CAS No 82571-53-7 , (E)-3-[4-(imidazol-1-ylmethyl)phenyl]prop-2-enoic acid

Title: Ozagrel
CAS Registry Number: 82571-53-7
CAS Name: (2E)-3-[4-(1H-Imidazol-1-ylmethyl)phenyl]-2-propenoic acid
Synonyms: (E)-4-(imidazol-1-ylmethyl)cinnamic acid
Manufacturers' Codes: OKY-046
Molecular Formula: C13H12N2O2
Molecular Weight: 228.25
Percent Composition: C 68.41%, H 5.30%, N 12.27%, O 14.02%
Literature References: Prepn: K. Iizuka et al., DE 2923815; eidem, US 4226878 (both 1980 to Ono; Kissei). Synthesis and thromboxane synthetase inhibitory activity: K. Iizuka et al., J. Med. Chem. 24, 1139 (1981). Pharmacology: S. Hiraku et al., Jpn. J. Pharmacol. 41, 393 (1986). Pulmonary vascular effects: R. Garcia-Szabo et al., Prostaglandins 28, 851 (1984). Metabolism in animals: M. Shimizu et al., Iyakuhin Kenkyu 17, 289 (1986), C.A. 105, 72012q (1986). HPLC determn in biological fluids: eidem, ibid. 298, C.A. 105, 72013r (1986). Clinical pharmacology and evaluation in myocardial infarction: T. Ito et al., Biomed. Biochim. Acta 43, S125 (1984). Clinical evaluation in prevention of cerebral vasospasm: S. Suzuki et al., Acta Neurochir. 77, 133 (1985); in coronary artery disease: M. Shikano et al., Jpn. Heart J. 28, 663 (1987). Toxicity data: T. Nishigake et al., Clin. Rep. 20, 2671 (1986). Series of articles on pharmacology: Pharmacometrics 31, 527-565 (1986), C.A. 105, 35349-35352 (1986).
Properties: Prisms from ethanol-ether, mp 223-224°.
Melting point: mp 223-224°
 
Derivative Type: Hydrochloride
CAS Registry Number: 78712-43-3
Molecular Formula: C13H12N2O2.HCl
Molecular Weight: 264.71
Percent Composition: C 58.98%, H 4.95%, N 10.58%, O 12.09%, Cl 13.39%
Properties: Crystals from ethanol-ether, mp 214-217°.
Melting point: mp 214-217°
 
Derivative Type: Sodium salt
Trademarks: Cataclot (Ono); Xanbon (Kissei)
Molecular Formula: C13H11N2NaO2
Molecular Weight: 250.23
Percent Composition: C 62.40%, H 4.43%, N 11.20%, Na 9.19%, O 12.79%
Properties: LD50 in male, female mice, male, female rats (mg/kg): 1940, 1580, 1150, 1300 i.v.; 3800, 3600, 5900, 5700 orally; 2450, 2100, 2300, 2250 s.c. (Nishigake).
Toxicity data: LD50 in male, female mice, male, female rats (mg/kg): 1940, 1580, 1150, 1300 i.v.; 3800, 3600, 5900, 5700 orally; 2450, 2100, 2300, 2250 s.c. (Nishigake)
 
Therap-Cat: Antithrombotic; antianginal.
Keywords: Antianginal; Antithrombotic; Thromboxane A2-Sythetase Inhibitor.