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Substance Name: Procainamide hydrochloride [USP:JAN]
RN: 614-39-1
UNII: SI4064O0LX
InChIKey: ABTXGJFUQRCPNH-UHFFFAOYSA-N

Notes

  • A benzoic-sulfonamide-furan. It is a diuretic with fast onset and short duration that is used for EDEMA and chronic RENAL INSUFFICIENCY.
  • A derivative of PROCAINE with less CNS action. It also acts as a non-nucleoside inhibitor of DNA METHYLATION and has led to SYSTEMIC LUPUS ERYTHEMATOSUS.

Molecular Formula

  • C13-H21-N3-O.Cl-H

Molecular Weight

  • 271.79
 

Classification Codes

  • Cardiac Depressant (Anti-Arrhythmic)
  • Drug / Therapeutic Agent
  • Human Data
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Names and Synonyms

Name of Substance

  • Procainamide hydrochloride [USP:JAN]

Synonyms

  • 4-Amino-N-(2-(diethylamino)ethyl)benzamide monohydrochloride
  • 4-Aminobenzoesaeure-2-diethylaminoethylester hydrochlorid
  • Benzamide, 4-amino-N-(2-(diethylamino)ethyl)-, monohydrochloride
  • CCRIS 7143
  • EINECS 210-381-7
  • Novocamid hydrochloride
  • p-Amino-N-(2-(diethylamino)ethyl)benzamide hydrochloride
  • p-Amino-N-(2-(diethylamino)ethyl)benzamide monohydrochloride
  • Procainamide HCl
  • Procainamide hydrochloride
  • Procaine amide hydrochloride
  • Procainhydrochlorid
  • Procaini hydrochloridum
  • Procainii chloridum
  • Procamide hydrochloride
  • Procan
  • Procan SR
  • Procan-SR hydrochloride
  • Procanbid
  • Procapan
  • Procapan hydrochloride
  • Procardyl hydrochloride
  • Promide hydrochloride
  • Pronestyl
  • Pronestyl-SR
  • Supicane amide hydrochloride
  • UNII-SI4064O0LX

Systematic Names

  • Benzamide, 4-amino-N-(2-(diethylamino)ethyl)-, hydrochloride (1:1)
  • Benzamide, 4-amino-N-(2-(diethylamino)ethyl)-, monohydrochloride
  • Benzamide, p-amino-N-(2-(diethylamino)ethyl)-, hydrochloride
  • Procainamide hydrochloride

Registry Numbers

CAS Registry Number

  • 614-39-1

FDA UNII

  • SI4064O0LX

Related Registry Number

  • 51-06-9 (Parent)

System Generated Number

  • 0000614391

Molecular Formulas

Molecular Formula

  • C13-H21-N3-O.Cl-H

Molecular Formula Fragments

  • C13-H21-N3-O
  • Cl-H
  • COMPONENT

Structure Descriptors

InChI

1S/C13H21N3O.ClH/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);1H

InChIKey

ABTXGJFUQRCPNH-UHFFFAOYSA-N

Smiles

Nc1ccc(cc1)C(NCCN(CC)CC)=O.Cl

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man LDLo oral 857mg/kg/60D- (857mg/kg) BLOOD: AGRANULOCYTOSIS American Heart Journal. Vol. 105, Pg. 1035, 1983.
man TDLo oral 200mg/kg/4W-I (200mg/kg) BLOOD: THROMBOCYTOPENIA Archives of Internal Medicine. Vol. 145, Pg. 700, 1985.
man TDLo oral 2786mg/kg/56W (2786mg/kg) BLOOD: LEUKOPENIA

MUSCULOSKELETAL: JOINTS
American Journal of Medicine. Vol. 80, Pg. 999, 1986.
mouse LD50 intramuscular 860mg/kg (860mg/kg)   Therapie. Vol. 9, Pg. 332, 1954.
mouse LD50 intraperitoneal 290mg/kg (290mg/kg)   Journal of Pharmaceutical Sciences. Vol. 59, Pg. 1405, 1970.
mouse LD50 intravenous 94640ug/kg (94.64mg/kg)   Drugs in Japan Vol. 6, Pg. 719, 1982.
mouse LD50 oral 1110mg/kg (1110mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 18, Pg. 1127, 1968.
mouse LD50 subcutaneous 800mg/kg (800mg/kg)   Proceedings of the Society for Experimental Biology and Medicine. Vol. 73, Pg. 236, 1950.
rat LD50 intravenous 95mg/kg (95mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 18, Pg. 1127, 1968.
rat LD50 oral 1509mg/kg (1509mg/kg)   Toksikologicheskii Vestnik. Vol. (2), Pg. 28, 1997.
rat LD50 subcutaneous > 2gm/kg (2000mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 18, Pg. 1127, 1968.
rat LD50 unreported 225mg/kg (225mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Journal of Pharmacy and Pharmacology. Vol. 14, Pg. 253, 1962.
women TDLo intravenous 10mg/kg/6M-C (10mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION Clinical Pharmacy. Vol. 4, Pg. 504, 1985.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 167 deg C   EXP
log P (octanol-water) -0.550 (none)   EST
Atmospheric OH Rate Constant 1.37E-10 cm3/molecule-sec 25 EST

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