20J

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

Created: 2013-08-13
Last modified:  2013-09-25

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Chemical Details

Formal Charge0
Atom Count21
Chiral Atom Count0
Bond Count22
Aromatic Bond Count6
2D diagram of 20J

Chemical Component Summary

Name7-chloro-3-methyl-2H-1,2,4-benzothiadiazine 1,1-dioxide
Systematic Name (OpenEye OEToolkits)7-chloranyl-3-methyl-2H-1$l^{6},2,4-benzothiadiazine 1,1-dioxide
FormulaC8 H7 Cl N2 O2 S
Molecular Weight230.671
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs12.01Clc1ccc2N=C(NS(=O)(=O)c2c1)C
SMILESCACTVS3.385CC1=Nc2ccc(Cl)cc2[S](=O)(=O)N1
SMILESOpenEye OEToolkits1.7.6CC1=Nc2ccc(cc2S(=O)(=O)N1)Cl
Canonical SMILESCACTVS3.385 CC1=Nc2ccc(Cl)cc2[S](=O)(=O)N1
Canonical SMILESOpenEye OEToolkits1.7.6 CC1=Nc2ccc(cc2S(=O)(=O)N1)Cl
InChIInChI1.03 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)
InChIKeyInChI1.03 GDLBFKVLRPITMI-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank IDDB01119 
NameDiazoxide
Groups approved
DescriptionDiazoxide is a non-diuretic benzothiadiazine derivative that activates ATP-sensitive potassium channels.[A255647,L44612] It is chemically related to thiazide diuretics but does not inhibit carbonic anhydrase and does not have chloriuretic or natriuretic activity.[A190372] Diazoxide is commonly used in the treatment of hyperinsulinaemic hypoglycemia due to its ability to inhibit insulin release.[A255647] Diazoxide also exhibits hypotensive activity and reduces arteriolar smooth muscle and vascular resistance.[A190372] When administered intravenously, diazoxide can be used to treat hypertensive emergencies;[L44622] however, this specific form of diazoxide is no longer available in the US. Diazoxide is usually well tolerated, and some of its more common side effects include fluid retention and electrolyte disturbances. In September 2015, the FDA issued a safety alert regarding post-marketing reports of pulmonary hypertension occurring in infants and neonates.[A255647,L44612]
Synonyms
  • Diazoxide choline
  • Diazoxidum
  • Diazoxide
  • Diazoxido
  • 7-chloro-3-methyl-2H-1,2,4-benzothiadiazine 1,1-dioxide
Brand Names
  • Diazoxide
  • Hyperstat
  • Truemed Group LLC
  • Proglycem Susp 50mg/ml
  • Diazoxide Oral Solution
IndicationOral diazoxide is indicated to manage hypoglycemia due to hyperinsulinism associated with conditions such as inoperable islet cell adenoma or carcinoma, and extrapancreatic malignancy in adults, or leucine sensitivity, islet cell hyperplasia, nesidioblastosis, extrapancreatic malignancy, islet cell adenoma, and adenomatosis in infants and children. In infants and children oral diazoxide may be used preoperatively as a temporary measure, and postoperatively, if hypoglycemia persists.[L44612] Diazoxide may also be used parentally or intravenously to treat hypertensive emergencies.[A255632,L44622]
Categories
  • Antihypertensive Agents
  • Arteriolar Smooth Muscle, Agents Acting On
  • Benzothiadiazines
  • Cardiovascular Agents
  • Direct Vasodilators
ATC-Code
  • G01AE10
  • C02DA01
  • V03AH01
CAS number364-98-7

Drug Targets

NameTarget SequencePharmacological ActionActions
ATP-sensitive inward rectifier potassium channel 11MLSRKGIIPEEYVLTRLAEDPAEPRYRARQRRARFVSKKGNCNVAHKNIR...unknowninducer
Mitochondrial ATP synthase F1 domainMLSVRVAAAVVRALPRRAGLVSRNALGSSFIAARNFHASNTHLQKTGTAE...unknowninhibitor
Serum albuminMKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...unknownbinder
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL181
PubChem 3019
ChEMBL CHEMBL1518123, CHEMBL181
ChEBI CHEBI:4495
CCDC/CSD DIAZOX