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Cingestol

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Cingestol
Clinical data
Trade namesLutisan
Other names19-Nor-17α-pregn-5-en-20-yn-17β-ol; O.V. 28[1][2]
Routes of
administration
Oral
Identifiers
  • (8R,9S,10R,13S,14S,17R)-17-ethynyl-13-methyl-2,3,4,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.037.225 Edit this at Wikidata
Chemical and physical data
FormulaC20H28O
Molar mass284.443 g·mol−1
3D model (JSmol)
  • C[C@]12CC[C@H]3[C@@H](CC=C4CCCC[C@H]34)[C@@H]1CC[C@@]2(O)C#C
  • InChI=1S/C20H28O/c1-3-20(21)13-11-18-17-9-8-14-6-4-5-7-15(14)16(17)10-12-19(18,20)2/h1,8,15-18,21H,4-7,9-13H2,2H3/t15-,16+,17+,18-,19-,20-/m0/s1
  • Key:HSYWFJBHXIUUCZ-XGXHKTLJSA-N

Cingestol (INN, USAN) (former tentative brand name Lutisan),[3] also known as 17α-ethynylestr-5-en-17β-ol,[4] is a steroidal progestin of the 19-nortestosterone group[5][6] that was never marketed.[7] It was synthesized in 1969[7] and was developed in the 1970s by Organon as a low-dose, progestogen-only contraceptive,[8][9][10][11] but in 1984, was still described as "under investigation".[12] The drug is an isomer of lynestrenol with the double bond between C5 and C6.[1]

See also

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References

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  1. ^ a b Tausk M (1975). Pharmacology of Hormones. Thieme. p. 126,129. ISBN 978-3-13-518901-7.
  2. ^ Concours médical. 1976. p. 1083.
  3. ^ Registry of Toxic Effects of Chemical Substances. National Institute for Occupational Safety and Health. 1987. p. 2995.
  4. ^ Brotherton J (1976). Sex hormone pharmacology. Academic Press. p. 12. ISBN 978-0-12-137250-7.
  5. ^ Korolkovas A (16 August 1988). Essentials of Medicinal Chemistry. Wiley. ISBN 978-0-471-88356-2.
  6. ^ WHO Technical Report Series. World Health Organization. 1981. p. 75. ISBN 9789241206570.
  7. ^ a b Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 279–. ISBN 978-1-4757-2085-3.
  8. ^ Tapingkae A (1974). Directory of selected scholars and researchers in Southeast Asia. Regional Institute of Higher Education and Development. p. 687.
  9. ^ Briggs MH, Briggs M (1976). Biochemical contraception: prospects for human development. Academic Press. p. 283. ISBN 978-0-12-134640-9.
  10. ^ Aref I, Hefnawi F, Kandil O, Aziz MT (August 1973). "Effect of minipills on physiologic responses of human cervical mucus, endometrium, and ovary". Fertility and Sterility. 24 (8): 578–583. doi:10.1016/s0015-0282(16)39850-8. PMID 4124151.
  11. ^ Kićović PM, Kovacević S, Djokic LJ, Milojević S, Janoskov J, Behlilović B, Jeremić N (1974). "Clinical evaluation of a new low dose progestagen-only contraceptive containing cingestol". International Journal of Fertility. 19 (3): 171–175. PMID 4375129.
  12. ^ Cutting WC, Csáky TZ, Barnes BA (1984). Cutting's Handbook of Pharmacology: The Actions and Uses of Drugs. Appleton-Century-Crofts. p. 439. ISBN 978-0-8385-1418-4.