Etynodiol

Etynodiol
Clinical data
Other names	Ethynodiol; 3β-Hydroxynorethisterone; 17α-Ethynylestr-4-ene-3β,17β-diol
Drug class	Progestin; Progestogen
ATC code	G03DC06 (WHO) ;
Identifiers
	IUPAC name (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	1231-93-2;
ChemSpider	14017;
UNII	9E01C36A9S;
CompTox Dashboard (EPA)	DTXSID1023025 ;
ECHA InfoCard	100.013.610
Chemical and physical data
Formula	C20H28O2
Molar mass	300.442 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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 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.

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]

v
t
e
Relative affinities (%) of norethisterone, metabolites, and prodrugs
Compound	Type^a	PRTooltip Progesterone receptor	ARTooltip Androgen receptor	ERTooltip Estrogen receptor	GRTooltip Glucocorticoid receptor	MRTooltip Mineralocorticoid receptor	SHBGTooltip Sex hormone-binding globulin	CBGTooltip Corticosteroid binding globulin
Norethisterone	–	67–75	15	0	0–1	0–3	16	0
5α-Dihydronorethisterone	Metabolite	25	27	0	0	?	?	?
3α,5α-Tetrahydronorethisterone	Metabolite	1	0	0–1	0	?	?	?
3α,5β-Tetrahydronorethisterone	Metabolite	?	0	0	?	?	?	?
3β,5α-Tetrahydronorethisterone	Metabolite	1	0	0–8	0	?	?	?
Ethinylestradiol	Metabolite	15–25	1–3	112	1–3	0	0.18	0
Norethisterone acetate	Prodrug	20	5	1	0	0	?	?
Norethisterone enanthate	Prodrug	?	?	?	?	?	?	?
Noretynodrel	Prodrug	6	0	2	0	0	0	0
Etynodiol	Prodrug	1	0	11–18	0	?	?	?
Etynodiol diacetate	Prodrug	1	0	0	0	0	?	?
Lynestrenol	Prodrug	1	1	3	0	0	?	?
Notes: Values are percentages (%). Reference ligands (100%) were promegestone for the PRTooltip progesterone receptor, metribolone for the ARTooltip androgen receptor, estradiol for the ERTooltip estrogen receptor, dexamethasone for the GRTooltip glucocorticoid receptor, aldosterone for the MRTooltip mineralocorticoid receptor, dihydrotestosterone for SHBGTooltip sex hormone-binding globulin, and cortisol for CBGTooltip 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

Society and culture

Generic names

Etynodiol is the generic name of the drug and its INNTooltip International Nonproprietary Name, while ethynodiol is its BANTooltip British Approved Name.^[1]^[2]

References

^ ^a ^b ^c Macdonald F (1997). Dictionary of Pharmacological Agents. CRC Press. p. 1454. ISBN 978-0-412-46630-4. Retrieved 12 May 2012.
^ ^a ^b ^c Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 422. ISBN 978-3-88763-075-1. Retrieved 30 May 2012.
^ 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.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 478. ISBN 9783527607495.
^ Shoupe D, Haseltine FP (6 December 2012). Contraception. Springer Science & Business Media. pp. 21–. ISBN 978-1-4612-2730-4.
^ Bhattacharya (1 January 2003). Pharmacology, 2/e. Elsevier India. pp. 378–. ISBN 978-81-8147-009-6.
^ 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.
^ 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.
^ 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.
^ 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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[Macdonald1997-1] Macdonald F (1997). Dictionary of Pharmacological Agents. CRC Press. p. 1454. ISBN 978-0-412-46630-4. Retrieved 12 May 2012.

[IndexNominum2000-2] Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 422. ISBN 978-3-88763-075-1. Retrieved 30 May 2012.

[SchindlerCampagnoli2003-3] 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.

[Fis2006-4] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 478. ISBN 9783527607495.

[ShoupeHaseltine2012-5] Shoupe D, Haseltine FP (6 December 2012). Contraception. Springer Science & Business Media. pp. 21–. ISBN 978-1-4612-2730-4.

[Bhattacharya2003-6] Bhattacharya (1 January 2003). Pharmacology, 2/e. Elsevier India. pp. 378–. ISBN 978-81-8147-009-6.

[HumansOrganization2007-7] 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.

[pmid2256526-8] 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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