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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
SynonymLanguageCode
BZQNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
BenzchinamideNot Available
Emete-conPfizer
EmeticonPfizer
PromeconEndo
QuantrilPfizer
Brand mixturesNot Available
Categories
CAS number63-12-7
WeightAverage: 404.4999
Monoisotopic: 404.231122144
Chemical FormulaC22H32N2O5
InChI KeyJSZILQVIPPROJI-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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassIsoquinolines and Derivatives
SubclassNot Available
Direct parentIsoquinolines and Derivatives
Alternative parentsPiperidinecarboxylic Acids; Anisoles; Alkyl Aryl Ethers; Tertiary Carboxylic Acid Amides; Carboxylic Acid Esters; Tertiary Amines; Polyamines; Carboxylic Acids; Enolates
Substituentsphenol ether; anisole; alkyl aryl ether; benzene; piperidine; tertiary carboxylic acid amide; carboxamide group; carboxylic acid ester; tertiary amine; ether; polyamine; carboxylic acid; enolate; carboxylic acid derivative; amine; organonitrogen compound
Classification descriptionThis compound belongs to the isoquinolines and derivatives. These are aromatic polycyclic compounds containing an isoquinoline moiety, which consists of a benzene ring fused to a pyridine ring and forming benzo[c]pyridine.
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
Metabolism
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
Property Value Probability
Human Intestinal Absorption + 0.8998
Blood Brain Barrier + 0.9383
Caco-2 permeable + 0.6206
P-glycoprotein substrate Substrate 0.7763
P-glycoprotein inhibitor I Inhibitor 0.7325
P-glycoprotein inhibitor II Non-inhibitor 0.5791
Renal organic cation transporter Non-inhibitor 0.5858
CYP450 2C9 substrate Non-substrate 0.8588
CYP450 2D6 substrate Non-substrate 0.7872
CYP450 3A4 substrate Substrate 0.7516
CYP450 1A2 substrate Non-inhibitor 0.8882
CYP450 2C9 substrate Non-inhibitor 0.9501
CYP450 2D6 substrate Non-inhibitor 0.9311
CYP450 2C19 substrate Non-inhibitor 0.7941
CYP450 3A4 substrate Non-inhibitor 0.8742
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7716
Ames test Non AMES toxic 0.7011
Carcinogenicity Non-carcinogens 0.8844
Biodegradation Not ready biodegradable 0.9795
Rat acute toxicity 2.5546 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9392
hERG inhibition (predictor II) Inhibitor 0.5894
Pharmacoeconomics
Manufacturers
  • Pfizer inc
  • Roerig div pfizer inc
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 Solubility0.49ALOGPS
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 RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
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 ReferenceNot Available
External Links
ResourceLink
KEGG DrugD00243
PubChem Compound2342
PubChem Substance46506155
ChemSpider2252
ChEBI27662
ChEMBLCHEMBL1201250
Therapeutic Targets DatabaseDAP000713
PharmGKBPA164749018
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
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 March 31, 2014 15:16