Etynodiol diacetate

Etynodiol diacetate
Clinical data
Trade namesOvulen, Demulen, others
Other namesEthynodiol diacetate; Norethindrol diacetate; 3β-Hydroxynorethisterone 3β,17β-diacetate;[1] 17α-Ethynylestr-4-ene-3β,17β-diyl diacetate; CB-8080; SC-11800
License data
Pregnancy
category
  • Contraindicated
Routes of
administration		By mouth
Drug classProgestogen; Progestin; Progestogen ester
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • US: ℞-only[2][3]
  • In general: ℞ (Prescription only)
Identifiers
  • [(3S,8R,9S,10R,13S,14S,17R)-17-acetyloxy-17-ethynyl-13-methyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.005.496 Edit this at Wikidata
Chemical and physical data
FormulaC24H32O4
Molar mass384.516 g·mol−1
3D model (JSmol)
  • O=C(O[C@@H]4/C=C3\[C@@H]([C@H]2CC[C@]1([C@@H](CC[C@]1(C#C)OC(=O)C)[C@@H]2CC3)C)CC4)C
  • InChI=1S/C24H32O4/c1-5-24(28-16(3)26)13-11-22-21-8-6-17-14-18(27-15(2)25)7-9-19(17)20(21)10-12-23(22,24)4/h1,14,18-22H,6-13H2,2-4H3/t18-,19-,20+,21+,22-,23-,24-/m0/s1
  • Key:ONKUMRGIYFNPJW-KIEAKMPYSA-N

Etynodiol diacetate, or ethynodiol diacetate, sold under the brand name Ovulen among others, is a progestin medication which is used in birth control pills.[4][5][6] The medication is available only in combination with an estrogen.[7] It is taken by mouth.[8]

Etynodiol diacetate is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.[9][10] It has weak androgenic and estrogenic activity and no other important hormonal activity.[11][12][13] The medication is a prodrug of norethisterone in the body, with etynodiol occurring as an intermediate.[9][10][14]

Etynodiol, a related compound, was discovered in 1954, and etynodiol diacetate was introduced for medical use in 1965.[15][16] The combination ethynodiol with mestranol (Ovulen) was approved for medical use in the United States in 1966.[17] The combination ethinylestradiol with ethynodiol (Demulen) was approved for medical use in the United States in 1970.[18]

In 2021, the combination with ethinylestradiol was the 276th most commonly prescribed medication in the United States, with more than 800,000 prescriptions.[19][20]

  1. ^ Schindler AE, Campagnoli C, Druckmann R, Huber J, Pasqualini JR, Schweppe KW, et al. (December 2003). "Classification and pharmacology of progestins". Maturitas. 46 (Suppl 1): S7–S16. doi:10.1016/j.maturitas.2003.09.014. PMID 14670641.
  2. ^ "Zovia 1/35- ethynodiol diacetate and ethinyl estradiol tablets kit". Archived from the original on 28 September 2022. Retrieved 20 January 2024.
  3. ^ "Kelnor 1/35- ethynodiol diacetate and ethinyl estradiol kit". Archived from the original on 29 March 2023. Retrieved 20 January 2024.
  4. ^ Shoupe D, Haseltine FP (6 December 2012). Contraception. Springer Science & Business Media. pp. 21–. ISBN 978-1-4612-2730-4.
  5. ^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 522–. ISBN 978-1-4757-2085-3.
  6. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 422. ISBN 978-3-88763-075-1. Retrieved 30 May 2012.
  7. ^ "Etynodiol". Drugs.com. Archived from the original on 5 February 2018. Retrieved 4 February 2018.
  8. ^ Cite error: The named reference Blum2013 was invoked but never defined (see the help page).
  9. ^ a b Cite error: The named reference pmid2256526 was invoked but never defined (see the help page).
  10. ^ a b Cite error: The named reference HumansOrganization2007 was invoked but never defined (see the help page).
  11. ^ Cite error: The named reference TashjianArmstrong2011 was invoked but never defined (see the help page).
  12. ^ Cite error: The named reference Becker2001 was invoked but never defined (see the help page).
  13. ^ Cite error: The named reference GorollMulley2009 was invoked but never defined (see the help page).
  14. ^ Cite error: The named reference pmid12215716 was invoked but never defined (see the help page).
  15. ^ Cite error: The named reference Petrow_1971 was invoked but never defined (see the help page).
  16. ^ Cite error: The named reference Publishing2013 was invoked but never defined (see the help page).
  17. ^ "Ovulen: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Archived from the original on 8 December 2022. Retrieved 20 January 2024.
  18. ^ "Demulen: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Archived from the original on 10 May 2021. Retrieved 20 January 2024.
  19. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  20. ^ "Ethinyl Estradiol; Ethynodiol - Drug Usage Statistics". ClinCalc. Archived from the original on 18 January 2024. Retrieved 14 January 2024.