(1S,2R,10R,11S,14R,15S)-15-methyl-14-(prop-2-en-1-yl)tetracyclo[8.7.0.02,7.011,15]heptadec-6-en-14-ol

• ChemBase编号: 1239
• 分子式: C21H32O
• 平均质量: 300.47818
• 单一同位素质量: 300.24531564
• SMILES: O[C@@]1([C@@]2([C@H]([C@H]3[C@H](CC2)[C@@H]2C(=CCCC2)CC3)CC1)C)CC=C
• Canonical SMILES: C=CC[C@]1(O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CCCC[C@H]12
• InChI: InChI=1S/C21H32O/c1-3-12-21(22)14-11-19-18-9-8-15-6-4-5-7-16(15)17(18)10-13-20(19,21)2/h3,6,16-19,22H,1,4-5,7-14H2,2H3/t16-,17+,18+,19-,20-,21-/m0/s1
• InChIKey: ATXHVCQZZJYMCF-XUDSTZEESA-N

名称和登记号

名称

• IUPAC标准名: (1S,2R,10R,11S,14R,15S)-15-methyl-14-(prop-2-en-1-yl)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-ol; (1S,2R,10R,11S,14R,15S)-15-methyl-14-(prop-2-en-1-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-ol
• IUPAC传统名: gestanin; allylestrenol
• 商标名: Perselin; Turinal; Gestanol; Gestanon; Gestormone; Orageston; Organon; Gestanin
• 别名: 17α-Allylestr-4-en-17β-ol; Allylestrenol

登记号

• CAS号: 432-60-0
• PubChem SID: 160964699; 46506946
• PubChem CID: 235905
• ATC码: G03DC01
• CHEMBL: 1445549
• Chemspider ID: 205855
• DrugBank ID: DB01431
• KEGG ID: D01374
• 美国药典/FDA物质标识码: I47VB5DZ8O
• 维基百科标题: Allylestrenol

理论计算性质

JChem

• 质子受体: 1
• 质子供体: 1
• LogD (pH = 5.5): 4.828528
• LogD (pH = 7.4): 4.8285284
• Log P: 4.8285284
• 摩尔折射率: 93.1439 cm^3
• 极化性: 36.66564 Å^3
• 极化表面积: 20.23 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 5.14
• LOG S: -5.73
• 溶解度: 5.58e-04 g/l

分子性质

药理学性质

• 妊娠期药物分类: Used in threatened miscarriage and RPL

详细说明

DrugBank - DB01431

• Drug Groups: approved
• Description: A synthetic steroid with progestational activity. [PubChem]
• Indication: Allylestrenol was designed to be used for miscarriage prevention, prevention of premature labour and has been investigated for possible use in men for treatment for benign prostatic hyperplasia.
• Pharmacology: Allylestrenol is a progestogen structurally related to progesterone that has been given in threatened and recurrent miscarriage, and to prevent premature labour. However, with the exception of proven progesterone deficiency, such use is no longer recommended. In threatened miscarriage in progesterone-deficient women a suggested dose is 5 mg three times daily by mouth for 5 to 7 days.
• Elimination: The glucuronide and sulfate conjugates of pregnanediol and pregnanolone are excreted in the urine and bile. Progesterone metabolites which are excreted in the bile may undergo enterohepatic recycling or may be excreted in the feces. Progesterone metabolites are excreted mainly by the kidneys.