Tocainide

Names

[ Name ]:
Tocainide

[Synonym ]:
R/S-Tocainide
2-amino-2',6'-propionoxylidide
MFCD00072010
EINECS 255-505-0
TOCAINIDE
6'-propionoxylidide,2-amino-2
alanyl-2,6-xylidide

Biological Activity

[Description]:

Tocainide hydrochloride is an orally activesodium channel blocker, it blocks the sodium channels in the pain-producing foci in the nerve membranes. Tocainide hydrochloride is a primary amine analog of lidocaine, can be used for the treatment of tinnitus[1][2].

[Related Catalog]:

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

Research Areas >> Cardiovascular Disease

[Target]

IC50: sodium channel[1]

[In Vivo]

Tocainide (100 mg/kg) effectively suppresses ventricular ectopic activity in unanesthetized dogs with coronary occlusion. Termination of tocainide infusion in both digitalis toxicity and coronary occlusion models results in prompt return of ventricular ectopic activity[1].

[References]

[1]. Alpert JS, et al. Chemistry, pharmacology, antiarrhythmic efficacy and adverse effects of tocainide hydrochloride, an orally active structural analog of lidocaine. Pharmacotherapy. 1983 Nov-Dec;3(6):316-23.

[2]. De Luca A,et al.Optimal requirements for high affinity and use-dependent block of skeletal muscle sodium channel by N-benzyl analogs of tocainide-like compounds.Mol Pharmacol. 2003 Oct;64(4):932-45.

Chemical & Physical Properties

[ Molecular Formula ]:
C₁₁H₁₆N₂O

[ Molecular Weight ]:
192.25800

[ Exact Mass ]:
192.12600

[ PSA ]:
55.12000

[ LogP ]:
2.36240

[ Storage condition ]:
2-8°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UG6305000

CHEMICAL NAME :: 2',6'-Propionoxylidide, 2-amino-

CAS REGISTRY NUMBER :: 41708-72-9

LAST UPDATED :: 199707

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C11-H16-N2-O

MOLECULAR WEIGHT :: 192.29

WISWESSER LINE NOTATION :: ZY1&VMR B1 F1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 229 mg/kg

TOXIC EFFECTS :: Behavioral - coma Cardiac - cardiomyopathy including infarction

REFERENCE :: BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 288,760,1984

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human

DOSE/DURATION :: 5714 ug/kg

TOXIC EFFECTS :: Behavioral - hallucinations, distorted perceptions Gastrointestinal - nausea or vomiting

REFERENCE :: DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year: 2,141,1977

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 2606 mg/kg/11W-I

TOXIC EFFECTS :: Blood - aplastic anemia

REFERENCE :: NEJMAG New England Journal of Medicine. (Massachusetts Medical Soc., 10 Shattuck St., Boston, MA 02115) V.198- 1928- Volume(issue)/page/year: 314,583,1986

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 94 mg/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - local anesthetic Behavioral - convulsions or effect on seizure threshold Behavioral - ataxia

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 24,1059,1981

Safety Information

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R22

[ HS Code ]:
2924299090

Synthetic Route

Click to get detail synthetic route

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%