Cingestol

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 isomer of lynestrenol with the double bond between C5 and C6.^[1]

Synthesis

The chemical synthesis was originally reported in 1969.^[13]

FGI of nandrolone benzoate [1474-55-1] into its corresponding enol acetate gives (1). The reduction of this with sodium borohydride gave a mixture of two epimeric alcohols, the beta-alcohol predominating (2). Halogenation of this alcohol gave the chloride (3). Lithium in ammonia cleaved of the halogen, the ester was also removed during this step, PC149159696 (4). Oxidation with Jones reagent gave the ketone PC140376320 (5). Favorskii reaction should smoothly form cingestol in a single step.

See also

• Allylestrenol

References

1. 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. 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.
13. Bolt, C. C., De Jongh, H. P., Siegmann, C. M., Van Vliet, N. P., Zeelen, F. J. (January 1969). "C 17 ‐substituted 5‐ and 5(10)‐estrenes and their 7α‐methyl homologues". Recueil des Travaux Chimiques des Pays-Bas. 88 (9): 1061–1069. doi:10.1002/recl.19690880906.