(1R,2S,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,8-dien-5-one

• ChemBase编号: 262
• 分子式: C21H28O2
• 平均质量: 312.44582
• 单一同位素质量: 312.20893014
• SMILES: O=C([C@@H]1[C@@]2([C@H]([C@H]3[C@@H](CC2)[C@]2(C(=CC(=O)CC2)C=C3)C)CC1)C)C
• Canonical SMILES: O=C1CC[C@@]2(C(=C1)C=C[C@@H]1[C@H]2CC[C@]2([C@H]1CC[C@@H]2C(=O)C)C)C
• InChI: InChI=1S/C21H28O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4-5,12,16-19H,6-11H2,1-3H3/t16-,17+,18-,19+,20+,21+/m0/s1
• InChIKey: JGMOKGBVKVMRFX-HQZYFCCVSA-N

名称和登记号

名称

• IUPAC标准名: (1R,2S,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,8-dien-5-one
• IUPAC传统名: dydrogesterone
• 商标名: Diphaston; Dufaston; Duphaston; Duvaron; Gestatron; Gynorest; Prodel; Retrone; Terolut
• 别名: 10alpha-Isopregnenone; Didrogesterone [DCIT]; Dydrogesterona [INN-Spanish]; Dydrogesteronum [INN-Latin]; Hydrogesterone; Hydrogestrone; Isopregnenone; Dydrogesterone

登记号

• CAS号: 152-62-5
• PubChem SID: 46506195; 160963725
• PubChem CID: 9051

理论计算性质

JChem

• Acid pKa: 19.291891
• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 3.7866828
• LogD (pH = 7.4): 3.7866828
• Log P: 3.7866828
• 摩尔折射率: 93.8219 cm^3
• 极化性: 36.159924 Å^3
• 极化表面积: 34.14 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: 3.27
• LOG S: -4.81
• 溶解度: 4.86e-03 g/l

分子性质

理化性质

• 疏水性(logP): 3.4

详细说明

DrugBank - DB00378

• Drug Groups: approved
• Description: A synthetic progestational hormone with no androgenic or estrogenic properties. Unlike many other progestational compounds, dydrogesterone produces no increase in temperature and does not inhibit ovulation. [PubChem]
• Indication: Used to treat irregular duration of cycles and irregular occurrence and duration of periods caused by progesterone deficiency. Also used to prevent natural abortion in patients who have a history of habitual abortions.
• Pharmacology: Dydrogesterone is an orally active progestogen which acts directly on the uterus, producing a complete secretory endometrium in an estrogen-primed uterus. At therapeutic levels, dydrogesterone has no contraceptive effect as it does not inhibit or interfere with ovulation or the corpus luteum. Furthermore, dydrogesterone is non-androgenic, non-estrogenic, non-corticoid, non-anabolic and is not excreted as pregnanediol. Dydrogesterone helps to regulate the healthy growth and normal shedding of the uterus lining. Therefore, it may be useful in the treatment of menstrual disorders such as absent, irregular or painful menstrual periods, infertility, premenstrual syndrome and endometriosis.
• Toxicity: No serious or unexpected toxicity has been observed with dydrogesterone. In acute toxicity studies, the LD50 doses in rats exceeded 4,640mg/kg for the oral route.
• Affected Organisms: Humans and other mammals
• Biotransformation: Metabolism is complete to a 20-dihydrodydrogesterone (DHD) metabolite.
• Absorption: Rapidly absorbed in the gastrointestinal tract with a bioavailability of 28%.
• Half Life: Dydrogesterone: 5-7 hours, 20-dihydrodydrogesterone (DHD) metabolite: 14-17 hours
• References: / [Link]
• External Links: Wikipedia

参考文献

• Link/