基本情報
- CAS
137071-32-0- 標準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- 分子式
- C43H68ClNO11
- 平均分子量
- 810.4 g/mol
- 単同位体質量
- 809.4480897
概要
Pimecrolimus is a lactam and a macrolide.
名称と識別子
- 優先名称
- 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
- 現地名
- ピメチルクロリムス(ELIエリデル
- 英語名
- Pimecrolimus
- 分子式
- C43H68ClNO11
- 分子量
- 810.45
名称と別名
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*))-
名称をさらに表示
ピメチルクロリムス(ELIエリデルピメチルクロリムスピメクロリムスピメクロリムス (JAN)(1R,9S,12S,13R,14S,17S,18E,21S,23S,24R,25S,27R)-12-[(1E)-1-[(1S,3R,4S)-4-クロロ-3-メトキシシクロヘキシル]プロパ-1-エン-2-イル]-17-エチル-1,14-ジヒドロキシ-23,25-ジメトキシ-13,19,21,27-テトラメチル-11,28-ジオキサ-4-アザトリシクロ[22.3.1.04,9]オクタコサ-18-エン-2,3,10,16-テトラオン(1R,9S,12S,13R,14S,17S,18E,21S,23S,24R,25S,27R)-1,14-ジヒドロキシ-12-[(E)-1-メチル-2-[(1S)-3β-メトキシ-4β-クロロシクロヘキシル]エテニル]-13,19,21,27-テトラメチル-17-エチル-23,25-ジメトキシ-11,28-ジオキサ-4-アザトリシクロ[22.3.1.04,9]オクタコサ-18-エン-2,3,10,16-テトラオン
物性
構造計算による物性
- XLogP
- 3.8
- 極性表面積
- 158 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 11
- 回転可能結合数
- 6
- 重原子数
- 56
- 形式電荷
- 0
- 複雑度
- 1,440
実験および物理化学的性質
Human Drugs
Breast Feeding; Lactation; Milk, Human; Dermatologic Agents; Immunosuppressive Agents
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
物理化学的性質
- 融点
- 135 · 135-136 °C
- 沸点
- 866.1 · 866.1±75.0 °C(Predicted)
- 比重(密度)
- 1.19 · 1.19
- 貯蔵温度
- 2 · Keep in dark place,Sealed in dry,2-8°C
- 溶解性
- DMSO（微量、超音波処理）、クロロホルム（微量）、メタノール（微量）
- 外見
- 個体
- 酸解離定数(Pka)
- 9.97 · 9.97±0.70(Predicted)
- 色
- ホワイトからオフホワイト
- InChIKey
- KASDHRXLYQOAKZ-JXCUAROPNA-N
化学的性質
化学的特性White Solid
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
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.
危険有害性情報
Hazard Classes and CategoriesAcute Tox. 4 (100%)
毒性情報
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
安全データ
- wgk
- WGK 3
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
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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