From Wikipedia, the free encyclopedia
Chemical compound
Norgesterone
Trade names Vestalin (with
EE Tooltip ethinylestradiol ) Other names Norvinodrel; Vinylestrenolone; Vinilestrenolone; Vinylnoretynodrel; 17α-Vinylestr-5(10)-en-17-ol-3-one; 17α-Vinyl-δ5(10) -19-nortestosterone
Routes of administration
By mouth
Drug class
Progestogen ;
Progestin
ATC code
(8R ,9S ,13S ,14S ,17R )-17-ethenyl-17-hydroxy-13-methyl-1,2,4,6,7,8,9,11,12,14,15,16-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 )
CC12CCC3C(C1CCC2(C=C)O)CCC4=C3CCC(=O)C4
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/h3,16-18,22H,1,4-12H2,2H3/t16-,17-,18+,19+,20+/m1/s1
Key:YPVUHOBTCWJYNQ-SLHNCBLASA-N
Norgesterone , also known as norvinodrel or vinylestrenolone and sold under the brand name Vestalin , is a
progestin medication which was formerly used in
birth control pills for women but is now no longer marketed.
[1]
[2]
[3]
[4] It was used in combination with the
estrogen
ethinylestradiol .
[2]
[3]
[4] It is taken
by mouth .
[5]
[6]
Norgesterone is a progestin, or a
synthetic
progestogen , and hence is an
agonist of the
progesterone receptor , the
biological target of progestogens like
progesterone .
[7] It has no
androgenic activity.
[7]
Norgesterone was first described in 1962.
[8]
[9] It is no longer available.
[10]
Medical uses
Norgesterone was used in combination with
ethinylestradiol in
birth control pills to prevent
pregnancy .
[2] It is no longer available.
[10]
Pharmacology
Pharmacodynamics
Norgesterone is a
progestogen , and hence is an
agonist of the
progesterone receptor .
[7] Unlike related progestins, it is virtually devoid of
androgenic activity in
animal
assays .
[7]
Chemistry
Norgesterone, also known as 17α-vinyl-δ5(10) -19-nortestosterone or as 17α-vinylestr-5(10)-en-17β-ol-3-one, is a
synthetic
estrane
steroid and a
derivative of
testosterone and
19-nortestosterone .
[1]
Analogues of norgesterone include
norvinisterone (17α-vinyl-19-nortestosterone) and
vinyltestosterone (17α-vinyltestosterone).
[1]
History
Norgesterone was first described in 1962.
[8]
[9]
Society and culture
Generic names
Norgesterone is the
generic name of the drug and its
INN Tooltip International Nonproprietary Name .
[1] It has also been referred to as norvinodrel , vinylestrenolone , and vinylnoretynodrel .
[1]
[11]
Brand names
Norgesterone was marketed in combination with
ethinylestradiol , an
estrogen , as a
birth control pill under the brand name Vestalin.
[2]
[3]
[4]
Availability
Norgesterone is no longer marketed and hence is no longer available in any country.
[10]
References
^
a
b
c
d
e Elks J (14 November 2014).
The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies . Springer. pp. 887–.
ISBN
978-1-4757-2085-3 .
^
a
b
c
d Wassef SA, Sami G, Hamid EA (June 1970). "Effect of switching with oral contraceptives". The Egyptian Population and Family Planning Review . 3 (1): 77–93.
PMID
12254511 .
^
a
b
c Bengtsson LP, Tausk M (September 1972).
Pharmacology of the endocrine system and related drugs: progesterone, progestational drugs and antifertility agents . Pergamon Press.
ISBN
9780080157450 .
^
a
b
c Challener CA (1 December 2001).
Chiral Drugs . Wiley.
ISBN
978-0-566-08411-9 .
^ Boris Rubio L (November 1966). "[Vinylestrenolone: a new progestational hormone. Results of its cyclic administration]". Minerva Ginecologica (in Italian). 18 (21): 1215–1217.
PMID
5997085 .
^ Samaja BA, Prandini B (March 1974).
"The influence of estrogenic and-or progestogenic treatment on some parameters of lipid metabolism (a controlled clinical study)" . Endokrinologie . 63 (1): 76–84.
PMID
4140086 . Archived from
the original on 2018-02-28.
^
a
b
c
d de Ruggieri P, Matscher R, Lupo C, Spazzoli G (1965). "Biological properties of 17α-vinyl-5(10)-estrene-17β-ol-3-one (norvinodrel) as a progestational and claudogenic compound". Steroids . 5 (1): 73–91.
doi :
10.1016/0039-128X(65)90133-9 .
ISSN
0039-128X .
^
a
b
"Steroid hormone compositions and method of using same" .
^
a
b D'Incerti Bonini L, Pagani C (April 1962). "[Clinical investigations of the progestational activity of vinylestrenolone]". Annali di Ostetricia e Ginecologia (in Italian). 84 : 279–285.
PMID
13883015 .
^
a
b
c
http://www.micromedexsolutions.com/micromedex2/ [
permanent dead link ]
^ Greydanus DE (6 December 2012).
"Contraception" . In Lavery JP, Sanfilippo JS (eds.). Pediatric and Adolescent Obstetrics and Gynecology . Springer Science & Business Media. pp. 236–.
ISBN
978-1-4612-5064-7 .
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 )