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Record Information
Version5.0
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 is only found in individuals that have used or taken this drug. It is a sulphonylurea hypoglycemic agent with actions and uses similar to those of chlorpropamide. [PubChem]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.
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
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point170 - 173 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.31 g/LNot Available
LogP2.5Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available173.317http://allccs.zhulab.cn/database/detail?ID=AllCCS00000736
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.31 g/LALOGPS
logP10(1.4) g/LALOGPS
logP10(1.91) g/LChemAxon
logS10(-3) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+174.2631661259
DarkChem[M-H]-168.6831661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TolazamideCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NN1CCCCCC13758.2Standard polar33892256
TolazamideCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NN1CCCCCC11938.6Standard non polar33892256
TolazamideCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NN1CCCCCC12673.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Tolazamide,1TMS,isomer #1CC1=CC=C(S(=O)(=O)N(C(=O)NN2CCCCCC2)[Si](C)(C)C)C=C12641.5Semi standard non polar33892256
Tolazamide,1TMS,isomer #1CC1=CC=C(S(=O)(=O)N(C(=O)NN2CCCCCC2)[Si](C)(C)C)C=C12512.1Standard non polar33892256
Tolazamide,1TMS,isomer #1CC1=CC=C(S(=O)(=O)N(C(=O)NN2CCCCCC2)[Si](C)(C)C)C=C13912.5Standard polar33892256
Tolazamide,1TMS,isomer #2CC1=CC=C(S(=O)(=O)NC(=O)N(N2CCCCCC2)[Si](C)(C)C)C=C12620.2Semi standard non polar33892256
Tolazamide,1TMS,isomer #2CC1=CC=C(S(=O)(=O)NC(=O)N(N2CCCCCC2)[Si](C)(C)C)C=C12553.7Standard non polar33892256
Tolazamide,1TMS,isomer #2CC1=CC=C(S(=O)(=O)NC(=O)N(N2CCCCCC2)[Si](C)(C)C)C=C13875.9Standard polar33892256
Tolazamide,2TMS,isomer #1CC1=CC=C(S(=O)(=O)N(C(=O)N(N2CCCCCC2)[Si](C)(C)C)[Si](C)(C)C)C=C12576.0Semi standard non polar33892256
Tolazamide,2TMS,isomer #1CC1=CC=C(S(=O)(=O)N(C(=O)N(N2CCCCCC2)[Si](C)(C)C)[Si](C)(C)C)C=C12720.2Standard non polar33892256
Tolazamide,2TMS,isomer #1CC1=CC=C(S(=O)(=O)N(C(=O)N(N2CCCCCC2)[Si](C)(C)C)[Si](C)(C)C)C=C13664.3Standard polar33892256
Tolazamide,1TBDMS,isomer #1CC1=CC=C(S(=O)(=O)N(C(=O)NN2CCCCCC2)[Si](C)(C)C(C)(C)C)C=C12894.5Semi standard non polar33892256
Tolazamide,1TBDMS,isomer #1CC1=CC=C(S(=O)(=O)N(C(=O)NN2CCCCCC2)[Si](C)(C)C(C)(C)C)C=C12743.2Standard non polar33892256
Tolazamide,1TBDMS,isomer #1CC1=CC=C(S(=O)(=O)N(C(=O)NN2CCCCCC2)[Si](C)(C)C(C)(C)C)C=C13987.9Standard polar33892256
Tolazamide,1TBDMS,isomer #2CC1=CC=C(S(=O)(=O)NC(=O)N(N2CCCCCC2)[Si](C)(C)C(C)(C)C)C=C12841.0Semi standard non polar33892256
Tolazamide,1TBDMS,isomer #2CC1=CC=C(S(=O)(=O)NC(=O)N(N2CCCCCC2)[Si](C)(C)C(C)(C)C)C=C12810.9Standard non polar33892256
Tolazamide,1TBDMS,isomer #2CC1=CC=C(S(=O)(=O)NC(=O)N(N2CCCCCC2)[Si](C)(C)C(C)(C)C)C=C13909.5Standard polar33892256
Tolazamide,2TBDMS,isomer #1CC1=CC=C(S(=O)(=O)N(C(=O)N(N2CCCCCC2)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C13070.6Semi standard non polar33892256
Tolazamide,2TBDMS,isomer #1CC1=CC=C(S(=O)(=O)N(C(=O)N(N2CCCCCC2)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C13214.0Standard non polar33892256
Tolazamide,2TBDMS,isomer #1CC1=CC=C(S(=O)(=O)N(C(=O)N(N2CCCCCC2)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C13717.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Tolazamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-9530000000-1efba84cf35a7c3462e82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tolazamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-06r6-9500000000-41e71d724a7515763bb72014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolazamide LC-ESI-qTof , Positive-QTOFsplash10-001i-0119000000-08f98037ec7196f2922f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolazamide LC-ESI-qTof , Positive-QTOFsplash10-00kg-6901000000-edb181b207ba0c040d5e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolazamide , positive-QTOFsplash10-001i-0119000000-08f98037ec7196f2922f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolazamide , positive-QTOFsplash10-00kg-6901000000-edb181b207ba0c040d5e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolazamide 15V, Positive-QTOFsplash10-03di-0209000000-bedb05b5a97e0908596d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolazamide 30V, Positive-QTOFsplash10-014i-4901000000-a1ee7e5f83476a046f2c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolazamide 60V, Positive-QTOFsplash10-014m-9400000000-3f489397c4cc0115550a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolazamide 45V, Positive-QTOFsplash10-014j-7900000000-2ef187297f5318cde5412021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolazamide 90V, Negative-QTOFsplash10-056r-9600000000-79b4a41348e060a885cb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolazamide 45V, Positive-QTOFsplash10-014j-7900000000-03a2caa6a6a16dcc961e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolazamide 15V, Negative-QTOFsplash10-0229-0908000000-8344640fb69c0a69b6412021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolazamide 30V, Negative-QTOFsplash10-00di-0900000000-9f30fc8ec61a1c86f54e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolazamide 90V, Positive-QTOFsplash10-006x-9000000000-7a341cee1d086348c0cd2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolazamide 75V, Positive-QTOFsplash10-00r7-9100000000-3c4b583b1c32a728bc9f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolazamide 75V, Negative-QTOFsplash10-0a4i-4900000000-2be60e1fa0ecff75b17a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolazamide 60V, Negative-QTOFsplash10-05fr-1900000000-035f71a8c50843cec3a62021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolazamide 10V, Positive-QTOFsplash10-03di-2916000000-f998a4bd881fca969a3a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolazamide 20V, Positive-QTOFsplash10-03di-3900000000-073057c545546aaa05112016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolazamide 40V, Positive-QTOFsplash10-0avm-9100000000-96cc995c9c21a62b02912016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolazamide 10V, Negative-QTOFsplash10-03di-1927000000-6672f320a126a06c90de2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolazamide 20V, Negative-QTOFsplash10-03k9-1900000000-fc714c59b068c2d0bfbd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolazamide 40V, Negative-QTOFsplash10-00fr-8910000000-7907f8e51f6cee4e2e2e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolazamide 10V, Positive-QTOFsplash10-03di-0209000000-b918c838d9ee432978cf2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolazamide 20V, Positive-QTOFsplash10-0007-9302000000-89635c793cbf932550ab2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolazamide 40V, Positive-QTOFsplash10-0006-9100000000-3d92be1e62349f90d27c2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00839 details
UrineExpected but not QuantifiedNot QuantifiedNot 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
MarkerDB IDNot Available
Good Scents 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 ]