Bezitramide

Identification

Name
Bezitramide
Accession Number
DB01459
Type
Small Molecule
Groups
Experimental, Illicit, Withdrawn
Description

Bezitramide is a narcotic analgesic which was discovered in 1961, clinically tested around the 1970's [1], and marketed under the name Burgodin(R). After cases of fatal overdose in the Netherlands in 2004 the drug was withdrawn from the market.

In the United States Bezitramide was never been approved for clinical use. It is presently an illegal substance classified under Schedule II of the Controlled Substances Act. [wiki]

Structure
Thumb
Synonyms
  • 1-[1-(3-Cyano-3,3-diphenylpropyl)-4-piperidinyl]-1,3-dihydro-3-(1-oxopropyl)-2H-benzimidazol-2-one
External IDs
IDS-NB-007 / N02AC05 / R 4845
International/Other Brands
Burgodin (Janssen Pharmceutica)
Categories
UNII
3KXW0Y310I
CAS number
15301-48-1
Weight
Average: 492.6114
Monoisotopic: 492.252526288
Chemical Formula
C31H32N4O2
InChI Key
FLKWNFFCSSJANB-UHFFFAOYSA-N
InChI
InChI=1S/C31H32N4O2/c1-2-29(36)35-28-16-10-9-15-27(28)34(30(35)37)26-17-20-33(21-18-26)22-19-31(23-32,24-11-5-3-6-12-24)25-13-7-4-8-14-25/h3-16,26H,2,17-22H2,1H3
IUPAC Name
4-[4-(2-oxo-3-propanoyl-2,3-dihydro-1H-1,3-benzodiazol-1-yl)piperidin-1-yl]-2,2-diphenylbutanenitrile
SMILES
CCC(=O)N1C(=O)N(C2CCN(CCC(C#N)(C3=CC=CC=C3)C3=CC=CC=C3)CC2)C2=CC=CC=C12

Pharmacology

Indication

A narcotic analgesic once used for the treatment of severe chronic pain. [1]

Pharmacodynamics

Bezitramide acts in the body to relieve pain with a potency 20 times that of methadone [1]. Its duration of action is relatively long, lasting up to 12 hours post oral administration, after the achievement of steady state. Its onset of action is slow, with a peak in analgesic effect noted between 2.5-3.5 hours after dosing.

It is noted to illicit a strong antitussive effect, which could be of benefit to patients with bronchial carcinoma.

Mechanism of action
Not Available
Absorption

Bezitramide has poor water solubility, thus administration is restricted to the oral route. [1]

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Bezitramide is a prodrug which undergoes rapid hydrolysis of a proprionyl-group to form the major metabolite, R-4618. R-4618 has analgesic properties similar to the parent compound.[1] Metabolism occurs in the gastrointestinal tract under both acidic and alkaline conditions [1].

Route of elimination

Less than 0.3% of the dose was excreted unchanged in the urine. High concentrations in feces suggested incomplete absorption of biliary excretion.

Experiments in rats demonstrated extensive (up to 70%) biliary excretion, and less than 3% urinary excretion. [1]

Half life

11-24h. [1]

Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may increase the analgesic activities of Bezitramide.Experimental, Illicit
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may increase the analgesic activities of Bezitramide.Experimental
3,4-Methylenedioxyamphetamine3,4-Methylenedioxyamphetamine may increase the analgesic activities of Bezitramide.Experimental, Illicit
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may increase the analgesic activities of Bezitramide.Experimental, Illicit
AcepromazineAcepromazine may increase the hypotensive activities of Bezitramide.Approved, Vet Approved
AceprometazineAceprometazine may increase the hypotensive activities of Bezitramide.Approved
AcetazolamideThe risk or severity of adverse effects can be increased when Bezitramide is combined with Acetazolamide.Approved, Vet Approved
AclidiniumThe risk or severity of adverse effects can be increased when Aclidinium is combined with Bezitramide.Approved
AgmatineThe risk or severity of adverse effects can be increased when Agmatine is combined with Bezitramide.Experimental, Investigational
AlaproclateBezitramide may increase the serotonergic activities of Alaproclate.Experimental
AlcuroniumThe risk or severity of adverse effects can be increased when Alcuronium is combined with Bezitramide.Experimental
AlimemazineAlimemazine may increase the hypotensive activities of Bezitramide.Approved, Vet Approved
AlvimopanThe risk or severity of adverse effects can be increased when Bezitramide is combined with Alvimopan.Approved, Investigational
AmilorideThe risk or severity of adverse effects can be increased when Bezitramide is combined with Amiloride.Approved
Ammonium chlorideAmmonium chloride may increase the excretion rate of Bezitramide which could result in a lower serum level and potentially a reduction in efficacy.Approved, Investigational, Vet Approved
AmphetamineAmphetamine may increase the analgesic activities of Bezitramide.Approved, Illicit, Investigational
Anisotropine MethylbromideThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Bezitramide.Approved
AtracuriumThe risk or severity of adverse effects can be increased when Atracurium is combined with Bezitramide.Approved, Experimental, Investigational
Atracurium besylateThe risk or severity of adverse effects can be increased when Atracurium besylate is combined with Bezitramide.Approved
AtropineThe risk or severity of adverse effects can be increased when Atropine is combined with Bezitramide.Approved, Vet Approved
AzosemideThe risk or severity of adverse effects can be increased when Bezitramide is combined with Azosemide.Investigational
BenactyzineThe risk or severity of adverse effects can be increased when Benactyzine is combined with Bezitramide.Withdrawn
BendroflumethiazideThe risk or severity of adverse effects can be increased when Bezitramide is combined with Bendroflumethiazide.Approved
BenzatropineThe risk or severity of adverse effects can be increased when Benzatropine is combined with Bezitramide.Approved
BenzphetamineThe risk or severity of serotonin syndrome can be increased when Bezitramide is combined with Benzphetamine.Approved, Illicit
BiperidenThe risk or severity of adverse effects can be increased when Biperiden is combined with Bezitramide.Approved, Investigational
BisacodylThe therapeutic efficacy of Bisacodyl can be decreased when used in combination with Bezitramide.Approved
BL-1020BL-1020 may increase the hypotensive activities of Bezitramide.Investigational
BornaprineThe risk or severity of adverse effects can be increased when Bornaprine is combined with Bezitramide.Experimental
BromotheophyllineThe risk or severity of adverse effects can be increased when Bezitramide is combined with Bromotheophylline.Approved
BrompheniramineThe risk or severity of adverse effects can be increased when Brompheniramine is combined with Bezitramide.Approved
BumetanideThe risk or severity of adverse effects can be increased when Bezitramide is combined with Bumetanide.Approved
BuprenorphineBuprenorphine may decrease the analgesic activities of Bezitramide.Approved, Illicit, Investigational, Vet Approved
BupropionThe risk or severity of adverse effects can be increased when Bupropion is combined with Bezitramide.Approved
ButorphanolButorphanol may decrease the analgesic activities of Bezitramide.Approved, Illicit, Vet Approved
ButylscopolamineThe risk or severity of adverse effects can be increased when Butylscopolamine is combined with Bezitramide.Approved, Investigational, Vet Approved
Canrenoic acidThe risk or severity of adverse effects can be increased when Bezitramide is combined with Canrenoic acid.Approved, Withdrawn
CanrenoneThe risk or severity of adverse effects can be increased when Bezitramide is combined with Canrenone.Investigational
ChlorothiazideThe risk or severity of adverse effects can be increased when Bezitramide is combined with Chlorothiazide.Approved, Vet Approved
ChlorphenoxamineThe risk or severity of adverse effects can be increased when Chlorphenoxamine is combined with Bezitramide.Withdrawn
ChlorphentermineChlorphentermine may increase the analgesic activities of Bezitramide.Illicit, Withdrawn
ChlorproethazineChlorproethazine may increase the hypotensive activities of Bezitramide.Experimental
ChlorpromazineChlorpromazine may increase the hypotensive activities of Bezitramide.Approved, Investigational, Vet Approved
ChlorthalidoneThe risk or severity of adverse effects can be increased when Bezitramide is combined with Chlorthalidone.Approved
CicletanineThe risk or severity of adverse effects can be increased when Bezitramide is combined with Cicletanine.Investigational
CitalopramBezitramide may increase the serotonergic activities of Citalopram.Approved
ClofenamideThe risk or severity of adverse effects can be increased when Bezitramide is combined with Clofenamide.Experimental
ClopamideThe risk or severity of adverse effects can be increased when Bezitramide is combined with Clopamide.Experimental
ClorexoloneThe risk or severity of adverse effects can be increased when Bezitramide is combined with Clorexolone.Experimental
CodeineThe risk or severity of adverse effects can be increased when Codeine is combined with Bezitramide.Approved, Illicit
ConivaptanThe risk or severity of adverse effects can be increased when Bezitramide is combined with Conivaptan.Approved, Investigational
CyclobenzaprineThe risk or severity of adverse effects can be increased when Bezitramide is combined with Cyclobenzaprine.Approved
CyclopenthiazideThe risk or severity of adverse effects can be increased when Bezitramide is combined with Cyclopenthiazide.Experimental
CyclopentolateThe risk or severity of adverse effects can be increased when Cyclopentolate is combined with Bezitramide.Approved
CyclothiazideThe risk or severity of adverse effects can be increased when Bezitramide is combined with Cyclothiazide.Approved
DapagliflozinThe therapeutic efficacy of Dapagliflozin can be decreased when used in combination with Bezitramide.Approved
DapoxetineBezitramide may increase the serotonergic activities of Dapoxetine.Investigational
DarifenacinThe risk or severity of adverse effects can be increased when Darifenacin is combined with Bezitramide.Approved, Investigational
DesloratadineThe risk or severity of adverse effects can be increased when Desloratadine is combined with Bezitramide.Approved, Investigational
DesmopressinThe risk or severity of hyponatremia can be increased when Bezitramide is combined with Desmopressin.Approved
DesvenlafaxineThe risk or severity of serotonin syndrome can be increased when Bezitramide is combined with Desvenlafaxine.Approved, Investigational
DexetimideThe risk or severity of adverse effects can be increased when Dexetimide is combined with Bezitramide.Withdrawn
DextroamphetamineDextroamphetamine may increase the analgesic activities of Bezitramide.Approved, Illicit
DextromethorphanThe risk or severity of adverse effects can be increased when Dextromethorphan is combined with Bezitramide.Approved
DicyclomineThe risk or severity of adverse effects can be increased when Dicyclomine is combined with Bezitramide.Approved
DiethylpropionDiethylpropion may increase the analgesic activities of Bezitramide.Approved, Illicit
DiphenhydramineThe risk or severity of adverse effects can be increased when Diphenhydramine is combined with Bezitramide.Approved, Investigational
DocusateThe therapeutic efficacy of Docusate can be decreased when used in combination with Bezitramide.Approved
DoxylamineThe risk or severity of adverse effects can be increased when Doxylamine is combined with Bezitramide.Approved, Vet Approved
DrospirenoneThe risk or severity of adverse effects can be increased when Bezitramide is combined with Drospirenone.Approved
DuloxetineBezitramide may increase the serotonergic activities of Duloxetine.Approved
EfonidipineThe therapeutic efficacy of Efonidipine can be decreased when used in combination with Bezitramide.Approved, Investigational
EluxadolineBezitramide may increase the constipating activities of Eluxadoline.Approved, Investigational
EmeproniumThe risk or severity of adverse effects can be increased when Emepronium is combined with Bezitramide.Experimental
EpitizideThe risk or severity of adverse effects can be increased when Bezitramide is combined with Epitizide.Experimental
EplerenoneThe risk or severity of adverse effects can be increased when Bezitramide is combined with Eplerenone.Approved
EscitalopramBezitramide may increase the serotonergic activities of Escitalopram.Approved, Investigational
Etacrynic acidThe risk or severity of adverse effects can be increased when Bezitramide is combined with Etacrynic acid.Approved, Investigational
EtanautineThe risk or severity of adverse effects can be increased when Etanautine is combined with Bezitramide.Experimental
EthopropazineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Bezitramide.Approved
EthoxzolamideThe risk or severity of adverse effects can be increased when Bezitramide is combined with Ethoxzolamide.Withdrawn
EtoperidoneBezitramide may increase the serotonergic activities of Etoperidone.Withdrawn
EtybenzatropineThe risk or severity of adverse effects can be increased when Etybenzatropine is combined with Bezitramide.Experimental
FenquizoneThe risk or severity of adverse effects can be increased when Bezitramide is combined with Fenquizone.Experimental
FentanylThe risk or severity of serotonin syndrome can be increased when Fentanyl is combined with Bezitramide.Approved, Illicit, Investigational, Vet Approved
FesoterodineThe risk or severity of adverse effects can be increased when Fesoterodine is combined with Bezitramide.Approved
FlavoxateThe risk or severity of adverse effects can be increased when Flavoxate is combined with Bezitramide.Approved
FluoxetineThe risk or severity of serotonin syndrome can be increased when Bezitramide is combined with Fluoxetine.Approved, Vet Approved
FluphenazineFluphenazine may increase the hypotensive activities of Bezitramide.Approved
FluspirileneThe risk or severity of adverse effects can be increased when Bezitramide is combined with Fluspirilene.Approved, Investigational
FluvoxamineThe risk or severity of adverse effects can be increased when Fluvoxamine is combined with Bezitramide.Approved, Investigational
FurosemideThe therapeutic efficacy of Furosemide can be decreased when used in combination with Bezitramide.Approved, Vet Approved
GallamineThe risk or severity of adverse effects can be increased when Gallamine is combined with Bezitramide.Experimental
Gallamine TriethiodideThe risk or severity of adverse effects can be increased when Gallamine Triethiodide is combined with Bezitramide.Approved
GepefrineGepefrine may increase the analgesic activities of Bezitramide.Experimental
GlycerinThe therapeutic efficacy of Glycerin can be decreased when used in combination with Bezitramide.Approved, Investigational
GlycopyrroniumThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Bezitramide.Approved, Investigational, Vet Approved
HomatropineThe risk or severity of adverse effects can be increased when Homatropine is combined with Bezitramide.Approved
HydrochlorothiazideThe therapeutic efficacy of Hydrochlorothiazide can be decreased when used in combination with Bezitramide.Approved, Vet Approved
HydrocodoneThe risk or severity of serotonin syndrome can be increased when Hydrocodone is combined with Bezitramide.Approved, Illicit
HydroflumethiazideThe risk or severity of adverse effects can be increased when Bezitramide is combined with Hydroflumethiazide.Approved, Investigational
HydroxyamphetamineHydroxyamphetamine may increase the analgesic activities of Bezitramide.Approved
HyoscyamineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Bezitramide.Approved
IbopamineThe risk or severity of adverse effects can be increased when Bezitramide is combined with Ibopamine.Experimental
IndalpineBezitramide may increase the serotonergic activities of Indalpine.Investigational, Withdrawn
IndapamideThe risk or severity of adverse effects can be increased when Bezitramide is combined with Indapamide.Approved
Iofetamine I-123Iofetamine I-123 may increase the analgesic activities of Bezitramide.Approved
IpratropiumThe risk or severity of adverse effects can be increased when Ipratropium is combined with Bezitramide.Approved
IsosorbideThe risk or severity of adverse effects can be increased when Bezitramide is combined with Isosorbide.Approved, Investigational
LactuloseThe therapeutic efficacy of Lactulose can be decreased when used in combination with Bezitramide.Approved
LamotrigineThe risk or severity of adverse effects can be increased when Lamotrigine is combined with Bezitramide.Approved, Investigational
LevomilnacipranBezitramide may increase the serotonergic activities of Levomilnacipran.Approved, Investigational
LisdexamfetamineLisdexamfetamine may increase the analgesic activities of Bezitramide.Approved, Investigational
Magnesium carbonateThe therapeutic efficacy of Magnesium carbonate can be decreased when used in combination with Bezitramide.Approved, Investigational
Magnesium citrateThe therapeutic efficacy of Magnesium citrate can be decreased when used in combination with Bezitramide.Approved
Magnesium hydroxideThe therapeutic efficacy of Magnesium hydroxide can be decreased when used in combination with Bezitramide.Approved, Investigational
Magnesium sulfateThe therapeutic efficacy of Magnesium sulfate can be decreased when used in combination with Bezitramide.Approved, Investigational, Vet Approved
MannitolThe risk or severity of adverse effects can be increased when Bezitramide is combined with Mannitol.Approved, Investigational
MazaticolThe risk or severity of adverse effects can be increased when Mazaticol is combined with Bezitramide.Experimental
MebutizideThe risk or severity of adverse effects can be increased when Bezitramide is combined with Mebutizide.Experimental
MecamylamineThe risk or severity of adverse effects can be increased when Mecamylamine is combined with Bezitramide.Approved, Investigational
MefrusideThe risk or severity of adverse effects can be increased when Bezitramide is combined with Mefruside.Experimental
MephedroneMephedrone may increase the analgesic activities of Bezitramide.Investigational
MephentermineMephentermine may increase the analgesic activities of Bezitramide.Approved
MersalylThe risk or severity of adverse effects can be increased when Bezitramide is combined with Mersalyl.Approved
MesoridazineMesoridazine may increase the hypotensive activities of Bezitramide.Approved, Investigational
MethamphetamineMethamphetamine may increase the analgesic activities of Bezitramide.Approved, Illicit
MethanthelineThe risk or severity of adverse effects can be increased when Methantheline is combined with Bezitramide.Approved, Investigational
MethazolamideThe risk or severity of adverse effects can be increased when Bezitramide is combined with Methazolamide.Approved
MethotrimeprazineMethotrimeprazine may increase the hypotensive activities of Bezitramide.Approved, Investigational
MethoxyphenamineMethoxyphenamine may increase the analgesic activities of Bezitramide.Experimental
MethscopolamineThe risk or severity of adverse effects can be increased when Methscopolamine is combined with Bezitramide.Approved
MethyclothiazideThe risk or severity of adverse effects can be increased when Bezitramide is combined with Methyclothiazide.Approved
Methylene blueMethylene blue may increase the hypotensive activities of Bezitramide.Approved, Investigational
Methylscopolamine bromideThe risk or severity of adverse effects can be increased when Methylscopolamine bromide is combined with Bezitramide.Approved
MeticraneThe risk or severity of adverse effects can be increased when Bezitramide is combined with Meticrane.Experimental
MetixeneThe risk or severity of adverse effects can be increased when Metixene is combined with Bezitramide.Approved
MetoclopramideThe risk or severity of serotonin syndrome can be increased when Metoclopramide is combined with Bezitramide.Approved, Investigational
MetolazoneThe risk or severity of adverse effects can be increased when Bezitramide is combined with Metolazone.Approved
MidomafetamineMidomafetamine may increase the analgesic activities of Bezitramide.Experimental, Illicit, Investigational
MilnacipranBezitramide may increase the serotonergic activities of Milnacipran.Approved, Investigational
Mineral oilThe therapeutic efficacy of Mineral oil can be decreased when used in combination with Bezitramide.Approved, Vet Approved
MMDAMMDA may increase the analgesic activities of Bezitramide.Experimental, Illicit
MoricizineMoricizine may increase the hypotensive activities of Bezitramide.Approved, Investigational, Withdrawn
MuzolimineThe risk or severity of adverse effects can be increased when Bezitramide is combined with Muzolimine.Experimental
NalbuphineNalbuphine may decrease the analgesic activities of Bezitramide.Approved
NaltrexoneThe therapeutic efficacy of Bezitramide can be decreased when used in combination with Naltrexone.Approved, Investigational, Vet Approved
NefazodoneBezitramide may increase the serotonergic activities of Nefazodone.Approved, Withdrawn
NicardipineThe risk or severity of adverse effects can be increased when Nicardipine is combined with Bezitramide.Approved, Investigational
OndansetronThe risk or severity of serotonin syndrome can be increased when Ondansetron is combined with Bezitramide.Approved
OrphenadrineThe risk or severity of adverse effects can be increased when Orphenadrine is combined with Bezitramide.Approved
OtiloniumThe risk or severity of adverse effects can be increased when Otilonium is combined with Bezitramide.Experimental, Investigational
OxitropiumThe risk or severity of adverse effects can be increased when Oxitropium is combined with Bezitramide.Investigational
OxybutyninThe risk or severity of adverse effects can be increased when Oxybutynin is combined with Bezitramide.Approved, Investigational
OxycodoneThe risk or severity of adverse effects can be increased when Oxycodone is combined with Bezitramide.Approved, Illicit, Investigational
OxymorphoneThe risk or severity of adverse effects can be increased when Oxymorphone is combined with Bezitramide.Approved, Investigational, Vet Approved
OxyphenoniumThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Bezitramide.Approved
PancuroniumThe risk or severity of adverse effects can be increased when Pancuronium is combined with Bezitramide.Approved
ParoxetineThe risk or severity of adverse effects can be increased when Paroxetine is combined with Bezitramide.Approved, Investigational
PegvisomantThe therapeutic efficacy of Pegvisomant can be decreased when used in combination with Bezitramide.Approved
PentazocinePentazocine may decrease the analgesic activities of Bezitramide.Approved, Vet Approved
PentoliniumThe risk or severity of adverse effects can be increased when Pentolinium is combined with Bezitramide.Approved
PerazinePerazine may increase the hypotensive activities of Bezitramide.Approved, Investigational
PerphenazinePerphenazine may increase the hypotensive activities of Bezitramide.Approved
PhenglutarimideThe risk or severity of adverse effects can be increased when Phenglutarimide is combined with Bezitramide.Experimental
PhenobarbitalThe risk or severity of adverse effects can be increased when Phenobarbital is combined with Bezitramide.Approved, Investigational
PhenterminePhentermine may increase the analgesic activities of Bezitramide.Approved, Illicit
PipecuroniumThe risk or severity of adverse effects can be increased when Pipecuronium is combined with Bezitramide.Approved
PirenzepineThe risk or severity of adverse effects can be increased when Pirenzepine is combined with Bezitramide.Approved
PiretanideThe risk or severity of adverse effects can be increased when Bezitramide is combined with Piretanide.Approved
PolythiazideThe risk or severity of adverse effects can be increased when Bezitramide is combined with Polythiazide.Approved
Potassium cationThe risk or severity of adverse effects can be increased when Bezitramide is combined with Potassium.Approved, Investigational
Potassium CitrateThe risk or severity of adverse effects can be increased when Bezitramide is combined with Potassium Citrate.Approved, Investigational, Vet Approved
ProchlorperazineThe risk or severity of hypotension and central nervous system depression can be increased when Prochlorperazine is combined with Bezitramide.Approved, Vet Approved
ProcyclidineThe risk or severity of adverse effects can be increased when Procyclidine is combined with Bezitramide.Approved
PromazinePromazine may increase the hypotensive activities of Bezitramide.Approved, Vet Approved
PromethazineThe risk or severity of hypotension and central nervous system depression can be increased when Promethazine is combined with Bezitramide.Approved, Investigational
PropanthelineThe risk or severity of adverse effects can be increased when Propantheline is combined with Bezitramide.Approved
PropericiazinePropericiazine may increase the hypotensive activities of Bezitramide.Approved, Investigational
PropiopromazinePropiopromazine may increase the hypotensive activities of Bezitramide.Vet Approved
PropiverineThe risk or severity of adverse effects can be increased when Propiverine is combined with Bezitramide.Approved, Investigational
PseudoephedrinePseudoephedrine may increase the analgesic activities of Bezitramide.Approved
QuetiapineThe risk or severity of adverse effects can be increased when Quetiapine is combined with Bezitramide.Approved
QuinethazoneThe risk or severity of adverse effects can be increased when Bezitramide is combined with Quinethazone.Approved
QuinidineThe risk or severity of adverse effects can be increased when Quinidine is combined with Bezitramide.Approved, Investigational
RamosetronBezitramide may increase the constipating activities of Ramosetron.Approved, Investigational
RitobegronRitobegron may increase the analgesic activities of Bezitramide.Investigational
RizatriptanThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Bezitramide.Approved
RolofyllineThe risk or severity of adverse effects can be increased when Bezitramide is combined with Rolofylline.Investigational
ScopolamineThe risk or severity of adverse effects can be increased when Scopolamine is combined with Bezitramide.Approved, Investigational
SertralineBezitramide may increase the serotonergic activities of Sertraline.Approved
Sodium phosphate, monobasicThe therapeutic efficacy of Sodium phosphate, monobasic can be decreased when used in combination with Bezitramide.Approved
SolifenacinThe risk or severity of adverse effects can be increased when Solifenacin is combined with Bezitramide.Approved
SpiradolineThe risk or severity of adverse effects can be increased when Bezitramide is combined with Spiradoline.Investigational
SpironolactoneThe therapeutic efficacy of Spironolactone can be decreased when used in combination with Bezitramide.Approved
SuccinylcholineSuccinylcholine may increase the bradycardic activities of Bezitramide.Approved
SumatriptanThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Bezitramide.Approved, Investigational
TheobromineThe risk or severity of adverse effects can be increased when Bezitramide is combined with Theobromine.Approved, Investigational
ThiazinamThiazinam may increase the hypotensive activities of Bezitramide.Experimental
ThiethylperazineThiethylperazine may increase the hypotensive activities of Bezitramide.Withdrawn
ThioproperazineThioproperazine may increase the hypotensive activities of Bezitramide.Approved
ThioridazineThioridazine may increase the hypotensive activities of Bezitramide.Approved, Withdrawn
TicrynafenThe risk or severity of adverse effects can be increased when Bezitramide is combined with Ticrynafen.Withdrawn
TiotropiumThe risk or severity of adverse effects can be increased when Tiotropium is combined with Bezitramide.Approved
TolterodineThe risk or severity of adverse effects can be increased when Tolterodine is combined with Bezitramide.Approved, Investigational
TolvaptanThe risk or severity of adverse effects can be increased when Bezitramide is combined with Tolvaptan.Approved
TorasemideThe risk or severity of adverse effects can be increased when Bezitramide is combined with Torasemide.Approved
TramadolThe risk or severity of adverse effects can be increased when Tramadol is combined with Bezitramide.Approved, Investigational
TriamtereneThe risk or severity of adverse effects can be increased when Bezitramide is combined with Triamterene.Approved
TrichlormethiazideThe risk or severity of adverse effects can be increased when Bezitramide is combined with Trichlormethiazide.Approved, Vet Approved
TrifluoperazineTrifluoperazine may increase the hypotensive activities of Bezitramide.Approved, Investigational
TriflupromazineTriflupromazine may increase the hypotensive activities of Bezitramide.Approved, Vet Approved
TrihexyphenidylThe risk or severity of adverse effects can be increased when Trihexyphenidyl is combined with Bezitramide.Approved
TrimebutineThe risk or severity of adverse effects can be increased when Trimebutine is combined with Bezitramide.Approved
TrimethaphanThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Bezitramide.Approved, Investigational
TropatepineThe risk or severity of adverse effects can be increased when Tropatepine is combined with Bezitramide.Experimental
TropicamideThe risk or severity of adverse effects can be increased when Tropicamide is combined with Bezitramide.Approved, Investigational
TrospiumThe risk or severity of adverse effects can be increased when Trospium is combined with Bezitramide.Approved
TubocurarineThe risk or severity of adverse effects can be increased when Tubocurarine is combined with Bezitramide.Approved
UlaritideThe risk or severity of adverse effects can be increased when Bezitramide is combined with Ularitide.Investigational
UmeclidiniumThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Bezitramide.Approved
VecuroniumThe risk or severity of adverse effects can be increased when Vecuronium is combined with Bezitramide.Approved
VemurafenibThe risk or severity of QTc prolongation can be increased when Vemurafenib is combined with Bezitramide.Approved
VenlafaxineThe risk or severity of serotonin syndrome can be increased when Bezitramide is combined with Venlafaxine.Approved
XipamideThe risk or severity of adverse effects can be increased when Bezitramide is combined with Xipamide.Experimental
ZimelidineBezitramide may increase the serotonergic activities of Zimelidine.Withdrawn
ZolmitriptanThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Bezitramide.Approved, Investigational
Food Interactions
Not Available

References

General References
  1. Meijer DK, Hovinga G, Versluis A, Broring J, van Aken K, Moolenaar F, Wesseling H: Pharmacokinetics of the oral narcotic analgesic bezitramide and preliminary observations on its effect on experimentally induced pain. Eur J Clin Pharmacol. 1984;27(5):615-8. [PubMed:6519169]
External Links
PubChem Compound
61791
PubChem Substance
46505037
ChemSpider
55675
ChEBI
135794
ChEMBL
CHEMBL2104149
Wikipedia
Bezitramide
ATC Codes
N02AC05 — Bezitramide

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)145-149 °CPhysProp
water solubilityPoor water solubility Meijer, D. K. F., et al. "Pharmacokinetics of the oral narcotic analgesic bezitramide and preliminary observations on its effect on experimentally induced pain." European journal of clinical pharmacology 27.5 (1984): 615-618.
logP4.80SANGSTER (1993)
Predicted Properties
PropertyValueSource
Water Solubility0.0067 mg/mLALOGPS
logP4.35ALOGPS
logP4.79ChemAxon
logS-4.9ALOGPS
pKa (Strongest Basic)8.32ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area67.65 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity155.25 m3·mol-1ChemAxon
Polarizability55.58 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9787
Caco-2 permeable-0.5631
P-glycoprotein substrateSubstrate0.6446
P-glycoprotein inhibitor IInhibitor0.8347
P-glycoprotein inhibitor IINon-inhibitor0.6466
Renal organic cation transporterNon-inhibitor0.518
CYP450 2C9 substrateNon-substrate0.7483
CYP450 2D6 substrateNon-substrate0.6835
CYP450 3A4 substrateSubstrate0.6644
CYP450 1A2 substrateNon-inhibitor0.9217
CYP450 2C9 inhibitorNon-inhibitor0.5586
CYP450 2D6 inhibitorNon-inhibitor0.7687
CYP450 2C19 inhibitorNon-inhibitor0.8888
CYP450 3A4 inhibitorInhibitor0.584
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6976
Ames testNon AMES toxic0.569
CarcinogenicityNon-carcinogens0.8409
BiodegradationNot ready biodegradable0.9939
Rat acute toxicity3.5117 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.5527
hERG inhibition (predictor II)Inhibitor0.6899
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
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

Taxonomy

Description
This compound belongs to the class of organic compounds known as diphenylacetonitriles. These are cyclic aromatic compounds containing a diphenylacetonitrile moiety, which consists of a diphenylmethane linked to and acetonitrile to form 2,2-diphenylacetonitrile.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Diphenylacetonitriles
Direct Parent
Diphenylacetonitriles
Alternative Parents
Diphenylmethanes / Benzimidazoles / N-acylimidazoles / N-acyl ureas / Carbonylimidazoles / Aralkylamines / Piperidines / Heteroaromatic compounds / Trialkylamines / Nitriles
show 5 more
Substituents
Diphenylacetonitrile / Diphenylmethane / Benzimidazole / N-acylimidazole / Imidazole-1-carbonyl group / N-acyl urea / Aralkylamine / Ureide / N-substituted imidazole / Piperidine
show 19 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Drug created on July 31, 2007 07:09 / Updated on August 02, 2018 04:36