QuickView for Drospirenone (compound)

Summary
General Info

PubChem

PubChem Compound 68873

Name:	drospirenone
PubChem Compound ID:	68873
Molecular formula:	C₂₄H₃₀O₃
Molecular weight:	366.493 g/mol
Synonyms:	CCRIS 6523; Drospirenonum [INN-Latin]; Drospirenone [INN]; Spiro(17H-dicyclopropa(6,7:15,16)cyclopenta(a)phenanthrene-17,2'(5'H)-furan)-3,5'(2H)-dione, 1,3',4',6,7,8,9,10,11,12,13,14,15,16,20,21-hexadecahydro-10,13-dimethyl-, (6R-(6alpha,7alpha,8beta,9alpha,10beta,13beta,14alpha,15alpha,16alpha,17beta))-; (6R,7R,8R,9S,10R,13S,14S,15S,16S,17S)-1,3',4',6,6a,7,8,9,10,11,12,13,14,15,15a,16-Hexadecahydro-10,13-dimethylspiro-(17H-dicyclopropa(6,7:15,16)cyclopenta(a)phenanthrene-17,2'(5'H)-furan)-3,5'(2H)-dione; 1, 2-Dihydrospirorenone; DRSP; 6-beta,7-beta;15-beta,16-beta-Dimethylene-3-oxo-17-alpha-pregn-4-ene-21,17-carbolactone; Drospirenone; EINECS 266-679-2. show more » CCRIS 6523; Drospirenonum [INN-Latin]; Drospirenone [INN]; Spiro(17H-dicyclopropa(6,7:15,16)cyclopenta(a)phenanthrene-17,2'(5'H)-furan)-3,5'(2H)-dione, 1,3',4',6,7,8,9,10,11,12,13,14,15,16,20,21-hexadecahydro-10,13-dimethyl-, (6R-(6alpha,7alpha,8beta,9alpha,10beta,13beta,14alpha,15alpha,16alpha,17beta))-; (6R,7R,8R,9S,10R,13S,14S,15S,16S,17S)-1,3',4',6,6a,7,8,9,10,11,12,13,14,15,15a,16-Hexadecahydro-10,13-dimethylspiro-(17H-dicyclopropa(6,7:15,16)cyclopenta(a)phenanthrene-17,2'(5'H)-furan)-3,5'(2H)-dione; 1, 2-Dihydrospirorenone; DRSP; 6-beta,7-beta;15-beta,16-beta-Dimethylene-3-oxo-17-alpha-pregn-4-ene-21,17-carbolactone; Drospirenone; EINECS 266-679-2; Dihydrospirorenone; 1,2-Dihydrospirorenone; ZK-30595; Drospirenona [INN-Spanish]; Dehydrospirorenone; ZK 30595; SH-470; BRN 4765500; 67392-87-4 show less «

DrugBank

Identification

Name:	drospirenone
Name (isomeric):	DB01395
Drug Type:	small molecule
Synonyms:	Drospirenona [inn-spanish]; Drospirenonum [inn-latin]; 6β,7β,15β,16β-dimethylene-3-oxo-17α-pregn-4-ene-21,17 carbolactone; DRSP
Brand name mixture:	Yasmin(drospirenone + ethinylestradiol), Yaz(drospirenone + ethinylestradiol)
Category:	Aldosterone Antagonists, Progestins
CAS number:	67392-87-4

Pharmacology

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.
Mechanism of Action:	Progestins such as drospirenone diffuse freely into target cells in the female reproductive tract, mammary gland, hypothalamus, and the pituitary and bind to the progesterone receptor. Once bound to the receptor, progestins slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory LH su... show more » Progestins such as drospirenone diffuse freely into target cells in the female reproductive tract, mammary gland, hypothalamus, and the pituitary and bind to the progesterone receptor. Once bound to the receptor, progestins slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory LH surge. show less «
Absorption:	Oral bioavailability is approximately 76%.
Protein binding:	97%
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.
Half Life:	30 hours
Affected organisms:	Humans and other mammals

Interactions

Food interaction:

Food reduces the rate of absorption, but not the extent of absorption.

Drug interaction:

Benazepril	Increased risk of hyperkalemia
Thiopental	Thiopental may decrease the effect of Drospirenone. Contraceptive failure may occur. Alternative nonhomomonal contraception should be used during concomitant therapy.
Colesevelam	Bile Acid Sequestrants may decrease the serum concentration of Contraceptives (Progestins). Administer oral progestin-containing contraceptives at least 1-4 hours prior to or 4-6 hours after administration of a bile acid sequestrant. Consider alternatives in order to avoid this combination when possible, due to the risk for impaired contraceptive effectiveness.
Ramipril	Increased risk of hyperkalemia
Trandolapril	Increased risk of hyperkalemia. Monitor serum potassium levels.

Benazepril	Increased risk of hyperkalemia
Thiopental	Thiopental may decrease the effect of Drospirenone. Contraceptive failure may occur. Alternative nonhomomonal contraception should be used during concomitant therapy.
Colesevelam	Bile Acid Sequestrants may decrease the serum concentration of Contraceptives (Progestins). Administer oral progestin-containing contraceptives at least 1-4 hours prior to or 4-6 hours after administration of a bile acid sequestrant. Consider alternatives in order to avoid this combination when possible, due to the risk for impaired contraceptive effectiveness.
Ramipril	Increased risk of hyperkalemia
Trandolapril	Increased risk of hyperkalemia. Monitor serum potassium levels.
Irbesartan	Increased risk of hyperkalemia
Quinapril	Increased risk of hyperkalemia
Heparin	Heparin can increase risk of hyperkalemia for patients on drospirenone
Losartan	Increased risk of hyperkalemia
Bexarotene	Bexarotene may decrease the serum concentration of Contraceptives (Progestins). Since bexarotene is teratogenic and can lower serum concentrations of drospirenone, it is advised that women of childbearing potential use two forms of contraception (including at least one non-hormonal form).
Treprostinil	Additive hypotensive effect. Monitor antihypertensive therapy during concomitant use.
Candesartan	Increased risk of hyperkalemia
Tretinoin	Oral Tretinoin may decrease the effect of oral contraceptive, Drospirenone. An alternate form of contraception should be used during concomitant therapy.
Fosinopril	Increased risk of hyperkalemia
Artemether	Artemether may decrease the effectiveness of drospirinone by increasing its metabolism via CYP3A4. Consider an alternate non-hormonal means of contraception during artemether therapy.
Eprosartan	Increased risk of hyperkalemia
Captopril	Increased risk of hyperkalemia
Potassium	Increased risk of hyperkalemia
Telmisartan	Telmisartan may increase the hyperkalemic effect of Drospirenone. Monitor for increased serum potassium concentrations during concomitant therapy.
Lisinopril	Increased risk of hyperkalemia
Perindopril	Increased risk of hyperkalemia
Cilazapril	Increased risk of hyperkalemia
Enalapril	Increased risk of hyperkalemia
Olmesartan	Increased risk of hyperkalemia
Warfarin	Drospirenone may alter the anticoagulant effect of warfarin. Concomitant therapy should be avoided. Monitor for changes in coagulation status if drospirenone is initiated, discontinued or dose changed.
Triamterene	Increased risk of hyperkalemia

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Targets

Progesterone receptor

Mineralocorticoid receptor

Androgen receptor