Tolbutamide (CED0003593)

Record Information
Version1.0
Creation Date2016-05-22 03:31:23 UTC
Update Date2026-08-18 19:41:00 UTC
Accession NumberCHEM016427
Identification
Common NameTolbutamide
ClassSmall Molecule
Description
Tolbutamide is an organic compound with the formula C12H18N2O3S and an average molecular weight of 270.35 g/mol. Tolbutamide belongs to the benzenesulfonamides, a subclass of benzene and substituted derivatives within the organic compounds. The compound is associated with 21 recorded sources across several categories. Within healthcare, pharmaceuticals, and veterinary products, it is found in blood glucose lowering drugs (excluding insulins), gynecologicals, and unclassified diagnostic agents. Other sources include food, food processing, and cookware, specifically in the preparation of wort, the preparation of wine or sparkling wine, the preparation of vinegar, and food preservation. It is also released from household cleaning and consumer products, such as tobacco smoke filters, perfumes within detergents and soaps, non electric simulated smoking devices, other smoking requisites, and cigar cigarettes. Additionally, it is found in electrical and electronic equipment, including electrodes, antennas, colour television systems, electrically stimulated smoking devices, and conductors or conductive bodies characterised by the conductive materials, among four other sources. The recorded exposure route for this compound is oral. At the molecular level, tolbutamide interacts with three recorded protein targets. It acts as a blocker or inhibitor of the ATP-sensitive inward rectifier potassium channel 1 (KCNJ1) and targets the ATP-binding cassette sub-family C member 8 (ABCC8) and the ATP-binding cassette sub-family C member 9 (ABCC9).
Contaminant Type
  • Human Neurotoxin
Chemical Structure
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
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0a4m-9620000000-80b8e46fa29dc771af14Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0190000000-7ff8ebe7a2c8d9b989ecNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-05fr-1920000000-defac8a82087405b74dfNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0190000000-7ff8ebe7a2c8d9b989ecNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-05fr-1920000000-defac8a82087405b74dfNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0aou-9700000000-4ddde0b1cb5c52cde5e9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0avi-6900000000-7a66f373c605dedbdacaNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-9630000000-2017f03bf9e28638cee8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-05fr-8900000000-2a951aa06eb51e26b18dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9000000000-c10cd87bcaddb53a298dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9200000000-9e34241200e278e9e064Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-9610000000-75888e656e58b74cf3eeNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0596-9200000000-f75d5d5d54176257be85Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0930000000-8d71b509124429eea629Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a6r-6900000000-96b6cdfc78c2cfa0a77bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0900000000-a8b79ea32dfd9e27bddaNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0930000000-9f5b4960f823b6c7b58aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ab9-1900000000-d6a5548288198dd86802Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a6r-5900000000-93ef59adf84191071087Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-06vi-9500000000-9a73e07e1dc0aa3f9d1dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0900000000-4ea0388906b86ffee63fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0900000000-31e3dc09c4de8bb3bfc6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-9510000000-3cf70a6698169bf6f749Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9000000000-c3c67f8d71759b260470Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0596-9200000000-912265ec35e53053bb0aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9000000000-8c60be7b587e29aed7feNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-9780000000-b9e42f04441a4750b9a9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05fr-9400000000-731942a1402d4374a5dbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4l-9000000000-11ce33c22d2669eeac48Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01b9-2590000000-33755b9fecfcb717c051Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-2910000000-c5e9ee1500acc1154c87Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00fu-9700000000-97a794e19f654b96f09bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-6930000000-3108a3e91eeeb0c61626Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-fc29912a244a34f06fe0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-1e9013bb1713df1dbda5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00xr-0940000000-9974ff6e325df0b15051Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-4910000000-848168ff979b969a67baNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00dl-7900000000-739757b922c3b4479b13Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2286.0Log mg/kg[1300:4100]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
263Blood glucose lowering drugs, excl. insulinsHealthcare, pharmaceuticals & veterinary productsNot Available
316GynecologicalsHealthcare, pharmaceuticals & veterinary productsNot Available
411Unclassified diagnostic agentsHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
509Colour Television SystemsElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
Pathways
2 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)62.3572
Click to view 3D structureProstaglandin E receptor 4Q9TU16Canis lupus familiarisPredicted (SEA)0.0778492
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)69.9865
Thromboxane A2 receptor structureClick to view 3D structureThromboxane A2 receptorP21731HumansPredicted (SEA)9.49761
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)78.472
Albumin structureClick to view 3D structureAlbuminP02768HumansPredicted (SEA)15.492
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)107.432
Click to view 3D structureProtein RecAP9WHJ3Mycobacterium tuberculosisPredicted (SEA)14.0129
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)150.249
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)74.6574
Click to view 3D structureProstaglandin E2 receptor EP1 subtypeP34995HumansPredicted (SEA)17.8275
Carbonic anhydrase 14 structureClick to view 3D structureCarbonic anhydrase 14Q9ULX7HumansPredicted (SEA)67.4953
Prostaglandin E2 receptor EP3 subtype structureClick to view 3D structureProstaglandin E2 receptor EP3 subtypeP43115HumansPredicted (SEA)20.3186
Click to view 3D structureAlbuminP02770Rattus norvegicusPredicted (SEA)0.0778492
72 kDa type IV collagenase structureClick to view 3D structure72 kDa type IV collagenaseP08253HumansPredicted (SEA)240.009
Macrophage metalloelastase structureClick to view 3D structureMacrophage metalloelastaseP39900HumansPredicted (SEA)123.391
Prostaglandin E2 receptor EP2 subtype structureClick to view 3D structureProstaglandin E2 receptor EP2 subtypeP43116HumansPredicted (SEA)20.4743
Matrix metalloproteinase-9 structureClick to view 3D structureMatrix metalloproteinase-9P14780HumansPredicted (SEA)254.645
Replicase polyprotein 1ab structureClick to view 3D structureReplicase polyprotein 1abP0DTD1SARS-CoV-2Predicted (SEA)103.929
Prostaglandin F2-alpha receptor structureClick to view 3D structureProstaglandin F2-alpha receptorP43088HumansPredicted (SEA)12.1445
D(3) dopamine receptor structureClick to view 3D structureD(3) dopamine receptorP35462HumansPredicted (SEA)459.466
Click to view 3D structureRAC-alpha serine/threonine-protein kinaseP31750MousePredicted (SEA)3.03612
Prostaglandin E2 receptor EP4 subtype structureClick to view 3D structureProstaglandin E2 receptor EP4 subtypeP35408HumansPredicted (SEA)26.3909
Carbonic anhydrase 6 structureClick to view 3D structureCarbonic anhydrase 6P23280HumansPredicted (SEA)79.6398
Click to view 3D structureCarbonic anhydrase 5A, mitochondrialP35218HumansPredicted (SEA)109.534
Concentrations
Not Available
External Links
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