(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 ID: 1206
• Molecular Formular: C24H30O3
• Molecular Mass: 366.4932
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (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 Traditional name: drospirenone; yasmin
• Synonyms: 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

Database IDs

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

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.3667614
• LogD (pH = 7.4): 3.3667614
• Log P: 3.3667614
• Molar Refractivity: 101.6772 cm^3
• Polarizability: 40.426884 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.36
• LOG S: -5.21
• Solubility (Water): 2.25e-03 g/l

PROPERTIES

Physical Property

• Solubility: DMSO: ≥15
• Apperance: white to tan powder
• Optical Rotation: [α]/D -180 to -195°, c = 1 in methanol

Safety Information

• Storage Condition: -20°C; desiccated
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: progestin receptor

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C24H30O3

DETAILS

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.

REFERENCES

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