DIAZOXIDE

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 Search

SMILES

CC1=NC2=C(C=C(Cl)C=C2)S(=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

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/017453s020lbl.pdf

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

Primary Target	Pharmacology	Condition	Potency
Sulfonylurea receptor 1, Kir6.2 13 Target ID: CHEMBL2096972 Sources: https://www.researchgate.net/publication/234093464_Diazoxide	Opener 34		10.94 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hyperinsulinemia 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/017453s020lbl.pdf	Primary		Approved 8429	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

C_max

Value	Dose	Co-administered	Analyte	Population
45 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28715810/	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

Value	Dose	Co-administered	Analyte	Population
345 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28715810/	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
30 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/017453s020lbl.pdf	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
14.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28715810/	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
10% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/017453s020lbl.pdf	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

Dose	Population	Adverse 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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/017453s020lbl.pdf	unhealthy, adult + children Health Status: unhealthy Age Group: adult + children Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/017453s020lbl.pdf	Disc. AE: Hyperosmolar (non-ketotic) coma... AEs leading to discontinuation/dose reduction: Hyperosmolar (non-ketotic) coma Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/017453s020lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/017453s020lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/017453s020lbl.pdf	Disc. AE: Diabetic hyperosmolar coma... AEs leading to discontinuation/dose reduction: Diabetic hyperosmolar coma Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/017453s020lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/017453s020lbl.pdf	unhealthy, children Health Status: unhealthy Age Group: children Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/017453s020lbl.pdf	Disc. AE: Cataracts... AEs leading to discontinuation/dose reduction: Cataracts Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/017453s020lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/017453s020lbl.pdf	unhealthy, children Health Status: unhealthy Condition: hypoglycemia hyperinsulinism Age Group: children Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/017453s020lbl.pdf	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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/017453s020lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/017453s020lbl.pdf	unhealthy, infant + neonates Health Status: unhealthy Age Group: infant + neonates Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/017453s020lbl.pdf	Disc. AE: Pulmonary hypertension... AEs leading to discontinuation/dose reduction: Pulmonary hypertension Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/017453s020lbl.pdf

AEs

AE	Significance	Dose	Population
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/017453s020lbl.pdf	unhealthy, adult + children Health Status: unhealthy Age Group: adult + children Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/017453s020lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/017453s020lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/017453s020lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/017453s020lbl.pdf	unhealthy, children Health Status: unhealthy Age Group: children Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/017453s020lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/017453s020lbl.pdf	unhealthy, children Health Status: unhealthy Condition: hypoglycemia hyperinsulinism Age Group: children Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/017453s020lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/017453s020lbl.pdf	unhealthy, infant + neonates Health Status: unhealthy Age Group: infant + neonates Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/017453s020lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
		GLUT2 4 GLUT4 2

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
GLUT2 8	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/15845921/	yes
GLUT4 17	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/14976464/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:4495	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:4495
ChemicalBook	CB8426893	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB8426893
MolPort	MolPort-003-666-772	https://www.molport.com/shop/molecule-link/MolPort-003-666-772
MolPort	MolPort-003-941-186	https://www.molport.com/shop/molecule-link/MolPort-003-941-186
ZINC	ZINC000003872277	http://zinc15.docking.org/substances/ZINC000003872277
eMolecules	1934615	https://www.emolecules.com/cgi-bin/more?vid=1934615
eMolecules	36757797	https://www.emolecules.com/cgi-bin/more?vid=36757797

PubMed

Title	Date	PubMed
Modulation of beta-cell ouabain-sensitive 86Rb+ influx (Na+/K+ pump) by D-glucose, glibenclamide or diazoxide.	2001	11467417
Overstimulation and beta-cell function.	2001 Feb	11272169
Characterization of a KATP channel-independent pathway involved in potentiation of insulin secretion by efaroxan.	2001 Feb	11272145
Hyperinsulinism of infancy: the regulated release of insulin by KATP channel-independent pathways.	2001 Feb	11272144
Defective stimulus-secretion coupling in islets of Psammomys obesus, an animal model for type 2 diabetes.	2001 Feb	11272141
Effects of glucose and amino acids on free ADP in betaHC9 insulin-secreting cells.	2001 Feb	11272139
Insulin autoimmune syndrome: the second Dutch case.	2001 Jan	11137746
Ischemic preconditioning with opening of mitochondrial adenosine triphosphate-sensitive potassium channels or Na/H exchange inhibition: which is the best protective strategy for heart transplants?	2001 Jan	11135172
Adenosine A1 receptor activation reduces reactive oxygen species and attenuates stunning in ventricular myocytes.	2001 Jan	11133228
K(ATP) channel blockers selectively interact with A(1)-adenosine receptor mediated modulation of acetylcholine release in the rat hippocampus.	2001 Jan 19	11166687
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 Jul	11480549
Diazoxide effects on hypothalamic and extra-hypothalamic NPY content in Zucker rats.	2001 Jun	11390019
Glucose-regulated pulsatile insulin release from mouse islets via the K(ATP) channel-independent pathway.	2001 Jun	11375802
Neurologic outcomes of 90 neonates and infants with persistent hyperinsulinemic hypoglycemia.	2001 Mar	11230585
Oxytocin antagonist disrupts hypotension-evoked renin secretion and other responses in conscious rats.	2001 Mar	11171655
Increased intracellular calcium is required for spreading of rat islet beta-cells on extracellular matrix.	2001 May	11334406
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	11713640
Mitochondrial K(ATP) channel as an end effector of cardioprotection during late preconditioning: triggering role of nitric oxide.	2001 Nov	11708847
Mitochondrial ATP-sensitive potassium channels attenuate matrix Ca(2+) overload during simulated ischemia and reperfusion: possible mechanism of cardioprotection.	2001 Nov 9	11701616
The KATP channel opener diazoxide protects cardiac myocytes during metabolic inhibition without causing mitochondrial depolarization or flavoprotein oxidation.	2001 Oct	11588107
Contribution to glucose tolerance of insulin-independent vs. insulin-dependent mechanisms in mice.	2001 Oct	11551845
Glucose effects on gastric motility and tone evoked from the rat dorsal vagal complex.	2001 Oct 1	11579164
Identification and properties of a novel intracellular (mitochondrial) ATP-sensitive potassium channel in brain.	2001 Sep 7	11441006

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 `Fri Dec 15 15:12:49 GMT 2023` Edited by `admin` on `Fri Dec 15 15:12:49 GMT 2023`
Record UNII	O5CB12L4FN
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIAZOXIDE

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

HYPERSTAT

Brand 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