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Cingestol

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Cingestol
Clinical data

Trade names	Lutisan
Other names	19-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	16915-71-2
PubChem CID	11954351
ChemSpider	10128646
UNII	VLJ9702J11
CompTox Dashboard (EPA)	DTXSID70168666
ECHA InfoCard	100.037.225
Chemical and physical data
Formula	C₂₀H₂₈O
Molar mass	284.443 g·mol⁻¹
3D model (JSmol)	Interactive image
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

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 isomeroflynestrenol with the double bond between C5 and C6.^[1]

References[edit]

^ ^a ^b Tausk M (1975). Pharmacology of Hormones. Thieme. p. 126,129. ISBN 978-3-13-518901-7.

^ Concours médical. 1976. p. 1083.

^ Registry of Toxic Effects of Chemical Substances. National Institute for Occupational Safety and Health. 1987. p. 2995.

^ Brotherton J (1976). Sex hormone pharmacology. Academic Press. p. 12. ISBN 978-0-12-137250-7.

^ Korolkovas A (16 August 1988). Essentials of Medicinal Chemistry. Wiley. ISBN 978-0-471-88356-2.

^ WHO Technical Report Series. World Health Organization. 1981. p. 75. ISBN 9789241206570.

^ ^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.

^ Tapingkae A (1974). Directory of selected scholars and researchers in Southeast Asia. Regional Institute of Higher Education and Development. p. 687.

^ Briggs MH, Briggs M (1976). Biochemical contraception: prospects for human development. Academic Press. p. 283. ISBN 978-0-12-134640-9.

^ 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.

^ 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.

^ 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.