O)CC1=O)[C@H](C)C[C@@H]2OC- InChIKey
KASDHRXLYQOAKZ-XDSKOBMDSA-N- 분자식
- C43H68ClNO11
- 평균 분자량
- 810.4 g/mol
- 단동위원소 질량
- 809.4480897
개요
Pimecrolimus is a lactam and a macrolide.
이름 및 식별자
- 우선 이름
- Pimecrolimus
- IUPAC
- (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
- 영어명
- Pimecrolimus
- 분자식
- C43H68ClNO11
- 분자량
- 810.45
이름 및 동의어
PimecrolimusElidel137071-32-0SDZ-ASM 981SDZ-ASM-981SDZ ASM 98133-epi-Chloro-33-desoxyascomycinPimecrolimusum(-)-PIMECROLIMUS7KYV510875D11AX1515,19-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*))-
이름 더 보기
PimecrolimuCS-1835PicrolimusPimerolimusPimecrolinusUnii-7kyv510875
DTXCID0026674RefChem:56730(1R,9S,12S,13S,14S,17R,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^(4,9))octacos-18-ene-2,3,10,16-tetrone15,19-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)-DTXSID2046674ASM 981Elidel (TN)C43H68ClNO11
물성
구조 계산 물성
- XLogP
- 3.8
- 극성 표면적
- 158 Ų
- 수소 결합 공여자 수
- 2
- 수소 결합 수용자 수
- 11
- 회전 가능 결합 수
- 6
- 무거운 원자 수
- 56
- 형식 전하
- 0
- 복잡도
- 1,440
실험 및 물리화학적 성질
Human Drugs
Breast Feeding; Lactation; Milk, Human; Dermatologic Agents; Immunosuppressive Agents
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
물리화학적 성질
- 녹는점
- 135 · 135-136 °C
- 끓는 점
- 866.1 · 866.1±75.0 °C(Predicted)
- 밀도
- 1.19 · 1.19
- 저장 조건
- 2 · Keep in dark place,Sealed in dry,2-8°C
- 용해도
- DMSO(약간 용해됨, 초음파처리), 클로로포름(약간 용해됨), 메탄올(약간 용해됨)
- 물리적 상태
- 고체
- 산도 계수 (pKa)
- 9.97 · 9.97±0.70(Predicted)
- 색상
- 흰색에서 황백색까지
- InChIKey
- KASDHRXLYQOAKZ-JXCUAROPNA-N
화학적 성질
White Solid
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
GHS 분류
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P260, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P318, P319, P321, P330, P362+P364, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 4 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
유해성 정보
Hazard Classes and CategoriesAcute Tox. 4 (100%)
독성 정보
Adverse Effects
The most common side effects of pimecrolimus cream are local sensations of burning, stinging, or pruritus; this may happen, especially when the site of the application is acutely inflamed. Generally, these side effects will improve with repetitive use or mitigated by using topical steroids before the initiation of pimecrolimus.
Toxicity SummaryTopical pimecrolimus is rated category C as there have been no adequate studies in pregnant women.
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Pimecrolimus
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
안전 데이터
- wgk
- WGK 3
- 스토리지 클래스
- 11 - Combustible Solids
화학 및 산업
약리 정보
ATC Code
D - Dermatologicals
QD - Dermatologicals
Protein Binding74%-87% (in vitro, bound to plasma proteins)
Pharmacodynamics
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.
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.
Metabolism/MetabolitesNo drug metabolism was observed in human skin in vitro. Oral administration yielded metabolites produced from O-demethylation and oxygenation reactions.
FDA Pharmacological Classification
7KYV510875
PIMECROLIMUS
Established Pharmacologic Class [EPC] - Calcineurin Inhibitor Immunosuppressant
Mechanisms of Action [MoA] - Calcineurin Inhibitors
Pimecrolimus is a Calcineurin Inhibitor Immunosuppressant. The mechanism of action of pimecrolimus is as a Calcineurin Inhibitor.
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