From Wikipedia, the free encyclopedia
Chemical compound
Cingestol
Trade names Lutisan Other names 19-Nor-17α-pregn-5-en-20-yn-17β-ol ; O.V. 28
[1]
[2]
Routes of administration
Oral
(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 InfoCard
100.037.225
Formula C 20 H 28 O
Molar mass 284.443 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
References
^
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 .
PR Tooltip Progesterone receptor
Agonists
Testosterone derivatives: Progestins:
6,6-Difluoronorethisterone
6,6-Difluoronorethisterone acetate
17α-Allyl-19-nortestosterone
Allylestrenol
Altrenogest
Chloroethynylnorgestrel
Cingestol
Danazol
Desogestrel
Dienogest
Ethinylandrostenediol
Ethisterone
Ethynerone
Etonogestrel
Etynodiol
Etynodiol diacetate
Gestodene
Gestrinone
Levonorgestrel
Levonorgestrel esters (e.g.,
levonorgestrel butanoate )
Lynestrenol
Lynestrenol phenylpropionate
Metynodiol
Metynodiol diacetate
Norelgestromin
Norethisterone (norethindrone)
Norethisterone esters (e.g.,
norethisterone acetate ,
norethisterone enanthate )
Noretynodrel
Norgesterone
Norgestimate
Norgestrel
Norgestrienone
Norvinisterone
Oxendolone
Quingestanol
Quingestanol acetate
Tibolone
Tigestol
Tosagestin ; Anabolic–androgenic steroids:
11β-Methyl-19-nortestosterone
11β-Methyl-19-nortestosterone dodecylcarbonate
19-Nor-5-androstenediol
19-Nor-5-androstenedione
19-Nordehydroepiandrosterone
Bolandiol
Bolandiol dipropionate
Bolandione
Dimethisterone
Dienedione
Dienolone
Dimethandrolone
Dimethandrolone buciclate
Dimethandrolone dodecylcarbonate
Dimethandrolone undecanoate
Dimethyldienolone
Dimethyltrienolone
Ethyldienolone
Ethylestrenol (ethylnandrol)
Methyldienolone
Metribolone (R-1881)
Methoxydienone (methoxygonadiene)
Mibolerone
Nandrolone
Nandrolone esters (e.g.,
nandrolone decanoate ,
nandrolone phenylpropionate )
Norethandrolone
Normethandrone (methylestrenolone, normethandrolone, normethisterone)
RU-2309
Tetrahydrogestrinone
Trenbolone (trienolone)
Trenbolone esters (e.g.,
trenbolone acetate ,
trenbolone enanthate )
Trendione
Trestolone
Trestolone acetate
Mixed (
SPRMs Tooltip Selective progesterone receptor modulators ) Antagonists
mPR Tooltip Membrane progesterone receptor (
PAQR Tooltip Progestin and adipoQ receptor )