For research use only. Not for therapeutic Use.
Tocainide (Cat.No:I009838) 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.
| Catalog Number | I009838 |
| CAS Number | 41708-72-9 |
| Synonyms | BRN 2416564; BRN 2416564; BRN 2416564; Tocainide; Tocainida; Tocainida;2-amino-N-(2,6-dimethylphenyl)propanamide |
| Molecular Formula | C11H16N2O |
| Purity | ≥95% |
| Target | Sodium Channel |
| Solubility | Soluble in DMSO, not in water |
| Storage | 0 - 4 °C for short term, or -20 °C for long term |
| IUPAC Name | 2-amino-N-(2,6-dimethylphenyl)propanamide |
| InChI | 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) |
| InChIKey | BUJAGSGYPOAWEI-UHFFFAOYSA-N |
| SMILES | CC1=C(C(=CC=C1)C)NC(=O)C(C)N |
| Reference | </br>1:Increased sodium channel use-dependent inhibition by a new potent analogue of tocainide greatly enhances in vivo antimyotonic activity. De Bellis M, Carbonara R, Roussel J, Farinato A, Massari A, Pierno S, Muraglia M, Corbo F, Franchini C, Carratù MR, De Luca A, Conte Camerino D, Desaphy JF.Neuropharmacology. 2017 Feb;113(Pt A):206-216. doi: 10.1016/j.neuropharm.2016.10.013. Epub 2016 Oct 13. PMID: 27743929 Free PMC Article</br>2:N-aryl-2,6-dimethylbenzamides, a new generation of tocainide analogues as blockers of skeletal muscle voltage-gated sodium channels. Muraglia M, De Bellis M, Catalano A, Carocci A, Franchini C, Carrieri A, Fortugno C, Bertucci C, Desaphy JF, De Luca A, Conte Camerino D, Corbo F.J Med Chem. 2014 Mar 27;57(6):2589-600. doi: 10.1021/jm401864b. Epub 2014 Mar 7. PMID: 24568674 </br>3:Species-dependent binding of tocainide analogues to albumin: affinity chromatography and circular dichroism study. Pistolozzi M, Fortugno C, Franchini C, Corbo F, Muraglia M, Roy M, Félix G, Bertucci C.J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Oct 1;968:69-78. doi: 10.1016/j.jchromb.2014.01.007. Epub 2014 Jan 10. PMID: 24472243 </br>4:Searching for novel anti-myotonic agents: pharmacophore requirement for use-dependent block of skeletal muscle sodium channels by N-benzylated cyclic derivatives of tocainide. De Luca A, De Bellis M, Corbo F, Franchini C, Muraglia M, Catalano A, Carocci A, Camerino DC.Neuromuscul Disord. 2012 Jan;22(1):56-65. doi: 10.1016/j.nmd.2011.07.001. Epub 2011 Jul 29. PMID: 21802953 Free PMC Article</br>5:Effects of a new potent analog of tocainide on hNav1.7 sodium channels and in vivo neuropathic pain models. Ghelardini C, Desaphy JF, Muraglia M, Corbo F, Matucci R, Dipalma A, Bertucci C, Pistolozzi M, Nesi M, Norcini M, Franchini C, Camerino DC.Neuroscience. 2010 Aug 25;169(2):863-73. doi: 10.1016/j.neuroscience.2010.05.019. Epub 2010 May 16. PMID: 20580661 </br>6:Tocainide analogues binding to human serum albumin: a HPLAC and circular dichroism study. Pistolozzi M, Franchini C, Corbo F, Muraglia M, De Giorgi M, Felix G, Bertucci C.J Pharm Biomed Anal. 2010 Oct 10;53(2):179-85. doi: 10.1016/j.jpba.2010.03.005. Epub 2010 Mar 7. PMID: 20359840 </br>7:2D- and 3D-QSAR of tocainide and mexiletine analogues acting as Na(v)1.4 channel blockers. Carrieri A, Muraglia M, Corbo F, Pacifico C.Eur J Med Chem. 2009 Apr;44(4):1477-85. doi: 10.1016/j.ejmech.2008.10.005. Epub 2008 Oct 14. PMID: 19027197 </br>8:Liquid chromatographic direct resolution of tocainide and its analogs on a (3,3/’-diphenyl-1,1/’-binaphthyl)-20-crown-6-based chiral stationary phase containing residual silanol protecting n-octyl groups. Choi HJ, Jin JS, Hyun MH.Chirality. 2009 Jan;21(1):11-5. doi: 10.1002/chir.20582. PMID: 18506839 </br>9:Constrained analogues of tocainide as potent skeletal muscle sodium channel blockers towards the development of antimyotonic agents. Catalano A, Carocci A, Corbo F, Franchini C, Muraglia M, Scilimati A, De Bellis M, De Luca A, Camerino DC, Sinicropi MS, Tortorella V.Eur J Med Chem. 2008 Nov;43(11):2535-40. doi: 10.1016/j.ejmech.2008.01.023. Epub 2008 Jan 31. PMID: 18342401 </br>10:New potent mexiletine and tocainide analogues evaluated in vivo and in vitro as antimyotonic agents on the myotonic ADR mouse. De Luca A, Pierno S, Liantonio A, Desaphy JF, Natuzzi F, Didonna MP, Ferrannini E, Jockusch H, Franchini C, Lentini G, Corbo F, Tortorella V, Camerino DC.Neuromuscul Disord. 2004 Jul;14(7):405-16. PMID: 15210163 |
