Identification
NameAcetohexamide
Accession NumberDB00414  (APRD00773)
TypeSmall Molecule
GroupsWithdrawn
Description

A sulfonylurea hypoglycemic agent that is metabolized in the liver to 1-hydrohexamide. Acetohexamide has been discontinued in the US market.

Structure
Thumb
Synonyms
1-((p-Acetylphenyl)sulfonyl)-3-cyclohexylurea
1-[(4-acetylbenzene)sulfonyl]-3-cyclohexylurea 4-acetyl-N-(cyclohexylcarbamoyl)benzenesulfonamide
Acetohexamid
Acetohexamida
Acétohexamide
Acetohexamide
Acetohexamidum
N-(p-Acetylphenylsulfonyl)-N'-cyclohexylurea
External IDs 33006
Product Ingredients Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Dimelor Tablet 1843 500mgTablet500 mgOralEli Lilly & Co. Ltd.1963-12-311998-08-04Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AcetohexamideWatson
DimelinShionogi Seiyaku
DymelorLilly
GamadiabetSalvat
Brand mixturesNot Available
Categories
UNIIQGC8W08I6I
CAS number968-81-0
WeightAverage: 324.395
Monoisotopic: 324.114377828
Chemical FormulaC15H20N2O4S
InChI KeyVGZSUPCWNCWDAN-UHFFFAOYSA-N
InChI
InChI=1S/C15H20N2O4S/c1-11(18)12-7-9-14(10-8-12)22(20,21)17-15(19)16-13-5-3-2-4-6-13/h7-10,13H,2-6H2,1H3,(H2,16,17,19)
IUPAC Name
3-(4-acetylbenzenesulfonyl)-1-cyclohexylurea
SMILES
CC(=O)C1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCC1
Pharmacology
Indication

Used in the management of diabetes mellitus type 2 (adult-onset).

Structured Indications Not Available
Pharmacodynamics

Acetohexamide is an intermediate-acting, first-generation oral sulfonylurea. It lowers blood sugar by stimulating the pancreatic beta cells to secrete insulin and by helping the body use insulin efficiently. The pancreas must produce insulin for this medication to work. Acetohexamide has one-third the potency of chlorpropamide, and twice the potency of tolbutamide; however, similar hypoglycemic efficacy occurs with equipotent dosage of sulfonylureas.

Mechanism of action

Sulfonylureas such as acetohexamide bind to an ATP-dependent K+ channel on the cell membrane of pancreatic beta cells. This inhibits a tonic, hyperpolarizing outflux of potassium, which causes the electric potential over the membrane to become more positive. This depolarization opens voltage-gated Ca2+ channels. The rise in intracellular calcium leads to increased fusion of insulin granulae with the cell membrane, and therefore increased secretion of (pro)insulin.

TargetKindPharmacological actionActionsOrganismUniProt ID
ATP-sensitive inward rectifier potassium channel 1Proteinyes
inhibitor
HumanP48048 details
Related Articles
Absorption

Rapidly absorbed from the GI tract.

Volume of distributionNot Available
Protein binding

90%

Metabolism

Extensively metabolized in the liver to the active metabolite hydroxyhexamide, which exhibits greater hypoglycemic potency than acetohexamide. Hydroxyhexamide is believed to be responsible for prolonged hypoglycemic effects.

SubstrateEnzymesProduct
Acetohexamide
Not Available
HydroxyhexamideDetails
Route of eliminationNot Available
Half life

Elimination half-life of the parent compound is 1.3 hours and the elimination half-life of the active metabolite is approximately 5-6 hours.

ClearanceNot Available
Toxicity

Oral, rat LD50: 5 gm/kg; Oral, mouse LD50: >2500 mg/kg. Symptoms of an acetohexamide overdose include hunger, nausea, anxiety, cold sweats, weakness, drowsiness, unconsciousness, and coma.

Affected organisms
  • Humans and other mammals
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
AcebutololAcebutolol may increase the hypoglycemic activities of Acetohexamide.Approved
AcenocoumarolAcetohexamide may increase the anticoagulant activities of Acenocoumarol.Approved
AlbiglutideAlbiglutide may increase the hypoglycemic activities of Acetohexamide.Approved
AlogliptinAlogliptin may increase the hypoglycemic activities of Acetohexamide.Approved
AlprenololAlprenolol may increase the hypoglycemic activities of Acetohexamide.Approved, Withdrawn
AripiprazoleThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Aripiprazole.Approved, Investigational
ArotinololArotinolol may increase the hypoglycemic activities of Acetohexamide.Approved
Arsenic trioxideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Arsenic trioxide.Approved, Investigational
ArticaineThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Articaine.Approved
AsenapineThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Asenapine.Approved
AtazanavirThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Atazanavir.Approved, Investigational
AtenololAtenolol may increase the hypoglycemic activities of Acetohexamide.Approved
AtorvastatinAtorvastatin may increase the hypoglycemic activities of Acetohexamide.Approved
BefunololBefunolol may increase the hypoglycemic activities of Acetohexamide.Experimental
BendroflumethiazideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Bendroflumethiazide.Approved
BetamethasoneThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Betamethasone.Approved, Vet Approved
BetaxololBetaxolol may increase the hypoglycemic activities of Acetohexamide.Approved
BevantololBevantolol may increase the hypoglycemic activities of Acetohexamide.Approved
BezafibrateBezafibrate may increase the hypoglycemic activities of Acetohexamide.Approved
BisoprololBisoprolol may increase the hypoglycemic activities of Acetohexamide.Approved
BopindololBopindolol may increase the hypoglycemic activities of Acetohexamide.Approved
BrexpiprazoleThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Brexpiprazole.Approved
BucindololBucindolol may increase the hypoglycemic activities of Acetohexamide.Investigational
BufuralolBufuralol may increase the hypoglycemic activities of Acetohexamide.Experimental, Investigational
BumetanideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Bumetanide.Approved
BupranololBupranolol may increase the hypoglycemic activities of Acetohexamide.Approved
BuserelinThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Buserelin.Approved
CanagliflozinCanagliflozin may increase the hypoglycemic activities of Acetohexamide.Approved
CarbocisteineThe risk or severity of adverse effects can be increased when Acetohexamide is combined with Carbocisteine.Approved
CarteololCarteolol may increase the hypoglycemic activities of Acetohexamide.Approved
CarvedilolCarvedilol may increase the hypoglycemic activities of Acetohexamide.Approved, Investigational
CeliprololCeliprolol may increase the hypoglycemic activities of Acetohexamide.Approved, Investigational
CeritinibThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Ceritinib.Approved
ChloramphenicolThe metabolism of Acetohexamide can be decreased when combined with Chloramphenicol.Approved, Vet Approved
ChlorothiazideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Chlorothiazide.Approved, Vet Approved
ChlorpropamideAcetohexamide may increase the hypoglycemic activities of Chlorpropamide.Approved
ChlorthalidoneThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Chlorthalidone.Approved
CimetidineThe serum concentration of Acetohexamide can be increased when it is combined with Cimetidine.Approved
ClofibrateClofibrate may increase the hypoglycemic activities of Acetohexamide.Approved
ClozapineThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Clozapine.Approved
CorticotropinThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Corticotropin.Approved, Vet Approved
Cortisone acetateThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Cortisone acetate.Approved
Cyproterone acetateThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Cyproterone acetate.Approved, Investigational
DabrafenibThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Dabrafenib.Approved
DanazolThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Danazol.Approved
DarunavirThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Darunavir.Approved
DesogestrelThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Desogestrel.Approved
DexamethasoneThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Dexamethasone.Approved, Investigational, Vet Approved
DiazoxideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Diazoxide.Approved
DicoumarolAcetohexamide may increase the anticoagulant activities of Dicoumarol.Approved
DienogestThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Dienogest.Approved
DisopyramideAcetohexamide may increase the hypoglycemic activities of Disopyramide.Approved
DrospirenoneThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Drospirenone.Approved
DulaglutideDulaglutide may increase the hypoglycemic activities of Acetohexamide.Approved
EmpagliflozinEmpagliflozin may increase the hypoglycemic activities of Acetohexamide.Approved
EpinephrineThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Epinephrine.Approved, Vet Approved
EsmololEsmolol may increase the hypoglycemic activities of Acetohexamide.Approved
EstradiolThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Estradiol.Approved, Investigational, Vet Approved
Estrone sulfateThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Estrone sulfate.Approved
Etacrynic acidThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Etacrynic acid.Approved
EthanolThe risk or severity of adverse effects can be increased when Acetohexamide is combined with Ethanol.Approved
Ethinyl EstradiolThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Ethinyl Estradiol.Approved
Ethyl biscoumacetateAcetohexamide may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
Ethynodiol diacetateThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Ethynodiol diacetate.Approved
EtofibrateEtofibrate may increase the hypoglycemic activities of Acetohexamide.Approved
EtonogestrelThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Etonogestrel.Approved, Investigational
EverolimusThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Everolimus.Approved
ExenatideExenatide may increase the hypoglycemic activities of Acetohexamide.Approved, Investigational
FenofibrateFenofibrate may increase the hypoglycemic activities of Acetohexamide.Approved
FluconazoleThe serum concentration of Acetohexamide can be increased when it is combined with Fluconazole.Approved
FludrocortisoneThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Fludrocortisone.Approved
FluindioneAcetohexamide may increase the anticoagulant activities of Fluindione.Investigational
FosamprenavirThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Fosamprenavir.Approved
FurosemideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Furosemide.Approved, Vet Approved
GemfibrozilGemfibrozil may increase the hypoglycemic activities of Acetohexamide.Approved
GliclazideAcetohexamide may increase the hypoglycemic activities of Gliclazide.Approved
GlimepirideAcetohexamide may increase the hypoglycemic activities of Glimepiride.Approved
GlipizideAcetohexamide may increase the hypoglycemic activities of Glipizide.Approved
GlyburideAcetohexamide may increase the hypoglycemic activities of Glyburide.Approved
GoserelinThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Goserelin.Approved
HistrelinThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Histrelin.Approved
HydrochlorothiazideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Hydrochlorothiazide.Approved, Vet Approved
HydrocortisoneThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Hydrocortisone.Approved, Vet Approved
HydroflumethiazideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Hydroflumethiazide.Approved
Hydroxyprogesterone caproateThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
IloperidoneThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Iloperidone.Approved
IndapamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Indapamide.Approved
IndenololIndenolol may increase the hypoglycemic activities of Acetohexamide.Withdrawn
IndinavirThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Indinavir.Approved
Insulin AspartAcetohexamide may increase the hypoglycemic activities of Insulin Aspart.Approved
Insulin DetemirAcetohexamide may increase the hypoglycemic activities of Insulin Detemir.Approved
Insulin GlargineAcetohexamide may increase the hypoglycemic activities of Insulin Glargine.Approved
Insulin GlulisineAcetohexamide may increase the hypoglycemic activities of Insulin Glulisine.Approved
Insulin HumanAcetohexamide may increase the hypoglycemic activities of Insulin Human.Approved, Investigational
Insulin LisproAcetohexamide may increase the hypoglycemic activities of Insulin Lispro.Approved
LabetalolLabetalol may increase the hypoglycemic activities of Acetohexamide.Approved
LandiololAop200704 may increase the hypoglycemic activities of Acetohexamide.Investigational
LanreotideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Lanreotide.Approved
LeuprolideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Leuprolide.Approved, Investigational
LevobunololLevobunolol may increase the hypoglycemic activities of Acetohexamide.Approved
LevonorgestrelThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Levonorgestrel.Approved, Investigational
LinagliptinLinagliptin may increase the hypoglycemic activities of Acetohexamide.Approved
Lipoic AcidLipoic Acid may increase the hypoglycemic activities of Acetohexamide.Approved, Nutraceutical
LiraglutideLiraglutide may increase the hypoglycemic activities of Acetohexamide.Approved
LopinavirThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Lopinavir.Approved
LurasidoneThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Lurasidone.Approved
MecaserminAcetohexamide may increase the hypoglycemic activities of Mecasermin.Approved, Investigational
Medroxyprogesterone acetateThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Medroxyprogesterone acetate.Approved, Investigational
Megestrol acetateThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Megestrol acetate.Approved, Vet Approved
MestranolThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Mestranol.Approved
MethotrimeprazineThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Methotrimeprazine.Approved
MethyclothiazideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Methyclothiazide.Approved
MethylprednisoloneThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Methylprednisolone.Approved, Vet Approved
MetipranololMetipranolol may increase the hypoglycemic activities of Acetohexamide.Approved
MetolazoneThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Metolazone.Approved
MetoprololMetoprolol may increase the hypoglycemic activities of Acetohexamide.Approved, Investigational
MetreleptinMetreleptin may increase the hypoglycemic activities of Acetohexamide.Approved
MiconazoleMiconazole may increase the hypoglycemic activities of Acetohexamide.Approved, Investigational, Vet Approved
MifepristoneAcetohexamide may increase the hypoglycemic activities of Mifepristone.Approved, Investigational
NadololNadolol may increase the hypoglycemic activities of Acetohexamide.Approved
NateglinideAcetohexamide may increase the hypoglycemic activities of Nateglinide.Approved, Investigational
NelfinavirThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Nelfinavir.Approved
NiacinThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Niacin.Approved, Investigational, Nutraceutical
NilotinibThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Nilotinib.Approved, Investigational
NorethisteroneThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Norethisterone.Approved
NorgestimateThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Norgestimate.Approved
OctreotideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Octreotide.Approved, Investigational
OlanzapineThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Olanzapine.Approved, Investigational
OxprenololOxprenolol may increase the hypoglycemic activities of Acetohexamide.Approved
PaliperidoneThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Paliperidone.Approved
PasireotideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Pasireotide.Approved
PenbutololPenbutolol may increase the hypoglycemic activities of Acetohexamide.Approved, Investigational
PentamidineThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Pentamidine.Approved
PhenindioneAcetohexamide may increase the anticoagulant activities of Phenindione.Approved
PhenprocoumonAcetohexamide may increase the anticoagulant activities of Phenprocoumon.Approved
PindololPindolol may increase the hypoglycemic activities of Acetohexamide.Approved
PioglitazonePioglitazone may increase the hypoglycemic activities of Acetohexamide.Approved, Investigational
PiperazineThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Piperazine.Approved, Vet Approved
PipotiazineThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Pipotiazine.Approved
PolythiazideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Polythiazide.Approved
PractololPractolol may increase the hypoglycemic activities of Acetohexamide.Approved
PrednisoloneThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Prednisolone.Approved, Vet Approved
PrednisoneThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Prednisone.Approved, Vet Approved
ProbenecidThe protein binding of Acetohexamide can be decreased when combined with Probenecid.Approved
ProgesteroneThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Progesterone.Approved, Vet Approved
PropranololPropranolol may increase the hypoglycemic activities of Acetohexamide.Approved, Investigational
QuetiapineThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Quetiapine.Approved
QuinethazoneThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Quinethazone.Approved
QuinineAcetohexamide may increase the hypoglycemic activities of Quinine.Approved
RanitidineThe serum concentration of Acetohexamide can be increased when it is combined with Ranitidine.Approved
RepaglinideAcetohexamide may increase the hypoglycemic activities of Repaglinide.Approved, Investigational
RifampicinThe serum concentration of Acetohexamide can be decreased when it is combined with Rifampicin.Approved
RisperidoneThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Risperidone.Approved, Investigational
RitonavirThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Ritonavir.Approved, Investigational
RosiglitazoneRosiglitazone may increase the hypoglycemic activities of Acetohexamide.Approved, Investigational
SaquinavirThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Saquinavir.Approved, Investigational
SaxagliptinSaxagliptin may increase the hypoglycemic activities of Acetohexamide.Approved
SirolimusThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Sirolimus.Approved, Investigational
SitagliptinSitagliptin may increase the hypoglycemic activities of Acetohexamide.Approved, Investigational
SotalolSotalol may increase the hypoglycemic activities of Acetohexamide.Approved
SulfadiazineAcetohexamide may increase the hypoglycemic activities of Sulfadiazine.Approved, Vet Approved
SulfamethoxazoleAcetohexamide may increase the hypoglycemic activities of Sulfamethoxazole.Approved
SulfisoxazoleAcetohexamide may increase the hypoglycemic activities of Sulfisoxazole.Approved, Vet Approved
SunitinibAcetohexamide may increase the hypoglycemic activities of Sunitinib.Approved, Investigational
TacrolimusThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Tacrolimus.Approved, Investigational
TemsirolimusThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Temsirolimus.Approved
TimololTimolol may increase the hypoglycemic activities of Acetohexamide.Approved
TipranavirThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Tipranavir.Approved, Investigational
TolazamideAcetohexamide may increase the hypoglycemic activities of Tolazamide.Approved
TolbutamideAcetohexamide may increase the hypoglycemic activities of Tolbutamide.Approved
TorasemideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Torasemide.Approved
TriamcinoloneThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Triamcinolone.Approved, Vet Approved
TrichlormethiazideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Trichlormethiazide.Approved, Vet Approved
TriptorelinThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Triptorelin.Approved, Vet Approved
TroglitazoneTroglitazone may increase the hypoglycemic activities of Acetohexamide.Withdrawn
VildagliptinVildagliptin may increase the hypoglycemic activities of Acetohexamide.Approved, Investigational
VoriconazoleThe serum concentration of Acetohexamide can be increased when it is combined with Voriconazole.Approved, Investigational
VorinostatThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Vorinostat.Approved, Investigational
WarfarinAcetohexamide may increase the anticoagulant activities of Warfarin.Approved
ZiprasidoneThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Ziprasidone.Approved
Food Interactions
  • Avoid alcohol.
  • Take without regard to meals.
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesA10BB31 — Acetohexamide
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentImpaired Glucose Tolerance (IGT) / Type 2 Diabetes Mellitus1
Not AvailableCompletedNot AvailableType 2 Diabetes Mellitus3
Pharmacoeconomics
Manufacturers
  • Barr laboratories inc
  • Usl pharma inc
  • Watson laboratories inc
  • Eli lilly industries inc
Packagers
Dosage forms
FormRouteStrength
TabletOral500 mg
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point (°C)188-190 °CSigal,M.V.,Jr.andVanArendonk,A.M.; US.Patent3,320,312;May16,1967;assigned to Eli Lilly and Company.
water solubility3430 mg/L (at 37 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP2.44SANGSTER (1993)
logS-2.06ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.0483 mg/mLALOGPS
logP1.72ALOGPS
logP1.81ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)4.31ChemAxon
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area92.34 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity82.77 m3·mol-1ChemAxon
Polarizability33.97 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9425
Blood Brain Barrier+0.8308
Caco-2 permeable-0.6272
P-glycoprotein substrateNon-substrate0.6406
P-glycoprotein inhibitor INon-inhibitor0.8731
P-glycoprotein inhibitor IINon-inhibitor0.8808
Renal organic cation transporterNon-inhibitor0.8538
CYP450 2C9 substrateSubstrate0.6473
CYP450 2D6 substrateNon-substrate0.8795
CYP450 3A4 substrateNon-substrate0.7171
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5913
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.8447
BiodegradationNot ready biodegradable0.8033
Rat acute toxicity2.1793 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8799
hERG inhibition (predictor II)Non-inhibitor0.8982
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
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
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentAlkyl-phenylketones
Alternative ParentsBenzenesulfonamides / Benzenesulfonyl compounds / Acetophenones / Benzoyl derivatives / Aryl alkyl ketones / Sulfonylureas / Organosulfonic acids and derivatives / Aminosulfonyl compounds / Propargyl-type 1,3-dipolar organic compounds / Carboximidic acids and derivatives
SubstituentsAlkyl-phenylketone / Benzenesulfonamide / Acetophenone / Benzenesulfonyl group / Benzoyl / Aryl alkyl ketone / Sulfonylurea / Benzenoid / Monocyclic benzene moiety / Aminosulfonyl compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsN-sulfonylurea, acetophenones (CHEBI:28052 )

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
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 out of it. Their voltage dependence is regulated by the concentration of extracellular potassium; as external potassium is raised, the voltage range of the channel opening shifts to more positive vol...
Gene Name:
KCNJ1
Uniprot ID:
P48048
Uniprot Name:
ATP-sensitive inward rectifier potassium channel 1
Molecular Weight:
44794.6 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Prostaglandin-e2 9-reductase activity
Specific Function:
NADPH-dependent reductase with broad substrate specificity. Catalyzes the reduction of a wide variety of carbonyl compounds including quinones, prostaglandins, menadione, plus various xenobiotics. Catalyzes the reduction of the antitumor anthracyclines doxorubicin and daunorubicin to the cardiotoxic compounds doxorubicinol and daunorubicinol. Can convert prostaglandin E2 to prostaglandin F2-alp...
Gene Name:
CBR1
Uniprot ID:
P16152
Uniprot Name:
Carbonyl reductase [NADPH] 1
Molecular Weight:
30374.73 Da
References
  1. Imamura Y, Shimada H: Differential pharmacokinetics of acetohexamide in male Wistar-Imamichi and Sprague-Dawley rats: role of microsomal carbonyl reductase. Biol Pharm Bull. 2005 Jan;28(1):185-7. [PubMed:15635190 ]
  2. Imamura Y, Koga T, Higuchi T, Otagiri M, Sugino E, Hibino S: Inhibitory effect of drugs with a ketone group on reduction of acetohexamide catalyzed by carbonyl reductase from rabbit kidney. J Enzyme Inhib. 1997 Feb;11(4):285-92. [PubMed:9208371 ]
  3. Kishimoto M, Kawamori R, Kamada T, Inaba T: Carbonyl reductase activity for acetohexamide in human erythrocytes. Drug Metab Dispos. 1994 May-Jun;22(3):367-70. [PubMed:8070312 ]

Carriers

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 colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
Gene Name:
ALB
Uniprot ID:
P02768
Uniprot Name:
Serum albumin
Molecular Weight:
69365.94 Da
References
  1. 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 ]
  2. Joseph KS, Anguizola J, Jackson AJ, Hage DS: Chromatographic analysis of acetohexamide binding to glycated human serum albumin. J Chromatogr B Analyt Technol Biomed Life Sci. 2010 Oct 15;878(28):2775-81. doi: 10.1016/j.jchromb.2010.08.021. Epub 2010 Aug 21. [PubMed:20829128 ]
  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 ]
  5. Tong Z, Joseph KS, Hage DS: Detection of heterogeneous drug-protein binding by frontal analysis and high-performance affinity chromatography. J Chromatogr A. 2011 Dec 9;1218(49):8915-24. doi: 10.1016/j.chroma.2011.04.078. Epub 2011 May 6. [PubMed:21612784 ]
Drug created on June 13, 2005 07:24 / Updated on July 21, 2017 17:44