Misplaced Pages

Norvinisterone

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
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
IUPAC name
  • (8R,9S,10R,13S,14S,17R)-17-ethenyl-17-hydroxy-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopentaphenanthren-3-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H28O2
Molar mass300.442 g·mol
3D model (JSmol)
Melting point169 to 171 °C (336 to 340 °F)
SMILES
  • O=C4\C=C2/(1CC3((O)(\C=C)CC31CC2)C)CC4
InChI
  • 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. 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. It has androgenic activity.

Norvinisterone was synthesized in 1953. It is no longer available.

Medical uses

Norvinisterone was used in hormonal contraception to prevent pregnancy.

Pharmacology

Pharmacodynamics

Norvinisterone is a progestogen. 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. However, it has also been reported to have little anabolic activity.

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. Analogues of norvinisterone include the progestin norgesterone and the AAS vinyltestosterone.

History

Norvinisterone was synthesized in 1953 and was studied in humans by 1960.

Society and culture

Generic names

Norvinisterone is the generic name of the drug and its INNTooltip International Nonproprietary Name. It is also known as vinylnortestosterone and is known by its developmental code name SC-4641.

Brand names

Norvinisterone was marketed under the brand names Neoprogestin and Nor-Progestelea by Syntex.

Availability

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

References

  1. ^ Budavari S, ed. (1989). "6637: Norvinisterone". Merck Index (11th ed.). Rahway, N.J.: Merck & Co. ISBN 978-0-911910-28-5.
  2. ^ 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.
  3. ^ Juo 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. ^ 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.
  6. ^ 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.
  7. ^ http://www.micromedexsolutions.com/micromedex2/
  8. ^ Martinez Montes EA, Bagnati EP, Zapata AC, Bur GE (March 1960). "". 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 and antiprogestogens
Progestogens
(and progestins)
PRTooltip Progesterone receptor agonists
Antiprogestogens
SPRMsTooltip Selective progesterone receptor modulators
PRTooltip Progesterone receptor antagonists
See also
Progesterone receptor modulators
Androgens and antiandrogens
Estrogens and antiestrogens
List of progestogens
Androgens and antiandrogens
Androgens
(incl. AASTooltip anabolic–androgenic steroid)
ARTooltip Androgen receptor agonists
Progonadotropins
Antiandrogens
ARTooltip Androgen receptor antagonists
Steroidogenesis
inhibitors
5α-Reductase
Others
Antigonadotropins
Others
See also
Androgen receptor modulators
Estrogens and antiestrogens
Progestogens and antiprogestogens
List of androgens/anabolic steroids
Progesterone receptor modulators
PRTooltip Progesterone receptor
Agonists
Mixed
(SPRMsTooltip Selective progesterone receptor modulators)
Antagonists
mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)
Agonists
Antagonists
See also
Receptor/signaling modulators
Progestogens and antiprogestogens
Androgen receptor modulators
Estrogen receptor modulators
List of progestogens
Androgen receptor modulators
ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists
See also
Receptor/signaling modulators
Androgens and antiandrogens
Estrogen receptor modulators
Progesterone receptor modulators
List of androgens and anabolic steroids
Categories: