Diazoxide
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
Structure for Diazoxide (DB01119)
- 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
- Indication
Used parentally to treat hypertensive emergencies. Also used to treat hypoglycemia secondary to insulinoma.
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- 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
Target Actions Organism AATP-sensitive inward rectifier potassium channel 11 inducerHumans ACarbonic anhydrase 1 inhibitorHumans ACarbonic anhydrase 2 inhibitorHumans USodium/potassium-transporting ATPase subunit alpha-1 otherHumans UCalcium-activated potassium channel subunit alpha-1 otherHumans - 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
Learn about our commercial Adverse Effects data.
Learn More- 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.
Drug Interaction Unlock Additional DataAbacavir Diazoxide may increase the excretion rate of Abacavir which could result in a lower serum level and potentially a reduction in efficacy. Acarbose The therapeutic efficacy of Acarbose can be increased when used in combination with Diazoxide. Acebutolol Diazoxide may increase the hypotensive activities of Acebutolol. Aceclofenac The therapeutic efficacy of Diazoxide can be decreased when used in combination with Aceclofenac. Acemetacin The therapeutic efficacy of Diazoxide can be decreased when used in combination with Acemetacin. Acetaminophen Diazoxide may increase the excretion rate of Acetaminophen which could result in a lower serum level and potentially a reduction in efficacy. Acetohexamide The therapeutic efficacy of Acetohexamide can be increased when used in combination with Diazoxide. Acetylsalicylic acid Acetylsalicylic acid may decrease the excretion rate of Diazoxide which could result in a higher serum level. Aclidinium Diazoxide may increase the excretion rate of Aclidinium which could result in a lower serum level and potentially a reduction in efficacy. Acrivastine Diazoxide may increase the excretion rate of Acrivastine which could result in a lower serum level and potentially a reduction in efficacy. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- No interactions found.
Products
- International/Other Brands
- Eudemine (Mercury)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataHyperstat Injection 300 mg/20mL Intravenous Merck Sharp & Dohme Limited 1973-01-22 2006-07-31 US 
Hyperstat Inj 15mg/ml Liquid Intravenous Schering Plough 1973-12-31 2003-07-14 Canada 
Proglycem Capsule 100 mg Oral Merck Ltd. 1985-12-31 Not applicable Canada Proglycem Suspension 50 mg/1mL Oral Teva Pharmaceuticals USA, Inc. 1990-09-30 Not applicable US Proglycem Susp 50mg/ml Suspension Oral Schering Plough 1984-12-31 2006-03-23 Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataDiazoxide Suspension 50 mg/1mL Oral E5 Pharma, Llc 2019-12-20 Not applicable US Diazoxide Suspension 50 mg/1mL Oral Par Pharmaceutical, Inc 2020-07-21 Not applicable US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
Categories
- ATC Codes
- G01AE10 — Combinations of sulfonamides
- G01AE — Sulfonamides
- G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
- G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- C02DA — Thiazide derivatives
- C02D — ARTERIOLAR SMOOTH MUSCLE, AGENTS ACTING ON
- C02 — ANTIHYPERTENSIVES
- C — CARDIOVASCULAR SYSTEM
- Drug Categories
- Amides
- Antihypertensive Agents
- Arteriolar Smooth Muscle, Agents Acting On
- Benzothiadiazines
- Cardiovascular Agents
- Direct Vasodilators
- Diuretics
- Drugs for Treatment of Hypoglycemia
- Genito Urinary System and Sex Hormones
- Gynecological Antiinfectives and Antiseptics
- Heterocyclic Compounds, Fused-Ring
- Hyperglycemia-Associated Agents
- Hypotensive Agents
- Sulfonamides
- Sulfones
- Sulfur Compounds
- Thiazide Derivatives
- Vasodilating Agents
- 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
- Koch-Weser J: Diazoxide. N Engl J Med. 1976 Jun 3;294(23):1271-3. doi: 10.1056/NEJM197606032942306. [PubMed:772431]
- FDA Approved Drug Products: Proglycem Diazoxide Oral Suspension [Link]
- External Links
- Human Metabolome Database
- HMDB0015251
- KEGG Drug
- D00294
- KEGG Compound
- C06949
- PubChem Compound
- 3019
- PubChem Substance
- 46508027
- ChemSpider
- 2911
- BindingDB
- 86248
- 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
Phase Status Purpose Conditions Count 4 Active Not Recruiting Basic Science Glucose Metabolism Disorders / Glucose, High Blood / Type 2 Diabetes Mellitus 1 4 Completed Prevention Type 1 Diabetes Mellitus 1 4 Completed Treatment Type 1 Diabetes Mellitus 1 4 Suspended Prevention Hypoglycemia / Hypoglycemia Unawareness / Type 1 Diabetes Mellitus 1 4 Withdrawn Treatment Gastro-enteropancreatic Neuroendocrine Tumor 1 3 Completed Treatment Hypothalamic-pituitary Lesions / Postsurgical craniopharyngioma 1 2 Completed Treatment BMI >30 kg/m2 1 2 Completed Treatment BMI >30 kg/m2 / Hyperinsulinism 1 2 Completed Treatment Hypothalamic Obesity 1 2 Suspended Basic Science Glucose Metabolism Disorders (Including Diabetes Mellitus) / Glucose, High Blood / Type 2 Diabetes Mellitus 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Ivax Pharmaceuticals
- Medisca Inc.
- Teva Pharmaceutical Industries Ltd.
- Dosage Forms
Form Route Strength Powder Not applicable 1 g/1g Suspension Oral 50 mg Injection Intravenous 300 mg/20mL Liquid Intravenous Capsule 25 mg Capsule Oral 100 MG Capsule Oral 25 MG Suspension Oral 50 mg/1mL Suspension Oral Suspension Oral 5 g - Prices
Unit description Cost Unit Proglycem 50 mg/ml Suspension 30ml Bottle 197.05USD bottle Diazoxide powder 85.07USD g Proglycem 100 mg Capsule 1.65USD capsule DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 330 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. water solubility 2850 mg/L Not Available logP 1.20 HANSCH,C ET AL. (1995) pKa 8.74 SANGSTER (1994) - Predicted Properties
Property Value Source Water Solubility 0.552 mg/mL ALOGPS logP 1.09 ALOGPS logP 1 ChemAxon logS -2.6 ALOGPS pKa (Strongest Acidic) 10.48 ChemAxon pKa (Strongest Basic) 1.33 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 58.53 Å2 ChemAxon Rotatable Bond Count 0 ChemAxon Refractivity 54.84 m3·mol-1 ChemAxon Polarizability 20.98 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.5923 Caco-2 permeable - 0.5765 P-glycoprotein substrate Non-substrate 0.6817 P-glycoprotein inhibitor I Non-inhibitor 0.6924 P-glycoprotein inhibitor II Non-inhibitor 0.6927 Renal organic cation transporter Non-inhibitor 0.8107 CYP450 2C9 substrate Non-substrate 0.5606 CYP450 2D6 substrate Non-substrate 0.8064 CYP450 3A4 substrate Non-substrate 0.5774 CYP450 1A2 substrate Inhibitor 0.9108 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Inhibitor 0.8932 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.831 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7977 Ames test Non AMES toxic 0.7888 Carcinogenicity Non-carcinogens 0.8304 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.3408 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9233 hERG inhibition (predictor II) Non-inhibitor 0.9271
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets
- 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
- 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]
- 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]
- 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]
- 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]
- 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
- 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]
- 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]
- 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]
- 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]
- 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
- 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]
- 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
- 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]
- 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]
- 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
- 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]
- 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]
- 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
- 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 07:24 / Updated on October 23, 2020 21:53
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