Etynodiol diacetate
 | |
| Systematic (IUPAC) name | |
|---|---|
|
(3β,17β)-17-ethynylestr-4-ene-3,17-diyl diacetate | |
| Clinical data | |
| Routes of administration | Oral |
| Legal status |
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| Identifiers | |
| CAS Number |
297-76-7 8056-92-6 |
| ATC code |
G03DC06 (WHO) G03AA01 G03FA06 (with an estrogen) |
| PubChem | CID 92709270 |
| DrugBank | DB00823 |
| ChemSpider | 8913 |
| Chemical data | |
| Formula | C24H32O4 |
| Molar mass | 384.509 g/mol |
| |
| |
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
Ethynodiol diacetate synthesis:[8] 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:[9]
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]
See also
- Methynodiol Diacetate (same structure but additional 11β-methyl group).
- Etynodiol
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.
- 1 2 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.
- 1 2 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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