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 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 [ ]
See also: List of progestogens and List of androgens/anabolic steroids
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 .[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 Merck Index , 11th edition, 6637
^ a b c d e f g h i j J. Elks (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 Pei-Show Juo (21 December 2001). Concise Dictionary of Biomedicine and Molecular Biology . CRC Press. pp. 774–. ISBN 978-1-4200-4130-9 .
^ P. H. List; L. Hörhammer (12 March 2013). Chemikalien und Drogen Teil A: N-Q . Springer Berlin Heidelberg. pp. 274–. ISBN 978-3-642-65035-2 .
^ a b Meyerson, Bengt J. (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 . ISSN 0013-7227 . PMID 4952012 .
^ a b Saunders, Francis J.; Drill, Victor A. (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 . ISSN 0013-7227 . PMID 13317831 .
^ a b http://www.micromedexsolutions.com/micromedex2/ [permanent dead link ]
^ a b Martinez Montes EA, Bagnati EP, Zapata AC, Bur GE (1960). "[Clinical trial of a new luteoid: norvinisterone]". Dia Med (in Spanish). 32 : 194–7. PMID 14421807 .
^ SCHEDL HP, DELEA C, BARTTER FC (August 1959). "Structure-activity relationships of anabolic steroids: role of the 19-methyl group". J. Clin. Endocrinol. Metab . 19 (8): 921–35. doi :10.1210/jcem-19-8-921 . PMID 14442516 .
Progestogens and antiprogestogens
Progestogens (and progestins )
PR agonists
Retroprogesterone derivatives: Dydrogesterone
Trengestone
Testosterone derivatives: Estranes: Danazol
Dimethisterone
Ethisterone
19-Nortestosterone derivatives: Estranes: Allylestrenol
Altrenogest
Dienogest
Etynodiol diacetate
Lynestrenol
Norethisterone (norethindrone) #
Norethisterone acetate
Norethisterone enanthate
Noretynodrel
Norgesterone
Norgestrienone
Normethandrone (methylestrenolone)
Norvinisterone
Oxendolone
Quingestanol acetate
Tibolone ; Gonanes: Desogestrel
Etonogestrel
Gestodene
Gestrinone
Levonorgestrel #
Norelgestromin
Norgestimate
Norgestrel
Spirolactone derivatives: Drospirenone
Antiprogestogens
SPRMs PR antagonists
Aglepristone
Mifepristone
# WHO-EM
‡ Withdrawn from market
Clinical trials :
† Phase III
§ Never to phase III
See also
Progesterone receptor modulators
Androgens and antiandrogens
Estrogens and antiestrogens
List of progestogens
Androgens and antiandrogens
Androgens (incl. AAS )
AR agonists
Testosterone derivatives: Androstenediol dipropionate
Boldenone undecylenate
Clostebol
Clostebol acetate
Clostebol caproate
Clostebol propionate
Cloxotestosterone acetate
Prasterone (dehydroepiandrosterone, DHEA)
Prasterone enanthate (DHEA enanthate)
Prasterone sulfate (DHEA sulfate)
Quinbolone
Testosterone #
Testosterone esters (e.g., testosterone cypionate , testosterone enanthate , testosterone propionate , testosterone undecanoate , testosterone ester mixtures (Deposterona , Omnadren , Sustanon , Testoviron Depot ))
17α-Ethynyltestosterone derivatives: Danazol
Gestrinone
Progestins (e.g., ethisterone (ethynyltestosterone) , levonorgestrel , norgestrel , norethisterone (norethindrone) , lynestrenol , norgestrienone )
Tibolone
Progesterone derivatives: Medroxyprogesterone acetate
Progonadotropins
Antiestrogens (e.g., tamoxifen , clomifene )
GnRH agonists (e.g., GnRH (gonadorelin) , leuprorelin )
Gonadotropins (e.g., LH , hCG )
Antiandrogens
AR antagonists
Steroidal: Abiraterone acetate
Canrenone
Chlormadinone acetate
Cyproterone acetate
Delmadinone acetate
Dienogest
Drospirenone
Medrogestone
Megestrol acetate
Nomegestrol acetate
Osaterone acetate
Oxendolone
Potassium canrenoate
Spironolactone
Nonsteroidal: Apalutamide
Bicalutamide
Cimetidine
Darolutamide
Enzalutamide
Flutamide
Ketoconazole
Nilutamide
Seviteronel †
Topilutamide (fluridil)
Steroidogenesis inhibitors
5α-Reductase
Alfatradiol
Dutasteride
Epristeride
Finasteride
Saw palmetto extract
Others
Abiraterone acetate
Aminoglutethimide
Bifluranol
Cyproterone acetate
Flutamide
Ketoconazole
Nilutamide
Seviteronel †
Spironolactone
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
# WHO-EM
‡ Withdrawn from market
Clinical trials :
† Phase III
§ Never to phase III
See also
Androgen receptor modulators
Estrogens and antiestrogens
Progestogens and antiprogestogens
List of androgens/anabolic steroids
PR
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
Spirolactone derivatives: Canrenoic acid
Canrenone
Drospirenone
Mespirenone
Potassium canrenoate
Prorenone
SC-5233 (spirolactone)
SC-8109
Spironolactone
Spirorenone
Mixed (SPRMs )
Nonsteroidal: Apigenin
Kaempferol
Naringenin
Syringic acid
Antagonists
Nonsteroidal: Darolutamide
Valproic acid
mPR (PAQR )
See also
Receptor/signaling modulators
Progestogens and antiprogestogens
Androgen receptor modulators
Estrogen receptor modulators
List of progestogens
AR
Agonists
Testosterone derivatives: 4-Androstenediol
4-Dehydroepiandrosterone (4-DHEA)
4-Hydroxytestosterone
5-Androstenedione
11-Ketotestosterone
11β-Hydroxyandrostenedione
Adrenosterone (11-ketoandrostenedione, 11-oxoandrostenedione)
Androstenediol (5-androstenediol)
Androstenedione (4-androstenedione)
Atamestane
Boldenone
Boldione (1,4-androstadienedione)
Clostebol
Clostebol acetate
Clostebol caproate
Clostebol propionate
Cloxotestosterone
Cloxotestosterone acetate
Dehydroandrosterone
DHEA (androstenolone, prasterone; 5-DHEA)
DHEA enanthate (prasterone enanthate)
DHEA sulfate
Exemestane
Formestane
Plomestane
Quinbolone
Silandrone
Testosterone # (+dutasteride )
17α-Ethynyl-19-nortestosterone derivatives: Δ4 -Tibolone
Desogestrel
Etonogestrel
Etynodiol
Gestodene
Gestrinone
Levonorgestrel
Levonorgestrel esters (e.g., levonorgestrel butanoate )
Lynestrenol
Lynestrenol phenylpropionate
Norethisterone
Norethisterone esters (e.g., norethisterone acetate , norethisterone enanthate )
Norgestrel
Norgestrienone
Quingestanol
Tibolone
Mixed (SARMs )
Steroidal:
MK-0773
TFM-4AS-1
YK-11
Antagonists
Nonsteroidal: 5N -Bicalutamide
AA560
Apalutamide
Atraric acid
Bakuchiol
Bicalutamide
Bisphenols (e.g., BADGE , , bisphenol A , bisphenol F , bisphenol S )
BMS-641988
Cimetidine
Cioteronel
Cyanonilutamide
Darolutamide
DDT (via metabolite p,p’-DDE )
Dieldrin
DIMP
Endosulfan
Enzalutamide
EPI-001
EPI-7386
Fenarimol
Flutamide
Hydroxyflutamide
Inocoterone
Inocoterone acetate
Ketoconazole
Ketodarolutamide
Lavender oil
LG-120907
Linuron
Methiocarb
N -Desmethylapalutamide
N -Desmethylenzalutamide
Nilutamide
Pentomone
Phenothrin
Prochloraz
Procymidone
Proxalutamide
Ralaniten (EPI-002)
Ralaniten acetate (EPI-506)
RD-162
Rezvilutamide
RU-22930
RU-56187
RU-57073
RU-58642
RU-58841
Seviteronel
Thalidomide
Topilutamide (fluridil)
Valproic acid
Vinclozolin
GPRC6A
Agonists
Cations (incl. aluminum , calcium , gadolinium , magnesium , strontium , zinc )
Dehydroandrosterone
Dihydrotestosterone
Estradiol
L -α-Amino acids (incl. L -arginine , L -lysine , L -ornithine )
Osteocalcin
SHBG
Testosterone
See also
Receptor/signaling modulators
Androgens and antiandrogens
Estrogen receptor modulators
Progesterone receptor modulators
List of androgens/anabolic steroids