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Lotrifen

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Lotrifen
Clinical data
Trade namesCanocenta, Privaprol
Other namesTrazisoquine; L-12717; DL-717-IT
Identifiers
  • 2-(4-chlorophenyl)-[1,2,4]triazolo[5,1-a]isoquinoline
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.060.340 Edit this at Wikidata
Chemical and physical data
FormulaC16H10ClN3
Molar mass279.73 g·mol−1
3D model (JSmol)
  • C1=CC=C2C(=C1)C=CN3C2=NC(=N3)C4=CC=C(C=C4)Cl
  • 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

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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

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  1. ^ 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.
  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. 

Further reading

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  • 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.