Ozagrel
Chemical compound
- none
- In general: ℞ (Prescription only)
- (2E)-3-[4-(1H-imidazol-1-ylmethyl)phenyl]acrylic acid
- 82571-53-7
Y
- 5282440
- 4445594
Y
- L256JB984D
- D08327
Y
- ChEMBL11662
Y
- DTXSID6048547
![Edit this at Wikidata](http://upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png)
- Interactive image
- 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
- ^ 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.
- ^ US 4175203, Cragoe Jr EJ, Bicking JB, "nterphenylene 11,12-secoprostaglandins", issued 20 November 1979, assigned to to Merck and Co Inc
- ^ 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.
- ^ "Ozagrel". Pharmaceutical Substances. Georg Thieme Verlag KG. Retrieved 2024-06-30.
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(ligands)
DP (D2)Tooltip Prostaglandin D2 receptor |
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EP (E2)Tooltip Prostaglandin E2 receptor |
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FP (F2α)Tooltip Prostaglandin F receptor |
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IP (I2)Tooltip Prostacyclin receptor |
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TP (TXA2)Tooltip Thromboxane receptor |
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Unsorted |
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(inhibitors)
- Precursors: Linoleic acid
- γ-Linolenic acid (gamolenic acid)
- Dihomo-γ-linolenic acid
- Diacylglycerol
- Arachidonic acid
- Prostaglandin G2
- Prostaglandin H2
- See also
- Receptor/signaling modulators
- Leukotriene signaling modulators
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