Lotrifen
{{Short description|Chemical compound}}
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| IUPAC_name = 2-(4-chlorophenyl)-[1,2,4]triazolo[5,1-a]isoquinoline
| image = Lotrifen.svg
| width = 160px
| tradename = Canocenta, Privaprol
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| CAS_number_Ref =
| CAS_number = 66535-86-2
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| PubChem = 68866
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| ChemSpiderID_Ref =
| ChemSpiderID = 62098
| UNII = K6J75G277H
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| ChEMBL = 94113
| synonyms = Trazisoquine; L-12717; DL-717-IT
| C=16 | H=10 | Cl=1 | N=3
| SMILES = C1=CC=C2C(=C1)C=CN3C2=NC(=N3)C4=CC=C(C=C4)Cl
| StdInChI_Ref =
| StdInChI = 1S/C16H10ClN3/c17-13-7-5-12(6-8-13)15-18-16-14-4-2-1-3-11(14)9-10-20(16)19-15/h1-10H
| StdInChIKey_Ref =
| StdInChIKey = DGWUVKLBXCWNTA-UHFFFAOYSA-N
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Lotrifen ({{abbrlink|INN|International Nonproprietary Name}}), also known as trazisoquine and sold under the brand names Canocenta and Privaprol, is an abortifacient which is used in veterinary medicine.{{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=PA743|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=743–}}{{cite book | vauthors = Negwer M, Scharnow HG |title=Organic-chemical drugs and their synonyms: (an international survey)|url=https://books.google.com/books?id=zWpqAAAAMAAJ|date=4 October 2001|publisher=Wiley-VCH|isbn=978-3-527-30247-5|page=1184}} It was described in 1978.
Synthesis
Reaction of the acyl hydrazide (1) and the carboximidate (2) gives compound (3). Heating this in the presence of sodium hydride cyclises this intermediate, forming the 1,2,4-triazole ring system of the drug. Oxidation of (4) with N-bromoacetamide yields lotrifen.{{cite web |url=https://www.chemdrug.com/article/8/3284/16419978.html |title=Lotrifen |website=chemdrug.com |access-date=2024-07-03}}{{cite patent |country=US |number=4075341 |inventor=Amedeo Omodei-Sale, Pietro Consonni and Leonard Lerner |title=2-Substituted phenyl-5-triazols [5,1-a]isoquinoline compounds |status=patent |gdate=1978-02-21 |fdate=1975-11-28 |pridate=1975-05-24 |assign1=Gruppo Lepetit S.P.A.}}
References
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Further reading
{{refbegin}}
- {{cite journal | vauthors = Lerner LJ | title = Development of novel embryotoxic compounds for interceptive fertility control in the dog | journal = Journal of Reproduction and Fertility. Supplement | volume = 39 | pages = 251–65 | date = 1989 | pmid = 2621727 }}
- {{cite journal | vauthors = Wanke R, Hermanns W | title = Adverse effects of the antifertility agent DL 717-IT (Canocenta, Byk Gulden, FRG). Pathological findings in the rabbit | journal = Research Communications in Chemical Pathology and Pharmacology | volume = 63 | issue = 1 | pages = 69–80 | date = January 1989 | pmid = 2916081 }}
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Category:4-Chlorophenyl compounds
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