AZM

5-ACETAMIDO-1,3,4-THIADIAZOLE-2-SULFONAMIDE

Created: 1999-07-08
Last modified:  2024-09-27

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Chemical Details

Formal Charge0
Atom Count19
Chiral Atom Count0
Bond Count19
Aromatic Bond Count5
2D diagram of AZM

Chemical Component Summary

Name5-ACETAMIDO-1,3,4-THIADIAZOLE-2-SULFONAMIDE
Systematic Name (OpenEye OEToolkits)N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)ethanamide
FormulaC4 H6 N4 O3 S2
Molecular Weight222.245
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=S(=O)(c1nnc(s1)NC(=O)C)N
SMILESCACTVS3.341CC(=O)Nc1sc(nn1)[S](N)(=O)=O
SMILESOpenEye OEToolkits1.5.0CC(=O)Nc1nnc(s1)S(=O)(=O)N
Canonical SMILESCACTVS3.341 CC(=O)Nc1sc(nn1)[S](N)(=O)=O
Canonical SMILESOpenEye OEToolkits1.5.0 CC(=O)Nc1nnc(s1)S(=O)(=O)N
InChIInChI1.03 InChI=1S/C4H6N4O3S2/c1-2(9)6-3-7-8-4(12-3)13(5,10)11/h1H3,(H2,5,10,11)(H,6,7,9)
InChIKeyInChI1.03 BZKPWHYZMXOIDC-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank IDDB00819 
NameAcetazolamide
Groups
  • approved
  • vet_approved
DescriptionOne of the carbonic anhydrase inhibitors that is sometimes effective against absence seizures. It is sometimes useful also as an adjunct in the treatment of tonic-clonic, myoclonic, and atonic seizures, particularly in women whose seizures occur or are exacerbated at specific times in the menstrual cycle. However, its usefulness is transient often because of rapid development of tolerance. Its antiepileptic effect may be due to its inhibitory effect on brain carbonic anhydrase, which leads to an increased transneuronal chloride gradient, increased chloride current, and increased inhibition. (From Smith and Reynard, Textbook of Pharmacology, 1991, p337)
Synonyms
  • N-[5-(aminosulfonyl)-1,3,5-thiadiazol-2-yl]acetamide
  • 5-acetylamino-1,3,4-thiadiazole-2-sulfonamide
  • Acetazolamidum
  • Acétazolamide
  • Acetazolamide
Brand Names
  • Diamox Sequels
  • AcetaZOLAMIDE
  • Acetazolamide
  • Diamox Tablets 250mg
  • Novo-zolamide Tab 250mg
IndicationFor adjunctive treatment of: edema due to congestive heart failure; drug-induced edema; centrencephalic epilepsies; chronic simple (open-angle) glaucoma
Categories
  • Anticonvulsants
  • Antiglaucoma Agents
  • Antiglaucoma Preparations and Miotics
  • Carbonic Anhydrase Inhibitors
  • Cardiovascular Agents
ATC-Code
  • G01AE10
  • S01EC01
CAS number59-66-5

Drug Targets

NameTarget SequencePharmacological ActionActions
Carbonic anhydrase 1MASPDWGYDDKNGPEQWSKLYPIANGNNQSPVDIKTSETKHDTSLKPISV...unknowninhibitor
Carbonic anhydrase 2MSHHWGYGKHNGPEHWHKDFPIAKGERQSPVDIDTHTAKYDPSLKPLSVS...unknowninhibitor
Carbonic anhydrase 4MRMLLALLALSAARPSASAESHWCYEVQAESSNYPCLVPVKWGGNCQKDR...unknowninhibitor
Carbonic anhydrase 12MPRRSLHAAAVLLLVILKEQPSSPAPVNGSKWTYFGPDGENSWSKKYPSC...unknowninhibitor
Carbonic anhydrase 14MLFSALLLEVIWILAADGGQHWTYEGPHGQDHWPASYPECGNNAQSPIDI...unknowninhibitor
View More
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 CHEMBL20
PubChem 1986
ChEMBL CHEMBL20
ChEBI CHEBI:27690
CCDC/CSD ATDZSA03, ATDZSA04, ATDZSA02, GUXVIH, ATDZSA, DACBIW, GUXTUR, GUXVON, MADTAP01, YIZGIA, RUYGUO, GUXSUQ, JIBNUD, GUXVAZ, GUXTOL, MADSIW, RUYGUO01, MADSOC, MADSAO, RUYGIC, MADSUI, YEVMUK, RUYGIC01, MADGIK, GUXTAX, MADGEG, JOFGOD, DATFAH, MADTET, MADTAP, DATDUZ, MADSES, DATFEL, DATFIP, XENJAF
COD 1545832, 1545833, 1545830, 1545834, 1545838, 1545837, 4510841, 4502906, 1545836, 1545835, 4502908, 1545831, 4502907, 4502909