4-amino-N-[2-(diethylamino)ethyl]benzamide

• ChemBase ID: 907
• Molecular Formular: C13H21N3O
• Molecular Mass: 235.32534
• Monoisotopic Mass: 235.16846231
• SMILES: O=C(NCCN(CC)CC)c1ccc(N)cc1
• Canonical SMILES: CCN(CCNC(=O)c1ccc(cc1)N)CC
• InChI: InChI=1S/C13H21N3O/c1-3-16(4-2)10-9-15-13(17)11-5-7-12(14)8-6-11/h5-8H,3-4,9-10,14H2,1-2H3,(H,15,17)
• InChIKey: REQCZEXYDRLIBE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-N-[2-(diethylamino)ethyl]benzamide
• IUPAC Traditional name: procainamide
• Brand Name: Biocoryl; Novocainamid; Novocainamide; Novocaine Amide; Novocamid; Procainamide Hcl; Procaine Amide; Procamide; Procan; Procan Sr; Procanbid; Procapan; Promine; Pronestyl; Pronestyl-Sr
• Synonyms: Procainamide

Database IDs

• CAS Number: 51-06-9
• PubChem SID: 46507313; 160964370
• PubChem CID: 4913

CALCULATED PROPERTIES

JChem

• Acid pKa: 15.7515745
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -2.27341
• LogD (pH = 7.4): -0.69723266
• Log P: 0.9508967
• Molar Refractivity: 72.2498 cm^3
• Polarizability: 26.875093 Å^3
• Polar Surface Area: 58.36 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.42
• LOG S: -1.89
• Solubility (Water): 3.02e+00 g/l

PROPERTIES

Physical Property

• Solubility: 5050 mg/L
• Hydrophobicity(logP): 1.3

DETAILS

DrugBank - DB01035

• Drug Groups: approved
• Description: A derivative of procaine with less CNS action. [PubChem]
• Indication: For the treatment of life-threatening ventricular arrhythmias.
• Pharmacology: Procainamide is an agent indicated for production of local or regional anesthesia and in the treatment of ventricular tachycardia occurring during cardiac manipulation, such as surgery or catheterization, or which may occur during acute myocardial infarction, digitalis toxicity, or other cardiac diseases. The mode of action of the antiarrhythmic effect of Procainamide appears to be similar to that of procaine and quinidine. Ventricular excitability is depressed and the stimulation threshold of the ventricle is increased during diastole. The sinoatrial node is, however, unaffected.
• Toxicity: LD₅₀=95 mg/kg (rat, IV); LD₅₀=312 mg/kg (mouse, oral); LD₅₀=103 mg/kg (mouse, IV); LD₅₀=250 mg/kg (rabbit, IV)
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: 75 to 95%
• Half Life: ~2.5-4.5 hours
• Protein Binding: 15 to 20%
• Elimination: Trace amounts may be excreted in the urine as free and conjugated p-aminobenzoic acid, 30 to 60 percent as unchanged PA, and 6 to 52 percent as the NAPA derivative.
• Distribution: * 2 L/kg
• External Links: Wikipedia; RxList; Drugs.com