Noretynodrel

Noretynodrel
Systematic (IUPAC) name
(8S,9S,13S,14S,17S)-17-ethynyl-17-hydroxy-13-methyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
Identifiers
CAS Number 68-23-5 N
ATC code G03FA09 (WHO)
PubChem CID 6231
ChemSpider 5995 YesY
UNII 88181ACA0M YesY
ChEMBL CHEMBL1387 YesY
Synonyms Noretynodrel; (17β)-17-ethynyl-17-hydroxyestr-5(10)-en-3-one; 17α-ethinyl-5(10)-19-nortestosterone; 5(10)-norethisterone; NSC-15432
Chemical data
Formula C20H26O2
Molar mass 298.419 g/mol
 NYesY (what is this?)  (verify)

Noretynodrel (INN), or norethynodrel (USAN, BAN), also known as 17α-ethinyl-δ5,10-19-nortestosterone or as 5(10)-norethisterone, is a steroidal progestin.[1] It was introduced in 1957 in Enovid, a combination formulation of noretynodrel and mestranol, for the treatment of gynecological and menstrual disorders.[2] A few years later, in May 1960, Enovid was also approved as the first oral contraceptive.[2][3] In addition to its progestogenic effects, noretynodrel, unlike most progestins but similarly to etynodiol diacetate, also has some estrogenic properties.[4] It has little or no androgenic action.[5][4][2] In accordance, noretynodrel has not been found to virilize female fetuses, in contrast to most other testosterone and 19-nortestosterone progestins such as ethisterone, norethisterone, and norethisterone acetate.[6]

References

  1. ↑ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 886–. ISBN 978-1-4757-2085-3.
  2. 1 2 3 Lara Marks (2010). Sexual Chemistry: A History of the Contraceptive Pill. Yale University Press. pp. 74–75. ISBN 0-300-16791-1.
  3. ↑ Mannfred A. Hollinger (19 October 2007). Introduction to Pharmacology, Third Edition. CRC Press. pp. 160–. ISBN 978-1-4200-4742-4.
  4. 1 2 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.
  5. ↑ Ethel Sloane (2002). Biology of Women. Cengage Learning. pp. 426–. ISBN 0-7668-1142-5.
  6. ↑ Simpson, Joe Leigh; Kaufman, Raymond H. (1998). "Fetal effects of estrogens, progestogens and diethylstilbestrol". In Fraser, Ian S. (ed.). Estrogens and Progestogens in Clinical Practice (3rd ed.). London: Churchill Livingstone. pp. 533–53. ISBN 0-443-04706-5.



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