Tolbutamide (CHEM016427)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:31:23 UTC
Update Date2016-11-09 01:15:23 UTC
Accession NumberCHEM016427
Identification
Common NameTolbutamide
ClassSmall Molecule
DescriptionTolbutamide is an oral antihyperglycemic agent used for the treatment of non-insulin-dependent diabetes mellitus (NIDDM). It is structurally similar to acetohexamide, chlorpropamide and tolazamide and belongs to the sulfonylurea class of insulin secretagogues, which act by stimulating β cells of the pancreas to release insulin. Sulfonylureas increase both basal insulin secretion and meal-stimulated insulin release. Medications in this class differ in their dose, rate of absorption, duration of action, route of elimination and binding site on their target pancreatic β cell receptor. Sulfonylureas also increase peripheral glucose utilization, decrease hepatic gluconeogenesis and may increase the number and sensitivity of insulin receptors. Sulfonylureas are associated with weight gain, though less so than insulin. Due to their mechanism of action, sulfonylureas may cause hypoglycemia and require consistent food intake to decrease this risk. The risk of hypoglycemia is increased in elderly, debilitated and malnourished individuals. Tolbutamide appears to be metabolized in the liver. Tolbutamide and its metabolites are excreted in urine (75-85%) and feces.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Butyl-3-(p-methylphenylsulfonyl)ureaChEBI
1-Butyl-3-(p-tolylsulfonyl)ureaChEBI
1-Butyl-3-tosylureaChEBI
1-p-Toluenesulfonyl-3-butylureaChEBI
3-(p-Tolyl-4-sulfonyl)-1-butylureaChEBI
N-(4-Methylbenzenesulfonyl)-n'-butylureaChEBI
N-(4-Methylphenylsulfonyl)-n'-butylureaChEBI
N-(p-Methylbenzenesulfonyl)-n'-butylureaChEBI
N-(Sulfonyl-p-methylbenzene)-n'-N-butylureaChEBI
N-Butyl-n'-(4-methylphenylsulfonyl)ureaChEBI
N-Butyl-n'-(p-tolylsulfonyl)ureaChEBI
N-Butyl-n'-p-toluenesulfonylureaChEBI
N-N-Butyl-n'-tosylureaChEBI
OrinaseChEBI
TolbutamidaChEBI
TolbutamidumChEBI
TolylsulfonylbutylureaChEBI
1-Butyl-3-(p-methylphenylsulphonyl)ureaGenerator
1-Butyl-3-(p-tolylsulphonyl)ureaGenerator
1-p-Toluenesulphonyl-3-butylureaGenerator
3-(p-Tolyl-4-sulphonyl)-1-butylureaGenerator
N-(4-Methylbenzenesulphonyl)-n'-butylureaGenerator
N-(4-Methylphenylsulphonyl)-n'-butylureaGenerator
N-(p-Methylbenzenesulphonyl)-n'-butylureaGenerator
N-(Sulphonyl-p-methylbenzene)-n'-N-butylureaGenerator
N-Butyl-n'-(4-methylphenylsulphonyl)ureaGenerator
N-Butyl-n'-(p-tolylsulphonyl)ureaGenerator
N-Butyl-n'-p-toluenesulphonylureaGenerator
TolylsulphonylbutylureaGenerator
Berlin chemie brand OF tolbutamideHMDB
Berlin-chemie brand OF tolbutamideHMDB
DiavalHMDB
RastinonHMDB
Tolbutamid r.a.n.HMDB
Yamanouchi brand OF tolbutamideHMDB
ArtosinHMDB
Hoechst brand OF tolbutamideHMDB
OrabetHMDB
Tolbutamide butamide brandHMDB
Tolbutamide hoechst brandHMDB
Apo-tolbutamideHMDB
Butamide brand OF tolbutamideHMDB
DolipolHMDB
Pfizer brand OF tolbutamideHMDB
Tolbutamide aventis brandHMDB
Valdecasas brand OF tolbutamideHMDB
Apotex brand OF tolbutamideHMDB
Aventis brand OF tolbutamideHMDB
DiabetolHMDB
R.A.N. brand OF tolbutamideHMDB
Tolbutamide pfizer brandHMDB
Chemical FormulaC12H18N2O3S
Average Molecular Mass270.348 g/mol
Monoisotopic Mass270.104 g/mol
CAS Registry Number64-77-7
IUPAC Name3-butyl-1-(4-methylbenzenesulfonyl)urea
Traditional Nametolbutamide
SMILESCCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1
InChI IdentifierInChI=1S/C12H18N2O3S/c1-3-4-9-13-12(15)14-18(16,17)11-7-5-10(2)6-8-11/h5-8H,3-4,9H2,1-2H3,(H2,13,14,15)
InChI KeyJLRGJRBPOGGCBT-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
  • Toluene
  • Sulfonylurea
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Aminosulfonyl compound
  • Carboximidic acid derivative
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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 Solubility0.2 g/LALOGPS
logP2.04ALOGPS
logP2.3ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)4.33ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.27 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity70.27 m³·mol⁻¹ChemAxon
Polarizability29.1 ųChemAxon
Number of Rings1ChemAxon
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, Positivesplash10-0a4m-9620000000-80b8e46fa29dc771af14Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0006-0190000000-7ff8ebe7a2c8d9b989ecSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-05fr-1920000000-defac8a82087405b74dfSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0006-0190000000-7ff8ebe7a2c8d9b989ecSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-05fr-1920000000-defac8a82087405b74dfSpectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-0aou-9700000000-4ddde0b1cb5c52cde5e9Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-0avi-6900000000-7a66f373c605dedbdacaSpectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-00di-9630000000-2017f03bf9e28638cee8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-05fr-8900000000-2a951aa06eb51e26b18dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-0006-9000000000-c10cd87bcaddb53a298dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-0006-9200000000-9e34241200e278e9e064Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00di-9610000000-75888e656e58b74cf3eeSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0596-9200000000-f75d5d5d54176257be85Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-0930000000-8d71b509124429eea629Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-6900000000-96b6cdfc78c2cfa0a77bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-a8b79ea32dfd9e27bddaSpectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-00di-0930000000-9f5b4960f823b6c7b58aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-0ab9-1900000000-d6a5548288198dd86802Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-0a6r-5900000000-93ef59adf84191071087Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-06vi-9500000000-9a73e07e1dc0aa3f9d1dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9780000000-b9e42f04441a4750b9a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-9400000000-731942a1402d4374a5dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-11ce33c22d2669eeac48Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-2590000000-33755b9fecfcb717c051Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-2910000000-c5e9ee1500acc1154c87Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00fu-9700000000-97a794e19f654b96f09bSpectrum
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 IDDB01124
HMDB IDHMDB0015256
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTolbutamide
Chemspider ID5304
ChEBI ID27999
PubChem Compound ID5505
Kegg Compound IDC07148
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19.
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11835228
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11840346
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=11911494
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=12042355
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=12355256
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=15207658
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=15317941
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=15620874
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=15655519
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=16290322
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=16426753
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=19059420
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=20880646
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=21178111
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=21193530
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=21471135
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=21535124
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=21712613
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=21757329
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=21827497
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=21831467
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=22028182
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=22079696