(1R,2R,4R,10R,11S,14S,15S,16S,18S,19S)-10,14-dimethylspiro[hexacyclo[9.8.0.0^{2,4}.0^{5,10}.0^{14,19}.0^{16,18}]nonadecane-15,2'-oxolan]-5-ene-5',7-dione

• ChemBase编号: 1206
• 分子式: C24H30O3
• 平均质量: 366.4932
• 单一同位素质量: 366.21949482
• SMILES: O1[C@]2([C@@H]3[C@H]([C@@H]4[C@@]2(CC[C@H]2[C@H]4[C@@H]4[C@@H](C4)C4=CC(=O)CC[C@]24C)C)C3)CCC1=O
• Canonical SMILES: O=C1CC[C@]2(C(=C1)[C@@H]1C[C@@H]1[C@@H]1[C@@H]2CC[C@]2([C@H]1[C@@H]1C[C@@H]1[C@]12CCC(=O)O1)C)C
• InChI: InChI=1S/C24H30O3/c1-22-6-3-12(25)9-17(22)13-10-14(13)20-16(22)4-7-23(2)21(20)15-11-18(15)24(23)8-5-19(26)27-24/h9,13-16,18,20-21H,3-8,10-11H2,1-2H3/t13-,14+,15-,16+,18+,20-,21+,22-,23+,24+/m1/s1
• InChIKey: METQSPRSQINEEU-HXCATZOESA-N

名称和登记号

名称

• IUPAC标准名: (1R,2R,4R,10R,11S,14S,15S,16S,18S,19S)-10,14-dimethylspiro[hexacyclo[9.8.0.0^{2,4}.0^{5,10}.0^{14,19}.0^{16,18}]nonadecane-15,2'-oxolan]-5-ene-5',7-dione; (1R,2R,4R,10R,11S,14S,15S,16S,18S,19S)-10,14-dimethylspiro[hexacyclo[9.8.0.0^2,^4.0^5,^1^0.0^1^4,^1^9.0^1^6,^1^8]nonadecane-15,2'-oxolan]-5-ene-5',7-dione
• IUPAC传统名: drospirenone; yasmin
• 别名: DRSP; Drospirenona [inn-spanish]; Drospirenonum [inn-latin]; 6β,7β,15β,16β-dimethylene-3-oxo-17α-pregn-4-ene-21,17 carbolactone; Drospirenone; Angeliq; 6β,7β,15β,16β -Dimethylene-3-oxo-17α-pregn-4-ene-21,17-carbolactone; Dihydrospirorenone; Drospirenone

登记号

• CAS号: 67392-87-4
• MDL号: MFCD00867350
• PubChem SID: 46507653; 160964668
• PubChem CID: 68873

理论计算性质

JChem

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 3.3667614
• LogD (pH = 7.4): 3.3667614
• Log P: 3.3667614
• 摩尔折射率: 101.6772 cm^3
• 极化性: 40.426884 Å^3
• 极化表面积: 43.37 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.36
• LOG S: -5.21
• 溶解度: 2.25e-03 g/l

分子性质

理化性质

• 溶解度: DMSO: ≥15
• 外观: white to tan powder
• 比旋光度: [α]/D -180 to -195°, c = 1 in methanol

安全信息

• 保存条件: -20°C; desiccated
• 保存温度: 2-8°C

药理学性质

• 作用靶点: progestin receptor

产品相关信息

• 纯度: ≥98% (HPLC)
• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C24H30O3

详细说明

DrugBank - DB01395

• Drug Groups: approved
• Description: Drospirenone is a synthetic progestin that is an analog to spironolactone. It is found in a number of birth control formulations. Drospirenone differs from other synthetic progestins in that its pharmacological profile in preclinical studies shows it to be closer to the natural progesterone. As such it has anti-mineralocorticoid properties, counteracts the estrogen-stimulated activity of the renin-angiotensin-aldosterone system, and is not androgenic.
• Indication: For the prevention of pregnancy in women who elect an oral contraceptive.
• Pharmacology: Drospirenone differs from other synthetic progestins in that its pharmacological profile in preclinical studies shows it to be closer to the natural progesterone. As such it has anti-mineralocorticoid properties, counteracts the estrogen-stimulated activity of the renin-angiotensin-aldosterone system, and is not androgenic.
• Affected Organisms: Humans and other mammals
• Biotransformation: Extensively metabolized following oral or intravenous administration. The two major metabolites are inactive and are formed independent of the CYP450 enzyme system. The metabolites are the acid form of drospirenone formed by opening of the lactone ring and the 4,5-dihydro-drospirenone-3-sulfate.
• Absorption: Oral bioavailability is approximately 76%.
• Half Life: 30 hours
• Protein Binding: 97%
• References: Krattenmacher R: Drospirenone: pharmacology and pharmacokinetics of a unique progestogen. Contraception. 2000 Jul;62(1):29-38. [Pubmed]
• External Links: Wikipedia

Selleck Chemicals - S1377

Research Area: Contraception
Biological Activity:
Drospirenone is a synthetic progestin that is an analog to spironolactone. Drospirenone is part of certain birth control formulations. The compound differs from other synthetic progestins in that its pharmacological profile in preclinical studies shows it to be closer to the natural progesterone. [1]

Sigma Aldrich - SML0147

Biochem/physiol Actions
Drospirenone is a fourth-generation progestin that has antimineralocorticoid, and antiandrogenic activity in addition to potent progestogenic activity. In two recent studies drospirenone appeared to double the risk of venous thromboembolism compared to levonorgestrel, although other studies found little added risk.

参考文献

• Krattenmacher R: Drospirenone: pharmacology and pharmacokinetics of a unique progestogen. Contraception. 2000 Jul;62(1):29-38. Pubmed
• http://en.wikipedia.org/wiki/Drospirenone