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Identification
NameChlorpropamide
Accession NumberDB00672  (APRD00029)
TypeSmall Molecule
GroupsApproved
Description

Chlorpropamide 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 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. 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
1-(P-Chlorobenzenesulfonyl)-3-propylurea
1-(P-Chlorophenylsulfonyl)-3-propylurea
1-Propyl-3-(P-chlorobenzenesulfonyl)urea
4-chloro-N-((Propylamino)carbonyl)benzenesulfonamide
4-chloro-N-[(Propylamino)carbonyl]benzenesulfonamide
Chlorpropamid
Chlorpropamide
Chlorpropamidum
Clorpropamida
N-(4-Chlorophenylsulfonyl)-n'-propylurea
N-(P-Chlorobenzenesulfonyl)-n'-propylurea
N-Propyl-n'-(P-chlorobenzenesulfonyl)urea
N-Propyl-n'-P-chlorophenylsulfonylcarbamide
External Identifiers
  • Hoechst 18810
  • P 607
  • U 9818
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Chlorpropamide 100 Tab USPtablet100 mgoralPro Doc Limitee1983-12-312009-07-23Canada
Chlorpropamide Tab 250mgtablet250 mgoralDuchesnay Inc1978-12-312003-07-18Canada
Chlorpropamide Tab 250mgtablet250 mgoralPro Doc Limitee1969-12-312009-07-23Canada
Diabinese Tab 100mgtablet100 mgoralPfizer Canada Inc1958-12-312000-10-18Canada
Diabinese Tab 250mgtablet250 mgoralPfizer Canada Inc1958-12-312000-07-26Canada
Novo-propamide 250mgtablet250 mgoralNovopharm Limited1969-12-312010-09-10Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo Chlorpropamide Tab 100mgtablet100 mgoralApotex Inc1977-12-31Not applicableCanada
Apo Chlorpropamide Tab 250mgtablet250 mgoralApotex Inc1974-12-31Not applicableCanada
Chlorpropamidetablet100 mg/1oralMylan Pharmaceuticals Inc.1984-06-01Not applicableUs
Chlorpropamidetablet250 mg/1oralPd Rx Pharmaceuticals, Inc.2011-05-04Not applicableUs
Chlorpropamidetablet250 mg/1oralMylan Pharmaceuticals Inc.1984-06-01Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AbemideKobayashi Kako
ChloronaseHoechst
DabinesePfizer
DiabeedolSriprasit Dispensary
DiabemideGuidotti
DiabezinPrince
DiabinesePfizer
DiabitexPlantex-Ikapharm
DibeconPharmasant
GlyceminSiam Bheasach
HypomideAspen Pharmacare
LitangenMing Ta
PropamideAtlantic
TraneOmega
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIWTM2C3IL2X
CAS number94-20-2
WeightAverage: 276.74
Monoisotopic: 276.033540689
Chemical FormulaC10H13ClN2O3S
InChI KeyInChIKey=RKWGIWYCVPQPMF-UHFFFAOYSA-N
InChI
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)
IUPAC Name
1-(4-chlorobenzenesulfonyl)-3-propylurea
SMILES
CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1
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
  • Sulfonylurea
  • Halobenzene
  • Chlorobenzene
  • Aryl halide
  • Aryl chloride
  • Aminosulfonyl compound
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonamide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationFor treatment of NIDDM in conjunction with diet and exercise.
PharmacodynamicsChlorpropamide, a second-generation sulfonylurea antidiabetic agent, is used with diet to lower blood glucose levels in patients with diabetes mellitus type II. Chlorpropamide is twice as potent as the related second-generation agent glipizide.
Mechanism of actionSulfonylureas such as chlorpropamide bind to ATP-sensitive potassium channels 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.
Related Articles
AbsorptionReadily absorbed from the GI tract. Peak plasma concentrations occur within 2-4 hours and the onset of action occurs within one hour. The maximal effect of chlorpropamide is seen 3-6 hours following oral administration.
Volume of distributionNot Available
Protein bindingHighly bound to plasma proteins.
Metabolism

Up to 80% of dose is metabolized likely through the liver to to 2-hydroxylchlorpropamide (2-OH CPA), p-chlorobenzenesulfonylurea (CBSU), 3-hydroxylchlorpropamide (3-OH CPA), and p-chlorobenzenesulfonamide (CBSA); CBSA may be produced by decomposition in urine. It is unknown whether chlorpropamide metabolites exert hypoglycemic effects.

SubstrateEnzymesProduct
Chlorpropamide
2-HydroxychlorpropamideDetails
Chlorpropamide
Not Available
3-HydroxychlorpropamideDetails
Chlorpropamide
Not Available
p-Chlorobenzene sulfonylureaDetails
p-Chlorobenzene sulfonylurea
Not Available
p-Chlorobenzene sulfonamideDetails
Route of elimination80-90% of a single oral dose is excreted in the urine as unchaged drug and metabolites within 96 hours.
Half lifeApproximately 36 hours with interindividual variation ranging from 25-60 hours. Duration of effect persists for at least 24 hours.
ClearanceNot Available
ToxicityIPN-RAT LD50 580 mg/kg
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9969
Blood Brain Barrier+0.8087
Caco-2 permeable-0.6198
P-glycoprotein substrateNon-substrate0.6087
P-glycoprotein inhibitor INon-inhibitor0.9009
P-glycoprotein inhibitor IINon-inhibitor0.9533
Renal organic cation transporterNon-inhibitor0.8747
CYP450 2C9 substrateSubstrate0.5553
CYP450 2D6 substrateNon-substrate0.8806
CYP450 3A4 substrateNon-substrate0.7042
CYP450 1A2 substrateNon-inhibitor0.9044
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.9592
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6454
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.7685
BiodegradationNot ready biodegradable0.9206
Rat acute toxicity2.1413 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9072
hERG inhibition (predictor II)Non-inhibitor0.9306
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Barr laboratories inc
  • Clonmel healthcare ltd
  • Duramed pharmaceuticals inc sub barr laboratories inc
  • Halsey drug co inc
  • Ivax pharmaceuticals inc
  • Mylan pharmaceuticals inc
  • Par pharmaceutical inc
  • Pliva inc
  • Sandoz inc
  • Superpharm corp
  • Teva pharmaceuticals usa inc
  • Usl pharma inc
  • Watson laboratories inc
  • Pfizer laboratories div pfizer inc
Packagers
Dosage forms
FormRouteStrength
Tabletoral100 mg
Tabletoral250 mg
Tabletoral100 mg/1
Tabletoral250 mg/1
Prices
Unit descriptionCostUnit
Diabinese 250 mg tablet1.34USD tablet
Diabinese 100 mg tablet0.61USD tablet
Chlorpropamide 250 mg tablet0.46USD tablet
Chlorpropamide 100 mg tablet0.33USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point129.2-129.8McLamore, W.M.; U S . Patent 3,349,124; October 24,1967; assigned to Chas. Pfizer Co., Inc.
water solubility258 mg/L (at 37 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP2.27HANSCH,C ET AL. (1995)
logS-3.03ADME Research, USCD
pKa5.13LIPINSKI,CA ET AL. (1991)
Predicted Properties
PropertyValueSource
Water Solubility0.157 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity65.43 m3·mol-1ChemAxon
Polarizability27.06 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

McLamore, W.M.; U S . Patent 3,349,124; October 24,1967; assigned to Chas. Pfizer Co.,
Inc.

General ReferencesNot Available
External Links
ATC CodesA10BB02
AHFS Codes
  • 68:20.20
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (35.8 KB)
Interactions
Drug Interactions
Drug
AcebutololAcebutolol may increase the hypoglycemic activities of Chlorpropamide.
AcenocoumarolChlorpropamide may increase the anticoagulant activities of Acenocoumarol.
AcetohexamideAcetohexamide may increase the hypoglycemic activities of Chlorpropamide.
Acetylsalicylic acidAcetylsalicylic acid may increase the hypoglycemic activities of Chlorpropamide.
AlbiglutideAlbiglutide may increase the hypoglycemic activities of Chlorpropamide.
AllopurinolThe serum concentration of Chlorpropamide can be increased when it is combined with Allopurinol.
AlogliptinAlogliptin may increase the hypoglycemic activities of Chlorpropamide.
AmitriptylineAmitriptyline may increase the hypoglycemic activities of Chlorpropamide.
Ammonium chlorideThe serum concentration of Chlorpropamide can be increased when it is combined with Ammonium chloride.
AmoxapineAmoxapine may increase the hypoglycemic activities of Chlorpropamide.
AripiprazoleThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Aripiprazole.
Arsenic trioxideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Arsenic trioxide.
ArticaineThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Articaine.
AsenapineThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Asenapine.
AtazanavirThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Atazanavir.
AtenololAtenolol may increase the hypoglycemic activities of Chlorpropamide.
BendroflumethiazideBendroflumethiazide may increase the hypoglycemic activities of Chlorpropamide.
BetamethasoneThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Betamethasone.
BetaxololBetaxolol may increase the hypoglycemic activities of Chlorpropamide.
BezafibrateBezafibrate may increase the hypoglycemic activities of Chlorpropamide.
BisoprololBisoprolol may increase the hypoglycemic activities of Chlorpropamide.
BrexpiprazoleThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Brexpiprazole.
BumetanideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Bumetanide.
BuserelinThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Buserelin.
CanagliflozinCanagliflozin may increase the hypoglycemic activities of Chlorpropamide.
CarbocisteineThe risk or severity of adverse effects can be increased when Chlorpropamide is combined with Carbocisteine.
CarteololCarteolol may increase the hypoglycemic activities of Chlorpropamide.
CarvedilolCarvedilol may increase the hypoglycemic activities of Chlorpropamide.
CeritinibThe serum concentration of Chlorpropamide can be increased when it is combined with Ceritinib.
ChloramphenicolThe metabolism of Chlorpropamide can be decreased when combined with Chloramphenicol.
ChlorothiazideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Chlorothiazide.
ChlorthalidoneThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Chlorthalidone.
CimetidineThe serum concentration of Chlorpropamide can be increased when it is combined with Cimetidine.
ClomipramineClomipramine may increase the hypoglycemic activities of Chlorpropamide.
ClozapineThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Clozapine.
CorticotropinThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Corticotropin.
Cortisone acetateThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Cortisone acetate.
Cyproterone acetateThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Cyproterone acetate.
DabrafenibThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Dabrafenib.
DanazolThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Danazol.
DapagliflozinDapagliflozin may increase the hypoglycemic activities of Chlorpropamide.
DarunavirThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Darunavir.
DesipramineDesipramine may increase the hypoglycemic activities of Chlorpropamide.
DesogestrelThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Desogestrel.
DexamethasoneThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Dexamethasone.
DexketoprofenThe risk or severity of adverse effects can be increased when Dexketoprofen is combined with Chlorpropamide.
DiazoxideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Diazoxide.
DicoumarolChlorpropamide may increase the anticoagulant activities of Dicoumarol.
DienogestThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Dienogest.
DihydrotestosteroneDihydrotestosterone may increase the hypoglycemic activities of Chlorpropamide.
DisopyramideChlorpropamide may increase the hypoglycemic activities of Disopyramide.
DoxepinDoxepin may increase the hypoglycemic activities of Chlorpropamide.
DrospirenoneThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Drospirenone.
DulaglutideDulaglutide may increase the hypoglycemic activities of Chlorpropamide.
EmpagliflozinEmpagliflozin may increase the hypoglycemic activities of Chlorpropamide.
EpinephrineThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Epinephrine.
ErythromycinErythromycin may increase the hypoglycemic activities of Chlorpropamide.
EsmololEsmolol may increase the hypoglycemic activities of Chlorpropamide.
EstradiolThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Estradiol.
Estrone sulfateThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Estropipate.
Etacrynic acidThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Ethacrynic acid.
EthanolThe risk or severity of adverse effects can be increased when Chlorpropamide is combined with Ethanol.
Ethinyl EstradiolThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Ethinyl Estradiol.
Ethynodiol diacetateThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Ethynodiol.
EtonogestrelThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Etonogestrel.
EverolimusThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Everolimus.
ExenatideExenatide may increase the hypoglycemic activities of Chlorpropamide.
FenofibrateFenofibrate may increase the hypoglycemic activities of Chlorpropamide.
FloxuridineThe metabolism of Chlorpropamide can be decreased when combined with Floxuridine.
FluconazoleThe metabolism of Chlorpropamide can be decreased when combined with Fluconazole.
FludrocortisoneThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Fludrocortisone.
FosamprenavirThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Fosamprenavir.
FurosemideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Furosemide.
GemfibrozilGemfibrozil may increase the hypoglycemic activities of Chlorpropamide.
GliclazideGliclazide may increase the hypoglycemic activities of Chlorpropamide.
GlimepirideChlorpropamide may increase the hypoglycemic activities of Glimepiride.
GlipizideChlorpropamide may increase the hypoglycemic activities of Glipizide.
GliquidoneGliquidone may increase the hypoglycemic activities of Chlorpropamide.
GlyburideGlyburide may increase the hypoglycemic activities of Chlorpropamide.
GoserelinThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Goserelin.
HexamethylenetetramineThe serum concentration of Chlorpropamide can be increased when it is combined with Hexamethylenetetramine.
HistrelinThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Histrelin.
HydrochlorothiazideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Hydrochlorothiazide.
HydrocortisoneThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Hydrocortisone.
Hydroxyprogesterone caproateThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Hydroxyprogesterone caproate.
IloperidoneThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Iloperidone.
ImipramineImipramine may increase the hypoglycemic activities of Chlorpropamide.
IndapamideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Indapamide.
IndinavirThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Indinavir.
Insulin AspartInsulin Aspart may increase the hypoglycemic activities of Chlorpropamide.
Insulin DegludecChlorpropamide may increase the hypoglycemic activities of Insulin degludec.
Insulin DetemirInsulin Detemir may increase the hypoglycemic activities of Chlorpropamide.
Insulin GlargineChlorpropamide may increase the hypoglycemic activities of Insulin Glargine.
Insulin GlulisineInsulin Glulisine may increase the hypoglycemic activities of Chlorpropamide.
Insulin HumanChlorpropamide may increase the hypoglycemic activities of Insulin Regular.
Insulin LisproChlorpropamide may increase the hypoglycemic activities of Insulin Lispro.
LabetalolLabetalol may increase the hypoglycemic activities of Chlorpropamide.
LanreotideChlorpropamide may increase the hypoglycemic activities of Lanreotide.
LeuprolideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Leuprolide.
LevonorgestrelThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Levonorgestrel.
LinagliptinLinagliptin may increase the hypoglycemic activities of Chlorpropamide.
Lipoic AcidLipoic Acid may increase the hypoglycemic activities of Chlorpropamide.
LiraglutideLiraglutide may increase the hypoglycemic activities of Chlorpropamide.
LopinavirThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Lopinavir.
LumacaftorThe serum concentration of Chlorpropamide can be decreased when it is combined with Lumacaftor.
LurasidoneThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Lurasidone.
MaprotilineMaprotiline may increase the hypoglycemic activities of Chlorpropamide.
MecamylamineThe risk or severity of adverse effects can be increased when Chlorpropamide is combined with Mecamylamine.
MecaserminChlorpropamide may increase the hypoglycemic activities of Mecasermin.
Medroxyprogesterone acetateThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Medroxyprogesterone Acetate.
Megestrol acetateThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Megestrol acetate.
MestranolThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Mestranol.
MetforminMetformin may increase the hypoglycemic activities of Chlorpropamide.
MethotrimeprazineThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Methotrimeprazine.
MethyclothiazideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Methyclothiazide.
MethylprednisoloneThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Methylprednisolone.
MetolazoneThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Metolazone.
MetoprololMetoprolol may increase the hypoglycemic activities of Chlorpropamide.
MetreleptinMetreleptin may increase the hypoglycemic activities of Chlorpropamide.
MiconazoleMiconazole may increase the hypoglycemic activities of Chlorpropamide.
MifepristoneThe serum concentration of Chlorpropamide can be increased when it is combined with Mifepristone.
NadololNadolol may increase the hypoglycemic activities of Chlorpropamide.
NateglinideChlorpropamide may increase the hypoglycemic activities of Nateglinide.
NebivololNebivolol may increase the hypoglycemic activities of Chlorpropamide.
NelfinavirThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Nelfinavir.
NiacinThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Niacin.
NilotinibThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Nilotinib.
NorethisteroneThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Norethindrone.
NorgestimateThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Norgestimate.
NortriptylineNortriptyline may increase the hypoglycemic activities of Chlorpropamide.
OctreotideChlorpropamide may increase the hypoglycemic activities of Octreotide.
OlanzapineThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Olanzapine.
OxandroloneOxandrolone may increase the hypoglycemic activities of Chlorpropamide.
PaliperidoneThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Paliperidone.
ParoxetineParoxetine may increase the hypoglycemic activities of Chlorpropamide.
PasireotideChlorpropamide may increase the hypoglycemic activities of Pasireotide.
PegvisomantPegvisomant may increase the hypoglycemic activities of Chlorpropamide.
PenbutololPenbutolol may increase the hypoglycemic activities of Chlorpropamide.
PentamidineChlorpropamide may increase the hypoglycemic activities of Pentamidine.
PhenelzinePhenelzine may increase the hypoglycemic activities of Chlorpropamide.
PhenytoinThe metabolism of Chlorpropamide can be increased when combined with Phenytoin.
PindololPindolol may increase the hypoglycemic activities of Chlorpropamide.
PioglitazonePioglitazone may increase the hypoglycemic activities of Chlorpropamide.
PipotiazineThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Pipotiazine.
PorfimerChlorpropamide may increase the photosensitizing activities of Porfimer.
PrednisoloneThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Prednisolone.
PrednisoneThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Prednisone.
ProbenecidThe protein binding of Chlorpropamide can be decreased when combined with Probenecid.
ProgesteroneThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Progesterone.
PropranololPropranolol may increase the hypoglycemic activities of Chlorpropamide.
ProtriptylineProtriptyline may increase the hypoglycemic activities of Chlorpropamide.
QuetiapineThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Quetiapine.
QuinineChlorpropamide may increase the hypoglycemic activities of Quinine.
RanitidineThe serum concentration of Chlorpropamide can be increased when it is combined with Ranitidine.
RepaglinideRepaglinide may increase the hypoglycemic activities of Chlorpropamide.
Repository corticotropinThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Repository corticotropin.
RifampicinThe serum concentration of Chlorpropamide can be decreased when it is combined with Rifampicin.
RisperidoneThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Risperidone.
RitonavirThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Ritonavir.
RosiglitazoneRosiglitazone may increase the hypoglycemic activities of Chlorpropamide.
SaquinavirThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Saquinavir.
SaxagliptinSaxagliptin may increase the hypoglycemic activities of Chlorpropamide.
SecobarbitalThe metabolism of Chlorpropamide can be increased when combined with Secobarbital.
SirolimusThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Sirolimus.
SitagliptinSitagliptin may increase the hypoglycemic activities of Chlorpropamide.
SotalolSotalol may increase the hypoglycemic activities of Chlorpropamide.
SparfloxacinSparfloxacin may increase the hypoglycemic activities of Chlorpropamide.
SulfadiazineSulfadiazine may increase the hypoglycemic activities of Chlorpropamide.
SulfamethoxazoleSulfamethoxazole may increase the hypoglycemic activities of Chlorpropamide.
SulfisoxazoleSulfisoxazole may increase the hypoglycemic activities of Chlorpropamide.
SunitinibChlorpropamide may increase the hypoglycemic activities of Sunitinib.
TacrolimusThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Tacrolimus.
TemsirolimusThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Temsirolimus.
TestosteroneTestosterone may increase the hypoglycemic activities of Chlorpropamide.
TimololTimolol may increase the hypoglycemic activities of Chlorpropamide.
TipranavirThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Tipranavir.
TolazamideChlorpropamide may increase the hypoglycemic activities of Tolazamide.
TolbutamideTolbutamide may increase the hypoglycemic activities of Chlorpropamide.
TorasemideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Torasemide.
TranylcypromineTranylcypromine may increase the hypoglycemic activities of Chlorpropamide.
TriamcinoloneThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Triamcinolone.
TrichlormethiazideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Trichlormethiazide.
TrimethoprimTrimethoprim may increase the hypoglycemic activities of Chlorpropamide.
TrimipramineTrimipramine may increase the hypoglycemic activities of Chlorpropamide.
TriptorelinThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Triptorelin.
TroglitazoneTroglitazone may increase the hypoglycemic activities of Chlorpropamide.
VerteporfinChlorpropamide may increase the photosensitizing activities of Verteporfin.
VildagliptinVildagliptin may increase the hypoglycemic activities of Chlorpropamide.
VoriconazoleThe serum concentration of Chlorpropamide can be increased when it is combined with Voriconazole.
VorinostatThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Vorinostat.
WarfarinChlorpropamide may increase the anticoagulant activities of Warfarin.
ZiprasidoneThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Ziprasidone.
Food Interactions
  • Avoid alcohol.
  • Food reduces the rate of absorption.
  • Take 30 minutes before meal.

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Sulfonylurea receptor activity
Specific Function:
Subunit of the beta-cell ATP-sensitive potassium channel (KATP). Regulator of ATP-sensitive K(+) channels and insulin release.
Gene Name:
ABCC8
Uniprot ID:
Q09428
Molecular Weight:
176990.36 Da
References
  1. Mizuno CS, Chittiboyina AG, Kurtz TW, Pershadsingh HA, Avery MA: Type 2 diabetes and oral antihyperglycemic drugs. Curr Med Chem. 2008;15(1):61-74. [PubMed:18220763 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Prostaglandin-endoperoxide synthase activity
Specific Function:
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gastric epithelial cells, it is a key step in the generation of prostaglandins, such as prostaglandin E2 (PGE2), which plays an important role in cytoprotection. In platelets, it is involved in the gener...
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular Weight:
68685.82 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular Weight:
141477.255 Da
References
  1. Ibrahim S, Peggins J, Knapton A, Licht T, Aszalos A: Influence of antipsychotic, antiemetic, and Ca(2+) channel blocker drugs on the cellular accumulation of the anticancer drug daunorubicin: P-glycoprotein modulation. J Pharmacol Exp Ther. 2000 Dec;295(3):1276-83. [PubMed:11082465 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
Gene Name:
SLC15A1
Uniprot ID:
P46059
Molecular Weight:
78805.265 Da
References
  1. Terada T, Sawada K, Saito H, Hashimoto Y, Inui K: Inhibitory effect of novel oral hypoglycemic agent nateglinide (AY4166) on peptide transporters PEPT1 and PEPT2. Eur J Pharmacol. 2000 Mar 24;392(1-2):11-7. [PubMed:10748266 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Peptide:proton symporter activity
Specific Function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
Gene Name:
SLC15A2
Uniprot ID:
Q16348
Molecular Weight:
81782.77 Da
References
  1. Terada T, Sawada K, Saito H, Hashimoto Y, Inui K: Inhibitory effect of novel oral hypoglycemic agent nateglinide (AY4166) on peptide transporters PEPT1 and PEPT2. Eur J Pharmacol. 2000 Mar 24;392(1-2):11-7. [PubMed:10748266 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS) (By similarity). Mediates the sodium-in...
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular Weight:
61815.78 Da
References
  1. Uwai Y, Saito H, Hashimoto Y, Inui K: Inhibitory effect of anti-diabetic agents on rat organic anion transporter rOAT1. Eur J Pharmacol. 2000 Jun 16;398(2):193-7. [PubMed:10854830 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23