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Details

Stereochemistry ACHIRAL
Molecular Formula C8H7ClN2O2S
Molecular Weight 230.671
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIAZOXIDE

SMILES

CC1=NC2=CC=C(Cl)C=C2S(=O)(=O)N1

InChI

InChIKey=GDLBFKVLRPITMI-UHFFFAOYSA-N
InChI=1S/C8H7ClN2O2S/c1-5-10-7-3-2-6(9)4-8(7)14(12,13)11-5/h2-4H,1H3,(H,10,11)

HIDE SMILES / InChI

Molecular Formula C8H7ClN2O2S
Molecular Weight 230.671
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Diazoxide is a drug which was approved by FDA for the treatment of secondary hyperinsulinemia. The drug exerts its action by binding to SUR1 subunit of ATP-sensitive potassium channel that leads to the channel opening.

CNS Activity

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
10.94 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PROGLYCEM
PubMed

PubMed

TitleDatePubMed
Modulation of beta-cell ouabain-sensitive 86Rb+ influx (Na+/K+ pump) by D-glucose, glibenclamide or diazoxide.
2001
Intracellular potassium and chloride channels: an update.
2001
Mitochondrial ATP-sensitive potassium channel plays a dominant role in ischemic preconditioning of rabbit heart.
2001
Restoration of Ca2+-inhibited oxidative phosphorylation in cardiac mitochondria by mitochondrial Ca2+ unloading.
2001 Apr
Interaction of sulfonylurea-conjugated polymer with insulinoma cell line of MIN6 and its effect on insulin secretion.
2001 Apr
Sulfonylurea receptors inhibit the epithelial sodium channel (ENaC) by reducing surface expression.
2001 Aug
Acute insulin responses to leucine in children with the hyperinsulinism/hyperammonemia syndrome.
2001 Aug
ATP-sensitive K+ channels and cellular actions of morphine in periaqueductal gray slices of neonatal and adult rats.
2001 Aug
Laparoscopic pancreatectomy for persistent hyperinsulinemic hypoglycemia of infancy.
2001 Aug
Inhibition of large-conductance calcium-activated potassium channel by 2-methoxyestradiol in cultured vascular endothelial (HUV-EC-C) cells.
2001 Aug 1
Modulation of islet ATP content by inhibition or stimulation of the Na(+)/K(+) pump.
2001 Aug 24
Effects of bezafibrate on beta-cell function of rat pancreatic islets.
2001 Aug 31
Intrinsic optical signals in respiratory brain stem regions of mice: neurotransmitters, neuromodulators, and metabolic stress.
2001 Jul
Oral agents for the treatment of type 2 diabetes mellitus: pharmacology, toxicity, and treatment.
2001 Jul
Distinct effect of diazoxide on insulin secretion stimulated by protein kinase A and protein kinase C in rat pancreatic islets.
2001 Jul
Downregulation of protein kinase C inhibits activation of mitochondrial K(ATP) channels by diazoxide.
2001 Jul 3
Increased calcium vulnerability of senescent cardiac mitochondria: protective role for a mitochondrial potassium channel opener.
2001 Jul 31
Transient hyperinsulinism in an asphyxiated newborn infant with hypoglycemia.
2001 Jun
Diazoxide effects on hypothalamic and extra-hypothalamic NPY content in Zucker rats.
2001 Jun
Glucose-regulated pulsatile insulin release from mouse islets via the K(ATP) channel-independent pathway.
2001 Jun
Mitochondrial ATP-sensitive potassium channels inhibit apoptosis induced by oxidative stress in cardiac cells.
2001 Jun 22
Glimepiride, a novel sulfonylurea, does not abolish myocardial protection afforded by either ischemic preconditioning or diazoxide.
2001 Jun 26
Role of intracellular Na(+) kinetics in preconditioned rat heart.
2001 Jun 8
Mitochondrial ATP-sensitive K+ channels play a role in cardioprotection by Na+-H+ exchange inhibition against ischemia/reperfusion injury.
2001 Mar 1
Failure to precondition pathological human myocardium.
2001 Mar 1
Mitochondrial ATP-sensitive channel opener does not induce vascular preconditioning, but potentiates the effect of a preconditioning ischemia on coronary reactive hyperemia in the anesthetized goat.
2001 Nov
The potential antidiabetic activity of some alpha-2 adrenoceptor antagonists.
2001 Nov
Mitochondrial K(ATP) channel as an end effector of cardioprotection during late preconditioning: triggering role of nitric oxide.
2001 Nov
Management of hyperinsulinemia with diazoxide in an elderly hemodialysis patient.
2001 Nov
Mitochondrial ATP-sensitive potassium channels attenuate matrix Ca(2+) overload during simulated ischemia and reperfusion: possible mechanism of cardioprotection.
2001 Nov 9
Opening of mitochondrial K(ATP) channels attenuates the ouabain-induced calcium overload in mitochondria.
2001 Nov 9
The KATP channel opener diazoxide protects cardiac myocytes during metabolic inhibition without causing mitochondrial depolarization or flavoprotein oxidation.
2001 Oct
Effect of aging on the ability of preconditioning to protect rat hearts from ischemia-reperfusion injury.
2001 Oct
Contribution to glucose tolerance of insulin-independent vs. insulin-dependent mechanisms in mice.
2001 Oct
Glucose effects on gastric motility and tone evoked from the rat dorsal vagal complex.
2001 Oct 1
Ischemic and pharmacological preconditioning in Girardi cells and C2C12 myotubes induce mitochondrial uncoupling.
2001 Oct 26
Incorporation of sulfonylurea into N-isopropylacrylamide as an extracellular matrix for an artificial pancreas.
2001 Sep
Critical timing of mitochondrial K(ATP) channel opening for enhancement of myocardial tolerance against infarction.
2001 Sep
[Activation of ATP-sensitive K+ channels by ADP and K+ channel openers: homology model of sulfonylurea receptor carboxyl-termini].
2001 Sep
Lidocaine and mexiletine inhibit mitochondrial oxidation in rat ventricular myocytes.
2001 Sep
Synthesis and characterization of a quinolinonic compound activating ATP-sensitive K(+) channels in endocrine and smooth muscle tissues.
2001 Sep
Mitochondrial K(ATP) channel opening protects a human atrial-derived cell line by a mechanism involving free radical generation.
2001 Sep
Diazoxide induced cardioprotection: what comes first, K(ATP) channels or reactive oxygen species?
2001 Sep
Contribution of both the sarcolemmal K(ATP) and mitochondrial K(ATP) channels to infarct size limitation by K(ATP) channel openers: differences from preconditioning in the role of sarcolemmal K(ATP) channels.
2001 Sep
Hyperinsulinism and hyperammonemia syndrome: report of twelve unrelated patients.
2001 Sep
Hepatothermic therapy of obesity: rationale and an inventory of resources.
2001 Sep
Mitochondrial K(ATP) channel activation reduces anoxic injury by restoring mitochondrial membrane potential.
2001 Sep
Amino acids and insulin are both required to regulate assembly of the eIF4E. eIF4G complex in rat skeletal muscle.
2001 Sep
Identification and pharmacological correction of a membrane trafficking defect associated with a mutation in the sulfonylurea receptor causing familial hyperinsulinism.
2001 Sep 21
Identification and properties of a novel intracellular (mitochondrial) ATP-sensitive potassium channel in brain.
2001 Sep 7
Patents

Sample Use Guides

In Vivo Use Guide
Adults and children: The usual daily dosage is 3 to 8 mg/kg, divided into two or three equal doses every 8 or 12 hours. Infants and newborns: The usual daily dosage is 8 to 15 mg/kg divided into two or three equal doses every 8 to 12 hours. An appropriate starting dosage is 10 mg/kg/day, divided into three equal doses every 8 hours.
Route of Administration: Oral
In Vitro Use Guide
Diazoxide inhibited glucagon secretion in rat pancreas at concentration of 325 uM.
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:40:11 UTC 2019
Edited
by admin
on Tue Oct 22 00:40:11 UTC 2019
Record UNII
O5CB12L4FN
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIAZOXIDE
EP   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
USAN   INN  
Official Name English
DIAZOXIDE [EP]
Common Name English
EUDEMINE INJECTION
Common Name English
7-CHLORO-3-METHYL-2H-1,2,4-BENZOTHIADIAZINE 1,1-DIOXIDE
Systematic Name English
DIAZOXIDE [MI]
Common Name English
SCH-6783
Code English
DIAZOXIDE [ORANGE BOOK]
Common Name English
SCH 6783
Code English
HYPERSTAT
Brand Name English
DIAZOXIDE [VANDF]
Common Name English
DIAZOXIDE [USP-RS]
Common Name English
2H-1,2,4-BENZOTHIADIAZINE, 7-CHLORO-3-METHYL-, 1,1-DIOXIDE
Systematic Name English
HYPERTONALUM
Common Name English
DIAZOXIDE [MART.]
Common Name English
DIAZOXIDE [JAN]
Common Name English
PROGLYCEM
Brand Name English
DIAZOXIDE [INN]
Common Name English
DIAZOXIDUM [WHO-IP LATIN]
Common Name English
SRG-95213
Code English
DIAZOXIDE [WHO-DD]
Common Name English
SRG 95213
Code English
NSC-76130
Code English
DIAZOXIDE [WHO-IP]
Common Name English
DIAZOXIDE [USAN]
Common Name English
NSC-64198
Code English
DIAZOXIDE [USP]
Common Name English
Classification Tree Code System Code
WHO-ATC V03AH01
Created by admin on Tue Oct 22 00:40:11 UTC 2019 , Edited by admin on Tue Oct 22 00:40:11 UTC 2019
WHO-ATC C02DA01
Created by admin on Tue Oct 22 00:40:11 UTC 2019 , Edited by admin on Tue Oct 22 00:40:11 UTC 2019
NCI_THESAURUS C29707
Created by admin on Tue Oct 22 00:40:11 UTC 2019 , Edited by admin on Tue Oct 22 00:40:11 UTC 2019
WHO-VATC QV03AH01
Created by admin on Tue Oct 22 00:40:11 UTC 2019 , Edited by admin on Tue Oct 22 00:40:11 UTC 2019
WHO-VATC QC02DA01
Created by admin on Tue Oct 22 00:40:11 UTC 2019 , Edited by admin on Tue Oct 22 00:40:11 UTC 2019
FDA ORPHAN DRUG 383712
Created by admin on Tue Oct 22 00:40:11 UTC 2019 , Edited by admin on Tue Oct 22 00:40:11 UTC 2019
Code System Code Type Description
MERCK INDEX
M4277
Created by admin on Tue Oct 22 00:40:11 UTC 2019 , Edited by admin on Tue Oct 22 00:40:11 UTC 2019
PRIMARY Merck Index
EPA CompTox
364-98-7
Created by admin on Tue Oct 22 00:40:11 UTC 2019 , Edited by admin on Tue Oct 22 00:40:11 UTC 2019
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
DIAZOXIDE
Created by admin on Tue Oct 22 00:40:11 UTC 2019 , Edited by admin on Tue Oct 22 00:40:11 UTC 2019
PRIMARY Description: A white, or almost white, crystalline powder; odourless. Solubility: Practically insoluble in water and ether R; freely soluble in dimethylformamide R; slightly soluble in ethanol (~750 g/l) TS. Category: Antihypertensive. Storage: Diazoxide should be kept in a well-closed container. Definition: Diazoxide contains not less than 98.0% and not more than 101.0% of C8H7ClN2O2S, calculated with reference to thedried substance.
INN
1294
Created by admin on Tue Oct 22 00:40:11 UTC 2019 , Edited by admin on Tue Oct 22 00:40:11 UTC 2019
PRIMARY
ECHA (EC/EINECS)
206-668-1
Created by admin on Tue Oct 22 00:40:11 UTC 2019 , Edited by admin on Tue Oct 22 00:40:11 UTC 2019
PRIMARY
MESH
D003981
Created by admin on Tue Oct 22 00:40:11 UTC 2019 , Edited by admin on Tue Oct 22 00:40:11 UTC 2019
PRIMARY
DRUG BANK
DB01119
Created by admin on Tue Oct 22 00:40:11 UTC 2019 , Edited by admin on Tue Oct 22 00:40:11 UTC 2019
PRIMARY
RXCUI
3327
Created by admin on Tue Oct 22 00:40:11 UTC 2019 , Edited by admin on Tue Oct 22 00:40:11 UTC 2019
PRIMARY RxNorm
CAS
364-98-7
Created by admin on Tue Oct 22 00:40:11 UTC 2019 , Edited by admin on Tue Oct 22 00:40:11 UTC 2019
PRIMARY
PUBCHEM
3019
Created by admin on Tue Oct 22 00:40:11 UTC 2019 , Edited by admin on Tue Oct 22 00:40:11 UTC 2019
PRIMARY
IUPHAR
2409
Created by admin on Tue Oct 22 00:40:11 UTC 2019 , Edited by admin on Tue Oct 22 00:40:11 UTC 2019
PRIMARY
ChEMBL
CHEMBL181
Created by admin on Tue Oct 22 00:40:11 UTC 2019 , Edited by admin on Tue Oct 22 00:40:11 UTC 2019
PRIMARY
WIKIPEDIA
DIAZOXIDE
Created by admin on Tue Oct 22 00:40:11 UTC 2019 , Edited by admin on Tue Oct 22 00:40:11 UTC 2019
PRIMARY
EVMPD
SUB07071MIG
Created by admin on Tue Oct 22 00:40:11 UTC 2019 , Edited by admin on Tue Oct 22 00:40:11 UTC 2019
PRIMARY
NCI_THESAURUS
C428
Created by admin on Tue Oct 22 00:40:11 UTC 2019 , Edited by admin on Tue Oct 22 00:40:11 UTC 2019
PRIMARY
Related Record Type Details
BINDER->LIGAND
BINDING
TARGET -> INHIBITOR
TARGET -> INHIBITOR
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC