Dazoxiben

Dazoxiben
Names
	Preferred IUPAC name 4-[2-(1H-Imidazol-1-yl)ethoxy]benzoic acid
Identifiers
CAS Number	78218-09-4 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL267473 ;
ChemSpider	47885 ;
DrugBank	DB03052 ;
IUPHAR/BPS	5175;
PubChem CID	53001;
UNII	09ZFC7974Q ;
CompTox Dashboard (EPA)	DTXSID9045639 ;
	InChI 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) Key: XQGZSYKGWHUSDH-UHFFFAOYSA-N ; 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;
	SMILES O=C(O)c2ccc(OCCn1ccnc1)cc2;
Properties
Chemical formula	C12H12N2O3
Molar mass	232.239 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Dazoxiben is an orally active thromboxane synthase inhibitor.^[1] It has shown a significant clinical improvement in patients with Raynaud's syndrome.^[2]

Synthesis

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

One convenient synthesis starts with the O-chloroethyl ether of p-hydroxybenzamide and proceeds bydisplacement with imidazole to give 2. Hydrolysis of the amide function completes the synthesis of dazoxiben.

References

^ 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.
^ 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.
^ 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 to Pfizer Corp.
^ 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.
^ 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.
^ 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.

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[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 to Pfizer 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.

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