Etynodiol diacetate

Etynodiol diacetate
Clinical data
Routes of; administration	Oral
ATC code	G03DC06 (WHO) ; G03AA01 (WHO) G03FA06 (WHO) (with an estrogen);
Legal status
Legal status	In general: ℞ (Prescription only);
Identifiers
	IUPAC name (3β,17β)-17-ethynylestr-4-ene-3,17-diyl diacetate;
CAS Number	297-76-7 ; 8056-92-6;
PubChem CID	92709270;
DrugBank	DB00823;
ChemSpider	8913;
CompTox Dashboard (EPA)	DTXSID4020614 ;
ECHA InfoCard	100.005.496
Chemical and physical data
Formula	C24H32O4
Molar mass	384.509 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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 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 (INN) (sold as Continuin, Femulen, Luteonorm, Luto-Metrodiol, and Metrodiol), or ethynodiol diacetate (USAN, BAN), also known as norethindrol diacetate,^[1] is a steroidal progestin which is used as a hormonal contraceptive.^[2]^[3] Relative to other 19-nortestosterone derivatives, it has relatively little or no potency as an androgen,^[4]^[5] and, unlike most progestins but similarly to noretynodrel,^[6] also has some estrogenic effects.^[7]^[4]

Synthesis

Reduction of norethisterone (1) affords the 3,17-diol. The 3β-hydroxy compound is the desired product; since reactions at C-3 do not show nearly the stereoselectivity as those at C-17 by virtue of the relative lack of stereo-directing proximate substituents, the formation of the desired isomer is engendered by use of a bulky reducing agent, Lithium tri-tert-butoxyaluminum hydride. Acetylation of the 3β,17β-diol affords Etynodiol diacetate (3), one of the most potent oral progestins.^[8]

References

^ Donna Shoupe; Florence P. Haseltine (6 December 2012). Contraception. Springer Science & Business Media. pp. 21–. ISBN 978-1-4612-2730-4.
^ F.. Macdonald (1997). Dictionary of Pharmacological Agents. CRC Press. p. 1454. ISBN 978-0-412-46630-4. Retrieved 12 May 2012.
^ Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 422. ISBN 978-3-88763-075-1. Retrieved 30 May 2012.
^ ^a ^b Kenneth L. Becker (24 April 2001). Principles and Practice of Endocrinology and Metabolism. Lippincott Williams & Wilkins. p. 1004. ISBN 978-0-7817-1750-2. Retrieved 30 May 2012.
^ Chaudhuri (1 January 2007). Practice Of Fertility Control: A Comprehensive Manual (7Th Edition). Elsevier India. p. 122. ISBN 978-81-312-1150-2. Retrieved 30 May 2012.
^ Benno Clemens Runnebaum; Thomas Rabe; Ludwig Kiesel (6 December 2012). Female Contraception: Update and Trends. Springer Science & Business Media. pp. 36–. ISBN 978-3-642-73790-9.
^ Allan H. Goroll; Albert G. Mulley (27 January 2009). Primary Care Medicine: Office Evaluation and Management of the Adult Patient. Lippincott Williams & Wilkins. p. 876. ISBN 978-0-7817-7513-7. Retrieved 30 May 2012.
^ ^a ^b Klimstra, P.; Colton, F. (1967). "The synthesis of 3β-hydroxyestr-4-en-17-one and 3β-hydroxiandrost-4-en-17-one". Steroids. 10 (4): 411. doi:10.1016/0039-128X(67)90119-5.
^ Sondheimer, F.; Klibansky, Y. (1959). "Synthesis of 3β-hydroxy analogues of steroidal hormones, a biologically active class of compounds". Tetrahedron. 5: 15. doi:10.1016/0040-4020(59)80066-1.

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[ShoupeHaseltine2012-1] Donna Shoupe; Florence P. Haseltine (6 December 2012). Contraception. Springer Science & Business Media. pp. 21–. ISBN 978-1-4612-2730-4.

[Macdonald1997-2] F.. Macdonald (1997). Dictionary of Pharmacological Agents. CRC Press. p. 1454. ISBN 978-0-412-46630-4. Retrieved 12 May 2012.

[Index_Nominum_2000:_International_Drug_Directory-3] Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 422. ISBN 978-3-88763-075-1. Retrieved 30 May 2012.

[Becker2001-4] Kenneth L. Becker (24 April 2001). Principles and Practice of Endocrinology and Metabolism. Lippincott Williams & Wilkins. p. 1004. ISBN 978-0-7817-1750-2. Retrieved 30 May 2012.

[Chaudhuri2007-5] Chaudhuri (1 January 2007). Practice Of Fertility Control: A Comprehensive Manual (7Th Edition). Elsevier India. p. 122. ISBN 978-81-312-1150-2. Retrieved 30 May 2012.

[RunnebaumRabe2012-6] Benno Clemens Runnebaum; Thomas Rabe; Ludwig Kiesel (6 December 2012). Female Contraception: Update and Trends. Springer Science & Business Media. pp. 36–. ISBN 978-3-642-73790-9.

[GorollMulley2009-7] Allan H. Goroll; Albert G. Mulley (27 January 2009). Primary Care Medicine: Office Evaluation and Management of the Adult Patient. Lippincott Williams & Wilkins. p. 876. ISBN 978-0-7817-7513-7. Retrieved 30 May 2012.

[Klimstra-8] Klimstra, P.; Colton, F. (1967). "The synthesis of 3β-hydroxyestr-4-en-17-one and 3β-hydroxiandrost-4-en-17-one". Steroids. 10 (4): 411. doi:10.1016/0039-128X(67)90119-5.

[9] Sondheimer, F.; Klibansky, Y. (1959). "Synthesis of 3β-hydroxy analogues of steroidal hormones, a biologically active class of compounds". Tetrahedron. 5: 15. doi:10.1016/0040-4020(59)80066-1.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

Synthesis

See also

References