Lotrifen

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;

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]

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]

References

^ ^a ^b Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 743–. ISBN 978-1-4757-2085-3.
^ Negwer M, Scharnow HG (4 October 2001). Organic-chemical drugs and their synonyms: (an international survey). Wiley-VCH. p. 1184. ISBN 978-3-527-30247-5.
^ "Lotrifen". chemdrug.com. Retrieved 2024-07-03.
^ US patent 4075341, Amedeo Omodei-Sale, Pietro Consonni and Leonard Lerner, "2-Substituted phenyl-5-triazols [5,1-a]isoquinoline compounds", issued 1978-02-21, assigned to Gruppo Lepetit S.P.A.

Lerner LJ (1989). "Development of novel embryotoxic compounds for interceptive fertility control in the dog". Journal of Reproduction and Fertility. Supplement. 39: 251–65. PMID 2621727.
Wanke R, Hermanns W (January 1989). "Adverse effects of the antifertility agent DL 717-IT (Canocenta, Byk Gulden, FRG). Pathological findings in the rabbit". Research Communications in Chemical Pathology and Pharmacology. 63 (1): 69–80. PMID 2916081.

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[Elks2014-1] Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 743–. ISBN 978-1-4757-2085-3.

[NegwerScharnow2001-2] Negwer M, Scharnow HG (4 October 2001). Organic-chemical drugs and their synonyms: (an international survey). Wiley-VCH. p. 1184. ISBN 978-3-527-30247-5.

[3] "Lotrifen". chemdrug.com. Retrieved 2024-07-03.

[4] US patent 4075341, Amedeo Omodei-Sale, Pietro Consonni and Leonard Lerner, "2-Substituted phenyl-5-triazols [5,1-a]isoquinoline compounds", issued 1978-02-21, assigned to Gruppo Lepetit S.P.A.

[1]

[2]

[3]

[4]

Synthesis

References

Further reading