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

Details

Stereochemistry ACHIRAL
Molecular Formula C8H7ClN2O2S
Molecular Weight 230.671
Optical Activity NONE
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 No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Sources: www.ncbi.nlm.nih.gov/pubmed/22056385

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
10.94 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PROGLYCEM

Approved Use

Proglycem (ORAL DIAZOXIDE) is useful in the management of hypoglycemia due to hyperinsulinism associated with the following conditions: Inoperable islet cell adenoma or carcinoma, or extrapancreatic malignancy in adults. Infants and Children: Leucine sensitivity, islet cell hyperplasia, nesidioblastosis, extrapancreatic malignancy, islet cell adenoma, or adenomatosis.

Launch Date

1976
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
45 μg/mL
2.5 mg 3 times / day steady-state, oral
dose: 2.5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
DIAZOXIDE plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
345 μg × h/mL
2.5 mg 3 times / day steady-state, oral
dose: 2.5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
DIAZOXIDE plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
14.3 h
2.5 mg 3 times / day steady-state, oral
dose: 2.5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
DIAZOXIDE plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: MALE
food status: UNKNOWN
30 h
2.5 mg/kg 3 times / day multiple, oral
dose: 2.5 mg/kg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
DIAZOXIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
10%
2.5 mg/kg 3 times / day multiple, oral
dose: 2.5 mg/kg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
DIAZOXIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
8 mg/kg 1 times / day multiple, oral
Dose: 8 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg/kg, 1 times / day
Sources:
unhealthy, adult + children
Health Status: unhealthy
Age Group: adult + children
Sources:
Disc. AE: Hyperosmolar (non-ketotic) coma...
AEs leading to
discontinuation/dose reduction:
Hyperosmolar (non-ketotic) coma
Sources:
8 mg/kg 1 times / day multiple, oral
Dose: 8 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg/kg, 1 times / day
Sources:
unhealthy, adult
Disc. AE: Diabetic hyperosmolar coma...
AEs leading to
discontinuation/dose reduction:
Diabetic hyperosmolar coma
Sources:
8 mg/kg 1 times / day multiple, oral
Dose: 8 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg/kg, 1 times / day
Sources:
unhealthy, children
Health Status: unhealthy
Age Group: children
Sources:
Disc. AE: Musculoskeletal and connective tissue deformities of skull, face and buccal cavity...
AEs leading to
discontinuation/dose reduction:
Musculoskeletal and connective tissue deformities of skull, face and buccal cavity (4 patients)
Sources:
8 mg/kg 1 times / day multiple, oral
Dose: 8 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg/kg, 1 times / day
Sources:
unhealthy, children
Health Status: unhealthy
Age Group: children
Sources:
Disc. AE: Cataracts...
AEs leading to
discontinuation/dose reduction:
Cataracts
Sources:
15 mg/kg 1 times / day multiple, oral
Dose: 15 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 15 mg/kg, 1 times / day
Sources:
unhealthy, infant + neonates
Health Status: unhealthy
Age Group: infant + neonates
Sources:
Disc. AE: Pulmonary hypertension...
AEs leading to
discontinuation/dose reduction:
Pulmonary hypertension
Sources:
AEs

AEs

AESignificanceDosePopulation
Hyperosmolar (non-ketotic) coma Disc. AE
8 mg/kg 1 times / day multiple, oral
Dose: 8 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg/kg, 1 times / day
Sources:
unhealthy, adult + children
Health Status: unhealthy
Age Group: adult + children
Sources:
Diabetic hyperosmolar coma Disc. AE
8 mg/kg 1 times / day multiple, oral
Dose: 8 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg/kg, 1 times / day
Sources:
unhealthy, adult
Musculoskeletal and connective tissue deformities of skull, face and buccal cavity 4 patients
Disc. AE
8 mg/kg 1 times / day multiple, oral
Dose: 8 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg/kg, 1 times / day
Sources:
unhealthy, children
Health Status: unhealthy
Age Group: children
Sources:
Cataracts Disc. AE
8 mg/kg 1 times / day multiple, oral
Dose: 8 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg/kg, 1 times / day
Sources:
unhealthy, children
Health Status: unhealthy
Age Group: children
Sources:
Pulmonary hypertension Disc. AE
15 mg/kg 1 times / day multiple, oral
Dose: 15 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 15 mg/kg, 1 times / day
Sources:
unhealthy, infant + neonates
Health Status: unhealthy
Age Group: infant + neonates
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes
yes
PubMed

PubMed

TitleDatePubMed
Mitochondrial ATP-sensitive potassium channels attenuate matrix Ca(2+) overload during simulated ischemia and reperfusion: possible mechanism of cardioprotection.
2001-11-09
Opening of mitochondrial K(ATP) channels attenuates the ouabain-induced calcium overload in mitochondria.
2001-11-09
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.
2001-11
The potential antidiabetic activity of some alpha-2 adrenoceptor antagonists.
2001-11
Mitochondrial K(ATP) channel as an end effector of cardioprotection during late preconditioning: triggering role of nitric oxide.
2001-11
Management of hyperinsulinemia with diazoxide in an elderly hemodialysis patient.
2001-11
Ischemic and pharmacological preconditioning in Girardi cells and C2C12 myotubes induce mitochondrial uncoupling.
2001-10-26
Glucose effects on gastric motility and tone evoked from the rat dorsal vagal complex.
2001-10-01
The KATP channel opener diazoxide protects cardiac myocytes during metabolic inhibition without causing mitochondrial depolarization or flavoprotein oxidation.
2001-10
Effect of aging on the ability of preconditioning to protect rat hearts from ischemia-reperfusion injury.
2001-10
Contribution to glucose tolerance of insulin-independent vs. insulin-dependent mechanisms in mice.
2001-10
Identification and pharmacological correction of a membrane trafficking defect associated with a mutation in the sulfonylurea receptor causing familial hyperinsulinism.
2001-09-21
Identification and properties of a novel intracellular (mitochondrial) ATP-sensitive potassium channel in brain.
2001-09-07
Incorporation of sulfonylurea into N-isopropylacrylamide as an extracellular matrix for an artificial pancreas.
2001-09
Critical timing of mitochondrial K(ATP) channel opening for enhancement of myocardial tolerance against infarction.
2001-09
[Activation of ATP-sensitive K+ channels by ADP and K+ channel openers: homology model of sulfonylurea receptor carboxyl-termini].
2001-09
Lidocaine and mexiletine inhibit mitochondrial oxidation in rat ventricular myocytes.
2001-09
Synthesis and characterization of a quinolinonic compound activating ATP-sensitive K(+) channels in endocrine and smooth muscle tissues.
2001-09
Mitochondrial K(ATP) channel opening protects a human atrial-derived cell line by a mechanism involving free radical generation.
2001-09
Diazoxide induced cardioprotection: what comes first, K(ATP) channels or reactive oxygen species?
2001-09
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.
2001-09
Hyperinsulinism and hyperammonemia syndrome: report of twelve unrelated patients.
2001-09
Hepatothermic therapy of obesity: rationale and an inventory of resources.
2001-09
Mitochondrial K(ATP) channel activation reduces anoxic injury by restoring mitochondrial membrane potential.
2001-09
Amino acids and insulin are both required to regulate assembly of the eIF4E. eIF4G complex in rat skeletal muscle.
2001-09
Effects of bezafibrate on beta-cell function of rat pancreatic islets.
2001-08-31
Modulation of islet ATP content by inhibition or stimulation of the Na(+)/K(+) pump.
2001-08-24
Inhibition of large-conductance calcium-activated potassium channel by 2-methoxyestradiol in cultured vascular endothelial (HUV-EC-C) cells.
2001-08-01
Sulfonylurea receptors inhibit the epithelial sodium channel (ENaC) by reducing surface expression.
2001-08
Acute insulin responses to leucine in children with the hyperinsulinism/hyperammonemia syndrome.
2001-08
Hyperinsulinism in short-chain L-3-hydroxyacyl-CoA dehydrogenase deficiency reveals the importance of beta-oxidation in insulin secretion.
2001-08
ATP-sensitive K+ channels and cellular actions of morphine in periaqueductal gray slices of neonatal and adult rats.
2001-08
Laparoscopic pancreatectomy for persistent hyperinsulinemic hypoglycemia of infancy.
2001-08
Downregulation of protein kinase C inhibits activation of mitochondrial K(ATP) channels by diazoxide.
2001-07-03
Effect on insulin release of compounds structurally related to the potassium-channel opener 7-chloro-3-isopropylamino-4H-1,2,4-benzothiadiazine 1,1-dioxide (BPDZ 73): introduction of heteroatoms on the 3-alkylamino side chain of the benzothiadiazine 1,1-dioxide ring.
2001-07
Intrinsic optical signals in respiratory brain stem regions of mice: neurotransmitters, neuromodulators, and metabolic stress.
2001-07
Oral agents for the treatment of type 2 diabetes mellitus: pharmacology, toxicity, and treatment.
2001-07
Glimepiride, a novel sulfonylurea, does not abolish myocardial protection afforded by either ischemic preconditioning or diazoxide.
2001-06-26
Mitochondrial ATP-sensitive potassium channels inhibit apoptosis induced by oxidative stress in cardiac cells.
2001-06-22
Role of intracellular Na(+) kinetics in preconditioned rat heart.
2001-06-08
Store-operated influx of Ca(2+) in pancreatic beta-cells exhibits graded dependence on the filling of the endoplasmic reticulum.
2001-06
Transient hyperinsulinism in an asphyxiated newborn infant with hypoglycemia.
2001-06
Restoration of Ca2+-inhibited oxidative phosphorylation in cardiac mitochondria by mitochondrial Ca2+ unloading.
2001-04
Interaction of sulfonylurea-conjugated polymer with insulinoma cell line of MIN6 and its effect on insulin secretion.
2001-04
Mitochondrial ATP-sensitive K+ channels play a role in cardioprotection by Na+-H+ exchange inhibition against ischemia/reperfusion injury.
2001-03-01
Failure to precondition pathological human myocardium.
2001-03-01
Disopyramide and its metabolite enhance insulin release from clonal pancreatic beta-cells by blocking K(ATP) channels.
2001-01
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
Patents

Sample Use Guides

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 Mon Mar 31 17:50:23 GMT 2025
Edited
by admin
on Mon Mar 31 17:50:23 GMT 2025
Record UNII
O5CB12L4FN
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
HYPERSTAT
Preferred Name English
DIAZOXIDE
EP   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
USAN   INN  
Official Name English
EUDEMINE INJECTION
Common Name English
DIAZOXIDE [EP MONOGRAPH]
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
Diazoxide [WHO-DD]
Common Name English
DIAZOXIDE [VANDF]
Common Name English
DIAZOXIDE [USP-RS]
Common Name English
DIAZOXIDE [USP MONOGRAPH]
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
SRG 95213
Code English
NSC-76130
Code English
DIAZOXIDE [WHO-IP]
Common Name English
DIAZOXIDE [USAN]
Common Name English
NSC-64198
Code English
Classification Tree Code System Code
WHO-ATC V03AH01
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
WHO-ATC C02DA01
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
NCI_THESAURUS C29707
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
WHO-VATC QV03AH01
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
WHO-VATC QC02DA01
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
FDA ORPHAN DRUG 383712
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
Code System Code Type Description
MERCK INDEX
m4277
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY Merck Index
EPA CompTox
DTXSID7022914
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
DIAZOXIDE
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
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 Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
ECHA (EC/EINECS)
206-668-1
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
MESH
D003981
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
DRUG BANK
DB01119
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
RXCUI
3327
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY RxNorm
RS_ITEM_NUM
1186000
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
DRUG CENTRAL
854
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
DAILYMED
O5CB12L4FN
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
SMS_ID
100000092606
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
CAS
364-98-7
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
PUBCHEM
3019
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
IUPHAR
2409
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
ChEMBL
CHEMBL181
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
WIKIPEDIA
DIAZOXIDE
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
NSC
64198
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
EVMPD
SUB07071MIG
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
CHEBI
4495
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
NCI_THESAURUS
C428
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
NSC
76130
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
FDA UNII
O5CB12L4FN
Created by admin on Mon Mar 31 17:50:23 GMT 2025 , Edited by admin on Mon Mar 31 17:50:23 GMT 2025
PRIMARY
Related Record Type Details
BINDER->LIGAND
BINDING
TARGET -> INHIBITOR
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC