Identification

Name
Tolbutamide
Accession Number
DB01124  (APRD00267)
Type
Small Molecule
Groups
Approved
Description

Tolbutamide 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.

Structure
Thumb
Synonyms
  • 1-Butyl-3-(P-methylphenylsulfonyl)urea
  • 1-Butyl-3-(P-tolylsulfonyl)urea
  • 1-Butyl-3-tosylurea
  • 1-P-Toluenesulfonyl-3-butylurea
  • 3-(P-Tolyl-4-sulfonyl)-1-butylurea
  • N-(4-Methylbenzenesulfonyl)-n'-butylurea
  • N-(4-Methylphenylsulfonyl)-n'-butylurea
  • N-(P-Methylbenzenesulfonyl)-n'-butylurea
  • N-(Sulfonyl-P-methylbenzene)-n'-N-butylurea
  • N-Butyl-n'-(4-methylphenylsulfonyl)urea
  • N-Butyl-N'-(p-tolylsulfonyl)urea
  • N-Butyl-n'-P-toluenesulfonylurea
  • N-N-Butyl-n'-tosylurea
  • Orinase (tn)
  • Tolbutamida
  • Tolbutamide
  • Tolbutamidum
  • Tolylsulfonylbutylurea
External IDs
NSC-23813 / NSC-87833
Product Ingredients
IngredientUNIICASInChI Key
Tolbutamide sodiumE830VC49W5473-41-6QKHDBRQBSNZFAK-UHFFFAOYSA-M
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Mobenol Tablets 500mgTablet500 mgOralCarter Horner Corp.1957-12-311997-08-14Canada
Orinase 0.5gmTablet500 mgOralHoechst Canada Inc.1957-12-311997-02-28Canada
Orinase 1gmTablet1 gOralHoechst Canada Inc.1966-12-311997-02-28Canada
TolbutamideTablet500 mgOralAa Pharma Inc1975-12-31Not applicableCanada
Tolbutamide Tab 500mgTablet500 mgOralPro Doc Limitee1962-12-312010-07-13Canada
Tolbutamide Tab 500mgTablet500 mgOralDuchesnay Inc.1978-12-312003-07-18Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Novo-butamide 500mgTablet500 mgOralNovopharm Limited1968-12-312005-08-10Canada
TolbutamideTablet500 mg/1OralMylan Pharmaceuticals1989-11-01Not applicableUs
International/Other Brands
Artosin / Butamide / Diabetol / Dirastan / Glyconon / Orinase / Rastinon
Categories
UNII
982XCM1FOI
CAS number
64-77-7
Weight
Average: 270.348
Monoisotopic: 270.103813142
Chemical Formula
C12H18N2O3S
InChI Key
JLRGJRBPOGGCBT-UHFFFAOYSA-N
InChI
InChI=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)
IUPAC Name
3-butyl-1-(4-methylbenzenesulfonyl)urea
SMILES
CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1

Pharmacology

Indication

For treatment of NIDDM (non-insulin-dependent diabetes mellitus) in conjunction with diet and exercise.

Structured Indications
Pharmacodynamics

Tolbutamide, a first-generation sulfonylurea antidiabetic agent, is used with diet to lower blood glucose levels in patients with diabetes mellitus type II. Tolbutamide is twice as potent as the related second-generation agent glipizide. Tolbutamide lowers blood sugar by stimulating the pancreas to secrete insulin and helping the body use insulin efficiently. The pancreas must be able to produce insulin for this drug to work.

Mechanism of action

Sulfonylureas lower blood glucose in patients with NIDDM by directly stimulating the acute release of insulin from functioning beta cells of pancreatic islet tissue by an unknown process that involves a sulfonylurea receptor (receptor 1) on the beta cell. Sulfonylureas inhibit the ATP-potassium channels on the beta cell membrane and potassium efflux, which results in depolarization and calcium influx, calcium-calmodulin binding, kinase activation, and release of insulin-containing granules by exocytosis, an effect similar to that of glucose.

TargetActionsOrganism
AATP-binding cassette sub-family C member 8
inhibitor
Human
UATP-sensitive inward rectifier potassium channel 1
inhibitor
Human
Absorption

Readily absorbed following oral administration. Tolbutamide is detectable in plasma 30-60 minutes following oral administration of a single dose with peak plasma concentrations occurring within 3-5 hours.

Absorption is unaltered if taken with food but is increased with high pH.

Volume of distribution
Not Available
Protein binding

Approximately 95% bound to plasma proteins.

Metabolism

Metabolized in the liver principally via oxidation of the p-methyl group producing the carboxyl metabolite, 1-butyl-3-p-carboxyphenylsulfonylurea. May also be metabolized to hydroxytolbutamide. Tolbutamide does not undergo acetylation like antibacterial sulfonamides as it does not have a p-amino group.

Route of elimination

Unchanged drug and metabolites are eliminated in the urine and feces. Approximately 75-85% of a single orally administered dose is excreted in the urine principally as the 1-butyl-3-p-carboxyphenylsulfonylurea within 24 hours.

Half life

Approximately 7 hours with interindividual variations ranging from 4-25 hours. Tolbutamide has the shortest duration of action, 6-12 hours, of the antidiabetic sulfonylureas.

Clearance
Not Available
Toxicity

Oral, mouse: LD50 = 2600 mg/kg

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Cytochrome P450 2C9CYP2C9*3(C;C) / (A;C)C AlleleEffect Directly StudiedPatients with this genotype have reduced metabolism of tolbutamide.Details
Cytochrome P450 2C9CYP2C9*6Not Available818delAEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*15Not Available485C>AEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*25Not Available353_362delAGAAATGGAAEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*35Not Available374G>T / 430C>TEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*2Not Available430C>TEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*4Not Available1076T>CEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*5Not Available1080C>GEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*8Not Available449G>AEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*11Not Available1003C>TEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*12Not Available1465C>TEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*13Not Available269T>CEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*14Not Available374G>AEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*16Not Available895A>GEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*18Not Available1075A>C / 1190A>C  … show all Effect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*26Not Available389C>GEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*28Not Available641A>TEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*30Not Available1429G>AEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2C9CYP2C9*33Not Available395G>AEffect InferredPoor drug metabolizer, lower dose requirementsDetails

Interactions

Drug Interactions
DrugInteractionDrug group
AbirateroneThe serum concentration of Tolbutamide can be increased when it is combined with Abiraterone.Approved
AcebutololAcebutolol may increase the hypoglycemic activities of Tolbutamide.Approved
AceclofenacThe metabolism of Aceclofenac can be decreased when combined with Tolbutamide.Approved, Investigational
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Tolbutamide.Approved
AcetaminophenThe metabolism of Acetaminophen can be decreased when combined with Tolbutamide.Approved
Acetylsalicylic acidThe metabolism of Acetylsalicylic acid can be decreased when combined with Tolbutamide.Approved, Vet Approved
AlogliptinAlogliptin may increase the hypoglycemic activities of Tolbutamide.Approved
AlosetronThe metabolism of Alosetron can be decreased when combined with Tolbutamide.Approved, Withdrawn
AlprazolamThe metabolism of Alprazolam can be decreased when combined with Tolbutamide.Approved, Illicit, Investigational
AlprenololAlprenolol may increase the hypoglycemic activities of Tolbutamide.Approved, Withdrawn
Aluminium clofibrateAluminium clofibrate may increase the hypoglycemic activities of Tolbutamide.Experimental
AminophenazoneThe metabolism of Aminophenazone can be decreased when combined with Tolbutamide.Approved, Withdrawn
AmiodaroneThe metabolism of Tolbutamide can be decreased when combined with Amiodarone.Approved, Investigational
AmitriptylineThe metabolism of Amitriptyline can be decreased when combined with Tolbutamide.Approved
AmodiaquineThe serum concentration of Amodiaquine can be increased when it is combined with Tolbutamide.Approved, Investigational
AmprenavirThe metabolism of Amprenavir can be decreased when combined with Tolbutamide.Approved
AntipyrineThe metabolism of Antipyrine can be decreased when combined with Tolbutamide.Approved
ApixabanThe metabolism of Apixaban can be decreased when combined with Tolbutamide.Approved
AprepitantThe serum concentration of Tolbutamide can be decreased when it is combined with Aprepitant.Approved, Investigational
Arachidonic AcidThe metabolism of Arachidonic Acid can be decreased when combined with Tolbutamide.Experimental
ArformoterolThe metabolism of Arformoterol can be decreased when combined with Tolbutamide.Approved, Investigational
ArmodafinilThe metabolism of Tolbutamide can be decreased when combined with Armodafinil.Approved, Investigational
ArotinololArotinolol may increase the hypoglycemic activities of Tolbutamide.Investigational
ArtemetherThe metabolism of Artemether can be decreased when combined with Tolbutamide.Approved
AtazanavirThe metabolism of Atazanavir can be decreased when combined with Tolbutamide.Approved, Investigational
AtenololAtenolol may increase the hypoglycemic activities of Tolbutamide.Approved
AtorvastatinAtorvastatin may increase the hypoglycemic activities of Tolbutamide.Approved
AzelastineThe metabolism of Azelastine can be decreased when combined with Tolbutamide.Approved
BefunololBefunolol may increase the hypoglycemic activities of Tolbutamide.Experimental
BendroflumethiazideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Bendroflumethiazide.Approved
BetaxololBetaxolol may increase the hypoglycemic activities of Tolbutamide.Approved
BevantololBevantolol may increase the hypoglycemic activities of Tolbutamide.Approved
BexaroteneThe metabolism of Bexarotene can be decreased when combined with Tolbutamide.Approved, Investigational
BezafibrateBezafibrate may increase the hypoglycemic activities of Tolbutamide.Approved
BisoprololBisoprolol may increase the hypoglycemic activities of Tolbutamide.Approved
BopindololBopindolol may increase the hypoglycemic activities of Tolbutamide.Approved
BortezomibThe metabolism of Bortezomib can be decreased when combined with Tolbutamide.Approved, Investigational
BosentanThe serum concentration of Bosentan can be increased when it is combined with Tolbutamide.Approved, Investigational
BrivaracetamThe metabolism of Brivaracetam can be decreased when combined with Tolbutamide.Approved, Investigational
BrompheniramineThe metabolism of Brompheniramine can be decreased when combined with Tolbutamide.Approved
BucindololBucindolol may increase the hypoglycemic activities of Tolbutamide.Investigational
BufuralolBufuralol may increase the hypoglycemic activities of Tolbutamide.Experimental, Investigational
BupranololBupranolol may increase the hypoglycemic activities of Tolbutamide.Approved
BuprenorphineThe metabolism of Buprenorphine can be decreased when combined with Tolbutamide.Approved, Illicit, Investigational, Vet Approved
BupropionThe metabolism of Bupropion can be decreased when combined with Tolbutamide.Approved
CabozantinibThe metabolism of Cabozantinib can be decreased when combined with Tolbutamide.Approved
CaffeineThe metabolism of Caffeine can be decreased when combined with Tolbutamide.Approved
CanagliflozinCanagliflozin may increase the hypoglycemic activities of Tolbutamide.Approved
CandesartanThe metabolism of Candesartan can be decreased when combined with Tolbutamide.Experimental
Candesartan cilexetilThe metabolism of Candesartan cilexetil can be decreased when combined with Tolbutamide.Approved
CannabidiolThe metabolism of Cannabidiol can be decreased when combined with Tolbutamide.Approved, Investigational
CapecitabineThe metabolism of Tolbutamide can be decreased when combined with Capecitabine.Approved, Investigational
CarbamazepineThe metabolism of Tolbutamide can be increased when combined with Carbamazepine.Approved, Investigational
CarbinoxamineThe metabolism of Carbinoxamine can be decreased when combined with Tolbutamide.Approved
CarbocisteineThe risk or severity of adverse effects can be increased when Tolbutamide is combined with Carbocisteine.Approved, Investigational
CarteololCarteolol may increase the hypoglycemic activities of Tolbutamide.Approved
CarvedilolThe serum concentration of Carvedilol can be increased when it is combined with Tolbutamide.Approved, Investigational
CelecoxibThe metabolism of Celecoxib can be decreased when combined with Tolbutamide.Approved, Investigational
CeliprololCeliprolol may increase the hypoglycemic activities of Tolbutamide.Approved, Investigational
CeritinibThe serum concentration of Tolbutamide can be increased when it is combined with Ceritinib.Approved
ChloramphenicolThe metabolism of Tolbutamide can be decreased when combined with Chloramphenicol.Approved, Vet Approved
ChlorothiazideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Chlorothiazide.Approved, Vet Approved
ChlorpropamideThe metabolism of Chlorpropamide can be decreased when combined with Tolbutamide.Approved
ChlorthalidoneThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Chlorthalidone.Approved
CholecalciferolThe metabolism of Tolbutamide can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CimetidineThe serum concentration of Tolbutamide can be increased when it is combined with Cimetidine.Approved
CinnarizineThe metabolism of Cinnarizine can be decreased when combined with Tolbutamide.Approved, Investigational
CiprofibrateCiprofibrate may increase the hypoglycemic activities of Tolbutamide.Approved, Investigational
CisaprideThe metabolism of Cisapride can be decreased when combined with Tolbutamide.Approved, Investigational, Withdrawn
CitalopramThe metabolism of Tolbutamide can be decreased when combined with Citalopram.Approved
ClofibrateClofibrate may increase the hypoglycemic activities of Tolbutamide.Approved, Investigational
ClofibrideClofibride may increase the hypoglycemic activities of Tolbutamide.Experimental
ClopidogrelThe metabolism of Clopidogrel can be decreased when combined with Tolbutamide.Approved
CloranololCloranolol may increase the hypoglycemic activities of Tolbutamide.Experimental
ClorindioneTolbutamide may increase the anticoagulant activities of Clorindione.Experimental
ClotrimazoleThe metabolism of Tolbutamide can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineThe metabolism of Clozapine can be decreased when combined with Tolbutamide.Approved
CrisaboroleThe metabolism of Tolbutamide can be decreased when combined with Crisaborole.Approved, Investigational
CyclopenthiazideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Cyclopenthiazide.Experimental
CyclophosphamideThe metabolism of Cyclophosphamide can be decreased when combined with Tolbutamide.Approved, Investigational
CyclosporineThe metabolism of Tolbutamide can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
DabrafenibThe serum concentration of Tolbutamide can be decreased when it is combined with Dabrafenib.Approved
DapagliflozinThe metabolism of Dapagliflozin can be decreased when combined with Tolbutamide.Approved
DapsoneThe metabolism of Dapsone can be decreased when combined with Tolbutamide.Approved, Investigational
DeferasiroxThe serum concentration of Tolbutamide can be increased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Tolbutamide can be decreased when combined with Delavirdine.Approved
DextromethorphanThe metabolism of Dextromethorphan can be decreased when combined with Tolbutamide.Approved
DiazepamThe metabolism of Diazepam can be decreased when combined with Tolbutamide.Approved, Illicit, Vet Approved
DiclofenacThe serum concentration of Diclofenac can be increased when it is combined with Tolbutamide.Approved, Vet Approved
DicoumarolThe metabolism of Dicoumarol can be decreased when combined with Tolbutamide.Approved
DiltiazemThe metabolism of Diltiazem can be decreased when combined with Tolbutamide.Approved
DiphenadioneTolbutamide may increase the anticoagulant activities of Diphenadione.Experimental
DiphenhydramineThe metabolism of Diphenhydramine can be decreased when combined with Tolbutamide.Approved
DoconexentThe metabolism of Doconexent can be decreased when combined with Tolbutamide.Approved, Investigational
DolasetronThe metabolism of Dolasetron can be decreased when combined with Tolbutamide.Approved
DonepezilThe metabolism of Donepezil can be decreased when combined with Tolbutamide.Approved
DopamineThe metabolism of Dopamine can be decreased when combined with Tolbutamide.Approved
DorzolamideThe metabolism of Dorzolamide can be decreased when combined with Tolbutamide.Approved
DosulepinThe metabolism of Tolbutamide can be decreased when combined with Dosulepin.Approved
DoxepinThe metabolism of Doxepin can be decreased when combined with Tolbutamide.Approved
DronabinolThe serum concentration of Dronabinol can be increased when it is combined with Tolbutamide.Approved, Illicit
EfavirenzThe metabolism of Tolbutamide can be decreased when combined with Efavirenz.Approved, Investigational
EletriptanThe metabolism of Eletriptan can be decreased when combined with Tolbutamide.Approved, Investigational
EmpagliflozinEmpagliflozin may increase the hypoglycemic activities of Tolbutamide.Approved
EnasidenibThe metabolism of Enasidenib can be decreased when combined with Tolbutamide.Approved
EpanololEpanolol may increase the hypoglycemic activities of Tolbutamide.Experimental
EpoprostenolThe metabolism of Epoprostenol can be decreased when combined with Tolbutamide.Approved
ErtugliflozinErtugliflozin may increase the hypoglycemic activities of Tolbutamide.Approved
Eslicarbazepine acetateThe metabolism of Tolbutamide can be decreased when combined with Eslicarbazepine acetate.Approved
EsmololEsmolol may increase the hypoglycemic activities of Tolbutamide.Approved
EsomeprazoleThe metabolism of Tolbutamide can be decreased when combined with Esomeprazole.Approved, Investigational
EstradiolThe metabolism of Estradiol can be decreased when combined with Tolbutamide.Approved, Investigational, Vet Approved
Estradiol acetateThe metabolism of Estradiol acetate can be decreased when combined with Tolbutamide.Approved, Investigational, Vet Approved
Estradiol benzoateThe metabolism of Estradiol benzoate can be decreased when combined with Tolbutamide.Approved, Investigational, Vet Approved
Estradiol cypionateThe metabolism of Estradiol cypionate can be decreased when combined with Tolbutamide.Approved, Investigational, Vet Approved
Estradiol dienanthateThe metabolism of Estradiol dienanthate can be decreased when combined with Tolbutamide.Approved, Investigational, Vet Approved
Estradiol valerateThe metabolism of Estradiol valerate can be decreased when combined with Tolbutamide.Approved, Investigational, Vet Approved
EstroneThe metabolism of Estrone can be decreased when combined with Tolbutamide.Approved
EszopicloneThe metabolism of Eszopiclone can be decreased when combined with Tolbutamide.Approved
EthanolThe risk or severity of adverse effects can be increased when Tolbutamide is combined with Ethanol.Approved
Ethyl biscoumacetateTolbutamide may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
EtodolacThe metabolism of Etodolac can be decreased when combined with Tolbutamide.Approved, Investigational, Vet Approved
EtofibrateEtofibrate may increase the hypoglycemic activities of Tolbutamide.Approved
EtoricoxibThe metabolism of Etoricoxib can be decreased when combined with Tolbutamide.Approved, Investigational
EtravirineThe metabolism of Etravirine can be decreased when combined with Tolbutamide.Approved
FelodipineThe metabolism of Tolbutamide can be decreased when combined with Felodipine.Approved, Investigational
FenofibrateFenofibrate may increase the hypoglycemic activities of Tolbutamide.Approved
Fenofibric acidFenofibric acid may increase the hypoglycemic activities of Tolbutamide.Approved
FloxuridineThe metabolism of Tolbutamide can be decreased when combined with Floxuridine.Approved
FluconazoleThe serum concentration of Tolbutamide can be increased when it is combined with Fluconazole.Approved
FluindioneTolbutamide may increase the anticoagulant activities of Fluindione.Investigational
FlunarizineThe metabolism of Flunarizine can be decreased when combined with Tolbutamide.Approved
FlunitrazepamThe metabolism of Flunitrazepam can be decreased when combined with Tolbutamide.Approved, Illicit
FluorouracilThe metabolism of Tolbutamide can be decreased when combined with Fluorouracil.Approved
FluoxetineThe metabolism of Fluoxetine can be decreased when combined with Tolbutamide.Approved, Vet Approved
FlurbiprofenThe metabolism of Flurbiprofen can be decreased when combined with Tolbutamide.Approved, Investigational
FluvastatinThe metabolism of Fluvastatin can be decreased when combined with Tolbutamide.Approved
FluvoxamineThe metabolism of Tolbutamide can be decreased when combined with Fluvoxamine.Approved, Investigational
FormoterolThe metabolism of Formoterol can be decreased when combined with Tolbutamide.Approved, Investigational
FosaprepitantThe serum concentration of Tolbutamide can be decreased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Tolbutamide can be increased when combined with Fosphenytoin.Approved
GavestinelThe metabolism of Gavestinel can be decreased when combined with Tolbutamide.Investigational
GemfibrozilThe metabolism of Tolbutamide can be decreased when combined with Gemfibrozil.Approved
GliclazideThe metabolism of Gliclazide can be decreased when combined with Tolbutamide.Approved
GlimepirideThe metabolism of Glimepiride can be decreased when combined with Tolbutamide.Approved
GlipizideThe metabolism of Glipizide can be decreased when combined with Tolbutamide.Approved
GlyburideThe metabolism of Glyburide can be decreased when combined with Tolbutamide.Approved
GuanfacineThe metabolism of Guanfacine can be decreased when combined with Tolbutamide.Approved, Investigational
HaloperidolThe metabolism of Haloperidol can be decreased when combined with Tolbutamide.Approved
HalothaneThe metabolism of Halothane can be decreased when combined with Tolbutamide.Approved, Vet Approved
HexobarbitalThe metabolism of Hexobarbital can be decreased when combined with Tolbutamide.Approved
HistamineThe metabolism of Histamine can be decreased when combined with Tolbutamide.Approved, Investigational
HydrochlorothiazideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Hydrochlorothiazide.Approved, Vet Approved
HydroflumethiazideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Hydroflumethiazide.Approved, Investigational
HydromorphoneThe metabolism of Hydromorphone can be decreased when combined with Tolbutamide.Approved, Illicit
IbuprofenThe metabolism of Ibuprofen can be decreased when combined with Tolbutamide.Approved
IdarubicinThe metabolism of Idarubicin can be decreased when combined with Tolbutamide.Approved
IfosfamideThe metabolism of Ifosfamide can be decreased when combined with Tolbutamide.Approved
ImatinibThe metabolism of Imatinib can be decreased when combined with Tolbutamide.Approved
IndapamideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Indapamide.Approved
IndenololIndenolol may increase the hypoglycemic activities of Tolbutamide.Withdrawn
IndinavirThe metabolism of Tolbutamide can be decreased when combined with Indinavir.Approved
IndisulamThe metabolism of Indisulam can be decreased when combined with Tolbutamide.Investigational
IndomethacinThe metabolism of Indomethacin can be decreased when combined with Tolbutamide.Approved, Investigational
IrbesartanThe metabolism of Irbesartan can be decreased when combined with Tolbutamide.Approved, Investigational
IsoniazidThe metabolism of Tolbutamide can be decreased when combined with Isoniazid.Approved
IxazomibThe metabolism of Ixazomib can be decreased when combined with Tolbutamide.Approved
KetamineThe metabolism of Ketamine can be decreased when combined with Tolbutamide.Approved, Vet Approved
KetobemidoneThe metabolism of Ketobemidone can be decreased when combined with Tolbutamide.Approved, Investigational
KetoconazoleThe metabolism of Tolbutamide can be decreased when combined with Ketoconazole.Approved, Investigational
KetoprofenThe metabolism of Ketoprofen can be decreased when combined with Tolbutamide.Approved, Vet Approved
LabetalolLabetalol may increase the hypoglycemic activities of Tolbutamide.Approved
LacosamideThe serum concentration of Lacosamide can be increased when it is combined with Tolbutamide.Approved
LandiololLandiolol may increase the hypoglycemic activities of Tolbutamide.Investigational
LansoprazoleThe metabolism of Lansoprazole can be decreased when combined with Tolbutamide.Approved, Investigational
LapatinibThe metabolism of Tolbutamide can be decreased when combined with Lapatinib.Approved, Investigational
LeflunomideThe serum concentration of Tolbutamide can be increased when it is combined with Leflunomide.Approved, Investigational
LesinuradThe metabolism of Lesinurad can be decreased when combined with Tolbutamide.Approved
LevobunololLevobunolol may increase the hypoglycemic activities of Tolbutamide.Approved
LicofeloneThe metabolism of Licofelone can be decreased when combined with Tolbutamide.Investigational
LidocaineThe metabolism of Lidocaine can be decreased when combined with Tolbutamide.Approved, Vet Approved
LinagliptinLinagliptin may increase the hypoglycemic activities of Tolbutamide.Approved
Lipoic AcidLipoic Acid may increase the hypoglycemic activities of Tolbutamide.Approved, Nutraceutical
LobeglitazoneThe metabolism of Tolbutamide can be decreased when combined with Lobeglitazone.Approved, Investigational
LopinavirThe metabolism of Tolbutamide can be increased when combined with Lopinavir.Approved
LoratadineThe metabolism of Loratadine can be decreased when combined with Tolbutamide.Approved
LornoxicamThe metabolism of Lornoxicam can be decreased when combined with Tolbutamide.Approved, Investigational
LosartanThe metabolism of Losartan can be decreased when combined with Tolbutamide.Approved
LovastatinThe metabolism of Tolbutamide can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Tolbutamide can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Tolbutamide can be increased when it is combined with Lumacaftor.Approved
LumiracoxibThe metabolism of Lumiracoxib can be decreased when combined with Tolbutamide.Approved, Investigational
ManidipineThe metabolism of Tolbutamide can be decreased when combined with Manidipine.Approved, Investigational
MedrogestoneThe serum concentration of Tolbutamide can be decreased when it is combined with Medrogestone.Approved
Mefenamic acidThe metabolism of Mefenamic acid can be decreased when combined with Tolbutamide.Approved
MelatoninThe metabolism of Melatonin can be decreased when combined with Tolbutamide.Approved, Nutraceutical, Vet Approved
MeloxicamThe metabolism of Meloxicam can be decreased when combined with Tolbutamide.Approved, Vet Approved
MephenytoinThe metabolism of Mephenytoin can be decreased when combined with Tolbutamide.Investigational, Withdrawn
MepindololMepindolol may increase the hypoglycemic activities of Tolbutamide.Experimental
MestranolThe metabolism of Mestranol can be decreased when combined with Tolbutamide.Approved
MethadoneThe metabolism of Methadone can be decreased when combined with Tolbutamide.Approved
MethoxyfluraneThe metabolism of Methoxyflurane can be decreased when combined with Tolbutamide.Approved, Investigational, Vet Approved
MethyclothiazideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Methyclothiazide.Approved
MetipranololMetipranolol may increase the hypoglycemic activities of Tolbutamide.Approved
MetolazoneThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Metolazone.Approved
MetoprololMetoprolol may increase the hypoglycemic activities of Tolbutamide.Approved, Investigational
MetreleptinMetreleptin may increase the hypoglycemic activities of Tolbutamide.Approved
MetronidazoleThe metabolism of Metronidazole can be decreased when combined with Tolbutamide.Approved
MiconazoleMiconazole may increase the hypoglycemic activities of Tolbutamide.Approved, Investigational, Vet Approved
MidostaurinThe metabolism of Tolbutamide can be decreased when combined with Midostaurin.Approved
MifepristoneThe serum concentration of Tolbutamide can be increased when it is combined with Mifepristone.Approved, Investigational
MirtazapineThe metabolism of Mirtazapine can be decreased when combined with Tolbutamide.Approved
MoclobemideThe metabolism of Moclobemide can be decreased when combined with Tolbutamide.Approved
ModafinilThe metabolism of Tolbutamide can be decreased when combined with Modafinil.Approved, Investigational
MontelukastThe metabolism of Montelukast can be decreased when combined with Tolbutamide.Approved
NadololNadolol may increase the hypoglycemic activities of Tolbutamide.Approved
NaproxenThe metabolism of Naproxen can be decreased when combined with Tolbutamide.Approved, Vet Approved
NateglinideThe metabolism of Nateglinide can be decreased when combined with Tolbutamide.Approved, Investigational
NebivololNebivolol may increase the hypoglycemic activities of Tolbutamide.Approved, Investigational
NelfinavirThe metabolism of Tolbutamide can be decreased when combined with Nelfinavir.Approved
NetupitantThe metabolism of Netupitant can be decreased when combined with Tolbutamide.Approved
NevirapineThe metabolism of Nevirapine can be decreased when combined with Tolbutamide.Approved
NicardipineThe metabolism of Tolbutamide can be decreased when combined with Nicardipine.Approved
NiclosamideThe metabolism of Niclosamide can be decreased when combined with Tolbutamide.Approved, Investigational, Vet Approved
NicotineThe metabolism of Nicotine can be decreased when combined with Tolbutamide.Approved
NilotinibThe metabolism of Tolbutamide can be decreased when combined with Nilotinib.Approved, Investigational
NortriptylineThe metabolism of Nortriptyline can be decreased when combined with Tolbutamide.Approved
OlodaterolThe metabolism of Olodaterol can be decreased when combined with Tolbutamide.Approved
OmeprazoleThe metabolism of Omeprazole can be decreased when combined with Tolbutamide.Approved, Investigational, Vet Approved
OndansetronThe metabolism of Ondansetron can be decreased when combined with Tolbutamide.Approved
OspemifeneThe serum concentration of Ospemifene can be increased when it is combined with Tolbutamide.Approved
OxaprozinThe metabolism of Oxaprozin can be decreased when combined with Tolbutamide.Approved
OxprenololOxprenolol may increase the hypoglycemic activities of Tolbutamide.Approved
PaclitaxelThe metabolism of Paclitaxel can be decreased when combined with Tolbutamide.Approved, Vet Approved
PantoprazoleThe metabolism of Tolbutamide can be decreased when combined with Pantoprazole.Approved
ParamethadioneThe metabolism of Paramethadione can be decreased when combined with Tolbutamide.Approved
ParecoxibThe serum concentration of Parecoxib can be increased when it is combined with Tolbutamide.Approved
PenbutololPenbutolol may increase the hypoglycemic activities of Tolbutamide.Approved, Investigational
PerphenazineThe metabolism of Perphenazine can be decreased when combined with Tolbutamide.Approved
PhenacetinThe metabolism of Phenacetin can be decreased when combined with Tolbutamide.Withdrawn
PhenindioneTolbutamide may increase the anticoagulant activities of Phenindione.Approved, Investigational
PhenobarbitalThe metabolism of Tolbutamide can be increased when combined with Phenobarbital.Approved
PhenprocoumonThe metabolism of Phenprocoumon can be decreased when combined with Tolbutamide.Approved, Investigational
PhenylbutazoneThe metabolism of Phenylbutazone can be decreased when combined with Tolbutamide.Approved, Vet Approved
PhenytoinThe metabolism of Tolbutamide can be increased when combined with Phenytoin.Approved, Vet Approved
PindololPindolol may increase the hypoglycemic activities of Tolbutamide.Approved
PioglitazoneThe metabolism of Pioglitazone can be decreased when combined with Tolbutamide.Approved, Investigational
PiroxicamThe metabolism of Piroxicam can be decreased when combined with Tolbutamide.Approved, Investigational
PitavastatinThe metabolism of Pitavastatin can be decreased when combined with Tolbutamide.Approved
Platelet Activating FactorPlatelet Activating Factor may increase the hypoglycemic activities of Tolbutamide.Experimental
PolythiazideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Polythiazide.Approved
PractololPractolol may increase the hypoglycemic activities of Tolbutamide.Approved
PrasugrelThe metabolism of Prasugrel can be decreased when combined with Tolbutamide.Approved
PravastatinThe metabolism of Pravastatin can be decreased when combined with Tolbutamide.Approved
PregabalinThe risk or severity of heart failure can be increased when Pregabalin is combined with Tolbutamide.Approved, Illicit, Investigational
PrimidoneThe metabolism of Tolbutamide can be increased when combined with Primidone.Approved, Vet Approved
ProbenecidThe protein binding of Tolbutamide can be decreased when combined with Probenecid.Approved
ProgesteroneThe metabolism of Progesterone can be decreased when combined with Tolbutamide.Approved, Vet Approved
ProguanilThe metabolism of Proguanil can be decreased when combined with Tolbutamide.Approved
PromazineThe metabolism of Promazine can be decreased when combined with Tolbutamide.Approved, Vet Approved
PropofolThe metabolism of Propofol can be decreased when combined with Tolbutamide.Approved, Investigational, Vet Approved
PropranololPropranolol may increase the hypoglycemic activities of Tolbutamide.Approved, Investigational
PyrimethamineThe metabolism of Tolbutamide can be decreased when combined with Pyrimethamine.Approved, Vet Approved
QuazepamThe metabolism of Quazepam can be decreased when combined with Tolbutamide.Approved, Illicit
QuinethazoneThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Quinethazone.Approved
QuinidineThe metabolism of Quinidine can be decreased when combined with Tolbutamide.Approved
QuinineThe metabolism of Quinine can be decreased when combined with Tolbutamide.Approved
RabeprazoleThe metabolism of Tolbutamide can be decreased when combined with Rabeprazole.Approved, Investigational
RamelteonThe serum concentration of Ramelteon can be increased when it is combined with Tolbutamide.Approved, Investigational
RanitidineThe serum concentration of Tolbutamide can be increased when it is combined with Ranitidine.Approved
RifampicinThe serum concentration of Tolbutamide can be decreased when it is combined with Rifampicin.Approved
RifapentineThe metabolism of Tolbutamide can be increased when combined with Rifapentine.Approved
RofecoxibThe metabolism of Rofecoxib can be decreased when combined with Tolbutamide.Investigational, Withdrawn
RonifibrateRonifibrate may increase the hypoglycemic activities of Tolbutamide.Experimental
RosiglitazoneThe metabolism of Rosiglitazone can be decreased when combined with Tolbutamide.Approved, Investigational
RosuvastatinThe metabolism of Rosuvastatin can be decreased when combined with Tolbutamide.Approved
RucaparibThe metabolism of Tolbutamide can be decreased when combined with Rucaparib.Approved, Investigational
RupatadineThe metabolism of Rupatadine can be decreased when combined with Tolbutamide.Approved
Salicylic acidThe metabolism of Salicylic acid can be decreased when combined with Tolbutamide.Approved, Vet Approved
SaxagliptinSaxagliptin may increase the hypoglycemic activities of Tolbutamide.Approved
SecobarbitalThe metabolism of Tolbutamide can be increased when combined with Secobarbital.Approved, Vet Approved
SelegilineThe metabolism of Selegiline can be decreased when combined with Tolbutamide.Approved, Investigational, Vet Approved
SeratrodastThe metabolism of Seratrodast can be decreased when combined with Tolbutamide.Approved
SertralineThe metabolism of Sertraline can be decreased when combined with Tolbutamide.Approved
SildenafilThe metabolism of Sildenafil can be decreased when combined with Tolbutamide.Approved, Investigational
SimfibrateSimfibrate may increase the hypoglycemic activities of Tolbutamide.Experimental
SitagliptinSitagliptin may increase the hypoglycemic activities of Tolbutamide.Approved, Investigational
SitaxentanThe metabolism of Sitaxentan can be decreased when combined with Tolbutamide.Approved, Investigational, Withdrawn
SorafenibThe metabolism of Tolbutamide can be decreased when combined with Sorafenib.Approved, Investigational
SotalolSotalol may increase the hypoglycemic activities of Tolbutamide.Approved
StiripentolThe metabolism of Tolbutamide can be decreased when combined with Stiripentol.Approved
SulfadiazineThe metabolism of Sulfadiazine can be decreased when combined with Tolbutamide.Approved, Vet Approved
SulfamethoxazoleThe metabolism of Sulfamethoxazole can be decreased when combined with Tolbutamide.Approved
SulfamoxoleThe metabolism of Sulfamoxole can be decreased when combined with Tolbutamide.Approved
SulfinpyrazoneThe metabolism of Sulfinpyrazone can be decreased when combined with Tolbutamide.Approved
SulfisoxazoleThe metabolism of Sulfisoxazole can be decreased when combined with Tolbutamide.Approved, Vet Approved
SuprofenThe metabolism of Suprofen can be decreased when combined with Tolbutamide.Approved, Withdrawn
TalinololTalinolol may increase the hypoglycemic activities of Tolbutamide.Investigational
TamoxifenThe metabolism of Tamoxifen can be decreased when combined with Tolbutamide.Approved
TapentadolThe metabolism of Tapentadol can be decreased when combined with Tolbutamide.Approved
TemazepamThe metabolism of Temazepam can be decreased when combined with Tolbutamide.Approved
TenoxicamThe metabolism of Tenoxicam can be decreased when combined with Tolbutamide.Approved
TerbinafineThe metabolism of Terbinafine can be decreased when combined with Tolbutamide.Approved, Investigational, Vet Approved
TerfenadineThe metabolism of Terfenadine can be decreased when combined with Tolbutamide.Withdrawn
TeriflunomideThe metabolism of Tolbutamide can be decreased when combined with Teriflunomide.Approved
TertatololTertatolol may increase the hypoglycemic activities of Tolbutamide.Experimental
TestosteroneThe metabolism of Testosterone can be decreased when combined with Tolbutamide.Approved, Investigational
Testosterone cypionateThe metabolism of Testosterone Cypionate can be decreased when combined with Tolbutamide.Approved
Testosterone enanthateThe metabolism of Testosterone Enanthate can be decreased when combined with Tolbutamide.Approved
Testosterone undecanoateThe metabolism of Testosterone Undecanoate can be decreased when combined with Tolbutamide.Approved, Investigational
ThalidomideThe metabolism of Thalidomide can be decreased when combined with Tolbutamide.Approved, Investigational, Withdrawn
TheophyllineThe metabolism of Theophylline can be decreased when combined with Tolbutamide.Approved
ThiamylalThe metabolism of Thiamylal can be decreased when combined with Tolbutamide.Approved, Vet Approved
TicagrelorThe metabolism of Tolbutamide can be decreased when combined with Ticagrelor.Approved
TiclopidineThe metabolism of Tolbutamide can be decreased when combined with Ticlopidine.Approved
TimololTimolol may increase the hypoglycemic activities of Tolbutamide.Approved
TioclomarolTolbutamide may increase the anticoagulant activities of Tioclomarol.Experimental
TolterodineThe metabolism of Tolterodine can be decreased when combined with Tolbutamide.Approved, Investigational
TopiramateThe metabolism of Tolbutamide can be decreased when combined with Topiramate.Approved
TopiroxostatThe metabolism of Tolbutamide can be decreased when combined with Topiroxostat.Approved, Investigational
TorasemideThe metabolism of Torasemide can be decreased when combined with Tolbutamide.Approved
TrabectedinThe metabolism of Trabectedin can be decreased when combined with Tolbutamide.Approved, Investigational
TranylcypromineThe metabolism of Tolbutamide can be decreased when combined with Tranylcypromine.Approved
TreprostinilThe metabolism of Treprostinil can be decreased when combined with Tolbutamide.Approved, Investigational
TretinoinThe metabolism of Tretinoin can be decreased when combined with Tolbutamide.Approved, Investigational, Nutraceutical
TrichlormethiazideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Trichlormethiazide.Approved, Vet Approved
TrimethadioneThe metabolism of Trimethadione can be decreased when combined with Tolbutamide.Approved
TrimethoprimThe metabolism of Trimethoprim can be decreased when combined with Tolbutamide.Approved, Vet Approved
TrimipramineThe metabolism of Trimipramine can be decreased when combined with Tolbutamide.Approved
TroglitazoneThe metabolism of Troglitazone can be decreased when combined with Tolbutamide.Investigational, Withdrawn
UbidecarenoneThe therapeutic efficacy of Tolbutamide can be increased when used in combination with Ubidecarenone.Approved, Investigational, Nutraceutical
ValdecoxibThe metabolism of Valdecoxib can be decreased when combined with Tolbutamide.Investigational, Withdrawn
Valproic AcidThe metabolism of Valproic Acid can be decreased when combined with Tolbutamide.Approved, Investigational
ValsartanThe metabolism of Valsartan can be decreased when combined with Tolbutamide.Approved, Investigational
VemurafenibThe serum concentration of Tolbutamide can be increased when it is combined with Vemurafenib.Approved
VenlafaxineThe metabolism of Venlafaxine can be decreased when combined with Tolbutamide.Approved
VerapamilThe metabolism of Verapamil can be decreased when combined with Tolbutamide.Approved
VicrivirocThe metabolism of Vicriviroc can be decreased when combined with Tolbutamide.Investigational
VildagliptinVildagliptin may increase the hypoglycemic activities of Tolbutamide.Approved, Investigational
VismodegibThe metabolism of Vismodegib can be decreased when combined with Tolbutamide.Approved
VoriconazoleThe serum concentration of Tolbutamide can be increased when it is combined with Voriconazole.Approved, Investigational
VortioxetineThe metabolism of Vortioxetine can be decreased when combined with Tolbutamide.Approved
WarfarinThe metabolism of Warfarin can be decreased when combined with Tolbutamide.Approved
XimelagatranThe metabolism of Ximelagatran can be decreased when combined with Tolbutamide.Approved, Investigational, Withdrawn
ZafirlukastThe metabolism of Zafirlukast can be decreased when combined with Tolbutamide.Approved, Investigational
ZalcitabineThe metabolism of Zalcitabine can be decreased when combined with Tolbutamide.Approved, Investigational
ZaltoprofenThe metabolism of Zaltoprofen can be decreased when combined with Tolbutamide.Approved, Investigational
ZidovudineThe metabolism of Zidovudine can be decreased when combined with Tolbutamide.Approved
ZileutonThe metabolism of Zileuton can be decreased when combined with Tolbutamide.Approved, Investigational, Withdrawn
ZolpidemThe metabolism of Zolpidem can be decreased when combined with Tolbutamide.Approved
ZopicloneThe metabolism of Zopiclone can be decreased when combined with Tolbutamide.Approved
ZucapsaicinThe metabolism of Tolbutamide can be decreased when combined with Zucapsaicin.Approved
Food Interactions
Not Available

References

Synthesis Reference

Yan-Ping Chen, Pai-Ching Lin, "Tolbutamide Particle And Preparing Method Thereof And Method Of Reducing A Blood Glucose." U.S. Patent US20120121707, issued May 17, 2012.

US20120121707
General 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]
External Links
Human Metabolome Database
HMDB0015256
KEGG Drug
D00380
KEGG Compound
C07148
PubChem Compound
5505
PubChem Substance
46508421
ChemSpider
5304
BindingDB
50027886
ChEBI
27999
ChEMBL
CHEMBL782
Therapeutic Targets Database
DAP000136
PharmGKB
PA451718
IUPHAR
2415
Guide to Pharmacology
GtP Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Tolbutamide
ATC Codes
A10BB03 — TolbutamideV04CA01 — Tolbutamide
AHFS Codes
  • 68:20.20 — Sulfonylureas
MSDS
Download (73.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailablePain, Chronic1
1CompletedBasic ScienceDrug Drug Interactions1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedTreatmentAdult Solid Neoplasm1
1CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection1
1CompletedTreatmentDrug Interactions1
1CompletedTreatmentHealthy Volunteers1
1TerminatedTreatmentCancer, Advanced / Malignant Lymphomas1
1TerminatedTreatmentHealthy Volunteers1
2CompletedTreatmentImpaired Glucose Tolerance (IGT) / Type 2 Diabetes Mellitus1
4RecruitingBasic ScienceType 2 Diabetes Mellitus1
Not AvailableCompletedNot AvailableType 2 Diabetes Mellitus3

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
TabletOral1 g
TabletOral500 mg
TabletOral500 mg/1
Prices
Unit descriptionCostUnit
Tolbutamide 500 mg tablet0.4USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)128.5 °CPhysProp
water solubility109 mg/L (at 37 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP2.34HANSCH,C ET AL. (1995)
logS-3.39ADME Research, USCD
pKa5.16SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.202 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity70.27 m3·mol-1ChemAxon
Polarizability29.1 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9959
Blood Brain Barrier+0.9321
Caco-2 permeable-0.6453
P-glycoprotein substrateNon-substrate0.5333
P-glycoprotein inhibitor INon-inhibitor0.9349
P-glycoprotein inhibitor IINon-inhibitor0.9131
Renal organic cation transporterNon-inhibitor0.8852
CYP450 2C9 substrateSubstrate0.5304
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.7558
CYP450 1A2 substrateNon-inhibitor0.9443
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9504
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9613
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.881
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.781
BiodegradationNot ready biodegradable0.8811
Rat acute toxicity2.0629 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9561
hERG inhibition (predictor II)Non-inhibitor0.9511
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (9.12 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0006-0190000000-7ff8ebe7a2c8d9b989ec
MS/MS Spectrum - , positiveLC-MS/MSsplash10-05fr-1920000000-defac8a82087405b74df

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzenesulfonamides
Direct Parent
Benzenesulfonamides
Alternative Parents
Tosyl compounds / Benzenesulfonyl compounds / Sulfonylureas / Organosulfonic acids and derivatives / Aminosulfonyl compounds / Propargyl-type 1,3-dipolar organic compounds / Carboximidic acids and derivatives / Organopnictogen compounds / Organooxygen compounds / Organic oxides
show 1 more
Substituents
Benzenesulfonamide / Tosyl compound / Benzenesulfonyl group / Toluene / Sulfonylurea / Organic sulfonic acid or derivatives / Organosulfonic acid or derivatives / Sulfonyl / Aminosulfonyl compound / Carboximidic acid derivative
show 11 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
N-sulfonylurea (CHEBI:27999)

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
Uniprot Name
ATP-binding cassette sub-family C member 8
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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Phosphatidylinositol-4,5-bisphosphate binding
Specific Function
In the kidney, probably plays a major role in potassium homeostasis. Inward rectifier potassium channels are characterized by a greater tendency to allow potassium to flow into the cell rather than...
Gene Name
KCNJ1
Uniprot ID
P48048
Uniprot Name
ATP-sensitive inward rectifier potassium channel 1
Molecular Weight
44794.6 Da
References
  1. Proks P, Jones P, Ashcroft FM: Interaction of stilbene disulphonates with cloned K(ATP) channels. Br J Pharmacol. 2001 Mar;132(5):973-82. [PubMed:11226127]
  2. Smith PA, Proks P: Inhibition of the ATP-sensitive potassium channel from mouse pancreatic beta-cells by surfactants. Br J Pharmacol. 1998 Jun;124(3):529-39. [PubMed:9647478]
  3. Liu X, Singh BB, Ambudkar IS: ATP-dependent activation of K(Ca) and ROMK-type K(ATP) channels in human submandibular gland ductal cells. J Biol Chem. 1999 Aug 27;274(35):25121-9. [PubMed:10455193]

Enzymes

Details
1. Cytochrome P450 2C9
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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 un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
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]
  3. Lasker JM, Wester MR, Aramsombatdee E, Raucy JL: Characterization of CYP2C19 and CYP2C9 from human liver: respective roles in microsomal tolbutamide, S-mephenytoin, and omeprazole hydroxylations. Arch Biochem Biophys. 1998 May 1;353(1):16-28. [PubMed:9578596]
  4. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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 un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. 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 im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
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]
  3. Lasker JM, Wester MR, Aramsombatdee E, Raucy JL: Characterization of CYP2C19 and CYP2C9 from human liver: respective roles in microsomal tolbutamide, S-mephenytoin, and omeprazole hydroxylations. Arch Biochem Biophys. 1998 May 1;353(1):16-28. [PubMed:9578596]
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 un...
Gene Name
CYP2C18
Uniprot ID
P33260
Uniprot Name
Cytochrome P450 2C18
Molecular Weight
55710.075 Da
References
  1. 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]

Carriers

Details
1. Serum albumin
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Marszall MP, Bucinski A: A protein-coated magnetic beads as a tool for the rapid drug-protein binding study. J Pharm Biomed Anal. 2010 Jul 8;52(3):420-4. doi: 10.1016/j.jpba.2009.06.023. Epub 2009 Jun 18. [PubMed:19596536]
  2. Joseph KS, Hage DS: Characterization of the binding of sulfonylurea drugs to HSA by high-performance affinity chromatography. J Chromatogr B Analyt Technol Biomed Life Sci. 2010 Jun 1;878(19):1590-8. doi: 10.1016/j.jchromb.2010.04.019. [PubMed:20435530]
  3. Yoo MJ, Hage DS: Use of peak decay analysis and affinity microcolumns containing silica monoliths for rapid determination of drug-protein dissociation rates. J Chromatogr A. 2011 Apr 15;1218(15):2072-8. doi: 10.1016/j.chroma.2010.09.070. Epub 2010 Oct 16. [PubMed:20956006]
  4. Basiaga SB, Hage DS: Chromatographic studies of changes in binding of sulfonylurea drugs to human serum albumin due to glycation and fatty acids. J Chromatogr B Analyt Technol Biomed Life Sci. 2010 Nov 15;878(30):3193-7. doi: 10.1016/j.jchromb.2010.09.033. Epub 2010 Oct 23. [PubMed:20974553]

Transporters

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
Uniprot Name
Solute carrier family 15 member 1
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
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibit...
Gene Name
SLCO1A2
Uniprot ID
P46721
Uniprot Name
Solute carrier organic anion transporter family member 1A2
Molecular Weight
74144.105 Da
References
  1. Shitara Y, Sugiyama D, Kusuhara H, Kato Y, Abe T, Meier PJ, Itoh T, Sugiyama Y: Comparative inhibitory effects of different compounds on rat oatpl (slc21a1)- and Oatp2 (Slc21a5)-mediated transport. Pharm Res. 2002 Feb;19(2):147-53. [PubMed:11883641]
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
Uniprot Name
Solute carrier family 15 member 2
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 ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost.
Gene Name
SLCO2B1
Uniprot ID
O94956
Uniprot Name
Solute carrier organic anion transporter family member 2B1
Molecular Weight
76709.98 Da
References
  1. Satoh H, Yamashita F, Tsujimoto M, Murakami H, Koyabu N, Ohtani H, Sawada Y: Citrus juices inhibit the function of human organic anion-transporting polypeptide OATP-B. Drug Metab Dispos. 2005 Apr;33(4):518-23. Epub 2005 Jan 7. [PubMed:15640378]

Drug created on June 13, 2005 07:24 / Updated on January 22, 2018 10:46