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Identification
NameBenzquinamide
Accession NumberDB00767  (APRD00820)
TypeSmall Molecule
GroupsWithdrawn
Description

Benzquinamide is a discontinued antiemetic compound with antihistaminic, mild anticholinergic, and sedative properties. The mechanism of action is not known, but presumably benzquinamide works via antagonism of muscarinic acetycholine receptors and histamine H1 receptors.

Structure
Thumb
Synonyms
BZQ
External Identifiers Not Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
BenzchinamideNot Available
Emete-conPfizer
EmeticonPfizer
PromeconEndo
QuantrilPfizer
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Benzquinamide hydrochloride
ThumbNot applicableDBSALT001425
Categories
UNII0475EA27Q3
CAS number63-12-7
WeightAverage: 404.4999
Monoisotopic: 404.231122144
Chemical FormulaC22H32N2O5
InChI KeyInChIKey=JSZILQVIPPROJI-UHFFFAOYSA-N
InChI
InChI=1S/C22H32N2O5/c1-6-23(7-2)22(26)17-13-24-9-8-15-10-20(27-4)21(28-5)11-16(15)18(24)12-19(17)29-14(3)25/h10-11,17-19H,6-9,12-13H2,1-5H3
IUPAC Name
3-(diethylcarbamoyl)-9,10-dimethoxy-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-yl acetate
SMILES
CCN(CC)C(=O)C1CN2CCC3=CC(OC)=C(OC)C=C3C2CC1OC(C)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrahydroisoquinolines
Sub ClassNot Available
Direct ParentTetrahydroisoquinolines
Alternative Parents
Substituents
  • Tetrahydroisoquinoline
  • Piperidinecarboxylic acid
  • Piperidinecarboxamide
  • 3-piperidinecarboxamide
  • Anisole
  • Aralkylamine
  • Alkyl aryl ether
  • Benzenoid
  • Piperidine
  • Acetate salt
  • Tertiary carboxylic acid amide
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid ester
  • Carboxamide group
  • Azacycle
  • Ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationUsed to prevent and treat nausea and vomiting associated with anesthesia and surgery, administered intramuscularly or intravenously.
PharmacodynamicsBenzquinamide is an antiemetic compound with antihistaminic, mild anticholinergic, and sedative properties.
Mechanism of actionThe mechanism of action is not known, but presumably benzquinamide works via antagonism of muscarinic acetycholine receptors and histamine H1 receptors.
AbsorptionIncomplete, with 33–39% bioavailability via the capsule and suppository routes, relative to the intramuscular route.
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half life1-1.6 hours (for all formulations)
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8998
Blood Brain Barrier+0.9383
Caco-2 permeable+0.6206
P-glycoprotein substrateSubstrate0.7763
P-glycoprotein inhibitor IInhibitor0.7325
P-glycoprotein inhibitor IINon-inhibitor0.5791
Renal organic cation transporterNon-inhibitor0.5858
CYP450 2C9 substrateNon-substrate0.8588
CYP450 2D6 substrateNon-substrate0.7872
CYP450 3A4 substrateSubstrate0.7516
CYP450 1A2 substrateNon-inhibitor0.8882
CYP450 2C9 inhibitorNon-inhibitor0.9501
CYP450 2D6 inhibitorNon-inhibitor0.9311
CYP450 2C19 inhibitorNon-inhibitor0.7941
CYP450 3A4 inhibitorNon-inhibitor0.8742
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7716
Ames testNon AMES toxic0.7011
CarcinogenicityNon-carcinogens0.8844
BiodegradationNot ready biodegradable0.9795
Rat acute toxicity2.5546 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9392
hERG inhibition (predictor II)Inhibitor0.5894
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point130-131.5Tretter, J.R.; US. Patent 3,053,845; September 11, 1962;assigned to Chas. Pfizer & Co., Inc. Lombardino, J.G. and McLamore, W.M.; U.S. Patent 3,055,894; September 25,1962; assigned to Chas. Pfizer & Co., Inc.
water solubility153 mg/LNot Available
logP1.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.49 mg/mLALOGPS
logP2.49ALOGPS
logP1.42ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)19.61ChemAxon
pKa (Strongest Basic)7.5ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area68.31 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity110.47 m3·mol-1ChemAxon
Polarizability45.27 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Tretter, J.R.; US. Patent 3,053,845; September 11, 1962; assigned to Chas. Pfizer & Co.,
Inc.
Lombardino, J.G. and McLamore, W.M.; U.S. Patent 3,055,894; September 25,1962;
assigned to Chas. Pfizer & Co., Inc.

General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with Benzquinamide.
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Benzquinamide.
AmoxapineThe risk or severity of adverse effects can be increased when Amoxapine is combined with Benzquinamide.
AmphetamineBenzquinamide may decrease the stimulatory activities of Amphetamine.
BenzphetamineBenzquinamide may decrease the stimulatory activities of Benzphetamine.
BuspironeThe risk or severity of adverse effects can be increased when Buspirone is combined with Benzquinamide.
CabergolineThe risk or severity of adverse effects can be increased when Cabergoline is combined with Benzquinamide.
CitalopramThe risk or severity of adverse effects can be increased when Citalopram is combined with Benzquinamide.
ClomipramineThe risk or severity of adverse effects can be increased when Clomipramine is combined with Benzquinamide.
CyclobenzaprineThe risk or severity of adverse effects can be increased when Cyclobenzaprine is combined with Benzquinamide.
DesipramineThe risk or severity of adverse effects can be increased when Desipramine is combined with Benzquinamide.
DesvenlafaxineThe risk or severity of adverse effects can be increased when Desvenlafaxine is combined with Benzquinamide.
DextroamphetamineBenzquinamide may decrease the stimulatory activities of Dextroamphetamine.
DextromethorphanThe risk or severity of adverse effects can be increased when Dextromethorphan is combined with Benzquinamide.
DihydroergotamineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Benzquinamide.
DonepezilDonepezil may increase the central neurotoxic activities of Benzquinamide.
DoxepinThe risk or severity of adverse effects can be increased when Doxepin is combined with Benzquinamide.
DuloxetineThe risk or severity of adverse effects can be increased when Duloxetine is combined with Benzquinamide.
EletriptanThe risk or severity of adverse effects can be increased when Eletriptan is combined with Benzquinamide.
Ergoloid mesylateThe risk or severity of adverse effects can be increased when Ergoloid mesylate is combined with Benzquinamide.
ErgonovineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Benzquinamide.
ErgotamineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Benzquinamide.
EscitalopramThe risk or severity of adverse effects can be increased when Escitalopram is combined with Benzquinamide.
FentanylThe risk or severity of adverse effects can be increased when Fentanyl is combined with Benzquinamide.
FluoxetineThe risk or severity of adverse effects can be increased when Fluoxetine is combined with Benzquinamide.
FluvoxamineThe risk or severity of adverse effects can be increased when Fluvoxamine is combined with Benzquinamide.
FrovatriptanThe risk or severity of adverse effects can be increased when Frovatriptan is combined with Benzquinamide.
GalantamineGalantamine may increase the central neurotoxic activities of Benzquinamide.
ImipramineThe risk or severity of adverse effects can be increased when Imipramine is combined with Benzquinamide.
IsocarboxazidThe risk or severity of adverse effects can be increased when Isocarboxazid is combined with Benzquinamide.
LevomilnacipranThe risk or severity of adverse effects can be increased when Levomilnacipran is combined with Benzquinamide.
LinezolidThe risk or severity of adverse effects can be increased when Linezolid is combined with Benzquinamide.
LisdexamfetamineBenzquinamide may decrease the stimulatory activities of Lisdexamfetamine.
LithiumLithium may increase the neurotoxic activities of Benzquinamide.
LorcaserinThe risk or severity of adverse effects can be increased when Lorcaserin is combined with Benzquinamide.
MaprotilineThe risk or severity of adverse effects can be increased when Maprotiline is combined with Benzquinamide.
MethadoneThe risk or severity of adverse effects can be increased when Methadone is combined with Benzquinamide.
MethamphetamineBenzquinamide may decrease the stimulatory activities of Methamphetamine.
MethylphenidateThe risk or severity of adverse effects can be increased when Benzquinamide is combined with Methylphenidate.
MetoclopramideThe risk or severity of adverse effects can be increased when Metoclopramide is combined with Benzquinamide.
MetyrosineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Benzquinamide.
MilnacipranThe risk or severity of adverse effects can be increased when Milnacipran is combined with Benzquinamide.
MoclobemideThe risk or severity of adverse effects can be increased when Moclobemide is combined with Benzquinamide.
NaratriptanThe risk or severity of adverse effects can be increased when Naratriptan is combined with Benzquinamide.
NefazodoneThe risk or severity of adverse effects can be increased when Nefazodone is combined with Benzquinamide.
NortriptylineThe risk or severity of adverse effects can be increased when Nortriptyline is combined with Benzquinamide.
ParoxetineThe risk or severity of adverse effects can be increased when Paroxetine is combined with Benzquinamide.
PethidineThe risk or severity of adverse effects can be increased when Pethidine is combined with Benzquinamide.
PhendimetrazineBenzquinamide may decrease the stimulatory activities of Phendimetrazine.
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Benzquinamide.
PhentermineBenzquinamide may decrease the stimulatory activities of Phentermine.
ProcarbazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Benzquinamide.
PromethazineThe risk or severity of adverse effects can be increased when Promethazine is combined with Benzquinamide.
ProtriptylineThe risk or severity of adverse effects can be increased when Protriptyline is combined with Benzquinamide.
QuinagolideThe therapeutic efficacy of Quinagolide can be decreased when used in combination with Benzquinamide.
RasagilineThe risk or severity of adverse effects can be increased when Rasagiline is combined with Benzquinamide.
RivastigmineRivastigmine may increase the central neurotoxic activities of Benzquinamide.
RizatriptanThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Benzquinamide.
SelegilineThe risk or severity of adverse effects can be increased when Selegiline is combined with Benzquinamide.
SertralineThe risk or severity of adverse effects can be increased when Sertraline is combined with Benzquinamide.
SumatriptanThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Benzquinamide.
Tedizolid PhosphateThe risk or severity of adverse effects can be increased when Tedizolid Phosphate is combined with Benzquinamide.
TetrabenazineThe risk or severity of adverse effects can be increased when Tetrabenazine is combined with Benzquinamide.
TramadolThe risk or severity of adverse effects can be increased when Tramadol is combined with Benzquinamide.
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Benzquinamide.
TrazodoneThe risk or severity of adverse effects can be increased when Trazodone is combined with Benzquinamide.
TrimipramineThe risk or severity of adverse effects can be increased when Trimipramine is combined with Benzquinamide.
VenlafaxineThe risk or severity of adverse effects can be increased when Venlafaxine is combined with Benzquinamide.
VilazodoneThe risk or severity of adverse effects can be increased when Vilazodone is combined with Benzquinamide.
VortioxetineThe risk or severity of adverse effects can be increased when Vortioxetine is combined with Benzquinamide.
ZolmitriptanThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Benzquinamide.
Food InteractionsNot Available

Targets

1. Histamine H1 receptor

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Histamine H1 receptor P35367 Details

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
  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
  3. Maurer H, Pfleger K: Identification and differentiation of alkylamine antihistamines and their metabolites in urine by computerized gas chromatography-mass spectrometry. J Chromatogr. 1988 Aug 19;430(1):31-41. Pubmed
  4. Niemegeers CJ: Antiemetic specificity of dopamine antagonists. Psychopharmacology (Berl). 1982;78(3):210-3. Pubmed

2. Muscarinic acetylcholine receptor M4

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M4 P08173 Details

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
  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

3. Muscarinic acetylcholine receptor M1

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M1 P11229 Details

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
  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

4. Muscarinic acetylcholine receptor M5

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M5 P08912 Details

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
  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

5. Muscarinic acetylcholine receptor M2

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M2 P08172 Details

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
  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

6. Muscarinic acetylcholine receptor M3

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M3 P20309 Details

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
  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

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Drug created on June 13, 2005 07:24 / Updated on November 30, 2015 12:10