(14R)-15-ethyl-14-ethynyl-14-hydroxy-17-methylidenetetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

• ChemBase编号: 179
• 分子式: C22H28O2
• 平均质量: 324.45652
• 单一同位素质量: 324.20893014
• SMILES: O[C@@]1(C2(C(C3C(C4C(=CC(=O)CC4)CC3)C(=C)C2)CC1)CC)C#C
• Canonical SMILES: C#C[C@]1(O)CCC2C1(CC)CC(=C)C1C2CCC2=CC(=O)CCC12
• InChI: InChI=1S/C22H28O2/c1-4-21-13-14(3)20-17-9-7-16(23)12-15(17)6-8-18(20)19(21)10-11-22(21,24)5-2/h2,12,17-20,24H,3-4,6-11,13H2,1H3/t17?,18?,19?,20?,21?,22-/m0/s1
• InChIKey: GCKFUYQCUCGESZ-KIIRVTSASA-N

名称和登记号

名称

• IUPAC标准名: (14R)-15-ethyl-14-ethynyl-14-hydroxy-17-methylidenetetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
• IUPAC传统名: etonogestrel
• 商标名: Implanon
• 别名: etonogestrel; Etonogestrel

登记号

• CAS号: 54048-10-1
• PubChem SID: 160963642
• PubChem CID: 40976

理论计算性质

JChem

• Acid pKa: 17.993504
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 3.6011698
• LogD (pH = 7.4): 3.6011698
• Log P: 3.6011698
• 摩尔折射率: 96.3516 cm^3
• 极化性: 37.451656 Å^3
• 极化表面积: 37.3 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.19
• LOG S: -4.64
• 溶解度: 7.37e-03 g/l

分子性质

理化性质

• 疏水性(logP): 3.4

详细说明

DrugBank - DB00294

• Drug Groups: approved; investigational
• Description: Etonogestrel is a molecule used in hormonal contraceptives, most notably the subdermal implant Implanon. [Wikipedia]
• Indication: For use as a female contraceptive (depot).
• Pharmacology: Etonogestrel is used as a female contraceptive. Etonogestrel is a progestin or a synthetic form of the naturally occurring female sex hormone, progesterone. In a woman's normal menstrual cycle, an egg matures and is released from the ovaries (ovulation). The ovary then produces progesterone, preventing the release of further eggs and priming the lining of the womb for a possible pregnancy. If pregnancy occurs, progesterone levels in the body remain high, maintaining the womb lining. If pregnancy does not occur, progesterone levels in the body fall, resulting in a menstrual period. Etonogestrel tricks the body processes into thinking that ovulation has already occurred, by maintaining high levels of the synthetic progesterone. This prevents the release of eggs from the ovaries.
• Toxicity: Symptoms of overdose include nausea, vomiting, vaginal bleeding, and other menstrual irregularities.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Half Life: 25 hours
• Elimination: Excretion of ENG and its metabolites, either as free steroid or as conjugates, is mainly in urine and to a lesser extent in feces.
• Distribution: * 201 L
• External Links: Wikipedia; PDRhealth; Drugs.com