DROSPIRENONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C24H30O3
Molecular Weight	366.4932
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 10
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12C[C@]1([H])[C@@]3([H])[C@]4([H])[C@]5([H])C[C@]5([H])[C@@]6(CCC(=O)O6)[C@@]4(C)CC[C@]3([H])[C@@]7(C)CCC(=O)C=C27

InChI

InChIKey=METQSPRSQINEEU-HXCATZOESA-N

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

HIDE SMILES / InChI

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021098s023lbl.pdf
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/7625729 | https://www.ncbi.nlm.nih.gov/pubmed/23530659 | https://www.ncbi.nlm.nih.gov/pubmed/7107766 | http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021355s006lbl.pdf

Drospirenone (INN, USAN), also known as 1,2-dihydrospirorenone, is a steroidal progestin of the spirolactone group. Drospirenone binds strongly to the progesterone receptor (PR) and mineralocorticoid receptor (MR), with lower affinity, to the androgen receptor (AR), and very low affinity for the glucocorticoid receptor (GR). Drospirenone is an ingredient in some birth control pills and hormone replacement therapy. In combination with ethinylestradiol it is used as contraception, and for women who want contraception it is also approved by the U.S. Food and Drug Administration (FDA) to treat vasomotor symptoms due to menopause.It is sold as a combined oral contraceptive under the brand names Yasmin (US, EU, Latin America), Jasmine (France), Yarina (Russia) in a dosage containing drospirenone 3 mg/ethinylestradiol 30 µg. In the United States, Bayer Schering released a pill based on Yasmin with the B vitamin folate (B9), which is marketed under the names Safyral and Beyaz.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Mineralocorticoid receptor 53 Target ID: CHEMBL1994 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7625729	Antagonist 2778
Progesterone receptor 61 Target ID: CHEMBL208 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7625729	Agonist 2678
Androgen Receptor 167 Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7625729	Antagonist 2778

Conditions

Condition	Modality	Highest Phase	Product
Pregnancy 65 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021098s023lbl.pdf	Primary	Approved 8429	YASMIN Approved Use INDICATIONS AND USAGE. Yasmin is an estrogen/progestin COC indicated for use by women to prevent pregnancy Launch Date 2001
Vasomotor symptoms due to menopause 4 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021355s006lbl.pdf	Primary	Approved 8429	Angeliq Approved Use Indications and Usage ANGELIQ is indicated in women who have a uterus for the: 1. Treatment of moderate to severe vasomotor symptoms associated with the menopause. 2. Treatment of moderate to severe symptoms of vulvar and vaginal atrophy associated with the menopause. When prescribing solely for the treatment of symptoms of vulvar and vaginal atrophy, topical vaginal products should be considered. Launch Date 2005
Vulvar and vaginal atrophy symptoms due to menopause 1 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021355s006lbl.pdf	Primary	Approved 8429	Angeliq Approved Use Indications and Usage ANGELIQ is indicated in women who have a uterus for the: 1. Treatment of moderate to severe vasomotor symptoms associated with the menopause. 2. Treatment of moderate to severe symptoms of vulvar and vaginal atrophy associated with the menopause. When prescribing solely for the treatment of symptoms of vulvar and vaginal atrophy, topical vaginal products should be considered. Launch Date 2005

C_max

Value	Dose	Analyte	Population
62.5 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22680989	6 mg single, oral dose: 6 mg route of administration: Oral experiment type: SINGLE co-administered:	DROSPIRENONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
9.85 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22680989	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	DROSPIRENONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
33.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22680989	3 mg single, oral dose: 3 mg route of administration: Oral experiment type: SINGLE co-administered:	DROSPIRENONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
27 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211367s000lbl.pdf	4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered:	DROSPIRENONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
41 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211367s000lbl.pdf	4 mg 1 times / day steady-state, oral dose: 4 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	DROSPIRENONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
1007 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22680989	6 mg single, oral dose: 6 mg route of administration: Oral experiment type: SINGLE co-administered:	DROSPIRENONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
140 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22680989	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	DROSPIRENONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
506 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22680989	3 mg single, oral dose: 3 mg route of administration: Oral experiment type: SINGLE co-administered:	DROSPIRENONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
26.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22680989	6 mg single, oral dose: 6 mg route of administration: Oral experiment type: SINGLE co-administered:	DROSPIRENONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
25.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22680989	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	DROSPIRENONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
28.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22680989	3 mg single, oral dose: 3 mg route of administration: Oral experiment type: SINGLE co-administered:	DROSPIRENONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
30 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211367s000lbl.pdf	4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered:	DROSPIRENONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
30 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211367s000lbl.pdf	4 mg 1 times / day steady-state, oral dose: 4 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	DROSPIRENONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
4% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211367s000lbl.pdf	4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered:		DROSPIRENONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
3 mg 1 times / day steady, oral Recommended Dose: 3 mg, 1 times / day Route: oral Route: steady Dose: 3 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021098s019lbl.pdf	healthy, 17 - 40 years n = 2837 Health Status: healthy Age Group: 17 - 40 years Sex: F Population Size: 2837 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021098s019lbl.pdf	Disc. AE: Premenstrual syndrome, Migraine headache... Other AEs: Premenstrual syndrome, Migraine headache... AEs leading to discontinuation/dose reduction: Premenstrual syndrome (6.7%) Migraine headache (1.5%) Other AEs: Premenstrual syndrome (13.2%) Migraine headache (10.7%) Breast discomfort (8.3%) Nausea and vomiting (4.5%) Abdominal discomfort (2.3%) Mood change (2.3%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021098s019lbl.pdf
3 mg 1 times / day steady, oral Recommended Dose: 3 mg, 1 times / day Route: oral Route: steady Dose: 3 mg, 1 times / day Co-administed with:: ethinylestradiol(20 mug) Sources: https://pubmed.ncbi.nlm.nih.gov/16542051/	healthy, mean 25.1 years n = 220 Health Status: healthy Age Group: mean 25.1 years Sex: F Population Size: 220 Sources: https://pubmed.ncbi.nlm.nih.gov/16542051/	Disc. AE: Weight gain, Headache... AEs leading to discontinuation/dose reduction: Weight gain (> 0.45) Headache (> 0.45) Depression (> 0.45) Menorrhagia (> 0.45) Skin disorder (> 0.45) Emotional lability (> 0.45) Sources: https://pubmed.ncbi.nlm.nih.gov/16542051/

AEs

AE	Significance	Dose	Population
Migraine headache	1.5% Disc. AE	3 mg 1 times / day steady, oral Recommended Dose: 3 mg, 1 times / day Route: oral Route: steady Dose: 3 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021098s019lbl.pdf	healthy, 17 - 40 years n = 2837 Health Status: healthy Age Group: 17 - 40 years Sex: F Population Size: 2837 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021098s019lbl.pdf
Migraine headache	10.7%	3 mg 1 times / day steady, oral Recommended Dose: 3 mg, 1 times / day Route: oral Route: steady Dose: 3 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021098s019lbl.pdf	healthy, 17 - 40 years n = 2837 Health Status: healthy Age Group: 17 - 40 years Sex: F Population Size: 2837 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021098s019lbl.pdf
Premenstrual syndrome	13.2%	3 mg 1 times / day steady, oral Recommended Dose: 3 mg, 1 times / day Route: oral Route: steady Dose: 3 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021098s019lbl.pdf	healthy, 17 - 40 years n = 2837 Health Status: healthy Age Group: 17 - 40 years Sex: F Population Size: 2837 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021098s019lbl.pdf
Abdominal discomfort	2.3%	3 mg 1 times / day steady, oral Recommended Dose: 3 mg, 1 times / day Route: oral Route: steady Dose: 3 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021098s019lbl.pdf	healthy, 17 - 40 years n = 2837 Health Status: healthy Age Group: 17 - 40 years Sex: F Population Size: 2837 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021098s019lbl.pdf
Mood change	2.3%	3 mg 1 times / day steady, oral Recommended Dose: 3 mg, 1 times / day Route: oral Route: steady Dose: 3 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021098s019lbl.pdf	healthy, 17 - 40 years n = 2837 Health Status: healthy Age Group: 17 - 40 years Sex: F Population Size: 2837 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021098s019lbl.pdf
Nausea and vomiting	4.5%	3 mg 1 times / day steady, oral Recommended Dose: 3 mg, 1 times / day Route: oral Route: steady Dose: 3 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021098s019lbl.pdf	healthy, 17 - 40 years n = 2837 Health Status: healthy Age Group: 17 - 40 years Sex: F Population Size: 2837 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021098s019lbl.pdf
Premenstrual syndrome	6.7% Disc. AE	3 mg 1 times / day steady, oral Recommended Dose: 3 mg, 1 times / day Route: oral Route: steady Dose: 3 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021098s019lbl.pdf	healthy, 17 - 40 years n = 2837 Health Status: healthy Age Group: 17 - 40 years Sex: F Population Size: 2837 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021098s019lbl.pdf
Breast discomfort	8.3%	3 mg 1 times / day steady, oral Recommended Dose: 3 mg, 1 times / day Route: oral Route: steady Dose: 3 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021098s019lbl.pdf	healthy, 17 - 40 years n = 2837 Health Status: healthy Age Group: 17 - 40 years Sex: F Population Size: 2837 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021098s019lbl.pdf
Depression	> 0.45 Disc. AE	3 mg 1 times / day steady, oral Recommended Dose: 3 mg, 1 times / day Route: oral Route: steady Dose: 3 mg, 1 times / day Co-administed with:: ethinylestradiol(20 mug) Sources: https://pubmed.ncbi.nlm.nih.gov/16542051/	healthy, mean 25.1 years n = 220 Health Status: healthy Age Group: mean 25.1 years Sex: F Population Size: 220 Sources: https://pubmed.ncbi.nlm.nih.gov/16542051/
Emotional lability	> 0.45 Disc. AE	3 mg 1 times / day steady, oral Recommended Dose: 3 mg, 1 times / day Route: oral Route: steady Dose: 3 mg, 1 times / day Co-administed with:: ethinylestradiol(20 mug) Sources: https://pubmed.ncbi.nlm.nih.gov/16542051/	healthy, mean 25.1 years n = 220 Health Status: healthy Age Group: mean 25.1 years Sex: F Population Size: 220 Sources: https://pubmed.ncbi.nlm.nih.gov/16542051/
Headache	> 0.45 Disc. AE	3 mg 1 times / day steady, oral Recommended Dose: 3 mg, 1 times / day Route: oral Route: steady Dose: 3 mg, 1 times / day Co-administed with:: ethinylestradiol(20 mug) Sources: https://pubmed.ncbi.nlm.nih.gov/16542051/	healthy, mean 25.1 years n = 220 Health Status: healthy Age Group: mean 25.1 years Sex: F Population Size: 220 Sources: https://pubmed.ncbi.nlm.nih.gov/16542051/
Menorrhagia	> 0.45 Disc. AE	3 mg 1 times / day steady, oral Recommended Dose: 3 mg, 1 times / day Route: oral Route: steady Dose: 3 mg, 1 times / day Co-administed with:: ethinylestradiol(20 mug) Sources: https://pubmed.ncbi.nlm.nih.gov/16542051/	healthy, mean 25.1 years n = 220 Health Status: healthy Age Group: mean 25.1 years Sex: F Population Size: 220 Sources: https://pubmed.ncbi.nlm.nih.gov/16542051/
Skin disorder	> 0.45 Disc. AE	3 mg 1 times / day steady, oral Recommended Dose: 3 mg, 1 times / day Route: oral Route: steady Dose: 3 mg, 1 times / day Co-administed with:: ethinylestradiol(20 mug) Sources: https://pubmed.ncbi.nlm.nih.gov/16542051/	healthy, mean 25.1 years n = 220 Health Status: healthy Age Group: mean 25.1 years Sex: F Population Size: 220 Sources: https://pubmed.ncbi.nlm.nih.gov/16542051/
Weight gain	> 0.45 Disc. AE	3 mg 1 times / day steady, oral Recommended Dose: 3 mg, 1 times / day Route: oral Route: steady Dose: 3 mg, 1 times / day Co-administed with:: ethinylestradiol(20 mug) Sources: https://pubmed.ncbi.nlm.nih.gov/16542051/	healthy, mean 25.1 years n = 220 Health Status: healthy Age Group: mean 25.1 years Sex: F Population Size: 220 Sources: https://pubmed.ncbi.nlm.nih.gov/16542051/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737 inhibitor 1587	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2C19 1478 CYP1A1 110

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021676s000_CLINPHARMR.pdf#page=25 Page: 25.0	minimum
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021676s000_CLINPHARMR.pdf#page=25 Page: 25.0	minimum
CYP3A4 1925	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021676s000_CLINPHARMR.pdf#page=25; https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/021098Orig1s022.pdf#page=24 Page: 25.0	moderate [IC50 31200 uM]	no (co-administration study) Comment: "IC50 units given are ""mM""; no significant effect of DRSP on the systemic clearance of the CYP3A4 product omeprazole sulfone was found" Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021676s000_CLINPHARMR.pdf#page=25; https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/021098Orig1s022.pdf#page=24 Page: 25.0
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021676s000_CLINPHARMR.pdf#page=25 Page: 25.0	moderate [IC50 36500 uM]
CYP1A1 218	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021676s000_CLINPHARMR.pdf#page=25 Page: 25.0	yes [IC50 14500 uM]
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021676s000_CLINPHARMR.pdf#page=25; https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/021098Orig1s022.pdf#page=24 Page: 25.0	yes [IC50 3390 uM]	no (co-administration study) Comment: "IC50 units given are ""mM""; daily oral administration of 3 mg DRSP for 14 days did not affect the oral clearance of omeprazole (40 mg, single oral dose) and the CYP2C19 product 5-hydroxy omeprazole" Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021676s000_CLINPHARMR.pdf#page=25; https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/021098Orig1s022.pdf#page=24 Page: 25.0

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 1737	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021676s000_CLINPHARMR.pdf#page=25 Page: 25.0	yes		no (co-administration study) Comment: simvastatin is not expected to affect DRSP's metabolism; When tested with midazolam, PK parameters of midazolam were similar regardless whether it was dosed with DSRP or with placebo. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021676s000_CLINPHARMR.pdf#page=25 Page: 25.0

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:50838	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:50838
ChemicalBook	CB8695608	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB8695608
MolPort	MolPort-003-847-034	https://www.molport.com/shop/molecule-link/MolPort-003-847-034
Selleck Chemicals	Drospirenone	http://www.selleckchem.com/products/Drospirenone.html
ZINC	ZINC000003927200	http://zinc15.docking.org/substances/ZINC000003927200
eMolecules	10229968	https://www.emolecules.com/cgi-bin/more?vid=10229968
eMolecules	29780522	https://www.emolecules.com/cgi-bin/more?vid=29780522
eMolecules	31588151	https://www.emolecules.com/cgi-bin/more?vid=31588151

PubMed

Title	Date	PubMed
Ethinylestradiol/drospirenone: a review of its use as an oral contraceptive.	2003	15871554
New progestogens: a review of their effects in perimenopausal and postmenopausal women.	2004	15493951
Safety of a new oral contraceptive containing drospirenone.	2004	15471507
Progestogens in combined oral contraceptives for contraception.	2004	15266546
Enhancing oral contraceptive success: the potential of new formulations.	2004 Apr	15105795
Ethinylestradiol-drospirenone, flutamide-metformin, or both for adolescents and women with hyperinsulinemic hyperandrogenism: opposite effects on adipocytokines and body adiposity.	2004 Apr	15070917
Pharmacological profile of progestins.	2004 Apr 15	15063480
Superiority of a combined contraceptive containing drospirenone to a triphasic preparation containing norgestimate in acne treatment.	2004 Aug	15379365
Flutamide-metformin plus an oral contraceptive (OC) for young women with polycystic ovary syndrome: switch from third- to fourth-generation OC reduces body adiposity.	2004 Aug	15229206
An observational study of Yasmin in the management of women with polycystic ovary syndrome.	2004 Jul	15222920
Estradiol and drospirenone for climacteric symptoms in postmenopausal women: a double-blind, randomized, placebo-controlled study of the safety and efficacy of three dose regimens.	2004 Jun	15497908
Drospirenone for the treatment of hirsute women with polycystic ovary syndrome: a clinical, endocrinological, metabolic pilot study.	2004 Jun	15181063
Safety and efficacy of drospirenone used in a continuous combination with 17beta-estradiol for prevention of postmenopausal osteoporosis.	2004 Mar	15259289
[Medication of the month. Angeliq: new hormonal therapy of menopause, with antialdosterone and antiandrogenic properties].	2004 Mar	15139405
Drospirenone, a progestogen with antimineralocorticoid properties: a short review.	2004 Mar 31	15134826
Ethinyl estradiol/drospirenone (Yasmin): a newer oral contraceptive.	2004 May 15	15168965
Prothrombotic changes in users of combined oral contraceptives containing drospirenone and cyproterone acetate.	2004 Nov	15550051
The effect on cartilage of different forms of application of postmenopausal estrogen therapy: comparison of oral and transdermal therapy.	2004 Nov	15542048
Short-term variations in bone remodeling markers of an oral contraception formulation containing 3 mg of drospirenone plus 30 microg of ethinyl estradiol: observational study in young postadolescent women.	2004 Oct	15451333
Flutamide-metformin plus ethinylestradiol-drospirenone for lipolysis and antiatherogenesis in young women with ovarian hyperandrogenism: the key role of early, low-dose flutamide.	2004 Sep	15356085
Efficacy and safety of a low-dose 24-day combined oral contraceptive containing 20 micrograms ethinylestradiol and 3 mg drospirenone.	2004 Sep	15325887
New contraception options.	2004 Sep-Oct	15586908
Effects of 17beta-oestradiol plus different doses of drospirenone on adipose tissue, adiponectin and atherogenic metabolites in postmenopausal women.	2005 Dec	16313478
Treatment of premenstrual dysphoric disorder with a new drospirenone-containing oral contraceptive formulation.	2005 Dec	16307962
Quantitative analysis of gene regulation by seven clinically relevant progestins suggests a highly similar mechanism of action through progesterone receptors in T47D breast cancer cells.	2005 Dec	16157482
Drospirenone and PCOS.	2005 Jan	15720866
A comparative study of monophasic oral contraceptives containing either drospirenone 3 mg or levonorgestrel 150 microg on premenstrual symptoms.	2005 Jan	15639064
Effects of an oral contraceptive containing drospirenone on bone turnover and bone mineral density.	2005 Jan	15625142
Venous thromboembolism after high-dose chemotherapy in a patient with Hodgkin's lymphoma receiving the new oral contraceptive ethinylestradiol and drospirenone ("Yasmine").	2005 Jan	15531905
Flutamide-metformin plus ethinylestradiol-drospirenone for lipolysis and antiatherogenesis in young women with ovarian hyperandrogenism: the key role of metformin at the start and after more than one year of therapy.	2005 Jan	15483105
Prospective study on sexual behavior of women using 30 microg ethinylestradiol and 3 mg drospirenone oral contraceptive.	2005 Jul	15964287
Systemic sclerosis following oral contraception.	2005 Jun	15940568
Effects of drospirenone/17-beta estradiol on blood pressure and potassium balance in hypertensive postmenopausal women.	2005 Jun	15925739
Effects of two combined oral contraceptives containing ethinyl estradiol 20 microg combined with either drospirenone or desogestrel on lipids, hemostatic parameters and carbohydrate metabolism.	2005 Jun	15914128
Differential effects of estrogens and progestins on the anticoagulant tissue factor pathway inhibitor in the rat.	2005 Mar	15857755
Different oral contraceptives and voice quality--an observational study.	2005 May	15854635
Long-term safety of drospirenone-estradiol for hormone therapy: a randomized, double-blind, multicenter trial.	2005 Nov-Dec	16278615
Effects of drospirenone/estrogen combinations on bone metabolism.	2005 Oct	16203654
Added benefits of drospirenone for compliance.	2005 Oct	16203653
Drospirenone in combination with estrogens: for contraception and hormone replacement therapy.	2005 Oct	16203652
Importance of controlling blood pressure.	2005 Oct	16203651
Pharmacology of different progestogens: the special case of drospirenone.	2005 Oct	16203650
Drospirenone, a progestin with a unique cardiovascular profile, for safe contraception and treatment of menopausal symptoms.	2005 Oct	16203649
Gateways to clinical trials.	2005 Sep	16258596
Efficacy of a new low-dose oral contraceptive with drospirenone in premenstrual dysphoric disorder.	2005 Sep	16135578
Antihypertensive effects of drospirenone with 17beta-estradiol, a novel hormone treatment in postmenopausal women with stage 1 hypertension.	2005 Sep 27	16186434
Discontinuous low-dose flutamide-metformin plus an oral or a transdermal contraceptive in patients with hyperinsulinaemic hyperandrogenism: normalizing effects on CRP, TNF-alpha and the neutrophil/lymphocyte ratio.	2006 Feb	16239318
The use of an oral contraceptive containing ethinylestradiol and drospirenone in an extended regimen over 126 days.	2006 Jan	16371292
Treating acne with oral contraceptives: use of lower doses.	2006 Jan	16371290
New progestagens for contraceptive use.	2006 Mar-Apr	16291771

Patents

Sample Use Guides

In Vivo Use Guide

To prevent pregnancy: One tablet (containing 3 mg drospirenone and 0.03 mg ethinyl estradiol) daily by mouth at the same time every day. To prevent symptoms due to menopause. one tablet (0.25 mg drospirenone/0.5 mg ethinyl estradiol) taken by mouth once daily

Route of Administration: Oral

In Vitro Use Guide

Activity of drospirenone was investigated by transiently transfecting the human MR (pRShMR) and pMMTV-CAT into COS 1 cells. Cells were treated with 10 nmol/l aldosterone and, in addition, with increasing amounts of the drospirenone (1nM – 1 mkM). After 48 hrs cells were harvested and duplicate dishes were assayed for activity

Name

Type

Language

DROSPIRENONE

Official Name

English

DROSPIRENONE [USP MONOGRAPH]

Common Name

English

NSC-760103

Code

English

DROSPIRENONE [MART.]

Common Name

English

DROSPIRENONE COMPONENT OF SAFYRAL

Common Name

English

DROSPIRENONE COMPONENT OF YASMIN

Common Name

English

(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

Common Name

English

DROSPIRENONE COMPONENT OF NEXTSTELLIS

Brand Name

English

DROSPIRENONE COMPONENT OF YAZ

Common Name

English

DROSPIRENONE [MI]

Common Name

English

SLYND

Brand Name

English

drospirenone [INN]

Common Name

English

ANGELIQ COMPONENT DROSPIRENONE

Common Name

English

ZK-30595

Code

English

DROSPIRENONE [USP-RS]

Common Name

English

YASMIN COMPONENT DROSPIRENONE

Common Name

English

YAZ COMPONENT DROSPIRENONE

Common Name

English

BEYAZ COMPONENT DROSPIRENONE

Common Name

English

DROSPIRENONE [JAN]

Common Name

English

DROSPIRENONE [EP MONOGRAPH]

Common Name

English

DROSPIRENONE COMPONENT OF BEYAZ

Common Name

English

SAFYRAL COMPONENT DROSPIRENONE

Common Name

English

DROSPIRENONE COMPONENT OF ANGELIQ

Common Name

English

DROSPIRENONE [USAN]

Common Name

English

DROSPIRENONE [VANDF]

Common Name

English

17-Hydroxy-6β,7β:15β,16β-dimethylene-3-oxo-17α-pregn-4-ene-21-carboxylic acid, γ-lactone

Common Name

English

ZK 30595

Code

English

DROSPIRENONE [ORANGE BOOK]

Common Name

English

Drospirenone [WHO-DD]

Common Name

English

NEXTSTELLIS COMPONENT DROSPIRENONE

Brand Name

English

DRSP

Common Name

English

Classification Tree Code System Code

WHO-ATC

G03AC10