Diazoxide

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Diazoxide
Diazoxide Structural Formula V.1.svg
Systematic (IUPAC) name
7-chloro-3-methyl-4H-1,2,4-benzothiadiazine 1,1-dioxide
Clinical data
Trade names Proglycem
AHFS/Drugs.com monograph
Pregnancy cat. C (AU) C (US)
Legal status POM (UK) -only (US)
Routes Oral, intravenous
Pharmacokinetic data
Protein binding 90%
Metabolism Hepatic oxidation and sulfate conjugation
Half-life 21-45 hours
Excretion Renal
Identifiers
CAS number 364-98-7 YesY
ATC code C02DA01 V03AH01
PubChem CID 3019
IUPHAR ligand 2409
DrugBank DB01119
ChemSpider 2911 YesY
UNII O5CB12L4FN YesY
KEGG D00294 YesY
ChEBI CHEBI:4495 YesY
ChEMBL CHEMBL181 YesY
Chemical data
Formula C8H7ClN2O2S 
Mol. mass 230.672 g/mol
 YesY (what is this?)  (verify)

Diazoxide (INN; brand name Proglycem[1]) is a potassium channel activator, which causes local relaxation in smooth muscle by increasing membrane permeability to potassium ions. This switches off voltage-gated calcium ion channels which inhibits the generation of an action potential.

Uses[edit]

Diazoxide is used as a vasodilator in the treatment of acute hypertension or malignant hypertension.[2]

Diazoxide also inhibits the secretion of insulin from the pancreas, thus it is used to counter hypoglycemia in disease states such as insulinoma (a tumor producing insulin)[3] or congenital hyperinsulinism.

Diazoxide acts as a positive allosteric modulator of the AMPA receptor, suggesting potential application as a cognitive enhancer.[4]

Synthesis[edit]

Diazoxide can be prepared from dichloronitrobenzene:

Diazoxide synthesis.[5]

Side effects[edit]

Diazoxide interferes with insulin release through its action on potassium channels.[citation needed] The efflux of potassium, as an effect of Diazoxide, will lead to hyperpolarization of cell membrane that leads to decrease calcium influx. The low calcium will decrease the release of insulin. Therefore this medicine is not given to non-insulin dependent diabetic patients.

References[edit]

  1. ^ Diazoxide, drugs.com
  2. ^ van Hamersvelt HW, Kloke HJ, de Jong DJ, Koene RA, Huysmans FT (August 1996). "Oedema formation with the vasodilators nifedipine and diazoxide: direct local effect or sodium retention?". J. Hypertens. 14 (8): 1041–5. doi:10.1097/00004872-199608000-00016. PMID 8884561. 
  3. ^ Huang Q, Bu S, Yu Y, et al. (January 2007). "Diazoxide prevents diabetes through inhibiting pancreatic beta-cells from apoptosis via Bcl-2/Bax rate and p38-beta mitogen-activated protein kinase". Endocrinology 148 (1): 81–91. doi:10.1210/en.2006-0738. PMID 17053028. 
  4. ^ PMID 8307099 (PubMed)
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  5. ^ doi:10.1126/science.133.3470.2067
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