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D9035

Sigma-Aldrich

Diazoxide

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Synonym(s):
7-Chloro-3-methyl-2H-1,2,4-benzothiadiazine 1,1-dioxide
Empirical Formula (Hill Notation):
C8H7ClN2O2S
CAS Number:
364-98-7
Molecular Weight:
230.67
EC Number:
206-668-1
MDL number:
MFCD00078578
PubChem Substance ID:
24277831
NACRES:
NA.77

form

powder

solubility

0.1 M NaOH: soluble
H2O: insoluble
methanol: soluble

originator

Schering Plough

SMILES string

CC1=Nc2ccc(Cl)cc2S(=O)(=O)N1

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)

InChI key

GDLBFKVLRPITMI-UHFFFAOYSA-N

Gene Information

human ... KCNA1(3736) , KCNJ11(3767) , KCNJ8(3764) , KCNMA1(3778)
mouse ... Kcnj1(56379) , Kcnj11(16514)
rat ... Gria1(50592) , Kcna1(24520) , Kcnj1(24521) , Kcnj11(83535) , Kcnj8(25472)

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General description

Diazoxide is a nondiuretic benzothiadiazine, which is used for the treatment of hypoglycemia, von Gierke′s disease, acute and malignant hypertension. It acts as a beta cell KATP channel opener. Diazoxide prevents the secretion of insulin.

Application

Diazoxide has been used for diazoxide infusion. It has also been used to prevent depolarization for K+-induced exocytosis.

Biochem/physiol Actions

Selective ATP-sensitive K+ channel activator in both vascular smooth muscle and pancreatic β-cells; antihypertensive.

Features and Benefits

This compound is featured on the Potassium Channels page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Schering Plough. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302 - H315 - H319 - H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Glucose-dependent granule docking limits insulin secretion and Is decreased in human type 2 diabetes
Gandasi NR, et al.
Cell Metabolism, 27(2), 470-478 (2018)
T Grimmsmann et al.
British journal of pharmacology, 123(5), 781-788 (1998-04-16)
1. The direct effects of diazoxide on mitochondrial membrane potential, Ca2+ transport, oxygen consumption and ATP generation were investigated in mouse pancreatic B-cells and rat liver mitochondria. 2. Diazoxide, at concentrations commonly used to open adenosine 5'-triphosphate (ATP)-dependent K+-channels (K(ATP)
Pharmacological Preconditioning with Diazoxide in the Experimental Hypothermic Circulatory Arrest Model
Haapanen H, et al.
The Heart Surgery Forum (2017)
Diazoxide for Lowering Insulin Levels in Breast Cancer Patients.
Fink MK and Klement RJ
Oncologist, 22(4), 491-491 (2017)
N D'hahan et al.
Proceedings of the National Academy of Sciences of the United States of America, 96(21), 12162-12167 (1999-10-16)
The pharmacological phenotype of ATP-sensitive potassium (K(ATP)) channels is defined by their tissue-specific regulatory subunit, the sulfonylurea receptor (SUR), which associates with the pore-forming channel core, Kir6.2. The potassium channel opener diazoxide has hyperglycemic and hypotensive properties that stem from
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