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D9035

Sigma-Aldrich

Diazoxide

≥98% (TLC), powder, ATP-sensitive K⁺ channel activator

Synonym(s):

7-Chloro-3-methyl-2H-1,2,4-benzothiadiazine 1,1-dioxide

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About This Item

Empirical Formula (Hill Notation):
C8H7ClN2O2S
CAS Number:
364-98-7
Molecular Weight:
230.67
EC Number:
206-668-1
MDL number:
MFCD00078578
UNSPSC Code:
12352119
PubChem Substance ID:
24277831
NACRES:
NA.77

product name

Diazoxide,

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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)
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)
Aharon Helman et al.
Cell metabolism, 31(5), 1004-1016 (2020-05-07)
A drastic transition at birth, from constant maternal nutrient supply in utero to intermittent postnatal feeding, requires changes in the metabolic system of the neonate. Despite their central role in metabolic homeostasis, little is known about how pancreatic β cells
Hiromi Nakai-Shimoda et al.
iScience, 25(1), 103609-103609 (2022-01-11)
Glucose-responsive ATP-sensitive potassium channels (KATP) are expressed in a variety of tissues including nervous systems. The depolarization of the membrane potential induced by glucose may lead to hyperexcitability of neurons and induce excitotoxicity. However, the roles of KATP in the
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