Azosemide (CHEM019346)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 06:02:25 UTC
Update Date2016-11-09 01:15:58 UTC
Accession NumberCHEM019346
Identification
Common NameAzosemide
ClassSmall Molecule
DescriptionA sulfonamide that is benzenesulfonamide which is substituted at positions 2, 4, and 5 by chlorine, (2-thienylmethyl)amino and 1H-tetrazol-5-yl groups, respectively. It is a diuretic that has been used in the management of oedema and hypertension.
Contaminant Sources
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Chloro-5-(1H-tetrazol-5-yl)-N(4)-2-thenylsulfanilamideChEBI
5-(4'-Chloro-5'-sulfamoyl-2'-thenylaminophenyl)tetrazoleChEBI
AzosemidaChEBI
AzosemidumChEBI
DiartChEBI
2-Chloro-5-(1H-tetrazol-5-yl)-N(4)-2-thenylsulphanilamideGenerator
5-(4'-Chloro-5'-sulphamoyl-2'-thenylaminophenyl)tetrazoleGenerator
2-Chloro-5-(1H-tetrazol-5-yl)-4-[(thiophen-2-ylmethyl)amino]benzenesulfonamideHMDB
2-Chloro-5-(1H-tetrazol-5-yl)-N4-2-thenylsulfanilamideHMDB
AzosemidHMDB
5-(4-Chloro-5-sulfamyl-2-thienylaminophenyl)tetrazoleHMDB
Chemical FormulaC12H11ClN6O2S2
Average Molecular Mass370.838 g/mol
Monoisotopic Mass370.007 g/mol
CAS Registry Number27589-33-9
IUPAC Name2-chloro-5-(2H-1,2,3,4-tetrazol-5-yl)-4-[(thiophen-2-ylmethyl)amino]benzene-1-sulfonamide
Traditional Nameazosemide
SMILESNS(=O)(=O)C1=C(Cl)C=C(NCC2=CC=CS2)C(=C1)C1=NNN=N1
InChI IdentifierInChI=1S/C12H11ClN6O2S2/c13-9-5-10(15-6-7-2-1-3-22-7)8(12-16-18-19-17-12)4-11(9)23(14,20)21/h1-5,15H,6H2,(H2,14,20,21)(H,16,17,18,19)
InChI KeyHMEDEBAJARCKCT-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenyltetrazoles and derivatives. Phenyltetrazoles and derivatives are compounds containing a phenyltetrazole skeleton, which consists of a tetrazole bound to a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassTetrazoles
Direct ParentPhenyltetrazoles and derivatives
Alternative Parents
Substituents
  • Aminobenzenesulfonamide
  • Phenyltetrazole
  • Benzenesulfonamide
  • Benzenesulfonyl group
  • Aniline or substituted anilines
  • Phenylalkylamine
  • Chlorobenzene
  • Halobenzene
  • Secondary aliphatic/aromatic amine
  • Aralkylamine
  • Aryl chloride
  • Benzenoid
  • Organosulfonic acid amide
  • Aryl halide
  • Monocyclic benzene moiety
  • Aminosulfonyl compound
  • Thiophene
  • Sulfonyl
  • Organosulfonic acid or derivatives
  • Organic sulfonic acid or derivatives
  • Heteroaromatic compound
  • Secondary amine
  • Azacycle
  • Organopnictogen compound
  • Organochloride
  • Organohalogen compound
  • Organic nitrogen compound
  • Amine
  • Organic oxygen compound
  • Organonitrogen compound
  • Organosulfur compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.093 g/LALOGPS
logP2.36ALOGPS
logP2.38ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)7.38ChemAxon
pKa (Strongest Basic)-0.77ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area126.65 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity102.08 m³·mol⁻¹ChemAxon
Polarizability34.56 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-3179000000-ab9cce02c68a2faedfa5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0019000000-4235353754d07f2eabb3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00g0-0059000000-3942e6570eaabb2100d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-054k-0191000000-9f7de4073d6c720917a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2009000000-49efb527af3e3895d8c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00or-9015000000-2e972e4ca5c8921631f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-f2169c50df45a7b901e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-78304d7d04dcd1a36029Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00pr-6019000000-8c32e4c4e0ad74156f00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9011000000-5a32e360207da8b1e194Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0009000000-d48728f26a4fcf28a99dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0009000000-3c3da5c3b9c593642134Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ls-6089000000-b92cde7661137efad26eSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB08961
HMDB IDHMDB0041831
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAzosemide
Chemspider ID2186
ChEBI ID31248
PubChem Compound ID2273
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=14520682
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=1563700
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=428188
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=512891
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=6617067
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=8785379
7. Suh OK, Kim SH, Lee MG: Pharmacokinetics and pharmacodynamics of azosemide. Biopharm Drug Dispos. 2003 Oct;24(7):275-97.
8. Lee SH, Lee MG: Stability, tissue metabolism, tissue distribution and blood partition of azosemide. Biopharm Drug Dispos. 1995 Oct;16(7):547-61.