Drospirenone

Drospirenone
Clinical data
PronunciationDroe-SPY-re-nown
Trade namesAlone: Slynd
With estradiol: Angeliq
With ethinylestradiol: Yasmin, Yasminelle, Yaz, others
With estetrol: Nextstellis
Other namesDihydrospirenone; Dihydrospirorenone; 1,2-Dihydrospirorenone; MSp; SH-470; ZK-30595; LF-111; 17β-Hydroxy-6β,7β:15β,16β-dimethylene-3-oxo-17α-pregn-4-ene-21-carboxylic acid, γ-lactone
AHFS/Drugs.comProfessional Drug Facts
License data
Routes of
administration
By mouth[1]
Drug classProgestogen; Progestin; Antimineralocorticoid; Steroidal antiandrogen
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability66–85%[1][4][5]
Protein binding95–97% (to albumin)[3][1][4]
MetabolismLiver (mostly CYP450-independent (reduction, sulfation, and cleavage of lactone ring), some CYP3A4 contribution)[4][6][7][8]
Metabolites• Drospirenone acid[3]
• 4,5-Dihydrodrospirenone 3-sulfate[3]
Elimination half-life25–33 hours[3][4][1]
ExcretionUrine, feces[3]
Identifiers
  • (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]phenantrene-17,2'(5'H)-furan]-3,5'(2H)-dione
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.060.599 Edit this at Wikidata
Chemical and physical data
FormulaC24H30O3
Molar mass366.501 g·mol−1
3D model (JSmol)
  • O=C7O[C@@]6([C@@]3([C@H]([C@@H]2[C@@H]4[C@H](/C1=C/C(=O)CC[C@]1(C)[C@H]2CC3)C4)[C@@H]5C[C@@H]56)C)CC7
  • 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 checkY
  • Key:METQSPRSQINEEU-HXCATZOESA-N checkY
  (verify)

Drospirenone is a progestin and antiandrogen medication which is used in birth control pills to prevent pregnancy and in menopausal hormone therapy, among other uses.[1][9] It is available both alone under the brand name Slynd and in combination with an estrogen under the brand name Yasmin among others.[9][3] The medication is an analog of the drug spironolactone.[10] Drospirenone is taken by mouth.[1][3]

Common side effects include acne, headache, breast tenderness, weight increase, and menstrual changes.[3] Rare side effects may include high potassium levels and blood clots (when taken as a combined oestrogen-progestogen pill), among others.[3][11] Drospirenone is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.[1] It has additional antimineralocorticoid and antiandrogenic activity and no other important hormonal activity.[1] Because of its antimineralocorticoid activity and lack of undesirable off-target activity, drospirenone is said to more closely resemble bioidentical progesterone than other progestins.[12][13]

Drospirenone was patented in 1976 and introduced for medical use in 2000.[14][15] It is available widely throughout the world.[9] The medication is sometimes referred to as a "fourth-generation" progestin.[16][17] It is available as a generic medication.[18] In 2020, a formulation of drospirenone with ethinylestradiol was the 145th most commonly prescribed medication in the United States, with more than 4 million prescriptions.[19][20]

  1. ^ a b c d e f g h Kuhl H (August 2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric. 8 Suppl 1 (sup1): 3–63. doi:10.1080/13697130500148875. PMID 16112947. S2CID 24616324.
  2. ^ "Health product highlights 2021: Annexes of products approved in 2021". Health Canada. 3 August 2022. Retrieved 25 March 2024.
  3. ^ a b c d e f g h i j Slynd-drospirenone tablet, film coated drug label/data at DailyMed from U.S. National Library of Medicine, National Institutes of Health.
  4. ^ a b c d Krattenmacher R (July 2000). "Drospirenone: pharmacology and pharmacokinetics of a unique progestogen". Contraception. 62 (1): 29–38. doi:10.1016/S0010-7824(00)00133-5. PMID 11024226.
  5. ^ Stanczyk FZ, Hapgood JP, Winer S, Mishell DR (April 2013). "Progestogens used in postmenopausal hormone therapy: differences in their pharmacological properties, intracellular actions, and clinical effects". Endocrine Reviews. 34 (2): 171–208. doi:10.1210/er.2012-1008. PMC 3610676. PMID 23238854.
  6. ^ Gaspard U, Endrikat J, Desager JP, Buicu C, Gerlinger C, Heithecker R (April 2004). "A randomized study on the influence of oral contraceptives containing ethinylestradiol combined with drospirenone or desogestrel on lipid and lipoprotein metabolism over a period of 13 cycles". Contraception. 69 (4): 271–278. doi:10.1016/j.contraception.2003.11.003. PMID 15033400.
  7. ^ Bachmann G, Kopacz S (November 2009). "Drospirenone/ethinyl estradiol 3 mg/20 mug (24/4 day regimen): hormonal contraceptive choices - use of a fourth-generation progestin". Patient Preference and Adherence. 3: 259–264. doi:10.2147/PPA.S3901. PMC 2778416. PMID 19936169.
  8. ^ Wiesinger H, Berse M, Klein S, Gschwend S, Höchel J, Zollmann FS, Schütt B (December 2015). "Pharmacokinetic interaction between the CYP3A4 inhibitor ketoconazole and the hormone drospirenone in combination with ethinylestradiol or estradiol". British Journal of Clinical Pharmacology. 80 (6): 1399–1410. doi:10.1111/bcp.12745. PMC 4693482. PMID 26271371.
  9. ^ a b c Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
  10. ^ Krattenmacher R (July 2000). "Drospirenone: pharmacology and pharmacokinetics of a unique progestogen". Contraception. 62 (1): 29–38. doi:10.1016/S0010-7824(00)00133-5. PMID 11024226.
  11. ^ Cite error: The named reference pmid26598309 was invoked but never defined (see the help page).
  12. ^ Oelkers W (December 2000). "Drospirenone--a new progestogen with antimineralocorticoid activity, resembling natural progesterone". The European Journal of Contraception & Reproductive Health Care (Review). 5 (Suppl 3): 17–24. doi:10.1080/14730782.2000.12288986. PMID 11246598. S2CID 35051390.
  13. ^ Oelkers W (December 2002). "Antimineralocorticoid activity of a novel oral contraceptive containing drospirenone, a unique progestogen resembling natural progesterone". The European Journal of Contraception & Reproductive Health Care (Review). 7 (Suppl 3): 19–26, discussion 42–3. doi:10.1080/14730782.2000.12288986. PMID 12659403.
  14. ^ Cite error: The named reference Ravina2011 was invoked but never defined (see the help page).
  15. ^ Alapi EM, Fischer J (2006). "Part III: Table of Selected Analogue Classes". In Fischer J, Ganellin CR (eds.). Analogue-based Drug Discovery. John Wiley & Sons. p. 459. ISBN 9783527607495.
  16. ^ Cite error: The named reference HatcherM.D.2007 was invoked but never defined (see the help page).
  17. ^ Cite error: The named reference RossoZeichner2016 was invoked but never defined (see the help page).
  18. ^ Generic Yasmin Availability via yasminat Drugs.com
  19. ^ "The Top 300 of 2020". ClinCalc. Retrieved 7 October 2022.
  20. ^ "Drospirenone; Ethinyl Estradiol - Drug Usage Statistics". ClinCalc. Retrieved 7 October 2022.