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词条 Norvinisterone
释义

  1. Medical uses

  2. Pharmacology

     Pharmacodynamics 

  3. Chemistry

  4. History

  5. Society and culture

     Generic names  Brand names  Availability 

  6. References

{{Drugbox
| 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
| image = Norvinisterone.svg
| width = 225px
| tradename = Neoprogestin, Nor-Progestelea
| Drugs.com =
| MedlinePlus =
| pregnancy_AU =
| pregnancy_US =
| pregnancy_category=
| legal_AU =
| legal_CA =
| legal_UK =
| legal_US =
| legal_status =
| routes_of_administration = By mouth
| class = Progestin; Progestogen; Androgen; Anabolic steroid
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
| CAS_number = 6795-60-4
| ATC_prefix = None
| ATC_suffix =
| PubChem = 65588
| ChemSpiderID = 59030
| DrugBank =
| synonyms = Vinylnortestosterone; SC-4641; 17α-Vinyl-19-nortestosterone; 17α-Vinylestr-4-en-17β-ol-3-one
| C=20 | H=28 | O=2
| molecular_weight = 300.435 g/mol
| 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
| StdInChI = 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
| StdInChIKey = VOJYZDFYEHKHAP-XGXHKTLJSA-N
| melting_point = 169
| melting_high = 171
| melting_notes = [1]
}}

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.[8]

Norvinisterone was synthesized in 1953.[2] It is no longer available.[10]

Medical uses

Norvinisterone was used in hormonal contraception to prevent pregnancy.[1][3]

Pharmacology

Pharmacodynamics

Norvinisterone is a progestogen.[2][14][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]

Chemistry

{{See also|List of progestogens|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.[7]

Society and culture

Generic names

Norvinisterone is the generic name of the drug and its {{abbrlink|INN|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.[8]

References

1. ^Merck Index, 11th edition, 6637
2. ^{{cite book|author=J. Elks|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA889|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=889–}}
3. ^{{cite book|author=Pei-Show Juo|title=Concise Dictionary of Biomedicine and Molecular Biology|url=https://books.google.com/books?id=Y4DLBQAAQBAJ&pg=PA774|date=21 December 2001|publisher=CRC Press|isbn=978-1-4200-4130-9|pages=774–}}
4. ^{{cite book|author1=P. H. List|author2=L. Hörhammer|title=Chemikalien und Drogen Teil A: N-Q|url=https://books.google.com/books?id=4TWnBgAAQBAJ&pg=PA274|date=12 March 2013|publisher=Springer Berlin Heidelberg|isbn=978-3-642-65035-2|pages=274–}}
5. ^{{cite journal|last1=Meyerson|first1=Bengt J.|title=Relationship Between the Anesthetic and Gestagenic Action and Estrous Behavior-Inducing Activity of Different Progestins|journal=Endocrinology|volume=81|issue=2|year=1967|pages=369–374|issn=0013-7227|doi=10.1210/endo-81-2-369|pmid=4952012}}
6. ^{{cite journal|last1=Saunders|first1=Francis J.|last2=Drill|first2=Victor A.|title=The Myotrophic and Androgenic Effects of 17-Ethyl-19-nortestosterone and Related Compounds|journal=Endocrinology|volume=58|issue=5|year=1956|pages=567–572|issn=0013-7227|doi=10.1210/endo-58-5-567|pmid=13317831}}
7. ^{{cite journal | vauthors = Martinez Montes EA, Bagnati EP, Zapata AC, Bur GE | title = [Clinical trial of a new luteoid: norvinisterone] | language = Spanish| journal = Dia Med | volume = 32 | issue = | pages = 194–7 | year = 1960 | pmid = 14421807 | doi = | url = }}
8. ^http://www.micromedexsolutions.com/micromedex2/
{{Progestogens and antiprogestogens}}{{Androgens and antiandrogens}}{{Progesterone receptor modulators}}{{Androgen receptor modulators}}

7 : Alkenes|Androgens and anabolic steroids|Estranes|Hepatotoxins|Hormonal contraception|Progestogens|Vinyl compounds

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