Chemical: Drug
drospirenone

PharmGKB contains no dosing guidelines for this . To report known genotype-based dosing guidelines, or if you are interested in developing guidelines, click here.


Annotated Labels

  1. FDA Label for drospirenone,ethinyl estradiol and CYP2C19
  2. HCSC Label for drospirenone,ethinyl estradiol and F5,PROC,PROS1,SERPINC1

last updated 09/01/2016

1. FDA Label for drospirenone,ethinyl estradiol and CYP2C19

Informative PGx
Full label available at DailyMed

Genes and/or phenotypes found in this label

  • CYP1A1
    • Precautions section
    • source: U.S. Food and Drug Administration
  • CYP1A2
    • Precautions section
    • source: U.S. Food and Drug Administration
  • CYP2C19
    • Precautions section
    • source: U.S. Food and Drug Administration
  • CYP2C9
    • Precautions section
    • source: U.S. Food and Drug Administration
  • CYP2D6
    • Precautions section
    • source: U.S. Food and Drug Administration
  • CYP3A4
    • metabolism/PK, Drug interactions section, Clinical pharmacology section, Precautions section
    • source: U.S. Food and Drug Administration


PharmGKB contains no Clinical Variants that meet the highest level of criteria.

Disclaimer: The PharmGKB's clinical annotations reflect expert consensus based on clinical evidence and peer-reviewed literature available at the time they are written and are intended only to assist clinicians in decision-making and to identify questions for further research. New evidence may have emerged since the time an annotation was submitted to the PharmGKB. The annotations are limited in scope and are not applicable to interventions or diseases that are not specifically identified.

The annotations do not account for individual variations among patients, and cannot be considered inclusive of all proper methods of care or exclusive of other treatments. It remains the responsibility of the health-care provider to determine the best course of treatment for a patient. Adherence to any guideline is voluntary, with the ultimate determination regarding its application to be made solely by the clinician and the patient. PharmGKB assumes no responsibility for any injury or damage to persons or property arising out of or related to any use of the PharmGKB clinical annotations, or for any errors or omissions.

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Overview

Generic Names
  • 6beta,7beta,15beta,16beta-dimethylene-3-oxo-17alpha-pregn-4-ene-21,17 carbolactone
  • DRSP
  • Drospirenona [inn-spanish]
  • Drospirenonum [inn-latin]
Trade Names
Brand Mixture Names
  • Yasmin (drospirenone + ethinylestradiol)
  • Yaz (drospirenone + ethinylestradiol)

PharmGKB Accession Id

PA164749409

Type(s):

Drug

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.

Source: Drug Bank

Indication

For the prevention of pregnancy in women who elect an oral contraceptive.

Source: Drug Bank

Other Vocabularies

Information pulled from DrugBank has not been reviewed by PharmGKB.

Pharmacology, Interactions, and Contraindications

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 surge.

Source: Drug Bank

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.

Source: Drug Bank

Food Interaction

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

Source: Drug Bank

Absorption, Distribution, Metabolism, Elimination & Toxicity

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.

Source: Drug Bank

Protein Binding

97%

Source: Drug Bank

Absorption

Oral bioavailability is approximately 76%.

Source: Drug Bank

Half-Life

30 hours

Source: Drug Bank

Chemical Properties

Chemical Formula

C24H30O3

Source: Drug Bank

Isomeric SMILES

C[C@]12CCC(=O)C=C1[C@@H]3C[C@@H]3[C@@H]4[C@@H]2CC[C@]5([C@H]4[C@@H]6C[C@@H]6[C@@]57CCC(=O)O7)C

Source: Drug Bank

[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

Source: Drug Bank

Canonical SMILES

C[C@]12CC[C@H]

Source: Drug Bank

Average Molecular Weight

366.4932

Source: Drug Bank

Monoisotopic Molecular Weight

366.219494826

Source: Drug Bank

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

Source: Drug Bank

InChI String

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

Source: Drug Bank

Genes that are associated with this drug in PharmGKB's database based on (1) variant annotations, (2) literature review, (3) pathways or (4) information automatically retrieved from DrugBank, depending on the "evidence" and "source" listed below.

Curated Information ?

Drug Targets

Gene Description
AR (source: Drug Bank )
ESR1 (source: Drug Bank )
NR3C2 (source: Drug Bank )
PGR (source: Drug Bank )

Curated Information ?

EvidenceDrug
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
ketoconazole

Drug Interactions

Interaction Description
benazepril - drospirenone Increased risk of hyperkaliemia (source: Drug Bank )
candesartan - drospirenone Increased risk of hyperkaliemia (source: Drug Bank )
candesartan - drospirenone Increased risk of hyperkaliemia (source: Drug Bank )
captopril - drospirenone Increased risk of hyperkaliemia (source: Drug Bank )
cilazapril - drospirenone Increased risk of hyperkaliemia (source: Drug Bank )
enalapril - drospirenone Increased risk of hyperkaliemia (source: Drug Bank )
eprosartan - drospirenone Increased risk of hyperkaliemia (source: Drug Bank )
eprosartan - drospirenone Increased risk of hyperkaliemia (source: Drug Bank )
fosinopril - drospirenone Increased risk of hyperkaliemia (source: Drug Bank )
heparin - drospirenone Increased risk of hyperkaliemia (source: Drug Bank )
irbesartan - drospirenone Increased risk of hyperkaliemia (source: Drug Bank )
irbesartan - drospirenone Increased risk of hyperkaliemia (source: Drug Bank )
lisinopril - drospirenone Increased risk of hyperkaliemia (source: Drug Bank )
losartan - drospirenone Increased risk of hyperkaliemia (source: Drug Bank )
losartan - drospirenone Increased risk of hyperkaliemia (source: Drug Bank )
olmesartan - drospirenone Increased risk of hyperkaliemia (source: Drug Bank )
perindopril - drospirenone Increased risk of hyperkaliemia (source: Drug Bank )
quinapril - drospirenone Increased risk of hyperkaliemia (source: Drug Bank )
ramipril - drospirenone Increased risk of hyperkaliemia (source: Drug Bank )
telmisartan - drospirenone Telmisartan may increase the hyperkalemic effect of Drospirenone. Monitor for increased serum potassium concentrations during concomitant therapy. (source: Drug Bank )
telmisartan - drospirenone Telmisartan may increase the hyperkalemic effect of Drospirenone. Monitor for increased serum potassium concentrations during concomitant therapy. (source: Drug Bank )
thiopental - drospirenone Thiopental may decrease the effect of Drospirenone. Contraceptive failure may occur. Alternative nonhomomonal contraception should be used during concomitant therapy. (source: Drug Bank )
thiopental - drospirenone Thiopental may decrease the effect of Drospirenone. Contraceptive failure may occur. Alternative nonhomomonal contraception should be used during concomitant therapy. (source: Drug Bank )
trandolapril - drospirenone Increased risk of hyperkalemia. Monitor serum potassium levels. (source: Drug Bank )
treprostinil - drospirenone Additive hypotensive effect. Monitor antihypertensive therapy during concomitant use. (source: Drug Bank )
triamterene - drospirenone Increased risk of hyperkaliemia (source: Drug Bank )
warfarin - drospirenone 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. (source: Drug Bank )

Relationships from National Drug File - Reference Terminology (NDF-RT)

May Prevent
Contraindicated With

Publications related to drospirenone: 1

No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Pharmacokinetic interaction between the CYP3A4 inhibitor ketoconazole and the hormone drospirenone in combination with ethinylestradiol or estradiol. British journal of clinical pharmacology. 2015. Wiesinger Herbert, et al. PubMed

LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB01395
ChEBI:
50838
KEGG Drug:
D03917
PubChem Compound:
68873
PubChem Substance:
12014580
46507653
Drugs Product Database (DPD):
2261731
ChemSpider:
62105
Therapeutic Targets Database:
DAP001206

Clinical Trials

These are trials that mention drospirenone and are related to either pharmacogenetics or pharmacogenomics.

No trials loaded.

NURSA Datasets

provided by nursa.org

No NURSA datasets available.

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Sources for PharmGKB drug information: DrugBank, PubChem.