Tolazamide (CHEM003722)

Record Information
Version1.0
Creation Date2014-09-11 05:15:40 UTC
Update Date2026-08-19 07:06:24 UTC
Accession NumberCHEM003722
Identification
Common NameTolazamide
ClassSmall Molecule
Description
A sulphonylurea hypoglycemic agent with actions and uses similar to those of chlorpropamide.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Drug
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-(Hexahydro-1-azepinyl)-3-p-tolylsulfonylureaChEBI
1-(Hexahydro-1H-azepin-1-yl)-3-(p-tolylsulfonyl)ureaChEBI
4-(p-Tolylsulfonyl)-1,1-hexamethylenesemicarbazideChEBI
BRN 1323565ChEBI
CCRIS 591ChEBI
DiabewasChEBI
EINECS 214-588-3ChEBI
N-(p-Toluenesulfonyl)-n'-hexamethyleniminoureaChEBI
N-{[(hexahydro-1H-azepin-1-yl)-amino]carbonyl}-4-methylbenzenesulfonamideChEBI
NorglycinChEBI
TolazamidaChEBI
TolazamidumChEBI
TolinaseChEBI
U 17835ChEBI
U-17835ChEBI
1-(Hexahydro-1-azepinyl)-3-p-tolylsulphonylureaGenerator
1-(Hexahydro-1H-azepin-1-yl)-3-(p-tolylsulphonyl)ureaGenerator
4-(p-Tolylsulphonyl)-1,1-hexamethylenesemicarbazideGenerator
N-(p-Toluenesulphonyl)-n'-hexamethyleniminoureaGenerator
N-{[(hexahydro-1H-azepin-1-yl)-amino]carbonyl}-4-methylbenzenesulphonamideGenerator
Pharmacia brand OF tolazamideHMDB
Chemical FormulaC14H21N3O3S
Average Molecular Mass311.400 g/mol
Monoisotopic Mass311.130 g/mol
CAS Registry Number1156-19-0
IUPAC Name1-(azepan-1-yl)-3-(4-methylbenzenesulfonyl)urea
Traditional Nametolazamide
SMILESCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NN1CCCCCC1
InChI IdentifierInChI=1S/C14H21N3O3S/c1-12-6-8-13(9-7-12)21(19,20)16-14(18)15-17-10-4-2-3-5-11-17/h6-9H,2-5,10-11H2,1H3,(H2,15,16,18)
InChI KeyOUDSBRTVNLOZBN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonamides
Direct ParentBenzenesulfonamides
Alternative Parents
Substituents
  • Benzenesulfonamide
  • Tosyl compound
  • Benzenesulfonyl group
  • Azepane
  • Toluene
  • Sulfonylurea
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Aminosulfonyl compound
  • Sulfonyl
  • Hydrazone
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point170-173°C
Boiling PointNot Available
Solubility65.4 mg/L (at 30°C)
Predicted Properties
PropertyValueSource
Water Solubility0.31 g/LALOGPS
logP1.4ALOGPS
logP1.91ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)4.07ChemAxon
pKa (Strongest Basic)1.61ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area78.51 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity81.34 m³·mol⁻¹ChemAxon
Polarizability32.82 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureRapidly and well absorbed from the gastrointestinal tract.
Mechanism of ToxicitySulfonylureas likely bind to ATP-sensitive potassium-channel receptors on the pancreatic cell surface, reducing potassium conductance and causing depolarization of the membrane. Depolarization stimulates calcium ion influx through voltage-sensitive calcium channels, raising intracellular concentrations of calcium ions, which induces the secretion, or exocytosis, of insulin.
MetabolismTolazamide is metabolized to five major metabolites ranging in hypoglycemic activity from 0 to 70%. Route of Elimination: Tolazamide is metabolized to five major metabolites ranging in hypoglycemic activity from 0% to 70%. They are excreted principally in the urine. Half Life: The average biological half-life of the drug is 7 hours.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor use as an adjunct to diet to lower the blood glucose in patients with non-insulin dependent diabetes mellitus (Type II) whose hyperglycemia cannot be satisfactorily controlled by diet alone.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsOverdosage of sulfonylureas can produce hypoglycemia. Severe hypoglycemic reactions with coma, seizure, or other neurological impairment occur infrequently, but constitute medical emergencies requiring immediate hospitalization.
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB00839
HMDB IDHMDB0014977
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTolazamide
Chemspider ID5302
ChEBI ID9613
PubChem Compound ID5503
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=15901207
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=8237731