Identification
- Generic Name
- Benzquinamide
- DrugBank Accession Number
- DB00767
- Background
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.
- Type
- Small Molecule
- Groups
- Withdrawn
- Structure
Structure for Benzquinamide (DB00767)
- Weight
- Average: 404.4999
Monoisotopic: 404.231122144 - Chemical Formula
- C22H32N2O5
- Synonyms
- benzquinamida
- Benzquinamide
- BZQ
Pharmacology
- Indication
Used to prevent and treat nausea and vomiting associated with anesthesia and surgery, administered intramuscularly or intravenously.
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Benzquinamide is an antiemetic compound with antihistaminic, mild anticholinergic, and sedative properties.
- Mechanism of action
The mechanism of action is not known, but presumably benzquinamide works via antagonism of muscarinic acetycholine receptors and histamine H1 receptors.
Target Actions Organism AHistamine H1 receptor antagonistHumans AMuscarinic acetylcholine receptor M4 antagonistHumans AMuscarinic acetylcholine receptor M1 antagonistHumans AMuscarinic acetylcholine receptor M5 antagonistHumans AMuscarinic acetylcholine receptor M2 antagonistHumans AMuscarinic acetylcholine receptor M3 antagonistHumans - Absorption
Incomplete, with 33–39% bioavailability via the capsule and suppository routes, relative to the intramuscular route.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
1-1.6 hours (for all formulations)
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAclidinium The risk or severity of adverse effects can be increased when Benzquinamide is combined with Aclidinium. Adenosine The risk or severity of Tachycardia can be increased when Adenosine is combined with Benzquinamide. Alfentanil The risk or severity of adverse effects can be increased when Benzquinamide is combined with Alfentanil. Alloin The therapeutic efficacy of Alloin can be decreased when used in combination with Benzquinamide. Amantadine The risk or severity of adverse effects can be increased when Benzquinamide is combined with Amantadine. Ambenonium The therapeutic efficacy of Benzquinamide can be decreased when used in combination with Ambenonium. Amitriptyline The risk or severity of adverse effects can be increased when Benzquinamide is combined with Amitriptyline. Amitriptylinoxide The risk or severity of adverse effects can be increased when Benzquinamide is combined with Amitriptylinoxide. Amobarbital The risk or severity of adverse effects can be increased when Benzquinamide is combined with Amobarbital. Amoxapine The risk or severity of adverse effects can be increased when Benzquinamide is combined with Amoxapine. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Not Available
Products
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Ingredient UNII CAS InChI Key Benzquinamide hydrochloride 3221WFM86J 113-69-9 KZLNXGBVFTWMPS-UHFFFAOYSA-N - International/Other Brands
- Benzchinamide / Emete-con (Pfizer) / Emeticon (Pfizer) / Promecon (Endo) / Quantril (Pfizer)
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Tetrahydroisoquinolines
- Sub Class
- Not Available
- Direct Parent
- Tetrahydroisoquinolines
- Alternative Parents
- Piperidinecarboxamides / Anisoles / Aralkylamines / Alkyl aryl ethers / Tertiary carboxylic acid amides / Trialkylamines / Carboxylic acid esters / Amino acids and derivatives / Monocarboxylic acids and derivatives / Azacyclic compounds show 4 more
- Substituents
- 3-piperidinecarboxamide / Alkyl aryl ether / Amine / Amino acid or derivatives / Anisole / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group show 18 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- monocarboxylic acid amide (CHEBI:27662)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 0475EA27Q3
- CAS number
- 63-12-7
- InChI Key
- 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
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 References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014905
- KEGG Drug
- D00243
- PubChem Compound
- 2342
- PubChem Substance
- 46506155
- ChemSpider
- 2252
- 19041
- ChEBI
- 27662
- ChEMBL
- CHEMBL1201250
- Therapeutic Targets Database
- DAP000713
- PharmGKB
- PA164749018
- Wikipedia
- Benzquinamide
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Pfizer inc
- Roerig div pfizer inc
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 130-131.5 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. water solubility 153 mg/L Not Available logP 1.7 Not Available - Predicted Properties
Property Value Source Water Solubility 0.49 mg/mL ALOGPS logP 2.49 ALOGPS logP 1.42 Chemaxon logS -2.9 ALOGPS pKa (Strongest Acidic) 19.61 Chemaxon pKa (Strongest Basic) 7.9 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 68.31 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 110.47 m3·mol-1 Chemaxon Polarizability 45.27 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - 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 inhibitor Non-inhibitor 0.9501 CYP450 2D6 inhibitor Non-inhibitor 0.9311 CYP450 2C19 inhibitor Non-inhibitor 0.7941 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Histamine receptor activity
- Specific Function
- In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamin...
- Gene Name
- HRH1
- Uniprot ID
- P35367
- Uniprot Name
- Histamine H1 receptor
- Molecular Weight
- 55783.61 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
- Niemegeers CJ: Antiemetic specificity of dopamine antagonists. Psychopharmacology (Berl). 1982;78(3):210-3. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Guanyl-nucleotide exchange factor activity
- Specific Function
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
- Gene Name
- CHRM4
- Uniprot ID
- P08173
- Uniprot Name
- Muscarinic acetylcholine receptor M4
- Molecular Weight
- 53048.65 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Phosphatidylinositol phospholipase c activity
- Specific Function
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
- Gene Name
- CHRM1
- Uniprot ID
- P11229
- Uniprot Name
- Muscarinic acetylcholine receptor M1
- Molecular Weight
- 51420.375 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Phosphatidylinositol phospholipase c activity
- Specific Function
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
- Gene Name
- CHRM5
- Uniprot ID
- P08912
- Uniprot Name
- Muscarinic acetylcholine receptor M5
- Molecular Weight
- 60073.205 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- G-protein coupled acetylcholine receptor activity
- Specific Function
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
- Gene Name
- CHRM2
- Uniprot ID
- P08172
- Uniprot Name
- Muscarinic acetylcholine receptor M2
- Molecular Weight
- 51714.605 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Receptor activity
- Specific Function
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
- Gene Name
- CHRM3
- Uniprot ID
- P20309
- Uniprot Name
- Muscarinic acetylcholine receptor M3
- Molecular Weight
- 66127.445 Da
References
Drug created at June 13, 2005 13:24 / Updated at March 03, 2023 17:39