Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:45 UTC
HMDB IDHMDB0014810
Secondary Accession Numbers
  • HMDB14810
Metabolite Identification
Common NameChlorpropamide
DescriptionChlorpropamide is an oral antihyperglycemic agent used for the treatment of non-insulin-dependent diabetes mellitus (NIDDM). It belongs to the sulfonylurea class of insulin secretagogues, which act by stimulating I 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 I 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. Chlorpropamide is not recommended for the treatment of NIDDM as it increases blood pressure and the risk of retinopathy (UKPDS-33). Up to 80% of the single oral dose of chlorpropramide is metabolized, likely in the liver; 80-90% of the dose is excreted in urine as unchanged drug and metabolites. Renal and hepatic dysfunction may increase the risk of hypoglycemia.
Structure
Data?1582753222
Synonyms
ValueSource
1-(p-Chlorobenzenesulfonyl)-3-propylureaChEBI
1-(p-Chlorophenylsulfonyl)-3-propylureaChEBI
1-Propyl-3-(p-chlorobenzenesulfonyl)ureaChEBI
4-Chloro-N-((propylamino)carbonyl)benzenesulfonamideChEBI
4-Chloro-N-[(propylamino)carbonyl]benzenesulfonamideChEBI
ChlorpropamidumChEBI
ClorpropamidaChEBI
N-(4-Chlorophenylsulfonyl)-n'-propylureaChEBI
N-(p-Chlorobenzenesulfonyl)-n'-propylureaChEBI
N-Propyl-n'-(p-chlorobenzenesulfonyl)ureaChEBI
N-Propyl-n'-p-chlorophenylsulfonylcarbamideChEBI
DiabineseKegg
1-(p-Chlorobenzenesulphonyl)-3-propylureaGenerator
1-(p-Chlorophenylsulphonyl)-3-propylureaGenerator
1-Propyl-3-(p-chlorobenzenesulphonyl)ureaGenerator
4-Chloro-N-((propylamino)carbonyl)benzenesulphonamideGenerator
4-Chloro-N-[(propylamino)carbonyl]benzenesulphonamideGenerator
N-(4-Chlorophenylsulphonyl)-n'-propylureaGenerator
N-(p-Chlorobenzenesulphonyl)-n'-propylureaGenerator
N-Propyl-n'-(p-chlorobenzenesulphonyl)ureaGenerator
N-Propyl-n'-p-chlorophenylsulphonylcarbamideGenerator
ChlorporpamideHMDB
Apotex brand OF chlorpropamideHMDB
Farmasierra brand OF chlorpropamideHMDB
InsogenHMDB
ClorpropamidHMDB
Pfizer brand OF chlorpropamideHMDB
Apo-chlorpropamideHMDB
Byk gulden brand OF chlorpropamideHMDB
GlucamideHMDB
MeldianHMDB
Chemical FormulaC10H13ClN2O3S
Average Molecular Weight276.74
Monoisotopic Molecular Weight276.033540689
IUPAC Name1-(4-chlorobenzenesulfonyl)-3-propylurea
Traditional Namechlorpropamide
CAS Registry Number94-20-2
SMILES
CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1
InChI Identifier
InChI=1S/C10H13ClN2O3S/c1-2-7-12-10(14)13-17(15,16)9-5-3-8(11)4-6-9/h3-6H,2,7H2,1H3,(H2,12,13,14)
InChI KeyRKWGIWYCVPQPMF-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
  • Benzenesulfonyl group
  • Chlorobenzene
  • Halobenzene
  • Sulfonylurea
  • Aryl chloride
  • Aryl halide
  • 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
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organopnictogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point127 - 129 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.16 g/LNot Available
LogP1.8Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available158.493http://allccs.zhulab.cn/database/detail?ID=AllCCS00000785
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.16 g/LALOGPS
logP2.15ALOGPS
logP1.94ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)4.33ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.27 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity65.43 m³·mol⁻¹ChemAxon
Polarizability27.06 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+159.59130932474
DeepCCS[M-H]-157.23230932474
DeepCCS[M-2H]-190.11830932474
DeepCCS[M+Na]+165.68430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ChlorpropamideCCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C13623.0Standard polar33892256
ChlorpropamideCCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C11659.8Standard non polar33892256
ChlorpropamideCCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C12229.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Chlorpropamide,1TMS,isomer #1CCCN(C(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C2240.7Semi standard non polar33892256
Chlorpropamide,1TMS,isomer #1CCCN(C(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C2331.4Standard non polar33892256
Chlorpropamide,1TMS,isomer #1CCCN(C(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C3146.6Standard polar33892256
Chlorpropamide,1TMS,isomer #2CCCNC(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(Cl)C=C12224.8Semi standard non polar33892256
Chlorpropamide,1TMS,isomer #2CCCNC(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(Cl)C=C12211.1Standard non polar33892256
Chlorpropamide,1TMS,isomer #2CCCNC(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(Cl)C=C13175.9Standard polar33892256
Chlorpropamide,2TMS,isomer #1CCCN(C(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C2184.8Semi standard non polar33892256
Chlorpropamide,2TMS,isomer #1CCCN(C(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C2462.0Standard non polar33892256
Chlorpropamide,2TMS,isomer #1CCCN(C(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C2867.2Standard polar33892256
Chlorpropamide,1TBDMS,isomer #1CCCN(C(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C2475.3Semi standard non polar33892256
Chlorpropamide,1TBDMS,isomer #1CCCN(C(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C2565.5Standard non polar33892256
Chlorpropamide,1TBDMS,isomer #1CCCN(C(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C3156.9Standard polar33892256
Chlorpropamide,1TBDMS,isomer #2CCCNC(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(Cl)C=C12465.9Semi standard non polar33892256
Chlorpropamide,1TBDMS,isomer #2CCCNC(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(Cl)C=C12454.0Standard non polar33892256
Chlorpropamide,1TBDMS,isomer #2CCCNC(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(Cl)C=C13199.8Standard polar33892256
Chlorpropamide,2TBDMS,isomer #1CCCN(C(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C2703.0Semi standard non polar33892256
Chlorpropamide,2TBDMS,isomer #1CCCN(C(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C2933.2Standard non polar33892256
Chlorpropamide,2TBDMS,isomer #1CCCN(C(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C2971.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Chlorpropamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0113-9540000000-ff74b5bd46b836406ce02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chlorpropamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chlorpropamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpropamide LC-ESI-qTof , Positive-QTOFsplash10-0002-0093000000-fa4d8bff1a5b0d68d8ea2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpropamide LC-ESI-qTof , Positive-QTOFsplash10-006x-0910000000-a09d8795a568a12a0da32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpropamide LC-ESI-qTof , Positive-QTOFsplash10-03dr-2910000000-7ee6a1f4754e3058ddb62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpropamide , positive-QTOFsplash10-0002-0093000000-fa4d8bff1a5b0d68d8ea2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpropamide , positive-QTOFsplash10-006x-0910000000-a09d8795a568a12a0da32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpropamide , positive-QTOFsplash10-03dr-2910000000-7ee6a1f4754e3058ddb62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpropamide 40V, Positive-QTOFsplash10-03di-1900000000-31862fa36dca6aa815d52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpropamide 15V, Negative-QTOFsplash10-000i-0930000000-a4253aba18424677d03f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpropamide 10V, Positive-QTOFsplash10-03kc-4920000000-e03da1b44dcb4895f9482021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpropamide 20V, Positive-QTOFsplash10-03k9-2900000000-a8d91ed685eb991c0ac72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpropamide 30V, Negative-QTOFsplash10-000i-0900000000-85959c7674668f778a7c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpropamide 45V, Negative-QTOFsplash10-000i-0900000000-f4650a1be90ea4cf89042021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpropamide 75V, Negative-QTOFsplash10-004i-9800000000-20116e7d84b9426dc3722021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpropamide 60V, Negative-QTOFsplash10-004r-1900000000-8e5466a5890f95e1d7f12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpropamide 90V, Positive-QTOFsplash10-004i-9100000000-c0d2de9234d984d4f5f52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpropamide 40V, Negative-QTOFsplash10-004i-9700000000-2dbf7aa3bcc58d7e7a0d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpropamide 20V, Negative-QTOFsplash10-000i-0900000000-5c15ec0e7d272f3993ed2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpropamide 90V, Negative-QTOFsplash10-004i-9100000000-f15d3a6d15e1e36c18002021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpropamide 10V, Negative-QTOFsplash10-000i-0930000000-87e8123fe243c4d02b512021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorpropamide 10V, Positive-QTOFsplash10-056u-8590000000-b6a0b930daf60d8907492016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorpropamide 20V, Positive-QTOFsplash10-052f-9300000000-86daf757c19ffd3a63352016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorpropamide 40V, Positive-QTOFsplash10-0006-9100000000-56249e018d50bc39c02c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorpropamide 10V, Negative-QTOFsplash10-00or-1290000000-3bb07392bdb6a7a3e6972016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorpropamide 20V, Negative-QTOFsplash10-000i-1930000000-99f0f1615af7f850d1802016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorpropamide 40V, Negative-QTOFsplash10-009i-6920000000-44e9f4535c61cee0a9c32016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00672 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00672 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00672
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2626
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkChlorpropamide
METLIN IDNot Available
PubChem Compound2727
PDB IDNot Available
ChEBI ID3650
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