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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2018-05-20 20:10:58 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
Thumb
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
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 chlorpropamideMeSH
DiabineseMeSH
Farmasierra brand OF chlorpropamideMeSH
InsogenMeSH
ClorpropamidMeSH
Pfizer brand OF chlorpropamideMeSH
apo-ChlorpropamideMeSH
Byk gulden brand OF chlorpropamideMeSH
GlucamideMeSH
MeldianMeSH
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
DescriptionThis compound 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:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point127 - 129 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.16 g/LNot Available
LogP1.8Not Available
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0113-9540000000-ff74b5bd46b836406ce0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0002-0093000000-fa4d8bff1a5b0d68d8eaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-006x-0910000000-a09d8795a568a12a0da3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03dr-2910000000-7ee6a1f4754e3058ddb6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0002-0093000000-fa4d8bff1a5b0d68d8eaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-006x-0910000000-a09d8795a568a12a0da3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03dr-2910000000-7ee6a1f4754e3058ddb6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056u-8590000000-b6a0b930daf60d890749View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052f-9300000000-86daf757c19ffd3a6335View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-56249e018d50bc39c02cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00or-1290000000-3bb07392bdb6a7a3e697View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1930000000-99f0f1615af7f850d180View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-009i-6920000000-44e9f4535c61cee0a9c3View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00672 details
UrineExpected but not Quantified Not 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
FoodDB 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
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available