Lotrifen

Lotrifen (INNTooltip 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.^[1][2] It was described in 1978.^[1]

Lotrifen

Clinical data
Trade names	Canocenta, Privaprol
Other names	Trazisoquine; L-12717; DL-717-IT
Identifiers
IUPAC name 2-(4-chlorophenyl)-[1,2,4]triazolo[5,1-a]isoquinoline
CAS Number	66535-86-2
PubChem CID	68866
ChemSpider	62098
UNII	K6J75G277H
ChEMBL	ChEMBL94113
CompTox Dashboard (EPA)	DTXSID6073603
ECHA InfoCard	100.060.340
Chemical and physical data
Formula	C16H10ClN3
Molar mass	279.73 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1=CC=C2C(=C1)C=CN3C2=NC(=N3)C4=CC=C(C=C4)Cl
InChI InChI=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 Key:DGWUVKLBXCWNTA-UHFFFAOYSA-N

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.^[3][4]