Identification

Name
Diazoxide
Accession Number
DB01119
Description

A benzothiadiazine derivative that is a peripheral vasodilator used for hypertensive emergencies. It lacks diuretic effect, apparently because it lacks a sulfonamide group.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 230.671
Monoisotopic: 229.991675875
Chemical Formula
C8H7ClN2O2S
Synonyms
  • Diazossido
  • Diazoxide
  • Diazoxido
  • Diazoxidum
External IDs
  • NSC-64198
  • NSC-76130
  • SCH 6783
  • SCH-6783
  • SRG 95213
  • SRG-95213

Pharmacology

Pharmacology
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Indication

Used parentally to treat hypertensive emergencies. Also used to treat hypoglycemia secondary to insulinoma.

Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Diazoxide is a potassium channel activator. Its mechanism of action revolves around enhancing cell membrane permeability to potassium ions. This action consequently elicits the relaxation of local smooth muscles. This switches off voltage-gated calcium ion channels which inhibits the generation of an action potential.

Mechanism of action

Diazoxide inhibits insulin release from the pancreas, by opening potassium channels in the beta cell membrane.2 Diazoxide is chemically related to thiazide diuretics but does not inhibit carbonic anhydrase and does not have chloriuretic or natriuretic activity.1 It also exhibits hypotensive activity by reducing arteriolar smooth muscle and vascular resistance.1

TargetActionsOrganism
AATP-sensitive inward rectifier potassium channel 11
inducer
Humans
ACarbonic anhydrase 1
inhibitor
Humans
ACarbonic anhydrase 2
inhibitor
Humans
USodium/potassium-transporting ATPase subunit alpha-1
other
Humans
UCalcium-activated potassium channel subunit alpha-1
other
Humans
Absorption

Readily absorbed following oral administration.

Volume of distribution
Not Available
Protein binding

Very high (more than 90%) to serum proteins.

Metabolism

Hepatic.

Route of elimination

Proglycem is extensively bound (more than 90%) to serum proteins, and is excreted in the kidneys.

Half-life

28 ±8.3 hours in normal adults.

Clearance
Not Available
Adverse Effects
Medicalerrors
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Toxicity

Oral LD50 in rat and mouse: 980 mg/kg and 444 mg/kg, respectively.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcarboseThe therapeutic efficacy of Acarbose can be increased when used in combination with Diazoxide.
AcebutololDiazoxide may increase the hypotensive activities of Acebutolol.
AceclofenacThe therapeutic efficacy of Diazoxide can be decreased when used in combination with Aceclofenac.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be increased when used in combination with Diazoxide.
AlbiglutideThe therapeutic efficacy of Albiglutide can be increased when used in combination with Diazoxide.
AlclofenacThe therapeutic efficacy of Diazoxide can be decreased when used in combination with Alclofenac.
AlfuzosinAlfuzosin may increase the hypotensive activities of Diazoxide.
AliskirenDiazoxide may increase the hypotensive activities of Aliskiren.
AlogliptinThe therapeutic efficacy of Alogliptin can be increased when used in combination with Diazoxide.
AmbrisentanDiazoxide may increase the hypotensive activities of Ambrisentan.
Interactions
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Food Interactions
No interactions found.

Products

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International/Other Brands
Eudemine (Mercury)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
HyperstatInjection300 mg/20mLIntravenousMerck Sharp & Dohme Limited1973-01-222006-07-31US flag
Hyperstat Inj 15mg/mlLiquidIntravenousSchering Plough1973-12-312003-07-14Canada flag
ProglycemCapsule100 mgOralMerck Ltd.1985-12-31Not applicableCanada flag
ProglycemSuspension50 mg/1mLOralTeva Pharmaceuticals USA, Inc.1990-09-30Not applicableUS flag
Proglycem Susp 50mg/mlSuspensionOralSchering Plough1984-12-312006-03-23Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
DiazoxideSuspension50 mg/1mLOralPar Pharmaceutical, Inc2020-07-21Not applicableUS flag
DiazoxideSuspension50 mg/1mLOralE5 Pharma, Llc2019-12-20Not applicableUS flag

Categories

ATC Codes
G01AE10 — Combinations of sulfonamidesC02DA01 — DiazoxideV03AH01 — Diazoxide
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 1,2,4-benzothiadiazine-1,1-dioxides. These are aromatic heterocyclic compounds containing a 1,2,4-benzothiadiazine ring system with two S=O bonds at the 1-position.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Thiadiazines
Sub Class
Benzothiadiazines
Direct Parent
1,2,4-benzothiadiazine-1,1-dioxides
Alternative Parents
Imidolactams / Benzenoids / Aryl chlorides / Organosulfonic acids and derivatives / Azacyclic compounds / Amidines / Organopnictogen compounds / Organochlorides / Organic oxides / Hydrocarbon derivatives
Substituents
1,2,4-benzothiadiazine-1,1-dioxide / Amidine / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzenoid / Hydrocarbon derivative / Imidolactam / Organic nitrogen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
sulfone, organochlorine compound, benzothiadiazine (CHEBI:4495)

Chemical Identifiers

UNII
O5CB12L4FN
CAS number
364-98-7
InChI Key
GDLBFKVLRPITMI-UHFFFAOYSA-N
InChI
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)
IUPAC Name
7-chloro-3-methyl-4H-1λ⁶,2,4-benzothiadiazine-1,1-dione
SMILES
CC1=NS(=O)(=O)C2=C(N1)C=CC(Cl)=C2

References

Synthesis Reference

Topliss, J.G., Sperber, N. and Rubin, A.A.; U.S. Patent 2,986,573; May 30, 1961; assigned to Schering Corporation. Topliss, J.G., Sperber, N. and Rubin, A.A.; U.S. Patent 3,345,365; October 3, 1967; assigned to Schering Corporation.

General References
  1. Koch-Weser J: Diazoxide. N Engl J Med. 1976 Jun 3;294(23):1271-3. doi: 10.1056/NEJM197606032942306. [PubMed:772431]
  2. FDA Approved Drug Products: Proglycem Diazoxide Oral Suspension [Link]
Human Metabolome Database
HMDB0015251
KEGG Drug
D00294
KEGG Compound
C06949
PubChem Compound
3019
PubChem Substance
46508027
ChemSpider
2911
BindingDB
86248
RxNav
3327
ChEBI
4495
ChEMBL
CHEMBL181
ZINC
ZINC000003872277
Therapeutic Targets Database
DAP000956
PharmGKB
PA449285
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
20J
Drugs.com
Drugs.com Drug Page
Wikipedia
Diazoxide
AHFS Codes
  • 24:08.20 — Direct Vasodilators
PDB Entries
4lv9
MSDS
Download (73 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingBasic ScienceGlucose Metabolism Disorders / Glucose, High Blood / Type 2 Diabetes Mellitus1
4CompletedPreventionType 1 Diabetes Mellitus1
4CompletedTreatmentType 1 Diabetes Mellitus1
4SuspendedPreventionHypoglycemia / Hypoglycemia Unawareness / Type 1 Diabetes Mellitus1
4WithdrawnTreatmentGastro-enteropancreatic Neuroendocrine Tumor1
3CompletedTreatmentHypothalamic-pituitary Lesions / Postsurgical craniopharyngioma1
2CompletedTreatmentBMI >30 kg/m21
2CompletedTreatmentBMI >30 kg/m2 / Hyperinsulinism1
2CompletedTreatmentHypothalamic Obesity1
2SuspendedBasic ScienceGlucose Metabolism Disorders (Including Diabetes Mellitus) / Glucose, High Blood / Type 2 Diabetes Mellitus1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Ivax Pharmaceuticals
  • Medisca Inc.
  • Teva Pharmaceutical Industries Ltd.
Dosage Forms
FormRouteStrength
PowderNot applicable1 g/1g
SuspensionOral50 mg
InjectionIntravenous300 mg/20mL
LiquidIntravenous
CapsuleOral
CapsuleOral100 mg
SuspensionOral50 mg/1mL
SuspensionOral
Prices
Unit descriptionCostUnit
Proglycem 50 mg/ml Suspension 30ml Bottle197.05USD bottle
Diazoxide powder85.07USD g
Proglycem 100 mg Capsule1.65USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)330Topliss, J.G., Sperber, N. and Rubin, A.A.; U.S. Patent 2,986,573; May 30, 1961; assigned to Schering Corporation. Topliss, J.G., Sperber, N. and Rubin, A.A.; U.S. Patent 3,345,365; October 3, 1967; assigned to Schering Corporation.
water solubility2850 mg/LNot Available
logP1.20HANSCH,C ET AL. (1995)
pKa8.74SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.552 mg/mLALOGPS
logP1.09ALOGPS
logP1ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)10.48ChemAxon
pKa (Strongest Basic)1.33ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area58.53 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity54.84 m3·mol-1ChemAxon
Polarizability20.98 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.5923
Caco-2 permeable-0.5765
P-glycoprotein substrateNon-substrate0.6817
P-glycoprotein inhibitor INon-inhibitor0.6924
P-glycoprotein inhibitor IINon-inhibitor0.6927
Renal organic cation transporterNon-inhibitor0.8107
CYP450 2C9 substrateNon-substrate0.5606
CYP450 2D6 substrateNon-substrate0.8064
CYP450 3A4 substrateNon-substrate0.5774
CYP450 1A2 substrateInhibitor0.9108
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.831
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7977
Ames testNon AMES toxic0.7888
CarcinogenicityNon-carcinogens0.8304
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.3408 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9233
hERG inhibition (predictor II)Non-inhibitor0.9271
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-0090000000-e862bca94c5672c9f532
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-0090000000-23cdf34c4eb3479d62ab
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-0590000000-b597fe9df00aeb0e5c42
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-0910000000-2dc8c72c747ff34f5534
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-1900000000-dded4e98b05043368b90
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-03di-0190000000-9f83244458c5cc11c589
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0bu3-1950000000-80f36d9e4aae5c2acf9c
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-004l-6900000000-49c0abb20e85be8d5cdc
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-004i-9200000000-044096d3b3178a811986
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-004i-9000000000-7a02d106750c03894a70
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-0a4l-0980000000-1d3e60eb1a3a4d4a314a
MS/MS Spectrum - , positiveLC-MS/MSsplash10-001i-1790000000-6ba824b6749ffd4b177d
MS/MS Spectrum - , positiveLC-MS/MSsplash10-01tc-4900000000-771b855118fab0901dba

Targets

Drugtargets
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inducer
General Function
Voltage-gated potassium channel activity
Specific Function
This receptor is controlled by G proteins. Inward rectifier potassium channels are characterized by a greater tendency to allow potassium to flow into the cell rather than out of it. Their voltage ...
Gene Name
KCNJ11
Uniprot ID
Q14654
Uniprot Name
ATP-sensitive inward rectifier potassium channel 11
Molecular Weight
43540.375 Da
References
  1. D'hahan N, Moreau C, Prost AL, Jacquet H, Alekseev AE, Terzic A, Vivaudou M: Pharmacological plasticity of cardiac ATP-sensitive potassium channels toward diazoxide revealed by ADP. Proc Natl Acad Sci U S A. 1999 Oct 12;96(21):12162-7. [PubMed:10518593]
  2. Sakura H, Trapp S, Liss B, Ashcroft FM: Altered functional properties of KATP channel conferred by a novel splice variant of SUR1. J Physiol. 1999 Dec 1;521 Pt 2:337-50. [PubMed:10581306]
  3. Shindo T, Katayama Y, Horio Y, Kurachi Y: MCC-134, a novel vascular relaxing agent, is an inverse agonist for the pancreatic-type ATP-sensitive K(+) channel. J Pharmacol Exp Ther. 2000 Jan;292(1):131-5. [PubMed:10604939]
  4. de Lonlay P, Fournet JC, Touati G, Groos MS, Martin D, Sevin C, Delagne V, Mayaud C, Chigot V, Sempoux C, Brusset MC, Laborde K, Bellane-Chantelot C, Vassault A, Rahier J, Junien C, Brunelle F, Nihoul-Fekete C, Saudubray JM, Robert JJ: Heterogeneity of persistent hyperinsulinaemic hypoglycaemia. A series of 175 cases. Eur J Pediatr. 2002 Jan;161(1):37-48. [PubMed:11808879]
  5. Russ U, Lange U, Loffler-Walz C, Hambrock A, Quast U: Binding and effect of K ATP channel openers in the absence of Mg2+. Br J Pharmacol. 2003 May;139(2):368-80. [PubMed:12770942]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
Gene Name
CA1
Uniprot ID
P00915
Uniprot Name
Carbonic anhydrase 1
Molecular Weight
28870.0 Da
References
  1. Domoki F, Bari F, Nagy K, Busija DW, Siklos L: Diazoxide prevents mitochondrial swelling and Ca2+ accumulation in CA1 pyramidal cells after cerebral ischemia in newborn pigs. Brain Res. 2004 Sep 3;1019(1-2):97-104. [PubMed:15306243]
  2. Erdemli G, Krnjevic K: Diazoxide suppresses slowly-inactivating outward and inward currents in CA1 hippocampal neurones. Neuroreport. 1993 Dec 13;5(3):249-51. [PubMed:8298083]
  3. Erdemli G, Krnjevic K: Actions of diazoxide on CA1 neurons in hippocampal slices from rats. Can J Physiol Pharmacol. 1995 May;73(5):608-18. [PubMed:7585327]
  4. Scuvee-Moreau J, Seutin V, Vrijens B, Pirotte B, De Tullio P, Massotte L, Albert A, Delarge J, Dresse A: Effect of potassium channel openers on the firing rate of hippocampal pyramidal cells and A10 dopaminergic neurons in vitro. Arch Physiol Biochem. 1997 Sep;105(5):421-8. [PubMed:9439778]
  5. Crepel V, Rovira C, Ben-Ari Y: The K+ channel opener diazoxide enhances glutamatergic currents and reduces GABAergic currents in hippocampal neurons. J Neurophysiol. 1993 Feb;69(2):494-503. [PubMed:7681475]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion in...
Gene Name
CA2
Uniprot ID
P00918
Uniprot Name
Carbonic anhydrase 2
Molecular Weight
29245.895 Da
References
  1. Munoz A, Nakazaki M, Goodman JC, Barrios R, Onetti CG, Bryan J, Aguilar-Bryan L: Ischemic preconditioning in the hippocampus of a knockout mouse lacking SUR1-based K(ATP) channels. Stroke. 2003 Jan;34(1):164-70. [PubMed:12511769]
  2. Sekine N, Ullrich S, Regazzi R, Pralong WF, Wollheim CB: Postreceptor signalling of growth hormone and prolactin and their effects in the differentiated insulin-secreting cell line, INS-1. Endocrinology. 1996 May;137(5):1841-50. [PubMed:8612523]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Other
General Function
Steroid hormone binding
Specific Function
This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates th...
Gene Name
ATP1A1
Uniprot ID
P05023
Uniprot Name
Sodium/potassium-transporting ATPase subunit alpha-1
Molecular Weight
112895.01 Da
References
  1. Lawrence CL, Rainbow RD, Davies NW, Standen NB: Effect of metabolic inhibition on glimepiride block of native and cloned cardiac sarcolemmal K(ATP) channels. Br J Pharmacol. 2002 Jul;136(5):746-52. [PubMed:12086984]
  2. Guo W, Chen N, Chen Y, Xia Q, Shen Y: Activation of Mitochondrial ATP-Sensitive Potassium Channel Contributes to Protective Effect in Prolonged Myocardial Preservation. Conf Proc IEEE Eng Med Biol Soc. 2005;4:4027-30. [PubMed:17281115]
  3. Comelli M, Metelli G, Mavelli I: Downmodulation of mitochondrial F0F1 ATP synthase by diazoxide in cardiac myoblasts: a dual effect of the drug. Am J Physiol Heart Circ Physiol. 2007 Feb;292(2):H820-9. [PubMed:17287451]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Other
General Function
Voltage-gated potassium channel activity
Specific Function
Potassium channel activated by both membrane depolarization or increase in cytosolic Ca(2+) that mediates export of K(+). It is also activated by the concentration of cytosolic Mg(2+). Its activati...
Gene Name
KCNMA1
Uniprot ID
Q12791
Uniprot Name
Calcium-activated potassium channel subunit alpha-1
Molecular Weight
137558.115 Da
References
  1. Klockner U, Trieschmann U, Isenberg G: Pharmacological modulation of calcium and potassium channels in isolated vascular smooth muscle cells. Arzneimittelforschung. 1989 Jan;39(1A):120-6. [PubMed:2541731]
  2. O'Malley D, Shanley LJ, Harvey J: Insulin inhibits rat hippocampal neurones via activation of ATP-sensitive K+ and large conductance Ca2+-activated K+ channels. Neuropharmacology. 2003 Jun;44(7):855-63. [PubMed:12726817]
  3. Zhang L, Li X, Zhou R, Xing G: Possible role of potassium channel, big K in etiology of schizophrenia. Med Hypotheses. 2006;67(1):41-3. Epub 2006 Jan 30. [PubMed:16446048]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Manganese ion binding
Specific Function
This enzyme has 2 functions: it catalyzes the production of glutamine and 4-aminobutanoate (gamma-aminobutyric acid, GABA), the latter in a pyridoxal phosphate-independent manner (By similarity). E...
Gene Name
GLUL
Uniprot ID
P15104
Uniprot Name
Glutamine synthetase
Molecular Weight
42064.15 Da
References
  1. Velloso LA, Bjork E, Ballagi AE, Funa K, Andersson A, Kampe O, Karlsson FA, Eizirik DL: Regulation of GAD expression in islets of Langerhans occurs both at the mRNA and protein level. Mol Cell Endocrinol. 1994 Jun;102(1-2):31-7. [PubMed:7926271]

Drug created on June 13, 2005 13:24 / Updated on April 11, 2021 00:58