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Substance Name: Procainamide [INN:BAN]
RN: 51-06-9
UNII: L39WTC366D
InChIKey: REQCZEXYDRLIBE-UHFFFAOYSA-N

Note

  • A class Ia antiarrhythmic drug that is structurally-related to PROCAINE.

Molecular Formula

  • C13-H21-N3-O

Molecular Weight

  • 235.3289
 

Classification Codes

  • Anti-Arrhythmia Agents
  • Cardiovascular Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Membrane Transport Modulators
  • Sodium Channel Blockers
  • Voltage-Gated Sodium Channel Blockers

Names and Synonyms

Name of Substance

  • Procainamide
  • Procainamide [INN:BAN]

MeSH Heading

  • Procainamide

Synonyms

  • 2-Diethylaminoethylamid kyseliny p-aminobenzoove
  • 2-Diethylaminoethylamid kyseliny p-aminobenzoove [Czech]
  • 4-14-00-01154 (Beilstein Handbook Reference)
  • 4-Amino-N-(2-(diethylamino)ethyl)benzamide
  • Benzamide, 4-amino-N-(2-(diethylamino)ethyl)-
  • Benzamide, p-amino-N-(2-(diethylamino)ethyl)-
  • Biocoryl
  • BRN 2214285
  • EINECS 200-078-8
  • HSDB 3170
  • Novocainamid
  • Novocainamide
  • Novocaine amide
  • Novocamid
  • NSC 27461
  • p-Amino-N-(2-diethylaminoethyl)benzamide
  • p-Aminobenzoic diethylaminoethylamide
  • Procainamida
  • Procainamida [INN-Spanish]
  • Procainamide
  • Procainamidum
  • Procainamidum [INN-Latin]
  • Procaine amide
  • Procamide
  • Procapan (free base)
  • Pronestyl
  • Rhythmin
  • UNII-L39WTC366D

Systematic Names

  • Benzamide, 4-amino-N-(2-(diethylamino)ethyl)- (9CI)
  • Benzamide, p-amino-N-(2-(diethylamino)ethyl)-
  • Procainamide

Registry Numbers

CAS Registry Number

  • 51-06-9

FDA UNII

  • L39WTC366D

Related Registry Number

  • 614-39-1 (hydrochloride)

System Generated Number

  • 0000051069

Structure Descriptors

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

Smiles

c1(C(=O)NCCN(CC)CC)ccc(cc1)N

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 intravenous 170mg/kg (170mg/kg)   Polish Journal of Pharmacology and Pharmacy. Vol. 32, Pg. 833, 1980.
dog LDLo oral 2210mg/kg (2210mg/kg)   Toxicology and Applied Pharmacology. Vol. 21, Pg. 253, 1972.
guinea pig LD50 intravenous 280mg/kg (280mg/kg)   Farmaco, Edizione Scientifica. Vol. 12, Pg. 77, 1957.
human TDLo oral 2280mg/kg/22W (2280mg/kg) MUSCULOSKELETAL: JOINTS British Heart Journal. Vol. 34, Pg. 284, 1972.
man TDLo intravenous 583mg/kg/12D- (583mg/kg) CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) American Heart Journal. Vol. 109, Pg. 375, 1985.
man TDLo oral 29mg/kg (29mg/kg) BEHAVIORAL: TREMOR American Journal of Cardiology. Vol. 57, Pg. 340, 1986.
man TDLo oral 8579mg/kg/43W (8579mg/kg) LUNGS, THORAX, OR RESPIRATION: FIBROSING ALVEOLITIS American Journal of Medicine. Vol. 76, Pg. 146, 1984.
man TDLo unreported 31gm/kg/3Y-I (31000mg/kg) VASCULAR: STRICTIRA; CJAMGES OM VESSE;S

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
Clinical and Experimental Rheumatology. Vol. 4, Pg. 290, 1986.
mouse LD50 intraperitoneal 178mg/kg (178mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Polish Journal of Pharmacology and Pharmacy. Vol. 37, Pg. 551, 1985.
mouse LD50 intravenous 49mg/kg (49mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Polish Journal of Pharmacology and Pharmacy. Vol. 37, Pg. 551, 1985.
mouse LD50 oral 525mg/kg (525mg/kg)   Collection of Czechoslovak Chemical Communications. Vol. 42, Pg. 3628, 1977.
mouse LD50 subcutaneous 720mg/kg (720mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Polish Journal of Pharmacology and Pharmacy. Vol. 37, Pg. 551, 1985.
rabbit LD50 intravenous 125mg/kg (125mg/kg)   Polish Journal of Pharmacology and Pharmacy. Vol. 32, Pg. 833, 1980.
rat LD50 intravenous 110mg/kg (110mg/kg)   Russian Pharmacology and Toxicology Vol. 33, Pg. 292, 1970.
rat LD50 oral 1950mg/kg (1950mg/kg)   Collection of Czechoslovak Chemical Communications. Vol. 42, Pg. 3628, 1977.
rat LD50 unreported 110mg/kg (110mg/kg)   Farmakologiya i Toksikologiya Vol. 54(3), Pg. 32, 1991.
women TDLo oral 1120mg/kg/4W- (1120mg/kg) BEHAVIORAL: WAKEFULNESS

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: TOXIC PSYCHOSIS
American Journal of Psychiatry. Vol. 145, Pg. 129, 1988.
women TDLo oral 1826mg/kg/13W (1826mg/kg) CARDIAC: OTHER CHANGES American Heart Journal. Vol. 83, Pg. 798, 1972.

Physical Properties

Physical Property Value Units Temp (deg C) Source
pKa Dissociation Constant 9.32 (none)   EXP
log P (octanol-water) 0.88 (none)   EXP
Water Solubility 5050 mg/L 25 EST
Vapor Pressure 9.57E-08 mm Hg 25 EST
Henry's Law Constant 1.99E-15 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.03E-10 cm3/molecule-sec 25 EST

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