Tocainide free base | CAS#41708-72-9

MedKoo Cat#: 318881 | Name: Tocainide

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Tocainide is a lidocaine analog, that does not have significant 1st pass metabolism. It is found in two enantiomers. The R isomer is 4x as potent as the S. Oral bioavailability is 0.9-1.0. In the blood tocainide is 10-20% protein bound. The Volume of distribution is 2.5-3.5 L/kg. 30-50% is excreted unchanged in the urine. The more active R-isomer is cleared faster in anephric patients or those with severe renal dysfunction. The main metabolite is the glucuronidated tocainide carbamic acid. The glucuronosyl transferase is apparently induced by rifampin. Weak inhibition of Cyp1A2 leads to a mild theophylline interaction.

Chemical Structure

Tocainide

CAS#41708-72-9 (free base)

Theoretical Analysis

MedKoo Cat#: 318881

Name: Tocainide

CAS#: 41708-72-9 (free base)

Chemical Formula: C11H16N2O

Exact Mass: 192.1263

Molecular Weight: 192.26

Elemental Analysis: C, 68.72; H, 8.39; N, 14.57; O, 8.32

Price and Availability

Size	Price	Availability
100mg	USD 250.00	2 Weeks
250mg	USD 450.00	2 Weeks
1g	USD 950.00	2 Weeks

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Related CAS #

71395-14-7 (HCl) 41708-72-9 (free base) 53984-74-0 (R-isomer HCl) 53984-76-2 (S-isomer HCl)

Synonym

BRN 2416564; BRN 2416564; BRN 2416564; Tocainide; Tocainida; Tocainida

IUPAC/Chemical Name

2-amino-N-(2,6-dimethylphenyl)propanamide

InChi Key

BUJAGSGYPOAWEI-UHFFFAOYSA-N

InChi Code

InChI=1S/C11H16N2O/c1-7-5-4-6-8(2)10(7)13-11(14)9(3)12/h4-6,9H,12H2,1-3H3,(H,13,14)

SMILES Code

CC(N)C(NC1=C(C)C=CC=C1C)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 192.26 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Feinberg L, Travis WD, Ferrans V, Sato N, Bernton HF. Pulmonary fibrosis associated with tocainide: report of a case with literature review. Am Rev Respir Dis. 1990 Feb;141(2):505-8. Review. PubMed PMID: 2137316. 2: Denaro CP, Benowitz NL. Poisoning due to class 1B antiarrhythmic drugs. Lignocaine, mexiletine and tocainide. Med Toxicol Adverse Drug Exp. 1989 Nov-Dec;4(6):412-28. Review. PubMed PMID: 2513464. 3: Snyder DW. Class IB antiarrhythmic drugs: tocainide, mexiletine, and moricizine. J La State Med Soc. 1989 May;141(5):21-5. Review. PubMed PMID: 2499645. 4: Kreeger RW, Hammill SC. New antiarrhythmic drugs: tocainide, mexiletine, flecainide, encainide, and amiodarone. Mayo Clin Proc. 1987 Nov;62(11):1033-50. Review. PubMed PMID: 3118116. 5: Rizzon P, Di Biase M, Favale S, Visani L. Class 1B agents lidocaine, mexiletine, tocainide, phenytoin. Eur Heart J. 1987 Mar;8 Suppl A:21-5. Review. PubMed PMID: 3107988. 6: Roden DM, Woosley RL. Drug therapy. Tocainide. N Engl J Med. 1986 Jul 3;315(1):41-5. Review. PubMed PMID: 3086724. 7: Dorociak A, Rewerski W, Walczak F. [Clinical pharmacology of tocainide]. Pol Tyg Lek. 1985 Dec 23-30;40(51-52):1440-4. Review. Polish. PubMed PMID: 3938534. 8: Morganroth J, Nestico PF, Horowitz LN. A review of the uses and limitations of tocainide--a class IB antiarrhythmic agent. Am Heart J. 1985 Oct;110(4):856-63. Review. PubMed PMID: 3931446. 9: Kutalek SP, Morganroth J, Horowitz LN. Tocainide: a new oral antiarrhythmic agent. Ann Intern Med. 1985 Sep;103(3):387-91. Review. PubMed PMID: 3927807. 10: Hasegawa GR. Tocainide: a new oral antiarrhythmic. Drug Intell Clin Pharm. 1985 Jul-Aug;19(7-8):514-7. Review. PubMed PMID: 3928308. 11: Roden DM. Tocainide and mexiletine. Orally effective lidocaine analogues. Arch Intern Med. 1985 Mar;145(3):417-8. Review. PubMed PMID: 3919665. 12: Camm AJ. Cardiac electrophysiology of four new antiarrhythmic drugs--encainide, flecainide, lorcainide and tocainide. Eur Heart J. 1984 Sep;5 Suppl B:75-9. Review. PubMed PMID: 6437820. 13: Vanhaleweyk G, Serruys PW, Hugenholtz PG. Haemodynamic effects of encainide, flecainide, lorcainide and tocainide. Eur Heart J. 1984 Sep;5 Suppl B:67-74. Review. PubMed PMID: 6437819. 14: Sedman AJ, Gal J, Mastropaolo W, Johnson P, Maloney JD, Moyer TP. Serum tocainide enantiomer concentrations in human subjects. Br J Clin Pharmacol. 1984 Jan;17(1):113-5. Review. PubMed PMID: 6419760; PubMed Central PMCID: PMC1463303. 15: Alpert JS, Haffajee CI, Young MD. 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. Review. PubMed PMID: 6419205. 16: Pottage A. Clinical profiles of newer class I antiarrhythmic agents--tocainide, mexiletine, encainide, flecainide and lorcainide. Am J Cardiol. 1983 Sep 22;52(6):24C-31C. Review. PubMed PMID: 6414279. 17: Holmes B, Brogden RN, Heel RC, Speight TM, Avery GS. Tocainide. A review of its pharmacological properties and therapeutic efficacy. Drugs. 1983 Aug;26(2):93-123. Review. PubMed PMID: 6411445. 18: Wulf BG. Mexiletine and tocainide: orally active congeners of lidocaine. Clin Pharm. 1983 Jul-Aug;2(4):340-6. Review. PubMed PMID: 6411416. 19: Touboul P, Kirkorian G, Atallah G, Moleur P. [New antiarrythmic drugs: mexiletine, tocainide, lorcainide, encainide, flecainide, propafenone, cipralan, sotalol]. Ann Cardiol Angeiol (Paris). 1982 Dec;31(7):531-7. Review. French. PubMed PMID: 6820620. 20: Witkowska M. [Clinical pharmacology of anti-arrhythymia agents. II. Lignocaine, mexiletine, tocainide, phenytoin]. Kardiol Pol. 1981;24(11-12):803-13. Review. Polish. PubMed PMID: 6804681.