DAZOXIBEN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H12N2O3
Molecular Weight	232.2353
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)C1=CC=C(OCCN2C=CN=C2)C=C1

InChI

InChIKey=XQGZSYKGWHUSDH-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6133076 | https://www.ncbi.nlm.nih.gov/pubmed/6337601 | https://www.ncbi.nlm.nih.gov/pubmed/3930740 | https://www.ncbi.nlm.nih.gov/pubmed/3921380

Dazoxiben is a selective inhibitor of thromboxane synthetase (IC50 3 nM), an enzyme that converts the endo-peroxide PGH2 into thromboxane A2, which is a potent vasoconstrictor and platelet aggregating agent. Dazoxiben has demonstrated efficacy in some clinical trial for the treatment of Raynaud's syndrome, an ischaemic condition manifested by the pallor of affected digits. In subsequent studies, however, no significant effect of dazoxiben was found. Dazoxiben was also evaluated in patients with sepsis, adult respiratory distress syndrome, stable angina, and other conditions.

Approval Year

PubMed

Title	Date	PubMed
UK-37, 248, a novel, selective thromboxane synthetase inhibitor with platelet anti-aggregatory and anti-thrombotic activity.	1981 Jul 1-15	6795753
[(1H-imidazol-1-yl)methyl]- and [(3-pyridinyl)methyl]pyrroles as thromboxane synthetase inhibitors.	1989 Apr	2704033
The mechanism of anti-thrombotic, thrombolytic and fibrinolytic actions of camonagrel--a new thromboxane synthase inhibitor.	1995	7778318
Effects of the selective inhibition of platelet thromboxane synthesis on the platelet-subendothelium interaction.	2002 Dec	12429581
Prostaglandin endoperoxides and thromboxane A2 activate the same receptor isoforms in human platelets.	2002 Jan	11848439
Cyclooxygenase contracting factors and altered pulmonary vascular responses in chronically hypoxic newborn pigs.	2002 Jan	11744644
Mechanisms involved in agonist-induced hyperaggregability of platelets from normal pregnancy.	2002 Jan-Feb	11810021
Sexual dimorphism in prostanoid-potentiated vascular contraction: roles of endothelium and ovarian steroids.	2002 Nov	12384486
Role of contaminating platelets in thromboxane synthesis in primary cultures of human umbilical vein endothelial cells.	2002 Sep	12428677
Study of the mechanisms involved in the bradykinin-induced contraction of the pig iris sphincter muscle in vitro.	2003 Jan 1	12498923
Effects of camonagrel, a selective inhibitor of platelet thromboxane synthase, on the platelet-subendothelium interaction.	2003 Sep	12886030
Chronic AT(1) receptor blockade alters mechanisms mediating responses to hypoxia in rat skeletal muscle resistance arteries.	2004 Aug	15044197
Role of platelet microparticles in the production of thromboxane by rabbit pulmonary artery.	2004 Feb	14718367
Role of endothelin-1 and thromboxane A2 in the pulmonary hypertension induced by heparin-protamine interaction in anesthetized dogs.	2004 Jan	14668575
BK2 but not BK1 receptors mediating contractile response in human umbilical arteries: role of thromboxane A2.	2004 May	15319801
Attenuation of lipopolysaccharide-induced hyperreactivity of human internal mammary arteries by melatonin.	2004 Sep	15298667
Redirection of eicosanoid metabolism in mPGES-1-deficient macrophages.	2005 Apr 29	15722356
Acetylcholine-induced endothelium-dependent contractions in the SHR aorta: the Janus face of prostacyclin.	2005 Nov	16158068
In SHR aorta, calcium ionophore A-23187 releases prostacyclin and thromboxane A2 as endothelium-derived contracting factors.	2006 Nov	16798820
Mechanisms underlying ATP-induced endothelium-dependent contractions in the SHR aorta.	2007 Feb 5	17126320
The calcium ionophore A23187 induces endothelium-dependent contractions in femoral arteries from rats with streptozotocin-induced diabetes.	2007 Mar	17245370
Effect of inhibitors of arachidonic acid conversion in platelets on thrombin-fibrinogen interaction and thrombin tolerance.	2007 Oct	18642704
Oral vasodilators for primary Raynaud's phenomenon.	2008 Apr 16	18425964
Roles of IL-6-gp130 Signaling in Vascular Inflammation.	2008 Aug	19936194
Estrogen potentiates constrictor prostanoid function in female rat aorta by upregulation of cyclooxygenase-2 and thromboxane pathway expression.	2008 Jun	18310519
Aspirin resistance with genetic dyslipidemia: contribution of vascular thromboxane generation.	2010 Aug	20530721

Name

Type

Language

DAZOXIBEN

Official Name

English

BENZOIC ACID, 4-(2-(1H-IMIDAZOL-1-YL)ETHOXY)-

Common Name

English

P-(2-IMIDAZOL-1-YLETHOXY)BENZOIC ACID

Common Name

English

dazoxiben [INN]

Common Name

English

4-(2-IMIDAZOL-1-YLETHOXY)BENZOIC ACID

Systematic Name

English

Code System Code Type Description

MESH

C029166