98123-83-2

Basic information

• Product Name: Epsiprantel
• Synonyms: Epsiprantel;Pyrazino2,1-a2benzazepin-4(1H)-one, 2-(cyclohexylcarbonyl)-2,3,6,7,8,12b-hexahydro-;2-(cyclohexanecarbonyl)-1,2,3,7,8,12b-hexahydrobenzo[c]pyrazino[1,2-a]azepin-4(6H)-one;2-(cyclohexanecarbonyl)-1,3,6,7,8,12b-hexahydropyrazino[2,1-a][2]benzazepin-4-one
• CAS NO: 98123-83-2
• Molecular Formula: C₂₀H₂₆N₂O₂
• Molecular Weight: 326.437
• Mol File: 98123-83-2.mol

Chemical Properties

• Melting Point: 189-190°
• Boiling Point: 553.7°Cat760mmHg
• Flash Point: 255.3°C
• Appearance: /
• Density: 1.2g/cm³
• Vapor Pressure: 2.65E-12mmHg at 25°C
• Refractive Index: 1.607
• PKA: -0.97±0.20(Predicted)
• CAS DataBase Reference: Epsiprantel(CAS DataBase Reference)
• NIST Chemistry Reference: Epsiprantel(98123-83-2)
• EPA Substance Registry System: Epsiprantel(98123-83-2)

Safety Data

• Hazardous Substances Data: 98123-83-2(Hazardous Substances Data)

Usage

Veterinary Drugs and Treatments

Epsiprantel is indicated for the treatment (removal) of Dipylidium caninum and Taenia pisiformis in dogs, and Dipylidium caninum and Taenia taeniaeformis in cats.

InChI:InChI=1/C20H26N2O2/c23-19-14-21(20(24)16-8-2-1-3-9-16)13-18-17-11-5-4-7-15(17)10-6-12-22(18)19/h4-5,7,11,16,18H,1-3,6,8-10,12-14H2

Upstream product

• 106206-88-6 1-(3-Phenylpropyl)-4-cyclohexylcarbonyl-6-hydroxypiperazin-2-one 
• 98123-84-3 1-(3-phenylpropyl)-4-benzyl-piperazine-2,6-dione 
• 121654-45-3 2-benzyl-4-oxo-1,2,3,4,6,7,8,12b-octahydropyrazino<2,1-a><2>benzazepine 
• 133958-40-4 1-(3-Phenylpropyl)-6-hydroxypiperazin-2-one 
• 98123-61-6 2H-4-oxo-1,2,3,4,6,7,8,12b-octahydropyrazino<2,1-a><2>benzazepine 
• 106206-86-4 1-(3-phenylpropyl)-piperazine-2,6-dione 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 1372607-34-5 1-cyclohexanecarbonyl-3-methoxy-1,2-dihydropyrazine 
• 52221-92-8 3-(2-bromo-phenyl)-propan-1-ol 
• 7664-93-9 sulfuric acid 
• 98123-85-4 1-(3-phenylpropyl)-4-benzyl-2-hydroxy-6-oxopiperazine 
• 2038-57-5 3-Phenylpropan-1-amine 

Downstream Products

• 121654-79-3 2-(cyclohexylcarbonyl)-4-thioxo-1,2,3,4,6,7,8,12b-octahydropyrazino<2,1-a><2>benzazepine 

Relevant articles and documents

A palladium-catalyzed intramolecular Heck/Hydrogenation approach towards the synthesis of praziquantel

Starting from 3-methoxy N-acylpyrazinium salts, a new approach towards the synthesis of the antischistosomal drug praziquantel (PZQ) has been developed. Utilization of a palladium-catalyzed intramolecular Heck reaction to form dehydro-PZQ followed by a Hydrogenation step, in a stepwise or one-pot manner, allowed for the gram scale synthesis of PZQ in 4 or 5 steps and in good overall yields. This methodology proved to be well suited for generating the pyrazino[1,2-a] isoindole and pyrazino[1,2-a] benzazepine analogues of PZQ.

SYNTHESIS OF TRICYCLIC SYSTEMS INCORPORATING THE AZEPINE RING

Some tricyclic compounds (derivatives of pyrazinobenzazepine, diazepinoisoquinoline, and some pyrimidoisoquinolines) which are analogs of the anthelmintic praziquantel have been synthesized.

Synthesis and Anthelmintic Activity of a Series of Pyrazinobenzazepine Derivatives

A series of 1,2,3,4,6,7,8,12b-octahydropyrazinobenzazepine derivatives was prepared and the cestocidal activity of the compounds evaluated in an in vitro Taenia crassiceps screen.Many of these derivatives proved to be highly active, and 2-(cyclohexylcarbonyl)-4-oxo-1,2,3,4,6,7,8,12b-octahydropyrazinobenzazepine, epsiprantel (BAN) (22), was selected for further development.The structure-activity relationships are discussed.

Benzazepines, and their use as anthelminthics

A compound of formula (I): STR1 in which R is optionally substituted phenyl; C3-8 cycloalkyl; C5-8 cycloalkenyl; C1-8 alkyl which may be straight or branched; C2-8 alkenyl which may be straight or branched; 5- or 6- membered heterocyclyl; or optionally substituted phenyl C1-4 alkyl, each of Y and Z, which may be the same or different, is oxygen or sulphur; and X is --CH2 -- or oxygen, a process for the preparation of such compounds and their use in human and veterinary medicine.