norgestomet
{{short description|Chemical compound}}
{{Distinguish|norgestimate}}
{{Drugbox
| Verifiedfields =
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| IUPAC_name = [(8R,9S,10R,11S,13S,14S,17R)-17-acetyl-11,13-dimethyl-3-oxo-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate
| image = Norgestomet.svg
| width = 225px
| tradename = Syncro-Mate B, Crestar
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| class = Progestogen; Progestin; Progestogen ester
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| CAS_number_Ref =
| CAS_number = 25092-41-5
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| PubChem = 9820838
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| ChemSpiderID_Ref =
| ChemSpiderID = 7996587
| UNII = 3L33UD42X4
| synonyms = Norgestamet; SC-21009; 11β-Methyl-17α-acetoxy-19-norprogesterone; 17α-Hydroxy-11β-methyl-19-norpregn-4-ene-3,20-dione acetate
| C=23 | H=32 | O=4
| SMILES = CC1CC2(C(CCC2(C(=O)C)OC(=O)C)C3C1C4CCC(=O)C=C4CC3)C
| StdInChI = 1S/C23H32O4/c1-13-12-22(4)20(9-10-23(22,14(2)24)27-15(3)25)19-7-5-16-11-17(26)6-8-18(16)21(13)19/h11,13,18-21H,5-10,12H2,1-4H3/t13-,18-,19-,20-,21+,22-,23-/m0/s1
| StdInChIKey = IWSXBCZCPVUWHT-VIFKTUCRSA-N
}}
Norgestomet, or norgestamet, sold under the brand name Syncro-Mate B and Crestar, is a progestin medication which is used in veterinary medicine to control estrus and ovulation in cattle.{{cite book | vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies |url= https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA887 |date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=887–}}{{cite book| vauthors = Favero RJ, Henderson EA, Kesler DJ | chapter = The Ability of Norgesomet Impregnated Poly(dimethylsiloxane) to Maintain Pregnancy Subsequent to Ovarietomy| veditors = Gebelein CG, Dunn RL |title=Progress in Biomedical Polymers| chapter-url = https://books.google.com/books?id=-qXTBH9-an0C&pg=PA356 |date=1 July 1990|publisher=Springer Science & Business Media|isbn=978-0-306-43523-2|pages=356–}}
Uses
=Veterinary=
Norgestomet is used in veterinary medicine.
Pharmacology
=Pharmacodynamics=
Norgestomet is a progestogen. In addition to the progesterone receptor, it possesses weak (micromolar) affinity for the glucocorticoid receptor.{{cite journal | vauthors = Moffatt RJ, Zollers WG, Welshons WV, Kieborz KR, Garverick HA, Smith MF | title = Basis of norgestomet action as a progestogen in cattle | journal = Domestic Animal Endocrinology | volume = 10 | issue = 1 | pages = 21–30 | date = January 1993 | pmid = 8467644 | doi = 10.1016/0739-7240(93)90005-v }}
Chemistry
{{See also|List of progestogens|Progestogen ester|List of progestogen esters}}
Norgestomet, also known as 11β-methyl-17α-acetoxy-19-norprogesterone or as 17α-hydroxy-11β-methyl-19-norpregn-4-ene-3,20-dione acetate, is a synthetic norpregnane steroid and a derivative of progesterone.
History
Norgestomet was developed and introduced for veterinary use in the mid-1970s.{{cite book| vauthors = Gordon U | chapter = Artificial Control O Oestrus and Ovulation |title=Controlled Breeding in Farm Animals| chapter-url= https://books.google.com/books?id=mEgvBQAAQBAJ&pg=PA40|date=22 October 2013|publisher=Elsevier|isbn=978-1-4832-8569-6|pages=40–}}
Society and culture
=Generic names=
Norgestomet is the generic name of the drug and its {{abbrlink|INN|International Nonproprietary Name}}, {{abbrlink|USAN|United States Adopted Name}}, and {{abbrlink|BAN|British Approved Name}}.{{cite web | title = Norgestomet | work = Drugs.com | url = https://www.drugs.com/international/norgestomet.html | archive-url = https://web.archive.org/web/20180228100752/https://www.drugs.com/international/norgestomet.html | archive-date = 28 February 2018 }} It also known as norgestamet and is known by its developmental code name SC-21009.{{cite web | url=http://krex.k-state.edu/dspace/handle/2097/27088 | title=Effect of time of insemination and calf removal after estrus synchronization in beef cattle | year=1979 | vauthors = Houghton PL }}
=Brand names=
References
{{Reflist}}
{{Progestogens and antiprogestogens}}
{{Progesterone receptor modulators}}
{{Glucocorticoid receptor modulators}}