基本情報
- CAS
13647-35-3- 標準SMILES
C[C@]12CC[C@H]3[C@@H](CC[C@@]45O[C@@H]4C(O)=C(C#N)C[C@]35C)[C@@H]1CC[C@@H]2O- InChIKey
KVJXBPDAXMEYOA-CXANFOAXSA-N- 分子式
- C20H27NO3
- 平均分子量
- 329.4 g/mol
- 単同位体質量
- 329.19909372
概要
Trilostane can cause developmental toxicity according to state or federal government labeling requirements.
名称と識別子
- 優先名称
- Trilostane
- IUPAC
- (1S,2R,6R,8S,11S,12S,15S,16S)-5,15-dihydroxy-2,16-dimethyl-7-oxapentacyclo[9.7.0.02,8.06,8.012,16]octadec-4-ene-4-carbonitrile
- 現地名
- トリロスタン
- 英語名
- Trilostane
- 分子式
- C20H27NO3
- 分子量
- 329.43
名称と別名
Trilostane13647-35-3ModrenalDesopanVetorylTrilostanoModrastaneTrilostanumWin-24540WIN 24,540DTXSID9023706L0FPV48Q5R
名称をさらに表示
トリロスタンデソパン4α,5-エポキシ-3,17β-ジヒドロキシ-5α-アンドロスタ-2-エン-2-カルボニトリル4α,5-エポキシ-3,17β-ジヒドロキシ-5α-アンドロスタン-2-エン-2-カルボニトリルトリロスタン (JAN)(1S,2R,6R,8S,11S,12S,15S,16S)-5,15-ジヒドロキシ-2,16-ジメチル-7-オキサペンタシクロ[9.7.0.02,8.06,8.012,16]オクタデカ-4-エン-4-カルボニトリルrilostaneTrilostan(1aS,4aR,4bS,6aS,7S,9aS,9bS,11aR)-2,7-Dihydroxy-4a,6a-dimethyl-1a,4,4a,4b,5,6,6a,7,8,9,9a,9b,10,11-tetradecahydrocyclopenta[7,8]phenanthro[1,10a-b]oxirene-3-carbonitrileModrefenTrostan*
Win 24540CHEBI:32260VETORYL CAPSULESNSC-758904Androst-2-ene-2-carbonitrile, 4,5-epoxy-3,17-dihydroxy-, (4alpha,5alpha,17beta)-DTXCID1037064alpha,5-epoxy-17beta-hydroxy-3-oxoandrostane-2-carbonitrile(1S,2R,6R,8S,11S,12S,15S,16S)-5,15-dihydroxy-2,16-dimethyl-7-oxapentacyclo[9.7.0.0^{2,8}.0^{6,8}.0^{12,16}]octadec-4-ene-4-carbonitrile
物性
構造計算による物性
- XLogP
- 2.9
- 極性表面積
- 76.8 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 4
- 回転可能結合数
- 0
- 重原子数
- 24
- 形式電荷
- 0
- 複雑度
- 692
実験および物理化学的性質
DrugsPharmaceuticals -> Listed in ZINC15
LogP3
Solubility5.93e-02 g/L
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Animal Drugs
EMA approved medicines: Veterinary medicine
EMA approved medicines: Veterinary medicine
FDA approved animal drugs -> Active ingredient
Pharmaceuticals -> UK Veterinary Medicines Directorate List
Melting Point264 °C
Physical DescriptionSolid
Collision Cross Section
186.2 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID9023706]
173.45 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
物理化学的性質
- 融点
- 264 °C · 264 °C
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
H315 (98%): Causes skin irritation [Warning Skin corrosion/irritation]
P203, P264, P264+P265, P280, P302+P352, P305+P351+P338, P318, P321, P332+P317, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 49 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Regulatory InformationHazard Traits - Developmental Toxicity
Hazard Classes and CategoriesSkin Irrit. 2 (98%)
安全データ
- wgk
- 3
- hs_code
- 29372900
- risk_code
- 36/37/38-62
- hazard_code
- Xi
- safety_code
- 26-36/37
- Hazard Classifications
- Eye Irrit. 2Repr. 2Skin Irrit. 2
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
ATC Code
H - Systemic hormonal preparations, excl. sex hormones and insulins
QH - Systemic hormonal preparations, excl. sex hormones and insulin
Pharmacodynamics
Trilostane blocks an enzyme involved in the production of several steroids including cortisol. Inhibiting this enzyme inhibits the production of cortisol. In Cushing's syndrome, the adrenal gland overproduces steroids. Although steroids are important for various functions of the body, too much can cause problems. Trilostane reduces the amount of steroids produced by the adrenal gland. This product was withdrawn from the U.S. market in April 1994.
Mechanism of ActionTrilostane produces suppression of the adrenal cortex by inhibiting enzymatic conversion of steroids by 3-beta-hydroxysteroid dehydrogenase/delta 5,4 ketosteroid isomerase, thus blocking synthesis of adrenal steroids.
Biological Half-Life8 hours.
Metabolism/MetabolitesHepatic.
MeSH Pharmacological Classification
Steroidal compounds with abortifacient activity.
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Cellular LocationsCytoplasm
応用分野
説明3β-hydroxysteroid dehydrogenase (3β-HSD) type 1 and type 2 isoforms are key enzymes for the biosynthesis of all active steroid hormones. 3β-HSD1 (type I) is expressed in placenta and peripheral tissues including breast tumors, whereas 3β-HSD2 (type 2) is expressed in the adrenal gland, ovary, and testis. Trilostane is an inhibitor of the 3β-HSDs: 3β-HSD1 and 3β-HSD2 with Ki values of 0.10 and 1.60 μM, respectively. Trilsotane has been approved for use in the treatment of Cushing’s syndrome in dogs to reduce cortisol, aldosterone, and corticosterone levels. Because human 3β-HSD (type 1) is a critical enzyme in the conversion of DHEA to estradiol in breast tumors, trilostane is also of interest for the treatment of breast cancer in postmenopausal women.
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