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Ozagrel

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
Ozagrel
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • (2E)-3-[4-(1H-imidazol-1-ylmethyl)phenyl]acrylic acid
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.122.039Edit this at Wikidata
Chemical and physical data
FormulaC13H12N2O2
Molar mass228.251 g·mol−1
3D model (JSmol)
  • C1=CC(=CC=C1CN2C=CN=C2)/C=C/C(=O)O
  • 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+ checkY
  • Key:SHZKQBHERIJWAO-AATRIKPKSA-N checkY

Ozagrel (INN) is anantiplatelet agent working as athromboxane A2 synthesis inhibitor.[1]

Synthesis

[edit]

Thefree-radical halogenation of ethyl 4-methylcinnamate (1) withN-bromosuccinimide in the presence ofbenzoyl peroxide gives ethyl 4-bromomethylcinnamate (2).[2]Alkylation ofimidazole (3) with this material gives the ethyl ester (4) of the drug, which issaponified to give ozagrel.[3][4]

References

[edit]
  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. Retrieved2024-06-30.
Receptor
(ligands)
DP (D2)Tooltip Prostaglandin D2 receptor
DP1Tooltip Prostaglandin D2 receptor 1
DP2Tooltip Prostaglandin D2 receptor 2
EP (E2)Tooltip Prostaglandin E2 receptor
EP1Tooltip Prostaglandin EP1 receptor
EP2Tooltip Prostaglandin EP2 receptor
EP3Tooltip Prostaglandin EP3 receptor
EP4Tooltip Prostaglandin EP4 receptor
Unsorted
FP (F)Tooltip Prostaglandin F receptor
IP (I2)Tooltip Prostacyclin receptor
TP (TXA2)Tooltip Thromboxane receptor
Unsorted
Enzyme
(inhibitors)
COX
(
PTGS)
PGD2STooltip Prostaglandin D synthase
PGESTooltip Prostaglandin E synthase
PGFSTooltip Prostaglandin F synthase
PGI2STooltip Prostacyclin synthase
TXASTooltip Thromboxane A synthase
Others
Stub icon

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