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Chemical compound
Norvinisterone
Trade names Neoprogestin, Nor-Progestelea Other names Vinylnortestosterone; SC-4641; 17α-Vinyl-19-nortestosterone; 17α-Vinylestr-4-en-17β-ol-3-one
Routes of administration
By mouth
Drug class
Progestogen ;
Progestin ;
Androgen ;
Anabolic steroid
ATC code
(8R ,9S ,10R ,13S ,14S ,17R )-17-ethenyl-17-hydroxy-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a ]phenanthren-3-one
CAS Number
PubChem
CID
ChemSpider
UNII
CompTox Dashboard (
EPA )
Formula C 20 H 28 O 2
Molar mass 300.442 g·mol−1 3D model (
JSmol )
Melting point 169 to 171 °C (336 to 340 °F)
[1]
O=C4\C=C2/[C@@H]([C@H]1CC[C@@]3([C@](O)(\C=C)CC[C@H]3[C@@H]1CC2)C)CC4
InChI=1S/C20H28O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h3,12,15-18,22H,1,4-11H2,2H3/t15-,16+,17+,18-,19-,20-/m0/s1
Key:VOJYZDFYEHKHAP-XGXHKTLJSA-N
Norvinisterone , sold under the brand names Neoprogestin and Nor-Progestelea , is a
progestin and
androgen /
anabolic steroid (AAS) medication which was used in
Europe but is now no longer marketed.
[1]
[2]
[3]
[4]
[5] It is taken
by mouth .
Norvinisterone is a progestin, or a
synthetic
progestogen , and hence is an
agonist of the
progesterone receptor , the
biological target of progestogens like
progesterone .
[2] It has
androgenic activity.
[6]
Norvinisterone was
synthesized in 1953.
[2] It is no longer available.
[7]
Medical uses
Norvinisterone was used in
hormonal contraception to prevent
pregnancy .
[1]
[3]
Pharmacology
Pharmacodynamics
Norvinisterone is a
progestogen .
[2]
[8]
[5] It appears to be quite
androgenic , with about one-third and one-fifth of the androgenic and
anabolic activity, respectively, of
nandrolone in
animal
bioassays .
[6] However, it has also been reported to have little anabolic activity.
[9]
Chemistry
Norvinisterone, also known as 17α-vinyl-19-nortestosterone or as 17α-vinylestr-4-en-17β-ol-3-one, is a
synthetic
estrane
steroid and a
derivative of
testosterone and
19-nortestosterone .
[2]
Analogues of norvinisterone include the progestin
norgesterone and the AAS
vinyltestosterone .
[2]
History
Norvinisterone was
synthesized in 1953
[2] and was studied in humans by 1960.
[8]
Society and culture
Generic names
Norvinisterone is the
generic name of the drug and its
INN Tooltip International Nonproprietary Name .
[2] It is also known as vinylnortestosterone and is known by its developmental code name SC-4641 .
[2]
[1]
Brand names
Norvinisterone was marketed under the brand names Neoprogestin and Nor-Progestelea by
Syntex .
[2]
[1]
Availability
Norgesterone is no longer marketed and hence is no longer available in any country.
[7]
References
^
a
b
c
d
e Budavari S, ed. (1989). "6637 : Norvinisterone".
Merck Index (11th ed.). Rahway, N.J.: Merck & Co.
ISBN
978-0-911910-28-5 .
^
a
b
c
d
e
f
g
h
i
j Elks J (14 November 2014).
The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies . Springer. pp. 889–.
ISBN
978-1-4757-2085-3 .
^
a
b Juo PS (21 December 2001).
Concise Dictionary of Biomedicine and Molecular Biology . CRC Press. pp. 774–.
ISBN
978-1-4200-4130-9 .
^ List PH, Hörhammer L (12 March 2013).
Chemikalien und Drogen Teil A: N-Q . Springer Berlin Heidelberg. pp. 274–.
ISBN
978-3-642-65035-2 .
^
a
b Meyerson BJ (August 1967). "Relationship between the anesthetic and gestagenic action and estrous behavior-inducing activity of different progestins". Endocrinology . 81 (2): 369–374.
doi :
10.1210/endo-81-2-369 .
PMID
4952012 .
^
a
b Saunders FJ, Drill VA (May 1956). "The myotrophic and androgenic effects of 17-ethyl-19-nortestosterone and related compounds". Endocrinology . 58 (5): 567–572.
doi :
10.1210/endo-58-5-567 .
PMID
13317831 .
^
a
b
http://www.micromedexsolutions.com/micromedex2/ [
permanent dead link ]
^
a
b Martinez Montes EA, Bagnati EP, Zapata AC, Bur GE (March 1960). "[Clinical trial of a new luteoid: norvinisterone]". El Dia Medico (in Spanish). 32 : 194–197.
PMID
14421807 .
^ Schedl HP, Delea C, Bartter FC (August 1959). "Structure-activity relationships of anabolic steroids: role of the 19-methyl group". The Journal of Clinical Endocrinology and Metabolism . 19 (8): 921–935.
doi :
10.1210/jcem-19-8-921 .
PMID
14442516 .
Androgens (incl.
AAS Tooltip anabolic–androgenic steroid )
Antiandrogens
AR Tooltip Androgen receptor
antagonists
Steroidogenesis inhibitors
Antigonadotropins
D2 receptor
antagonists (
prolactin releasers ) (e.g.,
domperidone ,
metoclopramide ,
risperidone ,
haloperidol ,
chlorpromazine ,
sulpiride )
Estrogens (e.g.,
bifluranol ,
diethylstilbestrol ,
estradiol ,
estradiol esters ,
ethinylestradiol ,
ethinylestradiol sulfonate ,
paroxypropione )
GnRH agonists (e.g.,
leuprorelin )
GnRH antagonists (e.g.,
cetrorelix )
Progestogens (incl.,
chlormadinone acetate ,
cyproterone acetate ,
hydroxyprogesterone caproate ,
gestonorone caproate ,
medroxyprogesterone acetate ,
megestrol acetate )
Others
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 )
AR Tooltip Androgen receptor
Agonists
SARMs Tooltip Selective androgen receptor modulator Antagonists
GPRC6A