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| CAS No.: | 51-06-9 |
|---|---|
| Name: | procainamide |
| Article Data: | 29 |
| Molecular Structure: | |
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| Formula: | C13H21 N3 O |
| Molecular Weight: | 235.329 |
| 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 |
| EINECS: | 200-078-8 |
| Density: | 1.060 |
| Melting Point: | 47°C |
| Boiling Point: | 421.8°Cat760mmHg |
| Flash Point: | 208.9°C |
| 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. |
| PSA: | 58.36000 |
| LogP: | 2.31250 |
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Chemistry
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
History
It was introduced in 1951.
Procanbid will no longer be manufactured.
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.
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. |
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.
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