Etynodiol

Last updated
Etynodiol
Etynodiol.svg
Clinical data
Other namesEthynodiol; 3β-Hydroxynorethisterone; 17α-Ethynylestr-4-ene-3β,17β-diol
Drug class Progestin; Progestogen
ATC code
Identifiers
  • (3S,8R,9S,10R,13S,14S,17R)-17-ethynyl-13-methyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol
CAS Number
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard 100.013.610 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C20H28O2
Molar mass 300.442 g·mol−1
3D model (JSmol)
  • O[C@@H]4/C=C3\[C@@H]([C@H]2CC[C@]1([C@@H](CC[C@]1(C#C)O)[C@@H]2CC3)C)CC4
  • InChI=1S/C20H28O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,12,14-18,21-22H,4-11H2,2H3/t14-,15-,16+,17+,18-,19-,20-/m0/s1
  • Key:JYILPERKVHXLNF-QMNUTNMBSA-N

Etynodiol, or ethynodiol, is a steroidal progestin of the 19-nortestosterone group which was never marketed. [1] [2] [3] A diacylated derivative, etynodiol diacetate, is used as a hormonal contraceptive. [1] [2] Etynodiol is sometimes used as a synonym for etynodiol diacetate.

Contents

It was patented in 1955. [4]

Pharmacology

Etynodiol is a prodrug of norethisterone, and is converted immediately and completely into norethisterone. [5] [6] [7] Etynodiol is an intermediate in the conversion of the prodrug lynestrenol into norethisterone. [8]

Relative affinities (%) of norethisterone, metabolites, and prodrugs
CompoundTypea PR Tooltip Progesterone receptor AR Tooltip Androgen receptor ER Tooltip Estrogen receptor GR Tooltip Glucocorticoid receptor MR Tooltip Mineralocorticoid receptor SHBG Tooltip Sex hormone-binding globulin CBG Tooltip Corticosteroid binding globulin
Norethisterone –67–751500–10–3160
5α-Dihydronorethisterone Metabolite252700 ? ? ?
3α,5α-TetrahydronorethisteroneMetabolite100–10 ? ? ?
3α,5β-TetrahydronorethisteroneMetabolite ?00 ? ? ? ?
3β,5α-TetrahydronorethisteroneMetabolite100–80 ? ? ?
Ethinylestradiol Metabolite15–251–31121–300.180
Norethisterone acetate Prodrug205100 ? ?
Norethisterone enanthate Prodrug ? ? ? ? ? ? ?
Noretynodrel Prodrug6020000
EtynodiolProdrug1011–180 ? ? ?
Etynodiol diacetate Prodrug10000 ? ?
Lynestrenol Prodrug11300 ? ?
Notes: Values are percentages (%). Reference ligands (100%) were promegestone for the PR Tooltip progesterone receptor, metribolone for the AR Tooltip androgen receptor, estradiol for the ER Tooltip estrogen receptor, dexamethasone for the GR Tooltip glucocorticoid receptor, aldosterone for the MR Tooltip mineralocorticoid receptor, dihydrotestosterone for SHBG Tooltip sex hormone-binding globulin, and cortisol for CBG Tooltip Corticosteroid-binding globulin. Footnotes:a = Active or inactive metabolite, prodrug, or neither of norethisterone. Sources: See template.

Chemistry

Etynodiol is a 19-nortestosterone derivative. Structurally, it is almost identical to norethisterone and lynestrenol, differing only in its C3 substituent. Whereas norethisterone has a ketone at C3 and lynestrenol has no substituent at C3, etynodiol has a hydroxyl group at the position.

Synthesis

Ethynodiol diacetate synthesis: F. B. Colton, U.S. patent 2,843,609 (1958 to Searle). Prepn of the 3-acetate, 17-acetate, and diacetate: P. D. Klimstra, U.S. patent 3,176,013 (1965 to Searle); see also: Ethynodiol diacetate synthesis.svg
Ethynodiol diacetate synthesis: F. B. Colton, U.S. patent 2,843,609 (1958 to Searle). Prepn of the 3-acetate, 17-acetate, and diacetate: P. D. Klimstra, U.S. patent 3,176,013 (1965 to Searle); see also:

Society and culture

Generic names

Etynodiol is the generic name of the drug and its INN Tooltip International Nonproprietary Name, while ethynodiol is its BAN Tooltip British Approved Name. [1] [2]

References

  1. 1 2 3 Macdonald F (1997). Dictionary of Pharmacological Agents. CRC Press. p. 1454. ISBN   978-0-412-46630-4 . Retrieved 12 May 2012.
  2. 1 2 3 Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 422. ISBN   978-3-88763-075-1 . Retrieved 30 May 2012.
  3. ↑ Schindler AE, Campagnoli C, Druckmann R, Huber J, Pasqualini JR, Schweppe KW, Thijssen JH (December 2003). "Classification and pharmacology of progestins". Maturitas. 46 (Suppl 1): S7 –S16. doi:10.1016/j.maturitas.2003.09.014. PMID   14670641.
  4. ↑ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 478. ISBN   9783527607495.
  5. ↑ Shoupe D, Haseltine FP (6 December 2012). Contraception. Springer Science & Business Media. pp. 21–. ISBN   978-1-4612-2730-4.
  6. ↑ Bhattacharya (1 January 2003). Pharmacology, 2/e. Elsevier India. pp. 378–. ISBN   978-81-8147-009-6.
  7. ↑ IARC Working Group on the Evaluation of Carcinogenic Risks to Humans; World Health Organization; International Agency for Research on Cancer (2007). Combined Estrogen-progestogen Contraceptives and Combined Estrogen-progestogen Menopausal Therapy. World Health Organization. pp. 146–. ISBN   978-92-832-1291-1.
  8. ↑ Hammerstein J (December 1990). "Prodrugs: advantage or disadvantage?". American Journal of Obstetrics and Gynecology. 163 (6 Pt 2): 2198–203. doi:10.1016/0002-9378(90)90561-K. PMID   2256526.
  9. ↑ Klimstra PD, Colton FB (October 1967). "The synthesis of 3beta-hydroxyestr-4-en-17-one and 3beta-hydroxyandrost-4-en-17-one". Steroids. 10 (4): 411–24. doi:10.1016/0039-128X(67)90119-5. PMID   6064262.
  10. ↑ Sondheimer F, Klibansky Y (1959). "Synthesis of 3β-hydroxy analogues of steroidal hormones, a biologically active class of compounds". Tetrahedron. 5: 15–26. doi:10.1016/0040-4020(59)80066-1.
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