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3737-09-5 molecular structure
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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 and InChIs

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

Cite this record

CBID:165 http://www.chembase.cn/molecule-165.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
Disopiramida [INN-Spanish]
Disopyramide Free Base
Disopyramide Phosphate
Disopyramidum [INN-Latin]
α-[2-[Bis(1-methylethyl)amino]ethyl]-α-phenyl-2-pyridine acetamide
α-Diisopropylaminoethyl-α-phenylpyridine-2-acetamide
Disopyramide
Disopyramide
双异丙吡胺
达舒平
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

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 16.190355  H Acceptors
H Donor LogD (pH = 5.5) -0.017306102 
LogD (pH = 7.4) 0.5726371  Log P 3.4684365 
Molar Refractivity 102.3002 cm3 Polarizability 40.196716 Å3
Polar Surface Area 59.22 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 3.21  LOG S -3.84 
Solubility (Water) 4.93e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
44.9 mg/L expand Show data source
Melting Point
85-87°C expand Show data source
Hydrophobicity(logP)
3.5 expand Show data source
Storage Condition
Room Temperature (15-30°C) expand Show data source
RTECS
UR8432000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22 expand Show data source
R:22-36/37/38 expand Show data source
Safety Statements
36 expand Show data source
S:25-26-36/37/39 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302-H361 expand Show data source
GHS Precautionary statements
P281 expand Show data source
Storage Temperature
2-8°C expand Show data source
Admin Routes
Oral, intravenous expand Show data source
Bioavailability
High expand Show data source
Excretion
Renal (80%) expand Show data source
Half Life
6.7 hours (range 4 to 10 hours) expand Show data source
Metabolism
Hepatic (CYP3A4-mediated) expand Show data source
Protein Bound
50% to 65%
(concentration-dependent)
expand Show data source
Legal Status
POM (UK) expand Show data source
Rx-only (US) expand Show data source
Pregnancy Category
B2 (Australia) expand Show data source
C (US) expand Show data source
Gene Information
human ... CYP1A2(1544), KCNH1(3756), SCN5A(6331) expand Show data source
Purity
98% expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Sigma Aldrich Sigma Aldrich MP Biomedicals MP Biomedicals Wikipedia Wikipedia
DrugBank - DB00280 external link
Item Information
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 external link
Biochem/physiol Actions
IA 类抗心律失常药;钠通道阻断剂
Sigma Aldrich - D7644 external link
Biochem/physiol Actions
IA 类抗心律失常药;钠通道阻断剂
MP Biomedicals - 02150996 external link
Purity: 98% minimum
m.p. 85-87°C

REFERENCES

REFERENCES

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PATENTS

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