3-(diethylcarbamoyl)-9,10-dimethoxy-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-yl acetate

• ChemBase ID: 647
• Molecular Formular: C22H32N2O5
• Molecular Mass: 404.49988
• Monoisotopic Mass: 404.23112213
• SMILES: O(C1C(CN2C(C1)c1c(CC2)cc(OC)c(OC)c1)C(=O)N(CC)CC)C(=O)C
• Canonical SMILES: CCN(C(=O)C1CN2CCc3c(C2CC1OC(=O)C)cc(c(c3)OC)OC)CC
• 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
• InChIKey: JSZILQVIPPROJI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(diethylcarbamoyl)-9,10-dimethoxy-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-yl acetate
• IUPAC Traditional name: benzquinamide
• Brand Name: BZQ; Benzchinamide; Emete-con; Emeticon; Promecon; Quantril
• Synonyms: Benzquinamide; Promecon; Quantrin; Emete-Con

Database IDs

• CAS Number: 63-12-7
• PubChem SID: 46506155; 160964110
• PubChem CID: 2342
• CHEMBL: 1201250
• KEGG ID: D00243
• Unique Ingredient Identifier: 0475EA27Q3
• Wikipedia Title: Benzquinamide

CALCULATED PROPERTIES

JChem

• Acid pKa: 19.607786
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): -0.5742615
• LogD (pH = 7.4): 1.064082
• Log P: 1.4195195
• Molar Refractivity: 110.471 cm^3
• Polarizability: 43.126442 Å^3
• Polar Surface Area: 68.31 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.49
• LOG S: -2.92
• Solubility (Water): 4.90e-01 g/l

PROPERTIES

Physical Property

• Solubility: 153 mg/L
• Hydrophobicity(logP): 1.7

Pharmacology Properties

• Admin Routes: Suppository, Injection
• US Licence: Quantril

DETAILS

DrugBank - DB00767

• Drug Groups: approved
• Description: Benzquinamide is an 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.
• Indication: Used to prevent and treat nausea and vomiting associated with anesthesia and surgery, administered intramuscularly or intravenously.
• Pharmacology: Benzquinamide is an antiemetic compound with antihistaminic, mild anticholinergic, and sedative properties.
• Affected Organisms: Humans and other mammals
• Absorption: Incomplete, with 33–39% bioavailability via the capsule and suppository routes, relative to the intramuscular route.
• Half Life: 1-1.6 hours (for all formulations)