Drospirenone

Identification

Summary

Drospirenone is a progestin used in oral contraceptive pills for the prevention of pregnancy and other conditions.

Brand Names

Angeliq 0.25/0.5 28 Day, Beyaz 28 Day, Gianvi 28-day, Jasmiel 28 Day, Lo-zumandimine 28 Day, Loryna, Nextstellis 28 Day, Nikki 28 Day, Ocella 28 Day, Safyral 28 Day, Slynd, Syeda 28 Day, Tydemy 28 Day, Vestura, Yasmin, Yasmin 28 Day, Yaz 28 Day, Yaz Plus, Zarah, Zumandimine 28 Day

Generic Name

Drospirenone

DrugBank Accession Number

DB01395

Background

Drospirenone is a synthetic progestin commonly found in the popular oral contraceptive, Yaz in combination with Ethinyl estradiol.¹⁹ Most recently, it was approved by both Health Canada and the FDA in combination with Estetrol as an oral contraceptive therapy.^27,28 Aside from its contraceptive effects, drospirenone is used with estrogens to control acne and premenstrual dysphoric disorder (PMDD).

Drospirenone has been the subject of widespread safety concern due to the possibility of an increased risk of venous thromboembolism associated with its use.^4,7 In 2012, however, a safety statement by the FDA concluded that the increase in the risk of thromboembolism resulting from the use of drospirenone remains unclear, as studies regarding this risk are conflicting. Some studies have demonstrated a significantly increased risk and some demonstrating no risk of thromboembolic events. In its statement, the FDA has mentioned that increased risk of venous thromboembolism with oral contraceptives such as drospirenone exists but remains lower than the risk of this condition during pregnancy and during the postpartum period, and this should be considered when assessing potential risks of hormonal contraceptive use.²¹

Type

Small Molecule

Groups

Approved

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Drospirenone (DB01395)

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Weight

Average: 366.4932
Monoisotopic: 366.219494826

Chemical Formula

C₂₄H₃₀O₃

Synonyms

• 1,2-Dihydrospirorenone
• 6β,7β;15β,16β-Dimethylene-3-oxo-17α-pregn-4-ene-21,17-carbolactone
• Dehydrospirorenone
• Drospirenona
• Drospirenone
• Drospirénone
• Drospirenonum
• DRSP

External IDs

• ZK 30595
• ZK-30595

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Pharmacology

Indication

Drospirenone, in combination with ethinyl estradiol or estetrol, is indicated as an oral contraceptive for the prevention of pregnancy.^19,28 In addition to its use for contraceptive effects, this combination is used to treat moderate acne vulgaris and the symptoms of premenstrual dysphoric disorder.^19,20 The drug has approved indications for combination with estrogens for the treatment of menopause-associated symptoms, such as vasomotor symptoms and vulvovaginal atrophy. Drospirenone combined with estrogen may also may aid in the prevention of osteoporosis in women who have been post-menopausal for at least a year and are not candidates for other therapies.^23,25 It can sometimes be found in preparations containing estrogen and folic acid for folic acid replenishment during oral contraception.²⁶

When used for the treatment of acne vulgaris, drospirenone-containing contraceptives should only be used in women ≥14 years of age who have experienced menarche, desire oral contraception, and do not have any contraindications to oral contraceptives.²⁰ Off-label uses for this drug include the treatment of menstrual irregularities, dysmenorrhea, hirsutism, and endometriosis.^1,11

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Used in combination to manage	Atrophy of vulva	Combination Product in combination with: Estradiol (DB00783)	••••••••••••		•••••••• •• •••••• ••••••••	••••••
Used in combination to manage	Moderate to severe vasomotor symptoms	Combination Product in combination with: Estradiol (DB00783)	••••••••••••			••••••
Used in combination to prevent	Neural tube defects (ntds)	Combination Product in combination with: Ethinylestradiol (DB00977), Levomefolic acid (DB11256)	••••••••••••		•••••••• •••••	•••• ••••••
Used in combination to manage	Premenstrual dysphoric disorder (pmdd)	Combination Product in combination with: Ethinylestradiol (DB00977), Levomefolic acid (DB11256)	••••••••••••			•••• ••••••
Used in combination to manage	Vulvo vaginal atrophy	Combination Product in combination with: Estradiol (DB00783)	••••••••••••		•••••••• •• •••••• ••••••••	••••••

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Associated Therapies

• Contraception
• Folate supplementation therapy

Contraindications & Blackbox Warnings

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Pharmacodynamics

Drospirenone inhibits the maturation of follicles and inhibits ovulation, preventing pregnancy. It has antiandrogen effects, improving acne and hirsutism. When combined with ethinyl estradiol, it has been shown to have favorable effects on the plasma lipid profile.²⁰ Due to its similarity to naturally occurring progesterone, drospirenone is thought to be associated with a lower incidence of progesterone contraceptive related adverse effects, such as breast tenderness and mood swings.¹

A note on venous thromboembolism risk and antimineralcorticoid effects

As with other oral contraceptives, the risk of venous thromboembolism and cardiovascular events may be increased when drospirenone is taken. The risk is especially higher in smokers and women aged 35 and older. Women taking this drug should be advised not to smoke. In addition, drospirenone, due to its antimineralcorticoid effects, may increase the risk of hyperkalemia. Patients at high risk for hyperkalemia should not be administered this drug. Consult the official prescribing information for detailed and updated information on the cardiovascular and other risks associated with drospirenone use.^19,20,23

Mechanism of action

Drospirenone and ethinyl estradiol in combination suppress the release of follicle stimulating hormone (FSH) and luteinizing hormone (LH), preventing ovulation. Other changes induced by this drug which may aid in the prevention of pregnancy include alterations in cervical mucus consistency, hindering sperm movement, and lowering the chance of embryo implantation.²⁰

Drospirenone is an analog of the diuretic spironolactone, which exerts anti-mineralocorticoid activity, blocking aldosterone receptors, which increases sodium and water excretion.¹ Studies in animals have demonstrated that drospirenone administration leads to antiandrogenic activity. This activity helps to oppose the effects of naturally occurring androgens, inhibiting the binding of dihydrotestosterone (DHT) to its receptor, and preventing androgen synthesis in the ovaries, helping to treat acne and hirsutism.^1,12,19 Drospirenone may also decrease the level of edema in sebaceous follicle during the second half of the menstrual cycle, when acne often appears.¹⁹

Target	Actions	Organism
AMineralocorticoid receptor	antagonist	Humans
AAndrogen receptor	antagonist	Humans
AProgesterone receptor	agonist	Humans
UGlucocorticoid receptor	binder	Humans

Absorption

The absolute bioavailability of drospirenone is approximately 76% due to first-pass effects.^13,19 The maximum plasma concentration of drospirenone occurs within 1 to 2 hours after oral administration and is estimated to range between 60 and 87 ng/mL.¹ A European prescribing monograph for the combination product of estradiol and drospirenone indicates that drospirenone is both completely and rapidly absorbed. It reports a Cmax of 21.9 ng/ml, achieved approximately 1-hour post-administration. The absolute bioavailability is reported to range between 76 to 85%.²³

Volume of distribution

The volume of distribution of drospirenone is estimated to be 4 L/kg, according to the FDA label for Yaz.¹⁹ Prescribing information from a combination of estradiol and drospirenone estimates the volume of distribution to range from 3.7- 4.2 L/kg.²³

Protein binding

Drospirenone is about 95% to 97% bound to serum plasma protein, likely to albumin.¹ During in vitro studies, drospirenone was found to bind with low affinity to sex hormone-binding globulin (SHBG).²⁰ Another reference indicates that drospirenone binds to serum albumin but does not bind to sex hormone-binding globulin (SHBG), nor corticoid binding globulin (CBG). Only 3-5% of the total drospirenone concentration is measured as a free steroid. ²³

Metabolism

Drospirenone is heavily metabolized. The two major inactive metabolites identified are the acid form of drospirenone produced by the opening of its lactone ring, known as M11, and the 4,5-dihydro-drospirenone-3-sulfate (M14).^1,13 Drospirenone also undergoes oxidative metabolism via the hepatic cytochrome enzyme CYP3A4.^17,18,23

Hover over products below to view reaction partners

• Drospirenone
  • 4,5-dihydro-drospirenone-3-sulfate

Route of elimination

Various metabolites of drospirenone are measured in the urine and feces. Drospirenone elimination from the body is almost after 10 days post-administration¹ when negligible amounts of drospirenone are found unchanged in both the urine and feces.²³ Between 38% to 47% of the metabolites are identified as glucuronide and sulfate conjugates in the urine. In the feces, approximately 17% to 20% of identifiable metabolites are found to be excreted as glucuronides and sulfates.¹

Half-life

The serum half-life of drospirenone is estimated to be 30 hours.¹³ The half-life of drospirenone metabolite excretion in the urine and feces is approximately 40 hours.²³

Clearance

Drospirenone is rapidly cleared, typically within 2-3 days of administration of the last active tablet.¹⁴ The rate of clearance of drospirenone calculated in the serum ranges from 1.2-1.5 ml/min/kg, however, this value can vary by up to 25% according to the patient.²³

Adverse Effects

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Toxicity

The oral LD50 of drospirenone in rats is >2000 mg/kg.²²

Overdose information An overdose of drospirenone, like other oral contraceptives, may lead to cause nausea or withdrawal bleeding. For drospirenone in particular, as an analog of spironolactone, may affect the levels of serum sodium and potassium. Their concentrations should be monitored in cases of overdose in addition to monitoring from metabolic acidosis and hyperkalemia, which may also result.^15,19

Pathways

Not Available

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Interactions

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This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Abacavir	Drospirenone may increase the excretion rate of Abacavir which could result in a lower serum level and potentially a reduction in efficacy.
Abametapir	The serum concentration of Drospirenone can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Drospirenone can be increased when combined with Abatacept.
Abciximab	The risk or severity of adverse effects can be increased when Drospirenone is combined with Abciximab.
Abemaciclib	The metabolism of Abemaciclib can be decreased when combined with Drospirenone.

Food Interactions

• Avoid St. John's Wort.
• Take at the same time every day.
• Take with or without food.

Products

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Product Images

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Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Slynd	Kit; Tablet, film coated	4 mg/1	Oral	Exeltis Usa, Inc.	2019-06-06	Not applicable
Slynd	Tablet	4 mg	Oral	Duchesnay Inc.	2022-04-20	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Aliane 0,02 mg/3 mg Filmtabletten	Drospirenone (3 mg) + Ethinylestradiol (0.02 mg)	Tablet, film coated	Oral	Bayer Austria Ges.M.B.H.	2006-05-26	Not applicable
Angeliq	Drospirenone (0.5 mg/1) + Estradiol (1 mg/1)	Tablet, film coated	Oral	Physicians Total Care, Inc.	2010-09-29	Not applicable
Angeliq	Drospirenone (0.25 mg/1) + Estradiol (0.5 mg/1)	Tablet, film coated	Oral	Bayer HealthCare Pharmaceuticals Inc.	2012-02-29	Not applicable
ANGELIQ	Drospirenone (2 mg) + Estradiol (1 mg)	Tablet, film coated	Oral	Bayer S.P.A.	2014-07-08	Not applicable
Angeliq	Drospirenone (0.5 mg/1) + Estradiol (1 mg/1)	Tablet, film coated	Oral	Bayer HealthCare Pharmaceuticals Inc.	2005-11-28	Not applicable

Categories

ATC Codes

G03AA18 — Drospirenone and estetrol

• G03AA — Progestogens and estrogens, fixed combinations
• G03A — HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE
• G03 — SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
• G — GENITO URINARY SYSTEM AND SEX HORMONES

G03AC10 — Drospirenone

• G03AC — Progestogens
• G03A — HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE
• G03 — SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
• G — GENITO URINARY SYSTEM AND SEX HORMONES

G03FA17 — Drospirenone and estrogen

• G03FA — Progestogens and estrogens, fixed combinations
• G03F — PROGESTOGENS AND ESTROGENS IN COMBINATION
• G03 — SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
• G — GENITO URINARY SYSTEM AND SEX HORMONES

G03AA12 — Drospirenone and ethinylestradiol

• G03AA — Progestogens and estrogens, fixed combinations
• G03A — HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE
• G03 — SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
• G — GENITO URINARY SYSTEM AND SEX HORMONES

Drug Categories

• Adrenal Cortex Hormones
• Agents causing hyperkalemia
• Androstanes
• Combination Contraceptives (with Estrogen and derivatives)
• Contraceptive Agents, Female
• Contraceptives, Oral
• Cytochrome P-450 CYP3A Substrates
• Cytochrome P-450 CYP3A4 Substrates
• Cytochrome P-450 CYP3A4 Substrates (strength unknown)
• Cytochrome P-450 Substrates
• Diuretics
• Fused-Ring Compounds
• Genito Urinary System and Sex Hormones
• Hormonal Contraceptives for Systemic Use
• Hormone Antagonists
• Hormones, Hormone Substitutes, and Hormone Antagonists
• Hyperglycemia-Associated Agents
• Mineralocorticoid Receptor Antagonists
• Natriuretic Agents
• Progesterone Congeners
• Progestin Contraceptives
• Progestins
• Sex Hormones and Modulators of the Genital System
• Steroids

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as spironolactones and derivatives. These are steroid lactones with a structure based on the spironolactone skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Spironolactones and derivatives

Alternative Parents

Cyclohexenones / Gamma butyrolactones / Tetrahydrofurans / Carboxylic acid esters / Oxacyclic compounds / Monocarboxylic acids and derivatives / Organic oxides / Hydrocarbon derivatives

Substituents

Aliphatic heteropolycyclic compound / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Cyclic ketone / Cyclohexenone / Gamma butyrolactone / Hydrocarbon derivative / Ketone / Lactone

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

3-oxo steroid, 3-oxo Delta(4)-steroid, steroid lactone (CHEBI:50838)

Affected organisms

• Humans and other mammals

Chemical Identifiers

UNII

N295J34A25

CAS number

67392-87-4

InChI Key

METQSPRSQINEEU-HXCATZOESA-N

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

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

SMILES

[H][C@@]12C[C@]1([H])[C@@]1([H])[C@]3([H])[C@]4([H])C[C@]4([H])[C@@]4(CCC(=O)O4)[C@@]3(C)CC[C@]1([H])[C@@]1(C)CCC(=O)C=C21

References

Synthesis Reference

DOI: 10.1002/cjoc.201201147

General References

1. Krattenmacher R: Drospirenone: pharmacology and pharmacokinetics of a unique progestogen. Contraception. 2000 Jul;62(1):29-38. [Article]
2. Wichianpitaya J, Taneepanichskul S: A comparative efficacy of low-dose combined oral contraceptives containing desogestrel and drospirenone in premenstrual symptoms. Obstet Gynecol Int. 2013;2013:487143. doi: 10.1155/2013/487143. Epub 2013 Feb 20. [Article]
3. Larivee N, Suissa S, Khosrow-Khavar F, Tagalakis V, Filion KB: Drospirenone-containing oral contraceptive pills and the risk of venous thromboembolism: a systematic review of observational studies. BJOG. 2017 Sep;124(10):1490-1499. doi: 10.1111/1471-0528.14623. Epub 2017 May 5. [Article]
4. Oedingen C, Scholz S, Razum O: Systematic review and meta-analysis of the association of combined oral contraceptives on the risk of venous thromboembolism: The role of the progestogen type and estrogen dose. Thromb Res. 2018 May;165:68-78. doi: 10.1016/j.thromres.2018.03.005. Epub 2018 Mar 15. [Article]
5. Li J, Ren J, Sun W: A comparative systematic review of Yasmin (drospirenone pill) versus standard treatment options for symptoms of polycystic ovary syndrome. Eur J Obstet Gynecol Reprod Biol. 2017 Mar;210:13-21. doi: 10.1016/j.ejogrb.2016.11.013. Epub 2016 Nov 16. [Article]
6. Lopez LM, Kaptein AA, Helmerhorst FM: Oral contraceptives containing drospirenone for premenstrual syndrome. Cochrane Database Syst Rev. 2012 Feb 15;(2):CD006586. doi: 10.1002/14651858.CD006586.pub4. [Article]
7. Authors unspecified: ACOG Committee Opinion Number 540: Risk of venous thromboembolism among users of drospirenone-containing oral contraceptive pills. Obstet Gynecol. 2012 Nov;120(5):1239-42. doi: http://10.1097/AOG.0b013e318277c93b. [Article]
8. Kluft C, Zimmerman Y, Mawet M, Klipping C, Duijkers IJ, Neuteboom J, Foidart JM, Bennink HC: Reduced hemostatic effects with drospirenone-based oral contraceptives containing estetrol vs. ethinyl estradiol. Contraception. 2017 Feb;95(2):140-147. doi: 10.1016/j.contraception.2016.08.018. Epub 2016 Sep 1. [Article]
9. Regidor PA, Schindler AE: Antiandrogenic and antimineralocorticoid health benefits of COC containing newer progestogens: dienogest and drospirenone. Oncotarget. 2017 Aug 3;8(47):83334-83342. doi: 10.18632/oncotarget.19833. eCollection 2017 Oct 10. [Article]
10. Momoeda M, Kondo M, Elliesen J, Yasuda M, Yamamoto S, Harada T: Efficacy and safety of a flexible extended regimen of ethinylestradiol/drospirenone for the treatment of dysmenorrhea: a multicenter, randomized, open-label, active-controlled study. Int J Womens Health. 2017 May 2;9:295-305. doi: 10.2147/IJWH.S134576. eCollection 2017. [Article]
11. Suvarna Y, Maity N, Kalra P, Shivamurthy MC: Comparison of efficacy of metformin and oral contraceptive combination of ethinyl estradiol and drospirenone in polycystic ovary syndrome. J Turk Ger Gynecol Assoc. 2016 Jan 12;17(1):6-9. doi: 10.5152/jtgga.2016.16129. eCollection 2016. [Article]
12. Mathur R, Levin O, Azziz R: Use of ethinylestradiol/drospirenone combination in patients with the polycystic ovary syndrome. Ther Clin Risk Manag. 2008 Apr;4(2):487-92. doi: 10.2147/tcrm.s6864. [Article]
13. Rapkin AJ, Winer SA: Drospirenone: a novel progestin. Expert Opin Pharmacother. 2007 May;8(7):989-99. doi: 10.1517/14656566.8.7.989 . [Article]
14. Breech LL, Braverman PK: Safety, efficacy, actions, and patient acceptability of drospirenone/ethinyl estradiol contraceptive pills in the treatment of premenstrual dysphoric disorder. Int J Womens Health. 2010 Aug 9;1:85-95. [Article]
15. Bird ST, Pepe SR, Etminan M, Liu X, Brophy JM, Delaney JA: The association between drospirenone and hyperkalemia: a comparative-safety study. BMC Clin Pharmacol. 2011 Dec 30;11:23. doi: 10.1186/1472-6904-11-23. [Article]
16. Zhang N, Shon J, Kim MJ, Yu C, Zhang L, Huang SM, Lee L, Tran D, Li L: Role of CYP3A in Oral Contraceptives Clearance. Clin Transl Sci. 2018 May;11(3):251-260. doi: 10.1111/cts.12499. Epub 2017 Oct 6. [Article]
17. Cadeddu G, Deidda A, Stochino ME, Velluti N, Burrai C, Del Zompo M: Clozapine toxicity due to a multiple drug interaction: a case report. J Med Case Rep. 2015 Apr 2;9:77. doi: 10.1186/s13256-015-0547-2. [Article]
18. Wiesinger H, Berse M, Klein S, Gschwend S, Hochel J, Zollmann FS, Schutt B: Pharmacokinetic interaction between the CYP3A4 inhibitor ketoconazole and the hormone drospirenone in combination with ethinylestradiol or estradiol. Br J Clin Pharmacol. 2015 Dec;80(6):1399-410. doi: 10.1111/bcp.12745. Epub 2015 Oct 28. [Article]
19. YAZ fda label [Link]
20. Yaz Bayer monograph [Link]
21. 2012 FDA safety statement, YAZ [Link]
22. FDA pharmacology review, Drospirenone [Link]
23. Angeliq EU label [Link]
24. drospirenone/ethinyl estradiol - Drug Summary [Link]
25. Angeliq FDA label [Link]
26. Safyral FDA label [Link]
27. Product monograph: Nexstellis (estetrol and drospirenone) oral tablets [Link]
28. FDA Approved Drug Products: NEXTSTELLIS (drospirenone and estetrol) tablets for oral use [Link]
29. FDA Approved Drug Products: YASMIN (drospirenone/ethinyl estradiol) tablets, for oral use [Link]

External Links

Human Metabolome Database

HMDB0015467

KEGG Drug

D03917

PubChem Compound

68873

PubChem Substance

46507653

ChemSpider

62105

BindingDB

150275

RxNav

11636

ChEBI

50838

ChEMBL

CHEMBL1509

ZINC

ZINC000003927200

Therapeutic Targets Database

DAP001206

PharmGKB

PA164749409

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

Wikipedia

Drospirenone

FDA label

Download (292 KB)

MSDS

Download (567 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Not Available	Blood Pressures / Contraception	1
4	Completed	Not Available	Polycystic Ovarian Syndrome (PCOS)	1
4	Completed	Basic Science	Adverse Effect of Oral Contraceptives, Subsequent Encounter	1
4	Completed	Diagnostic	Joint Stabilioty	1
4	Completed	Prevention	Breastfeeding / Contraception	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Tablet, film coated	Oral
Kit; tablet, film coated	Oral
Tablet, film coated	Oral	0.03 MG
Tablet	Oral	20.000 mcg
Tablet, coated	Oral	4 mg
Solution	Oral
Tablet	Oral	3.000 mg
Kit; tablet	Oral
Tablet, film coated	Oral
Tablet, film coated	Oral	4 MG
Kit; tablet, film coated	Oral	4 mg/1
Tablet	Oral	4 mg
Capsule, liquid filled	Oral
Tablet	Oral
Tablet, coated	Oral
Tablet, film coated	Oral	3 mg
Kit	Oral
Tablet, film coated	Oral	0.02 MG

Prices

Not Available

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US6787531	No	2004-09-07	2020-08-31
US6933395	No	2005-08-23	2017-08-11
US8906890	No	2014-12-09	2031-10-22
US6987101	No	2006-01-17	2017-12-22
US7163931	No	2007-01-16	2021-12-20
US6958326	No	2005-10-25	2021-12-20
US5798338	No	1998-08-25	2015-07-10
US6441168	No	2002-08-27	2022-07-30
US8617597	No	2013-12-31	2030-02-08
US10179140	No	2019-01-15	2031-06-28
US9603860	No	2017-03-28	2031-06-28
US10603281	No	2020-03-31	2031-06-08
US10849857	No	2020-12-01	2031-06-28
US7732430	No	2010-06-08	2025-03-02
US10987364	No	2021-04-27	2031-06-28
US11123299	No	2021-09-21	2031-06-28
US11291633	No	2011-06-28	2031-06-28
US11291632	No	2011-06-28	2031-06-28
US11351122	No	2011-06-28	2031-06-28
US11413249	No	2011-06-28	2031-06-28
US11439598	No	2011-06-28	2031-06-28
US11478487	No	2011-06-28	2031-06-28
US11504334	No	2011-06-28	2031-06-28
US11617751	No	2010-07-17	2030-07-17
US11793760	No	2016-06-17	2036-06-17

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	196-200	https://www.chemicalbook.com/ChemicalProductProperty_US_CB8695608.aspx
boiling point (°C)	552.2	https://www.lookchem.com/Drospirenone/
logP	3.08	https://pdf.hres.ca/dpd_pm/00042999.PDF
logS	-5.2	http://www.hmdb.ca/metabolites/HMDB0015467
pKa	-5	http://www.hmdb.ca/metabolites/HMDB0015467

Predicted Properties

Property	Value	Source
Water Solubility	0.00225 mg/mL	ALOGPS
logP	2.36	ALOGPS
logP	3.37	Chemaxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	18.52	Chemaxon
pKa (Strongest Basic)	-5	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	2	Chemaxon
Hydrogen Donor Count	0	Chemaxon
Polar Surface Area	43.37 Å2	Chemaxon
Rotatable Bond Count	0	Chemaxon
Refractivity	101.68 m3·mol-1	Chemaxon
Polarizability	41.81 Å3	Chemaxon
Number of Rings	7	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	1.0
Blood Brain Barrier	+	0.9383
Caco-2 permeable	+	0.6376
P-glycoprotein substrate	Substrate	0.6524
P-glycoprotein inhibitor I	Inhibitor	0.6171
P-glycoprotein inhibitor II	Non-inhibitor	0.6726
Renal organic cation transporter	Non-inhibitor	0.7005
CYP450 2C9 substrate	Non-substrate	0.796
CYP450 2D6 substrate	Non-substrate	0.9116
CYP450 3A4 substrate	Substrate	0.6964
CYP450 1A2 substrate	Non-inhibitor	0.5534
CYP450 2C9 inhibitor	Non-inhibitor	0.8665
CYP450 2D6 inhibitor	Non-inhibitor	0.9336
CYP450 2C19 inhibitor	Non-inhibitor	0.7754
CYP450 3A4 inhibitor	Non-inhibitor	0.8355
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.8541
Ames test	Non AMES toxic	0.9163
Carcinogenicity	Non-carcinogens	0.9505
Biodegradation	Not ready biodegradable	0.9757
Rat acute toxicity	1.9430 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9393
hERG inhibition (predictor II)	Non-inhibitor	0.8215

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Download (37.1 KB)

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-0w9c-0169000000-37155c35a2dfebdf3836
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-014i-0009000000-d2c2b3f0083127b93331
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-014j-0009000000-fec0b9559b578e9c9431
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-014i-0009000000-e83f0561c8b894209b60
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-014j-0209000000-16e3f1168fe085039712
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00xu-1019000000-7ac789c15184524f4e22
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-066r-0629000000-80294d71e68e61c9f972
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	198.3961196	predicted	DarkChem Lite v0.1.0
[M-H]-	198.4750196	predicted	DarkChem Lite v0.1.0
[M-H]-	197.7604196	predicted	DarkChem Lite v0.1.0
[M-H]-	188.11028	predicted	DeepCCS 1.0 (2019)
[M+H]+	198.9765196	predicted	DarkChem Lite v0.1.0
[M+H]+	199.0630196	predicted	DarkChem Lite v0.1.0
[M+H]+	197.9431196	predicted	DarkChem Lite v0.1.0
[M+H]+	189.834	predicted	DeepCCS 1.0 (2019)
[M+Na]+	199.4102196	predicted	DarkChem Lite v0.1.0
[M+Na]+	198.7850196	predicted	DarkChem Lite v0.1.0
[M+Na]+	196.16295	predicted	DeepCCS 1.0 (2019)

Targets

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Details1. Mineralocorticoid receptor

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Antagonist

General Function

Zinc ion binding

Specific Function

Receptor for both mineralocorticoids (MC) such as aldosterone and glucocorticoids (GC) such as corticosterone or cortisol. Binds to mineralocorticoid response elements (MRE) and transactivates targ...

Gene Name

NR3C2

Uniprot ID

P08235

Uniprot Name

Mineralocorticoid receptor

Molecular Weight

107066.575 Da

References

1. Krattenmacher R: Drospirenone: pharmacology and pharmacokinetics of a unique progestogen. Contraception. 2000 Jul;62(1):29-38. [Article]
2. Fuhrmann U, Krattenmacher R, Slater EP, Fritzemeier KH: The novel progestin drospirenone and its natural counterpart progesterone: biochemical profile and antiandrogenic potential. Contraception. 1996 Oct;54(4):243-51. [Article]
3. Muhn P, Fuhrmann U, Fritzemeier KH, Krattenmacher R, Schillinger E: Drospirenone: a novel progestogen with antimineralocorticoid and antiandrogenic activity. Ann N Y Acad Sci. 1995 Jun 12;761:311-35. doi: 10.1111/j.1749-6632.1995.tb31386.x. [Article]
4. Oelkers WK: Effects of estrogens and progestogens on the renin-aldosterone system and blood pressure. Steroids. 1996 Apr;61(4):166-71. [Article]
5. Oelkers W: Antimineralocorticoid activity of a novel oral contraceptive containing drospirenone, a unique progestogen resembling natural progesterone. Eur J Contracept Reprod Health Care. 2002 Dec;7 Suppl 3:19-26; discussion 42-3. [Article]
6. Oelkers W: Drospirenone, a progestogen with antimineralocorticoid properties: a short review. Mol Cell Endocrinol. 2004 Mar 31;217(1-2):255-61. doi: 10.1016/j.mce.2003.10.030. [Article]

Details2. Androgen receptor

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Antagonist

Curator comments

References indicate a lower affinity to the androgen receptor.

General Function

Zinc ion binding

Specific Function

Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription ...

Gene Name

AR

Uniprot ID

P10275

Uniprot Name

Androgen receptor

Molecular Weight

98987.9 Da

References

1. Krattenmacher R: Drospirenone: pharmacology and pharmacokinetics of a unique progestogen. Contraception. 2000 Jul;62(1):29-38. [Article]
2. Muhn P, Fuhrmann U, Fritzemeier KH, Krattenmacher R, Schillinger E: Drospirenone: a novel progestogen with antimineralocorticoid and antiandrogenic activity. Ann N Y Acad Sci. 1995 Jun 12;761:311-35. doi: 10.1111/j.1749-6632.1995.tb31386.x. [Article]
3. Oelkers W: Drospirenone, a progestogen with antimineralocorticoid properties: a short review. Mol Cell Endocrinol. 2004 Mar 31;217(1-2):255-61. doi: 10.1016/j.mce.2003.10.030. [Article]
4. Yaz Bayer monograph [Link]

Details3. Progesterone receptor

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Agonist

General Function

Zinc ion binding

Specific Function

The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Progesterone receptor ...

Gene Name

PGR

Uniprot ID

P06401

Uniprot Name

Progesterone receptor

Molecular Weight

98979.96 Da

References

1. Krattenmacher R: Drospirenone: pharmacology and pharmacokinetics of a unique progestogen. Contraception. 2000 Jul;62(1):29-38. [Article]
2. Bray JD, Jelinsky S, Ghatge R, Bray JA, Tunkey C, Saraf K, Jacobsen BM, Richer JK, Brown EL, Winneker RC, Horwitz KB, Lyttle CR: 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. J Steroid Biochem Mol Biol. 2005 Dec;97(4):328-41. Epub 2005 Sep 12. [Article]
3. Fuhrmann U, Krattenmacher R, Slater EP, Fritzemeier KH: The novel progestin drospirenone and its natural counterpart progesterone: biochemical profile and antiandrogenic potential. Contraception. 1996 Oct;54(4):243-51. [Article]
4. Arias-Loza PA, Hu K, Schafer A, Bauersachs J, Quaschning T, Galle J, Jazbutyte V, Neyses L, Ertl G, Fritzemeier KH, Hegele-Hartung C, Pelzer T: Medroxyprogesterone acetate but not drospirenone ablates the protective function of 17 beta-estradiol in aldosterone salt-treated rats. Hypertension. 2006 Nov;48(5):994-1001. Epub 2006 Sep 25. [Article]
5. Sitruk-Ware R: New progestagens for contraceptive use. Hum Reprod Update. 2006 Mar-Apr;12(2):169-78. Epub 2005 Nov 16. [Article]
6. Sitruk-Ware R: New progestogens: a review of their effects in perimenopausal and postmenopausal women. Drugs Aging. 2004;21(13):865-83. [Article]
7. Muhn P, Fuhrmann U, Fritzemeier KH, Krattenmacher R, Schillinger E: Drospirenone: a novel progestogen with antimineralocorticoid and antiandrogenic activity. Ann N Y Acad Sci. 1995 Jun 12;761:311-35. doi: 10.1111/j.1749-6632.1995.tb31386.x. [Article]

Details4. Glucocorticoid receptor

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Binder

Curator comments

References indicate a weak binding affinity to the glucocorticoid receptor.

General Function

Zinc ion binding

Specific Function

Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modula...

Gene Name

NR3C1

Uniprot ID

P04150

Uniprot Name

Glucocorticoid receptor

Molecular Weight

85658.57 Da

References

1. Krattenmacher R: Drospirenone: pharmacology and pharmacokinetics of a unique progestogen. Contraception. 2000 Jul;62(1):29-38. [Article]
2. Muhn P, Fuhrmann U, Fritzemeier KH, Krattenmacher R, Schillinger E: Drospirenone: a novel progestogen with antimineralocorticoid and antiandrogenic activity. Ann N Y Acad Sci. 1995 Jun 12;761:311-35. doi: 10.1111/j.1749-6632.1995.tb31386.x. [Article]

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Drug created at July 08, 2007 17:03 / Updated at May 31, 2023 07:29