Diazoxide Choline

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H6ClN2O2S.C5H14NO
Molecular Weight	333.834
Optical Activity	NONE
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[N+](C)(C)CCO.CC1=NC2=CC=C(Cl)C=C2S(=O)(=O)[N-]1

InChI

InChIKey=YLLWQNAEYILHLV-UHFFFAOYSA-N

InChI=1S/C8H6ClN2O2S.C5H14NO/c1-5-10-7-3-2-6(9)4-8(7)14(12,13)11-5;1-6(2,3)4-5-7/h2-4H,1H3;7H,4-5H2,1-3H3/q-1;+1

HIDE SMILES / InChI

Molecular Formula	C5H13NO
Molecular Weight	103.1628
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	NONE

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 8583	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
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
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

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: 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
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
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
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 Age Group: children 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
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 5

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
GLUT2 8	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/15845921/	yes
GLUT4 20	inducer 1966 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
eMolecules	1934615	https://www.emolecules.com/cgi-bin/more?vid=1934615
eMolecules	36757797	https://www.emolecules.com/cgi-bin/more?vid=36757797
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

PubMed

Title	Date	PubMed
Mitochondrial ATP-sensitive potassium channels attenuate matrix Ca(2+) overload during simulated ischemia and reperfusion: possible mechanism of cardioprotection.	2001-11-09	11701616
Opening of mitochondrial K(ATP) channels attenuates the ouabain-induced calcium overload in mitochondria.	2001-11-09	11701611
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	11713640
The potential antidiabetic activity of some alpha-2 adrenoceptor antagonists.	2001-11	11712871
Mitochondrial K(ATP) channel as an end effector of cardioprotection during late preconditioning: triggering role of nitric oxide.	2001-11	11708847
Management of hyperinsulinemia with diazoxide in an elderly hemodialysis patient.	2001-11	11598399
Ischemic and pharmacological preconditioning in Girardi cells and C2C12 myotubes induce mitochondrial uncoupling.	2001-10-26	11679408
Glucose effects on gastric motility and tone evoked from the rat dorsal vagal complex.	2001-10-01	11579164
The KATP channel opener diazoxide protects cardiac myocytes during metabolic inhibition without causing mitochondrial depolarization or flavoprotein oxidation.	2001-10	11588107
Effect of aging on the ability of preconditioning to protect rat hearts from ischemia-reperfusion injury.	2001-10	11557553
Contribution to glucose tolerance of insulin-independent vs. insulin-dependent mechanisms in mice.	2001-10	11551845
Identification and pharmacological correction of a membrane trafficking defect associated with a mutation in the sulfonylurea receptor causing familial hyperinsulinism.	2001-09-21	11457841
Identification and properties of a novel intracellular (mitochondrial) ATP-sensitive potassium channel in brain.	2001-09-07	11441006
Incorporation of sulfonylurea into N-isopropylacrylamide as an extracellular matrix for an artificial pancreas.	2001-09	11676014
Critical timing of mitochondrial K(ATP) channel opening for enhancement of myocardial tolerance against infarction.	2001-09	11605991
[Activation of ATP-sensitive K+ channels by ADP and K+ channel openers: homology model of sulfonylurea receptor carboxyl-termini].	2001-09	11577458
Lidocaine and mexiletine inhibit mitochondrial oxidation in rat ventricular myocytes.	2001-09	11575552
Synthesis and characterization of a quinolinonic compound activating ATP-sensitive K(+) channels in endocrine and smooth muscle tissues.	2001-09	11564656
Mitochondrial K(ATP) channel opening protects a human atrial-derived cell line by a mechanism involving free radical generation.	2001-09	11530102
Diazoxide induced cardioprotection: what comes first, K(ATP) channels or reactive oxygen species?	2001-09	11530096
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	11521165
Hyperinsulinism and hyperammonemia syndrome: report of twelve unrelated patients.	2001-09	11518822
Hepatothermic therapy of obesity: rationale and an inventory of resources.	2001-09	11516225
Mitochondrial K(ATP) channel activation reduces anoxic injury by restoring mitochondrial membrane potential.	2001-09	11514300
Amino acids and insulin are both required to regulate assembly of the eIF4E. eIF4G complex in rat skeletal muscle.	2001-09	11500312
Effects of bezafibrate on beta-cell function of rat pancreatic islets.	2001-08-31	11527545
Modulation of islet ATP content by inhibition or stimulation of the Na(+)/K(+) pump.	2001-08-24	11525782
Inhibition of large-conductance calcium-activated potassium channel by 2-methoxyestradiol in cultured vascular endothelial (HUV-EC-C) cells.	2001-08-01	11547343
Sulfonylurea receptors inhibit the epithelial sodium channel (ENaC) by reducing surface expression.	2001-08	11512032
Acute insulin responses to leucine in children with the hyperinsulinism/hyperammonemia syndrome.	2001-08	11502802
Hyperinsulinism in short-chain L-3-hydroxyacyl-CoA dehydrogenase deficiency reveals the importance of beta-oxidation in insulin secretion.	2001-08	11489939
ATP-sensitive K+ channels and cellular actions of morphine in periaqueductal gray slices of neonatal and adult rats.	2001-08	11454910
Laparoscopic pancreatectomy for persistent hyperinsulinemic hypoglycemia of infancy.	2001-08	11443431
Downregulation of protein kinase C inhibits activation of mitochondrial K(ATP) channels by diazoxide.	2001-07-03	11435343
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	11480549
Intrinsic optical signals in respiratory brain stem regions of mice: neurotransmitters, neuromodulators, and metabolic stress.	2001-07	11431521
Oral agents for the treatment of type 2 diabetes mellitus: pharmacology, toxicity, and treatment.	2001-07	11423816
Glimepiride, a novel sulfonylurea, does not abolish myocardial protection afforded by either ischemic preconditioning or diazoxide.	2001-06-26	11425777
Mitochondrial ATP-sensitive potassium channels inhibit apoptosis induced by oxidative stress in cardiac cells.	2001-06-22	11420303
Role of intracellular Na(+) kinetics in preconditioned rat heart.	2001-06-08	11397784
Store-operated influx of Ca(2+) in pancreatic beta-cells exhibits graded dependence on the filling of the endoplasmic reticulum.	2001-06	11493653
Transient hyperinsulinism in an asphyxiated newborn infant with hypoglycemia.	2001-06	11444360
Restoration of Ca2+-inhibited oxidative phosphorylation in cardiac mitochondria by mitochondrial Ca2+ unloading.	2001-04	11451373
Interaction of sulfonylurea-conjugated polymer with insulinoma cell line of MIN6 and its effect on insulin secretion.	2001-04	11426400
Mitochondrial ATP-sensitive K+ channels play a role in cardioprotection by Na+-H+ exchange inhibition against ischemia/reperfusion injury.	2001-03-01	11693777
Failure to precondition pathological human myocardium.	2001-03-01	11693741
Disopyramide and its metabolite enhance insulin release from clonal pancreatic beta-cells by blocking K(ATP) channels.	2001-01	11504161
Modulation of beta-cell ouabain-sensitive 86Rb+ influx (Na+/K+ pump) by D-glucose, glibenclamide or diazoxide.	2001	11467417
Intracellular potassium and chloride channels: an update.	2001	11440163
Mitochondrial ATP-sensitive potassium channel plays a dominant role in ischemic preconditioning of rabbit heart.	2001	11399869

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 `Mon Mar 31 18:34:16 GMT 2025` Edited by `admin` on `Mon Mar 31 18:34:16 GMT 2025`
Record UNII	2U8NRZ7P8L
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIAZOXIDE CHOLINE [USAN]

Preferred Name

English

Diazoxide Choline

Official Name

English

Ethanaminium, 2-hydroxy-N,N,N-trimethyl-, compd. with 7-chloro-3-methyl-2H-1,2,4-benzothiadiazine dioxide (1:1)

Systematic Name

English

2-Hydroxy-N,N,N-trimethylethan-1-aminium 7-chloro-3-methylbenzo[e][1,2,4]thiadiazin-2-ide 1,1-dioxide

Systematic Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

428214