Ozagrel

Ozagrel

Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name (2E)-3-[4-(1H-imidazol-1-ylmethyl)phenyl]acrylic acid
CAS Number	82571-53-7  Y
PubChem CID	5282440
ChemSpider	4445594  Y
UNII	L256JB984D
KEGG	D08327  Y
ChEMBL	ChEMBL11662  Y
CompTox Dashboard (EPA)	DTXSID6048547
ECHA InfoCard	100.122.039
Chemical and physical data
Formula	C13H12N2O2
Molar mass	228.251 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1=CC(=CC=C1CN2C=CN=C2)/C=C/C(=O)O
InChI InChI=1S/C13H12N2O2/c16-13(17)6-5-11-1-3-12(4-2-11)9-15-8-7-14-10-15/h1-8,10H,9H2,(H,16,17)/b6-5+ Y Key:SHZKQBHERIJWAO-AATRIKPKSA-N Y

Ozagrel (INN) is an antiplatelet agent working as a thromboxane A2 synthesis inhibitor. ^[1]

Synthesis

The free-radical halogenation of ethyl 4-methylcinnamate (1) with N-bromosuccinimide in the presence of benzoyl peroxide gives ethyl 4-bromomethylcinnamate (2). ^[2] Alkylation of imidazole (3) with this material gives the ethyl ester (4) of the drug, which is saponified to give ozagrel. ^{[3] [4]}

References

1. Loo MH, Egan D, Vaughan ED, Marion D, Felsen D, Weisman S (March 1987). "The effect of the thromboxane A2 synthesis inhibitor OKY-046 on renal function in rabbits following release of unilateral ureteral obstruction". The Journal of Urology. 137 (3): 571–576. doi:10.1016/s0022-5347(17)44108-5. PMID   3820396.
2. US 4175203,Cragoe Jr EJ, Bicking JB,"nterphenylene 11,12-secoprostaglandins",issued 20 November 1979, assigned to to Merck and Co Inc 
3. Iizuka K, Akahane K, Momose D, Nakazawa M, Tanouchi T, Kawamura M, et al. (October 1981). "Highly selective inhibitors of thromboxane synthetase. 1. Imidazole derivatives". Journal of Medicinal Chemistry. 24 (10): 1139–1148. doi:10.1021/jm00142a005. PMID   7199088.
4. "Ozagrel". Pharmaceutical Substances. Georg Thieme Verlag KG. Retrieved 2024-06-30.