N-Acetylprocainamide

Names

[ Name ]:
N-Acetylprocainamide

[Synonym ]:
NAPA
4-acetamido-N-(2-diethylaminoethyl)benzamide
Acecainide [INN]
MFCD00009052
4-acetamido-N-[2-(diethylamino)ethyl]benzamide
N-Acetyloprokainamid
Acecainidum
Acekainid
N-Acetylnovocainamide
Acekainid [Polish]
Acecainide
4-acetylamino-N-(2-diethylamino-ethyl)-benzamide
Acecainida
N-Acetylprocainamide

Biological Activity

[Description]:

N-Acetylprocainamide is a class III antiarrhythmic, which blocks K+ channels.

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> Potassium Channel

Research Areas >> Cardiovascular Disease

[Target]

K+ channel[1]

[In Vitro]

N-Acetylprocainamide is a K+ blocker. N-Acetylprocainamide decreases the tensions induced by K+ and methacholine. The pIC50 values for N-acetylprocainamide against the contractions induced by 0.3 and 1 μM methacholine are 2.80 ± 0.03 and 2.65 ± 0.02, respectively. And such a relaxant effect of N-Acetylprocainamide is inhibited by K+ channel blockers[1]. N-Acetylprocainamide shows no effect on Na+ absorption or Cl- secretion[2].

[References]

[1]. Nakahara T, et al. Role of K+ channels in N-acetylprocainamide-induced relaxation of bovine tracheal smooth muscle. Eur J Pharmacol. 2001 Mar 9;415(1):73-8.

[2]. Plass H, et al. Class I antiarrhythmics inhibit Na+ absorption and Cl- secretion in rabbit descending colon epithelium. Naunyn Schmiedebergs Arch Pharmacol. 2005 Jun;371(6):492-9.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.097g/cm3

[ Boiling Point ]:
500ºC at 760mmHg

[ Melting Point ]:
138-140ºC(lit.)

[ Molecular Formula ]:
C₁₅H₂₃N₃O₂

[ Molecular Weight ]:
277.36200

[ Flash Point ]:
256.2ºC

[ Exact Mass ]:
277.17900

[ PSA ]:
61.44000

[ LogP ]:
2.18050

[ Storage condition ]:
-20°C

[ Water Solubility ]:
soluble1%, clear, colorless to faintly yellow (1N HCl)

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AE1974350

CHEMICAL NAME :: Acetanilide, 4'-((2-(diethylamino)ethyl)carbamoyl)-

CAS REGISTRY NUMBER :: 32795-44-1

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C15-H23-N3-O2

MOLECULAR WEIGHT :: 277.41

WISWESSER LINE NOTATION :: 2N2&2MVR DMV1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 380 mg/kg

TOXIC EFFECTS :: Cardiac - other changes

REFERENCE :: PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 169,156,1982 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X3173 No. of Facilities: 71 (estimated) No. of Industries: 2 No. of Occupations: 2 No. of Employees: 758 (estimated) No. of Female Employees: 361 (estimated)

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
36/37/38

[ Safety Phrases ]:
26-36

[ RIDADR ]:
UN 3249

[ WGK Germany ]:
3

[ RTECS ]:
AE1974350

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

[ HS Code ]:
2924299090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2924299090

[ Summary ]:
2924299090. other cyclic amides (including cyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Articles

Drug-herb interaction: effect of St John's wort on bioavailability and metabolism of procainamide in mice.

Arch. Pathol. Lab. Med. 131(7) , 1094-8, (2007)

St John's wort induces the activity of the cytochrome P450 enzyme system causing treatment failure because of increased metabolism of many drugs. Procainamide is metabolized by a different pathway to ...

Application of computer-assisted radiotelemetry in the pharmacokinetic and pharmacodynamic modeling of procainamide and N-acetylprocainamide.

J. Pharm. Sci. 85(6) , 595-9, (1996)

The cardiovascular pharmacodynamics (PD) of procainamide and N-acetylprocainamide have not been well characterized in small rodents without the presence of anesthesia or restraint. This study was unde...

The discordant influences of infarct healing on the electrophysiologic effects of procainamide and N-acetylprocainamide.

J. Pharmacol. Exp. Ther. 273(1) , 315-9, (1995)

Ischemic zone refractoriness and conduction delay respond differently to infarct healing and, hypothetically, may exert discordant influences on the electrophysiologic action of different classes of a...