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Procainamide

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Name

Procainamide

EINECS 200-078-8
CAS No. 51-06-9 Density 1.060
PSA 58.36000 LogP 2.31250
Solubility N/A Melting Point 47°C
Formula C13H21 N3 O Boiling Point 421.8°Cat760mmHg
Molecular Weight 235.329 Flash Point 208.9°C
Transport Information N/A Appearance N/A
Safety Poison by intravenous and intraperitoneal routes. Moderately toxic by ingestion. Human systemic effects by ingestion: cardiac abnormalities, joint effects, cough, tremors, dyspnea, and other lung effects. When heated to decomposition it emits toxic fumes of NOx. Risk Codes N/A
Molecular Structure Molecular Structure of 51-06-9 (procainamide) Hazard Symbols N/A
Synonyms

Benzamide,p-amino-N-[2-(diethylamino)ethyl]- (8CI);4-Amino-N-(diethylaminoethyl)benzamide; 4-Amino-N-[2-(diethylamino)ethyl]benzamide;N-(2-(Diethylamino)ethyl)-4-aminobenzamide; NSC 27461; Novocainamid;Novocainamide; Novocaine amide; Novocamid; Procainamide; Procaine amide;Procanbid; SP 100; SP 100 (pharmaceutical);p-Amino-N-(2-diethylaminoethyl)benzamide; p-Aminobenzoic diethylaminoethylamide

Article Data 29

Procainamide Chemical Properties

IUPAC Name: 4-Amino-N-(2-diethylaminoethyl)benzamide  
Synonyms: 4-Aminobenzoic acid 2-diethylaminoethylamide ; 4-Amino-N-[2-(diethylamino)ethyl]benzamid ; 4-Amino-N-[2-(diethylamino)ethyl]benzamide ; 4-Amino-N-[2-(diéthylamino)éthyl]benzamide ; Benzamide, 4-amino-N-(2-(diethylamino)ethyl)-
CAS NO:51-06-9
Molecular Formula of p-Amino-n-(2-diethylaminoethyl)-benzamide (CAS NO.51-06-9) :C13H21N3O
Molecular Weight of p-Amino-n-(2-diethylaminoethyl)-benzamide (CAS NO.51-06-9) :235.3253
Molecular Structure of p-Amino-n-(2-diethylaminoethyl)-benzamide (CAS NO.51-06-9) :
Index of Refraction: 1.553
Surface Tension: 43.8 dyne/cm 
Density: 1.06 g/cm3 
Flash Point: 208.9 °C 
Enthalpy of Vaporization: 67.58 kJ/mol 
Boiling Point: 421.8 °C at 760 mmHg 
Vapour Pressure: 2.54E-07 mmHg at 25°C 

Procainamide History

It was introduced in 1951.
Procanbid will no longer be manufactured.

Procainamide Uses

 P-Amino-n-(2-diethylaminoethyl)-benzamide (CAS NO.51-06-9) is used for both supraventricular and ventricular arrhythmias. For example, it can be used to convert new-onset atrial fibrillation, though it is suboptimal for this purpose. It can also be used to treat Wolf-Parkinson-White syndrome by prolonging the refractory period of the accessory pathway. Typically use is secondary to lidocaine in patients who are allergic to lidocaine or dysrhythmias that are refractory to lidocaine.

Procainamide Toxicity Data With Reference

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: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

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

BEHAVIORAL: ATAXIA
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: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA
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.

Procainamide Safety Profile

Poison by intravenous and intraperitoneal routes. Moderately toxic by ingestion. Human systemic effects by ingestion: cardiac abnormalities, joint effects, cough, tremors, dyspnea, and other lung effects. When heated to decomposition it emits toxic fumes of NOx.

Procainamide Specification

Administration:Procainamide is administered intravenously or orally. When administered intravenously, a loading dose should first be given, though care should be taken not to cause hypotension. Procainamide's active metabolite is N-acetyl procainamide, which is stronger than procainamide and excreted by the kidneys and the renal system. Loading dose is 100mg IV bolus given slowly over 5 minutes. Max dose is 17mg/kg. Use is discontinued when dysrhythmia is suppressed, or if hypotension ensues, QRS complex widens by 50% or more, or maximum dose is achieved.
Side effects:Adverse effects include rash, myalgia, hypersensitivity reactions (fever, agranulocytosis), Drug-Induced Lupus Erythematosus (particularly in slow-acetylators), and proarrhythmic effects (e.g., torsades de pointes). Treatment with procainamide can cause antibody production against cellular components, accounting for the systemic lupus erythematosus-like adverse reactions

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