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

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	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
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

Primary Target	Pharmacology	Condition	Potency
Sulfonylurea receptor 1, Kir6.2 13	Opener 34		10.94 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hyperinsulinemia 2	Primary		Approved 8,429	PROGLYCEM

C_max

Value	Dose	Co-administered	Analyte	Population
45 μg/mL	2.5 mg 3 times / day steady-state, oral		DIAZOXIDE plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
345 μg × h/mL	2.5 mg 3 times / day steady-state, oral		DIAZOXIDE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
30 h	2.5 mg/kg 3 times / day multiple, oral		DIAZOXIDE plasma	Homo sapiens
14.3 h	2.5 mg 3 times / day steady-state, oral		DIAZOXIDE plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
10%	2.5 mg/kg 3 times / day multiple, oral		DIAZOXIDE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
8 mg/kg 1 times / day multiple, oral	unhealthy, adult + children	Disc. AE: Hyperosmolar (non-ketotic) coma...
8 mg/kg 1 times / day multiple, oral	unhealthy, adult	Disc. AE: Diabetic hyperosmolar coma...
8 mg/kg 1 times / day multiple, oral	unhealthy, children	Disc. AE: Cataracts...
8 mg/kg 1 times / day multiple, oral	unhealthy, children	Disc. AE: Musculoskeletal and connective tissue deformities of skull, face and buccal cavity...
15 mg/kg 1 times / day multiple, oral	unhealthy, infant + neonates	Disc. AE: Pulmonary hypertension...

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AEs

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

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
		GLUT2 4 GLUT4 2

Drug as perpetrator

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Target	Modality	Activity	Metabolite	Clinical evidence
GLUT2 8	inducer 1,573	yes
GLUT4 17	inducer 1,573	yes

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Sourcing

Sourcing

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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

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PubMed

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Title	Date	PubMed
Development and management of extrapyramidal symptoms in hypertensive patients treated with diazoxide.	1975 Mar	1114967
Opening of mitochondrial ATP-sensitive potassium channels enhances cardioplegic protection.	2001 Apr	11308175
Modulation of islet ATP content by inhibition or stimulation of the Na(+)/K(+) pump.	2001 Aug 24	11525782
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

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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
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

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Classification Tree

Code System

Code

Drugs for treatment of hypoglycemia

WHO-ATC

V03AH01

Thiazide derivatives

WHO-ATC

C02DA01

Agent Affecting Cardiovascular System

NCI_THESAURUS

C29707

Drugs for treatment of hypoglycemia

WHO-VATC

QV03AH01

Thiazide derivatives

WHO-VATC

QC02DA01

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Code System

Code

Type

Description

MERCK INDEX

m4277

PRIMARY

Merck Index

EPA CompTox

DTXSID7022914

PRIMARY

WHO INTERNATIONAL PHARMACOPEIA

DIAZOXIDE

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

PRIMARY

ECHA (EC/EINECS)

206-668-1

PRIMARY

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