{{short description|Chemical compound}} {{Distinguish|norgestimate}} {{Drugbox | Verifiedfields = | Watchedfields = | verifiedrevid = | IUPAC_name = [(8''R'',9''S'',10''R'',11''S'',13''S'',14''S'',17''R'')-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 | image_class = skin-invert-image | width = 225px
<!--Clinical data--> | tradename = Syncro-Mate B, Crestar | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_category = | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = | class = Progestogen; Progestin; Progestogen ester
<!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =
<!--Identifiers--> | CAS_number_Ref = | CAS_number = 25092-41-5 | CAS_supplemental = | ATC_prefix = | ATC_suffix = | PubChem = 9820838 | DrugBank_Ref = | DrugBank = | 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
<!--Chemical data--> | 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.<ref name="Elks2014">{{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–}}</ref><ref name="GebeleinDunn1990">{{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–}}</ref>
==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.<ref name="pmid8467644">{{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 }}</ref>
==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.<ref name="Elks2014" /><ref name="Drugs.com" />
==History== Norgestomet was developed and introduced for veterinary use in the mid-1970s.<ref name="Gordon2013">{{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–}}</ref>
==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}}.<ref name="Elks2014" /><ref name="Drugs.com">{{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 }}</ref> It also known as ''norgestamet'' and is known by its developmental code name SC-21009.<ref name="Elks2014" /><ref name="Drugs.com" /><ref>{{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 }}</ref>
===Brand names=== Norgestomet is marketed under the brand names Syncro-Mate B and Crestar.<ref name="Elks2014" /><ref name="Drugs.com" />
== References == {{Reflist}}
{{Progestogens and antiprogestogens}} {{Progesterone receptor modulators}} {{Glucocorticoid receptor modulators}}
Category:Acetate esters Category:Diketones Category:Glucocorticoids Category:Norpregnanes Category:Progestogen esters Category:Progestogens Category:Veterinary drugs