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Norvinisterone

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Norvinisterone
Clinical data
Trade namesNeoprogestin, Nor-Progestelea
Other namesVinylnortestosterone; SC-4641; 17α-Vinyl-19-nortestosterone; 17α-Vinylestr-4-en-17β-ol-3-one
Routes of
administration
By mouth
Drug classProgestogen;Progestin;Androgen;Anabolic steroid
ATC code
  • None
Identifiers
  • (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
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC20H28O2
Molar mass300.442 g·mol−1
3D model (JSmol)
Melting point169 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 namesNeoprogestin andNor-Progestelea, is aprogestin andandrogen/anabolic steroid (AAS) medication which was used inEurope but is now no longer marketed.[1][2][3][4][5] It is takenby mouth.

Norvinisterone is a progestin, or asyntheticprogestogen, and hence is anagonist of theprogesterone receptor, thebiological target of progestogens likeprogesterone.[2] It hasandrogenic activity.[6]

Norvinisterone wassynthesized in 1953.[2] It is no longer available.[7]

Medical uses

[edit]

Norvinisterone was used inhormonal contraception to preventpregnancy.[1][3]

Pharmacology

[edit]

Pharmacodynamics

[edit]

Norvinisterone is aprogestogen.[2][8][5] It appears to be quiteandrogenic, with about one-third and one-fifth of the androgenic andanabolic activity, respectively, ofnandrolone inanimalbioassays.[6] However, it has also been reported to have little anabolic activity.[9]

Chemistry

[edit]
See also:List of progestogens andList of androgens/anabolic steroids

Norvinisterone, also known as 17α-vinyl-19-nortestosterone or as 17α-vinylestr-4-en-17β-ol-3-one, is asyntheticestranesteroid and aderivative oftestosterone and19-nortestosterone.[2]Analogues of norvinisterone include the progestinnorgesterone and the AASvinyltestosterone.[2]

History

[edit]

Norvinisterone wassynthesized in 1953[2] and was studied in humans by 1960.[8]

Society and culture

[edit]

Generic names

[edit]

Norvinisterone is thegeneric name of the drug and itsINNTooltip International Nonproprietary Name.[2] It is also known asvinylnortestosterone and is known by its developmental code nameSC-4641.[2][1]

Brand names

[edit]

Norvinisterone was marketed under the brand names Neoprogestin and Nor-Progestelea bySyntex.[2][1]

Availability

[edit]

Norgesterone is no longer marketed and hence is no longer available in any country.[7]

References

[edit]
  1. ^abcdeBudavari S, ed. (1989). "6637: Norvinisterone".Merck Index (11th ed.). Rahway, N.J.: Merck & Co.ISBN 978-0-911910-28-5.
  2. ^abcdefghijElks J (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 889–.ISBN 978-1-4757-2085-3.
  3. ^abJuo PS (21 December 2001).Concise Dictionary of Biomedicine and Molecular Biology. CRC Press. pp. 774–.ISBN 978-1-4200-4130-9.
  4. ^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.
  5. ^abMeyerson 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.
  6. ^abSaunders 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.
  7. ^abhttp://www.micromedexsolutions.com/micromedex2/[permanent dead link]
  8. ^abMartinez 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.
  9. ^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.
Progestogens
(andprogestins)
PRTooltip Progesterone receptoragonists
Antiprogestogens
SPRMsTooltip Selective progesterone receptor modulators
PRTooltip Progesterone receptorantagonists
Androgens
(incl.AASTooltip anabolic–androgenic steroid)
ARTooltip Androgen receptoragonists
Progonadotropins
Antiandrogens
ARTooltip Androgen receptorantagonists
Steroidogenesis
inhibitors
5α-Reductase
Others
Antigonadotropins
Others
PRTooltip Progesterone receptor
Agonists
Mixed
(SPRMsTooltip Selective progesterone receptor modulators)
Antagonists
mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)
Agonists
Antagonists
ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists
Retrieved from "https://en.wikipedia.org/w/index.php?title=Norvinisterone&oldid=1184634205"
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