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

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 of DAZOXIBEN

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

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

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
UK-37, 248, a novel, selective thromboxane synthetase inhibitor with platelet anti-aggregatory and anti-thrombotic activity.
1981 Jul 1-15
[(1H-imidazol-1-yl)methyl]- and [(3-pyridinyl)methyl]pyrroles as thromboxane synthetase inhibitors.
1989 Apr
The mechanism of anti-thrombotic, thrombolytic and fibrinolytic actions of camonagrel--a new thromboxane synthase inhibitor.
1995
Prostaglandin endoperoxides and thromboxane A2 activate the same receptor isoforms in human platelets.
2002 Jan
Cyclooxygenase contracting factors and altered pulmonary vascular responses in chronically hypoxic newborn pigs.
2002 Jan
Mechanisms involved in agonist-induced hyperaggregability of platelets from normal pregnancy.
2002 Jan-Feb
Sexual dimorphism in prostanoid-potentiated vascular contraction: roles of endothelium and ovarian steroids.
2002 Nov
Chronic AT(1) receptor blockade alters mechanisms mediating responses to hypoxia in rat skeletal muscle resistance arteries.
2004 Aug
Role of platelet microparticles in the production of thromboxane by rabbit pulmonary artery.
2004 Feb
Role of endothelin-1 and thromboxane A2 in the pulmonary hypertension induced by heparin-protamine interaction in anesthetized dogs.
2004 Jan
BK2 but not BK1 receptors mediating contractile response in human umbilical arteries: role of thromboxane A2.
2004 May
Attenuation of lipopolysaccharide-induced hyperreactivity of human internal mammary arteries by melatonin.
2004 Sep
Redirection of eicosanoid metabolism in mPGES-1-deficient macrophages.
2005 Apr 29
The calcium ionophore A23187 induces endothelium-dependent contractions in femoral arteries from rats with streptozotocin-induced diabetes.
2007 Mar
Effect of inhibitors of arachidonic acid conversion in platelets on thrombin-fibrinogen interaction and thrombin tolerance.
2007 Oct
Oral vasodilators for primary Raynaud's phenomenon.
2008 Apr 16
Roles of IL-6-gp130 Signaling in Vascular Inflammation.
2008 Aug
Estrogen potentiates constrictor prostanoid function in female rat aorta by upregulation of cyclooxygenase-2 and thromboxane pathway expression.
2008 Jun
Aspirin resistance with genetic dyslipidemia: contribution of vascular thromboxane generation.
2010 Aug
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:36:28 GMT 2023
Edited
by admin
on Fri Dec 15 16:36:28 GMT 2023
Record UNII
09ZFC7974Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DAZOXIBEN
INN  
INN  
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
Created by admin on Fri Dec 15 16:36:28 GMT 2023 , Edited by admin on Fri Dec 15 16:36:28 GMT 2023
PRIMARY
EVMPD
SUB06925MIG
Created by admin on Fri Dec 15 16:36:28 GMT 2023 , Edited by admin on Fri Dec 15 16:36:28 GMT 2023
PRIMARY
NCI_THESAURUS
C171920
Created by admin on Fri Dec 15 16:36:28 GMT 2023 , Edited by admin on Fri Dec 15 16:36:28 GMT 2023
PRIMARY
PUBCHEM
53001
Created by admin on Fri Dec 15 16:36:28 GMT 2023 , Edited by admin on Fri Dec 15 16:36:28 GMT 2023
PRIMARY
DRUG BANK
DB03052
Created by admin on Fri Dec 15 16:36:28 GMT 2023 , Edited by admin on Fri Dec 15 16:36:28 GMT 2023
PRIMARY
SMS_ID
100000083448
Created by admin on Fri Dec 15 16:36:28 GMT 2023 , Edited by admin on Fri Dec 15 16:36:28 GMT 2023
PRIMARY
CAS
78218-09-4
Created by admin on Fri Dec 15 16:36:28 GMT 2023 , Edited by admin on Fri Dec 15 16:36:28 GMT 2023
PRIMARY
WIKIPEDIA
DAZOXIBEN
Created by admin on Fri Dec 15 16:36:28 GMT 2023 , Edited by admin on Fri Dec 15 16:36:28 GMT 2023
PRIMARY
EPA CompTox
DTXSID9045639
Created by admin on Fri Dec 15 16:36:28 GMT 2023 , Edited by admin on Fri Dec 15 16:36:28 GMT 2023
PRIMARY
FDA UNII
09ZFC7974Q
Created by admin on Fri Dec 15 16:36:28 GMT 2023 , Edited by admin on Fri Dec 15 16:36:28 GMT 2023
PRIMARY
INN
5130
Created by admin on Fri Dec 15 16:36:28 GMT 2023 , Edited by admin on Fri Dec 15 16:36:28 GMT 2023
PRIMARY
ChEMBL
CHEMBL267473
Created by admin on Fri Dec 15 16:36:28 GMT 2023 , Edited by admin on Fri Dec 15 16:36:28 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY