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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:44 UTC
HMDB IDHMDB0014977
Secondary Accession Numbers
  • HMDB14977
Metabolite Identification
Common NameTolazamide
DescriptionTolazamide, also known as tolinase or BRN 1323565, 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. Tolazamide is an oral blood glucose lowering drug of the sulfonylurea class. Some patients who are initially responsive to oral hypoglycemic drugs, including tolazamide, may become unresponsive or poorly responsive over time. Tolazamide is a drug which is used for 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. They are excreted principally in the urine. Tolazamide is a moderately basic compound (based on its pKa). Tolazamide is a potentially toxic compound. Sulfonylureas 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. Severe hypoglycemic reactions with coma, seizure, or other neurological impairment occur infrequently, but constitute medical emergencies requiring immediate hospitalization.
Structure
Data?1582753244
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 Weight311.4
Monoisotopic Molecular Weight311.130362243
IUPAC Name1-(azepan-1-yl)-3-(4-methylbenzenesulfonyl)urea
Traditional Nametolazamide
CAS Registry Number1156-19-0
SMILES
CC1=CC=C(C=C1)S(=O)(=O)NC(=O)NN1CCCCCC1
InChI Identifier
InChI=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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point170 - 173 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.31 g/LNot Available
LogP2.5Not Available
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
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-9530000000-1efba84cf35a7c3462e8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-001i-0119000000-08f98037ec7196f2922fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00kg-6901000000-edb181b207ba0c040d5eSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-0119000000-08f98037ec7196f2922fSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00kg-6901000000-edb181b207ba0c040d5eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-2916000000-f998a4bd881fca969a3aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3900000000-073057c545546aaa0511Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0avm-9100000000-96cc995c9c21a62b0291Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1927000000-6672f320a126a06c90deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03k9-1900000000-fc714c59b068c2d0bfbdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00fr-8910000000-7907f8e51f6cee4e2e2eSpectrum
MSMass Spectrum (Electron Ionization)splash10-06r6-9500000000-41e71d724a7515763bb7Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00839 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00839 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00839
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5302
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTolazamide
METLIN IDNot Available
PubChem Compound5503
PDB IDNot Available
ChEBI ID9613
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in inward rectifier potassium channel activity
Specific function:
In the kidney, probably plays a major role in potassium homeostasis. Inward rectifier potassium channels are characterized by a greater tendency to allow potassium to flow into the cell rather than out of it. Their voltage dependence is regulated by the concentration of extracellular potassium; as external potassium is raised, the voltage range of the channel opening shifts to more positive voltages. The inward rectification is mainly due to the blockage of outward current by internal magnesium. This channel is activated by internal ATP and can be blocked by external barium
Gene Name:
KCNJ1
Uniprot ID:
P48048
Molecular weight:
44794.6
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Szabo C, Salzman AL: Inhibition of ATP-activated potassium channels exerts pressor effects and improves survival in a rat model of severe hemorrhagic shock. Shock. 1996 Jun;5(6):391-4. [PubMed:8799949 ]
  4. Asano K, Cortes P, Garvin JL, Riser BL, Rodriguez-Barbero A, Szamosfalvi B, Yee J: Characterization of the rat mesangial cell type 2 sulfonylurea receptor. Kidney Int. 1999 Jun;55(6):2289-98. [PubMed:10354277 ]