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Chemical compound
Gestadienol acetate
Other names CIBA-31458-Ba; CIBA-31458; Norhydroxy-δ6 -progesterone acetate; 6-Dehydro-17α-acetoxy-19-norprogesterone; 17α-Acetoxy-19-norpregn-4,6-diene-3,20-dione
Routes of administration
By mouth
[1]
[2]
Drug class
Progestogen ;
Progestogen ester
[(8R ,9S ,10R ,13S ,14S ,17R )-17-acetyl-13-methyl-3-oxo-1,2,8,9,10,11,12,14,15,16-decahydrocyclopenta[a ]phenanthren-17-yl] acetate
CAS Number
PubChem
CID
ECHA InfoCard
100.224.529
Formula C 22 H 28 O 4
Molar mass 356.462 g·mol−1 3D model (
JSmol )
CC(=O)[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2C=CC4=CC(=O)CC[C@H]34)C)OC(=O)C
InChI=1S/C22H28O4/c1-13(23)22(26-14(2)24)11-9-20-19-6-4-15-12-16(25)5-7-17(15)18(19)8-10-21(20,22)3/h4,6,12,17-20H,5,7-11H2,1-3H3/t17-,18+,19+,20-,21-,22-/m0/s1
Key:TUFRQQROGGMVOC-ZCPXKWAGSA-N
Gestadienol acetate (developmental code name CIBA-31458-Ba or CIBA-31458 ) an
orally active
progestin which was described in the literature in 1967 and was never marketed.
[3]
[1]
[2]
[4]
[5] It has no
androgenic or
estrogenic effects.
[6] The effects of gestadienol acetate on the
endometrium and its general
pharmacology were studied in a
clinical trial in women.
[2]
[5] It has also been studied in a clinical trial for
benign prostatic hyperplasia in men, but was ineffective.
[6]
Chemistry
Gestadienol acetate, also known as norhydroxy-δ6 -progesterone acetate, 6-dehydro-17α-hydroxy-19-norprogesterone 17α-acetate, or 17α-hydroxy-19-norpregn-4,6-diene-3,20-dione 17α-acetate, is a
synthetic
norpregnane
steroid and a
derivative of
progesterone .
[3] It is specifically a combined derivative of
17α-hydroxyprogesterone and
19-norprogesterone , or of
gestronol (17α-hydroxy-19-norprogesterone), with an
acetate
ester at the C17α position and a
double bond between the C6 and C7 positions.
[3] Gestadienol acetate is the C17α
acetate
ester of
gestadienol .
[3]
Analogues of gestadienol acetate include
algestone acetophenide (dihydroxyprogesterone acetophenide),
demegestone ,
gestonorone caproate (norhydroxyprogesterone caproate),
hydroxyprogesterone acetate ,
hydroxyprogesterone caproate ,
nomegestrol acetate ,
norgestomet , and
segesterone acetate (nestorone).
[3]
References
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
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Methyldienolone
Metribolone (R-1881)
Methoxydienone (methoxygonadiene)
Mibolerone
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Nandrolone esters (e.g.,
nandrolone decanoate ,
nandrolone phenylpropionate )
Norethandrolone
Normethandrone (methylestrenolone, normethandrolone, normethisterone)
RU-2309
Tetrahydrogestrinone
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Trenbolone esters (e.g.,
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Trendione
Trestolone
Trestolone acetate
Mixed (
SPRMs Tooltip Selective progesterone receptor modulators ) Antagonists
mPR Tooltip Membrane progesterone receptor (
PAQR Tooltip Progestin and adipoQ receptor )