Norvinisterone

Norvinisterone
Clinical data
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	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-dodecahydrocyclopenta[a]phenanthren-3-one;
CAS Number	6795-60-4;
PubChem CID	65588;
ChemSpider	59030;
UNII	7Q843V12Q0;
CompTox Dashboard (EPA)	DTXSID501016506 ;
Chemical and physical data
Formula	C20H28O2
Molar mass	300.442 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	169 to 171 °C (336 to 340 °F)
	SMILES 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 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 INNTooltip 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/
^ ^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.

[Merck-1] Budavari S, ed. (1989). "6637: Norvinisterone". Merck Index (11th ed.). Rahway, N.J.: Merck & Co. ISBN 978-0-911910-28-5.

[Elks2014-2] ^ ^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.

[Juo2001-3] Juo PS (21 December 2001). Concise Dictionary of Biomedicine and Molecular Biology. CRC Press. pp. 774–. ISBN 978-1-4200-4130-9.

[ListHörhammer2013-4] 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.

[Meyerson1967-5] 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.

[SaundersDrill1956-6] 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.

[Micromedex-7] ttp://www.micromedexsolutions.com/micromedex2/

[pmid14421807-8] 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.

[pmid14442516-9] 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.

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