U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C12H12N2O3.ClH
Molecular Weight 268.696
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DAZOXIBEN HYDROCHLORIDE

SMILES

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

InChI

InChIKey=PVKDFUXBDJPRGU-UHFFFAOYSA-N
InChI=1S/C12H12N2O3.ClH/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);1H

HIDE SMILES / InChI

Molecular Formula C12H12N2O3
Molecular Weight 232.2353
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

PubMed

TitleDatePubMed
Aspirin resistance with genetic dyslipidemia: contribution of vascular thromboxane generation.
2010-08
Roles of IL-6-gp130 Signaling in Vascular Inflammation.
2008-08
Estrogen potentiates constrictor prostanoid function in female rat aorta by upregulation of cyclooxygenase-2 and thromboxane pathway expression.
2008-06
Oral vasodilators for primary Raynaud's phenomenon.
2008-04-16
Effect of inhibitors of arachidonic acid conversion in platelets on thrombin-fibrinogen interaction and thrombin tolerance.
2007-10
The calcium ionophore A23187 induces endothelium-dependent contractions in femoral arteries from rats with streptozotocin-induced diabetes.
2007-03
Mechanisms underlying ATP-induced endothelium-dependent contractions in the SHR aorta.
2007-02-05
In SHR aorta, calcium ionophore A-23187 releases prostacyclin and thromboxane A2 as endothelium-derived contracting factors.
2006-11
Acetylcholine-induced endothelium-dependent contractions in the SHR aorta: the Janus face of prostacyclin.
2005-11
Redirection of eicosanoid metabolism in mPGES-1-deficient macrophages.
2005-04-29
Attenuation of lipopolysaccharide-induced hyperreactivity of human internal mammary arteries by melatonin.
2004-09
Chronic AT(1) receptor blockade alters mechanisms mediating responses to hypoxia in rat skeletal muscle resistance arteries.
2004-08
BK2 but not BK1 receptors mediating contractile response in human umbilical arteries: role of thromboxane A2.
2004-05
Role of platelet microparticles in the production of thromboxane by rabbit pulmonary artery.
2004-02
Role of endothelin-1 and thromboxane A2 in the pulmonary hypertension induced by heparin-protamine interaction in anesthetized dogs.
2004-01
Effects of camonagrel, a selective inhibitor of platelet thromboxane synthase, on the platelet-subendothelium interaction.
2003-09
Study of the mechanisms involved in the bradykinin-induced contraction of the pig iris sphincter muscle in vitro.
2003-01-01
Effects of the selective inhibition of platelet thromboxane synthesis on the platelet-subendothelium interaction.
2002-12
Sexual dimorphism in prostanoid-potentiated vascular contraction: roles of endothelium and ovarian steroids.
2002-11
Role of contaminating platelets in thromboxane synthesis in primary cultures of human umbilical vein endothelial cells.
2002-09
Mechanisms involved in agonist-induced hyperaggregability of platelets from normal pregnancy.
2002-01-26
Prostaglandin endoperoxides and thromboxane A2 activate the same receptor isoforms in human platelets.
2002-01
Cyclooxygenase contracting factors and altered pulmonary vascular responses in chronically hypoxic newborn pigs.
2002-01
The mechanism of anti-thrombotic, thrombolytic and fibrinolytic actions of camonagrel--a new thromboxane synthase inhibitor.
1995
[(1H-imidazol-1-yl)methyl]- and [(3-pyridinyl)methyl]pyrroles as thromboxane synthetase inhibitors.
1989-04
UK-37, 248, a novel, selective thromboxane synthetase inhibitor with platelet anti-aggregatory and anti-thrombotic activity.
1981-07-01
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:34:00 GMT 2025
Edited
by admin
on Mon Mar 31 17:34:00 GMT 2025
Record UNII
G5AI939LWF
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DAZOXIBEN HYDROCHLORIDE
USAN  
USAN  
Official Name English
UK-37,248-01
Preferred Name English
DAZOXIBEN HYDROCHLORIDE [USAN]
Common Name English
UK-37248-01
Code English
BENZOIC ACID, 4-(2-(1H-IMIDAZOL-1-YL)ETHOXY)-, MONOHYDROCHLORIDE
Common Name English
DAZOXIBEN HCL
Common Name English
P-(2-IMIDAZOL-1-YLETHOXY)BENZOIC ACID MONOHYDROCHLORIDE
Common Name English
Code System Code Type Description
SMS_ID
300000055413
Created by admin on Mon Mar 31 17:34:00 GMT 2025 , Edited by admin on Mon Mar 31 17:34:00 GMT 2025
PRIMARY
CAS
74226-22-5
Created by admin on Mon Mar 31 17:34:00 GMT 2025 , Edited by admin on Mon Mar 31 17:34:00 GMT 2025
PRIMARY
EPA CompTox
DTXSID40225215
Created by admin on Mon Mar 31 17:34:00 GMT 2025 , Edited by admin on Mon Mar 31 17:34:00 GMT 2025
PRIMARY
PUBCHEM
53000
Created by admin on Mon Mar 31 17:34:00 GMT 2025 , Edited by admin on Mon Mar 31 17:34:00 GMT 2025
PRIMARY
NCI_THESAURUS
C169879
Created by admin on Mon Mar 31 17:34:00 GMT 2025 , Edited by admin on Mon Mar 31 17:34:00 GMT 2025
PRIMARY
ChEMBL
CHEMBL267473
Created by admin on Mon Mar 31 17:34:00 GMT 2025 , Edited by admin on Mon Mar 31 17:34:00 GMT 2025
PRIMARY
FDA UNII
G5AI939LWF
Created by admin on Mon Mar 31 17:34:00 GMT 2025 , Edited by admin on Mon Mar 31 17:34:00 GMT 2025
PRIMARY
DRUG BANK
DBSALT002937
Created by admin on Mon Mar 31 17:34:00 GMT 2025 , Edited by admin on Mon Mar 31 17:34:00 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY