4-[bis(propan-2-yl)amino]-2-phenyl-2-(pyridin-2-yl)butanamide

• ChemBase ID: 165
• Molecular Formular: C21H29N3O
• Molecular Mass: 339.47446
• Monoisotopic Mass: 339.23106256
• SMILES: O=C(N)C(CCN(C(C)C)C(C)C)(c1ccccc1)c1ncccc1
• Canonical SMILES: CC(N(C(C)C)CCC(c1ccccn1)(c1ccccc1)C(=O)N)C
• InChI: InChI=1S/C21H29N3O/c1-16(2)24(17(3)4)15-13-21(20(22)25,18-10-6-5-7-11-18)19-12-8-9-14-23-19/h5-12,14,16-17H,13,15H2,1-4H3,(H2,22,25)
• InChIKey: UVTNFZQICZKOEM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[bis(propan-2-yl)amino]-2-phenyl-2-(pyridin-2-yl)butanamide
• IUPAC Traditional name: disopyramide
• Brand Name: Dicorantil; Isorythm; Lispine; Norpace; Norpace CR; Ritmodan; Rythmodan; Rythmodan P; Rythmodan-La; Searle 703; Xi-Disopyramide
• Synonyms: Disopyramide; α-[2-[Bis(1-methylethyl)amino]ethyl]-α-phenyl-2-pyridine acetamide; α-Diisopropylaminoethyl-α-phenylpyridine-2-acetamide; Disopiramida [INN-Spanish]; Disopyramide Free Base; Disopyramide Phosphate; Disopyramidum [INN-Latin]; Disopyramide; 双异丙吡胺; 达舒平

Database IDs

• CAS Number: 3737-09-5
• EC Number: 223-110-2
• MDL Number: MFCD00057366
• PubChem SID: 46508226; 24278384; 160963628
• PubChem CID: 3114
• CHEBI ID: 4657
• ATC CODE: C01BA03
• CHEMBL: 517
• Chemspider ID: 3002
• DrugBank ID: DB00280
• KEGG ID: D00303
• Unique Ingredient Identifier: GFO928U8MQ
• Wikipedia Title: Disopyramide
• Medline Plus: a682408

CALCULATED PROPERTIES

JChem

• Acid pKa: 16.190355
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.017306102
• LogD (pH = 7.4): 0.5726371
• Log P: 3.4684365
• Molar Refractivity: 102.3002 cm^3
• Polarizability: 40.196716 Å^3
• Polar Surface Area: 59.22 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.21
• LOG S: -3.84
• Solubility (Water): 4.93e-02 g/l

PROPERTIES

Physical Property

• Solubility: 44.9 mg/L
• Melting Point: 85-87°C
• Hydrophobicity(logP): 3.5

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: UR8432000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22; R:22-36/37/38
• Safety Statements: 36; S:25-26-36/37/39
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H361
• GHS Precautionary statements: P281
• Storage Temperature: 2-8°C

Pharmacology Properties

• Admin Routes: Oral, intravenous
• Bioavailability: High
• Excretion: Renal (80%)
• Half Life: 6.7 hours (range 4 to 10 hours)
• Metabolism: Hepatic (CYP3A4-mediated)
• Protein Bound: 50% to 65%; (concentration-dependent)
• Legal Status: POM (UK); Rx-only (US)
• Pregnancy Category: B2 (Australia); C (US)
• Gene Information: human ... CYP1A2(1544), KCNH1(3756), SCN5A(6331)

Product Information

• Purity: 98%

DETAILS

MP Biomedicals - 02150996

Purity: 98% minimum
m.p. 85-87°C

DrugBank - DB00280

• Drug Groups: approved
• Description: A class I anti-arrhythmic agent (one that interferes directly with the depolarization of the cardiac membrane and thus serves as a membrane-stabilizing agent) with a depressant action on the heart similar to that of guanidine. It also possesses some anticholinergic and local anesthetic properties. [PubChem]
• Indication: For the treatment of documented ventricular arrhythmias, such as sustained ventricular tachycardia, ventricular pre-excitation and cardiac dysrhythmias. It is a Class Ia antiarrhythmic drug.
• Pharmacology: Disopyramide is an antiarrhythmic drug indicated for the treatment of documented ventricular arrhythmias, such as sustained ventricular tachycardia that are life-threatening. In man, Disopyramide at therapeutic plasma levels shortens the sinus node recovery time, lengthens the effective refractory period of the atrium, and has a minimal effect on the effective refractory period of the AV node. Little effect has been shown on AV-nodal and His-Purkinje conduction times or QRS duration. However, prolongation of conduction in accessory pathways occurs.
• Toxicity: LD₅₀=580 mg/kg in rats
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Nearly complete
• Half Life: 6.7 hours (range 4-10 hours)
• Protein Binding: 50%-65%
• Elimination: In healthy men, about 50% of a given dose of disopyramide is excreted in the urine as the unchanged drug, about 20% as the mono-N-dealkylated metabolite and 10% as the other metabolites.
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - D7275

Biochem/physiol Actions
IA 类抗心律失常药；钠通道阻断剂

Sigma Aldrich - D7644

Biochem/physiol Actions
IA 类抗心律失常药；钠通道阻断剂