ozagrel

{{Drugbox

| IUPAC_name = (2E)-3-[4-(1H-imidazol-1-ylmethyl)phenyl]acrylic acid

| image = Ozagrel.svg

| tradename =

| Drugs.com = {{drugs.com|international|ozagrel}}

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| legal_status = Rx-only

| routes_of_administration = Oral

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 82571-53-7

| ATC_prefix = none

| ATC_suffix =

| ATC_supplemental =

| PubChem = 5282440

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = L256JB984D

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D08327

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 11662

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 4445594

| chemical_formula =

| C=13 | H=12 | N=2 | O=2

| smiles = C1=CC(=CC=C1CN2C=CN=C2)/C=C/C(=O)O

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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+

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = SHZKQBHERIJWAO-AATRIKPKSA-N

}}

Ozagrel (INN) is an antiplatelet agent working as a thromboxane A2 synthesis inhibitor.{{cite journal | vauthors = Loo MH, Egan D, Vaughan ED, Marion D, Felsen D, Weisman S | title = The effect of the thromboxane A2 synthesis inhibitor OKY-046 on renal function in rabbits following release of unilateral ureteral obstruction | journal = The Journal of Urology | volume = 137 | issue = 3 | pages = 571–576 | date = March 1987 | pmid = 3820396 | doi = 10.1016/s0022-5347(17)44108-5 }}

Synthesis

:upright=2

The free-radical halogenation of ethyl 4-methylcinnamate (1) with N-bromosuccinimide in the presence of benzoyl peroxide gives ethyl 4-bromomethylcinnamate (2).{{cite patent | inventor = Cragoe Jr EJ, Bicking JB | title = nterphenylene 11,12-secoprostaglandins | country = US | number = 4175203 | gdate = 20 November 1979 | assign = to Merck and Co Inc | url = https://patents.google.com/patent/US4175203 }} Alkylation of imidazole (3) with this material gives the ethyl ester (4) of the drug, which is saponified to give ozagrel.{{cite journal | vauthors = Iizuka K, Akahane K, Momose D, Nakazawa M, Tanouchi T, Kawamura M, Ohyama I, Kajiwara I, Iguchi Y, Okada T, Taniguchi K, Miyamoto T, Hayashi M | title = Highly selective inhibitors of thromboxane synthetase. 1. Imidazole derivatives | journal = Journal of Medicinal Chemistry | volume = 24 | issue = 10 | pages = 1139–1148 | date = October 1981 | pmid = 7199088 | doi = 10.1021/jm00142a005 }}{{cite web |url=https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-15-0068 |title=Ozagrel | work = Pharmaceutical Substances |publisher=Georg Thieme Verlag KG |access-date=2024-06-30}}

References

Category:Imidazoles