Cingestol

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]

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
IUPAC name
  • (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
Chemical and physical data
FormulaC20H28O
Molar mass284.443 g·mol−1
3D model (JSmol)
SMILES
  • C[C@]12CC[C@H]3[C@@H](CC=C4CCCC[C@H]34)[C@@H]1CC[C@@]2(O)C#C
InChI
  • 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

See also

References
  1. M. Tausk (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. Janet Brotherton (1976). Sex hormone pharmacology. Academic Press. p. 12. ISBN 978-0-12-137250-7.
  5. Andrejus Korolkovas (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. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 279–. ISBN 978-1-4757-2085-3.
  8. Amnuay Tapingkae (1974). Directory of selected scholars and researchers in Southeast Asia. Regional Institute of Higher Education and Development. p. 687.
  9. Michael H. Briggs; Maxine Briggs (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 (1973). "Effect of minipills on physiologic responses of human cervical mucus, endometrium, and ovary". Fertil. Steril. 24 (8): 578–83. 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". Int. J. Fertil. 19 (3): 171–5. PMID 4375129.
  12. Windsor Cooper Cutting; T. Z. Csáky; Byron A. Barnes (1984). Cutting's Handbook of Pharmacology: The Actions and Uses of Drugs. Appleton-Century-Crofts. p. 439. ISBN 978-0-8385-1418-4.


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