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Substance Name: Disopyramide [USAN:INN:BAN:JAN]
RN: 3737-09-5
UNII: GFO928U8MQ
InChIKey: UVTNFZQICZKOEM-UHFFFAOYSA-N

Note

  • 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.

Molecular Formula

  • C21-H29-N3-O

Molecular Weight

  • 339.4801
 

Classification Codes

  • Anti-Arrhythmia Agents
  • Cardiac Depressant (Anti-Arrhythmic)
  • Cardiovascular Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Membrane Transport Modulators
  • Reproductive Effect
  • Sodium Channel Blockers
  • Voltage-Gated Sodium Channel Blockers

Names and Synonyms

Name of Substance

  • Disopyramide
  • Disopyramide [USAN:INN:BAN:JAN]

MeSH Heading

  • Disopyramide

Synonyms

  • 2-Pyridineacetamide, alpha-(2-(bis(1-methylethyl)amino)ethyl)-alpha-phenyl-
  • alpha-(2-(Diisopropylamino)ethyl)-alpha-phenyl-2-pyridineacetamide
  • Dicorantil
  • Disopiramida
  • Disopiramida [INN-Spanish]
  • Disopyramide
  • Disopyramidum
  • Disopyramidum [INN-Latin]
  • EINECS 223-110-2
  • gamma-Diisopropylamino-alpha-phenyl-alpha-(2-pyridyl)butyramide
  • H 3292
  • Ritmodan
  • SC 7031
  • SC-7031
  • Searle 703
  • UNII-GFO928U8MQ

Systematic Names

  • 2-Pyridineacetamide, alpha-(2-(bis(1-methylethyl)amino)ethyl)-alpha-phenyl-
  • 2-Pyridineacetamide, alpha-(2-(diisopropylamino)ethyl)-alpha-phenyl-
  • Disopyramide

Registry Numbers

CAS Registry Number

  • 3737-09-5

FDA UNII

  • GFO928U8MQ

Related Registry Numbers

  • 22059-60-5 (phosphate (1:1))
  • 54687-36-4 (mono-hydrochloride)

System Generated Number

  • 0003737095

Structure Descriptors

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

Smiles

CC(C)N(CCC(C(=O)N)(c1ccccc1)c2ccccn2)C(C)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child LDLo oral 46154ug/kg (46.154mg/kg) BEHAVIORAL: COMA

CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE

LUNGS, THORAX, OR RESPIRATION: CYANOSIS		 Medical Journal of Australia. Vol. 2, Pg. 335, 1978.
dog LDLo intravenous 36mg/kg (36mg/kg) BEHAVIORAL: REGIDITY

SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION		 Journal of Pharmacology and Experimental Therapeutics. Vol. 136, Pg. 114, 1962.
guinea pig LDLo intravenous 24900ug/kg (24.9mg/kg)   Farmaco, Edizione Pratica. Vol. 35, Pg. 49, 1980.
human TDLo oral 4286ug/kg (4.286mg/kg) CARDIAC: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 New England Journal of Medicine. Vol. 302, Pg. 614, 1980.
man LDLo oral 11429ug/kg (11.429mg/kg)   Journal of Forensic Sciences. Vol. 32, Pg. 1813, 1987.
mouse LD50 intraperitoneal 114mg/kg (114mg/kg) BLOOD: CHANGES IN SPLEEN

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 Kiso to Rinsho. Clinical Report. Vol. 5, Pg. 1628, 1971.
mouse LD50 intravenous 26mg/kg (26mg/kg) BEHAVIORAL: REGIDITY

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: TREMOR		 United States Patent Document. Vol. #4237139,
mouse LD50 oral 352mg/kg (352mg/kg)   Farmaco, Edizione Pratica. Vol. 35, Pg. 49, 1980.
mouse LD50 subcutaneous 305mg/kg (305mg/kg)   Drugs in Japan Vol. 6, Pg. 319, 1982.
rabbit LDLo intravenous 42200ug/kg (42.2mg/kg)   Farmaco, Edizione Pratica. Vol. 35, Pg. 49, 1980.
rat LD50 intraperitoneal 170mg/kg (170mg/kg)   Drugs in Japan Vol. 6, Pg. 319, 1982.
rat LD50 intravenous 39100ug/kg (39.1mg/kg)   Farmaco, Edizione Pratica. Vol. 35, Pg. 49, 1980.
rat LD50 oral 333mg/kg (333mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: ATAXIA

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)		 Arzneimittel-Forschung. Drug Research. Vol. 38, Pg. 1398, 1988.
rat LD50 subcutaneous 800mg/kg (800mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 9, Pg. 829, 1978.
women TDLo oral 84mg/kg/3W-I (84mg/kg) LUNGS, THORAX, OR RESPIRATION: STRUCTURAL OR FUNCTIONAL CHANGE IN TRACHEA OR BRONCHI

SENSE ORGANS AND SPECIAL SENSES: INCREASED INTRAOCULAR PRESSURE: EYE

BEHAVIORAL: HEADACHE		 Mayo Clinic Proceedings. Vol. 65, Pg. 1030, 1990.
women TDLo unreported 700mg/kg/13W- (700mg/kg) BEHAVIORAL: COMA

ENDOCRINE: HYPOGLYCEMIA		 Annales de Medecine Interne. Vol. 146, Pg. 209, 1995.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 94.5-95 deg C   EXP
log P (octanol-water) 2.58 (none)   EXP
Water Solubility 44.9 mg/L 25 EST
Vapor Pressure 1.35E-09 mm Hg 25 EST
Henry's Law Constant 2.59E-16 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.25E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.