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Dazoxiben

From Wikipedia, the free encyclopedia
Dazoxiben
Names
Preferred IUPAC name
4-[2-(1H-Imidazol-1-yl)ethoxy]benzoic acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
DrugBank
UNII
  • InChI=1S/C12H12N2O3/c15-12(16)10-1-3-11(4-2-10)17-8-7-14-6-5-13-9-14/h1-6,9H,7-8H2,(H,15,16) checkY
    Key: XQGZSYKGWHUSDH-UHFFFAOYSA-N checkY
  • InChI=1/C12H12N2O3/c15-12(16)10-1-3-11(4-2-10)17-8-7-14-6-5-13-9-14/h1-6,9H,7-8H2,(H,15,16)
    Key: XQGZSYKGWHUSDH-UHFFFAOYAY
  • O=C(O)c2ccc(OCCn1ccnc1)cc2
Properties
C12H12N2O3
Molar mass232.239 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Dazoxiben is an orally activethromboxane synthase inhibitor.[1] It has shown a significant clinical improvement in patients withRaynaud's syndrome.[2]

Synthesis

[edit]
Dazoxiben synthesis:[3][4][5][6]

One convenient synthesis starts with the O-chloroethylether of p-hydroxybenzamide and proceeds bydisplacement withimidazole to give2.Hydrolysis of the amide function completes the synthesis of dazoxiben.

References

[edit]
  1. ^Belch, J. J.; Cormie, J.; Newman, P.; McLaren, M.; Barbenel, J.; Capell, H.; Leiberman, P.; Forbes, C. D.; Prentice, C. R. (1983)."Dazoxiben, a thromboxane synthetase inhibitor, in the treatment of Raynaud's syndrome: A double-blind trial".British Journal of Clinical Pharmacology. 15 Suppl 1 (Suppl 1):113S –116S.doi:10.1111/j.1365-2125.1983.tb02119.x.PMC 1427695.PMID 6337601.
  2. ^Belch, J. J.; Cormie, J.; Newman, P.; McLaren, M.; Barbenel, J.; Capell, H.; Leiberman, P.; Forbes, C. D.; Prentice, C. R. (1983)."Dazoxiben, a thromboxane synthetase inhibitor, in the treatment of Raynaud's syndrome: A double-blind trial".British Journal of Clinical Pharmacology. 15 Suppl 1 (Suppl 1):113S –116S.doi:10.1111/j.1365-2125.1983.tb02119.x.PMC 1427695.PMID 6337601.
  3. ^DE 2950019, Cross, Peter Edward & Dickinson, Roger Peter, "Imidazolderivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel [Imidazol derivatives, processes for their production and pharmaceuticals containing them]", published 1980-07-10, assigned toPfizer Corp. 
  4. ^Kochergin, P. M.; Palei, R. M.; Balandina, L. V.; Kharitonova, A. E.; Kravchenko, A. N.; Persanova, L. V.; Govorukhina, E. I.; Frolova, M. A. (1995). "Simplified synthesis of dazoxiben".Pharmaceutical Chemistry Journal.29 (2): 139.doi:10.1007/BF02226528.S2CID 37387182.
  5. ^Iizuka, Kinji; Akahane, Kenji; Momose, Denichi; Nakazawa, Masayuki; Tanouchi, Tadao; Kawamura, Masanori; Ohyama, Isao; Kajiwara, Ikuo; Iguchi, Yohichi (1981). "Highly selective inhibitors of thromboxane synthetase. 1. Imidazole derivatives".Journal of Medicinal Chemistry.24 (10):1139–1148.doi:10.1021/jm00142a005.PMID 7199088.
  6. ^Cross, Peter E.; Dickinson, Roger P.; Parry, M. John; Randall, Michael J. (1985). "Selective thromboxane synthetase inhibitors. 1. 1-[(Aryloxy)alkyl]-1H-imidazoles".Journal of Medicinal Chemistry.28 (10):1427–1432.doi:10.1021/jm00148a009.PMID 3930740.
Antiplatelet drugs
Glycoprotein IIb/IIIa inhibitors
ADP receptor/P2Y12inhibitors
Prostaglandin analogue (PGI2)
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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 (F2α)Tooltip Prostaglandin F receptor
IP (I2)Tooltip Prostacyclin receptor
TP (TXA2)Tooltip Thromboxane receptor
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Enzyme
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(PTGS)
PGD2STooltip Prostaglandin D synthase
PGESTooltip Prostaglandin E synthase
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TXASTooltip Thromboxane A synthase
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