Fantofarone

• CAT Number: M021975
• CAS Number: 114432-13-2
• Molecular Formula: C31H38N2O5S
• Molecular Weight: 550.714
• Purity: ≥95%
• Storage: Desiccate at -20C
• IUPAC Name: N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methyl-3-[4-(2-propan-2-ylindolizin-1-yl)sulfonylphenoxy]propan-1-amine
• InChI: InChI=1S/C31H38N2O5S/c1-23(2)27-22-33-18-7-6-9-28(33)31(27)39(34,35)26-13-11-25(12-14-26)38-20-8-17-32(3)19-16-24-10-15-29(36-4)30(21-24)37-5/h6-7,9-15,18,21-23H,8,16-17,19-20H2,1-5H3
• InChIKey: ITAMRBIZWGDOHW-UHFFFAOYSA-N
• SMILES: CC(C)C1=CN2C=CC=CC2=C1S(=O)(=O)C3=CC=C(C=C3)OCCCN(C)CCC4=CC(=C(C=C4)OC)OC

Fantofarone, also known as SR 33557, is a highly potent calcium channel antagonist representative of a new class of slow channel blockers. Fantofarone can significantly modify cardiac function and in particular, decrease MO2C consumption during periods of elevated heart rate. Fantofarone is able to induce submaximal peripheral vasodilating effects at doses that are devoid of any clinically significant cardiac effect.

Reference

1:Pharmacokinetic-pharmacodynamic model for fantofarone cardiac and brachial haemodynamic effects in healthy volunteers. Bellissant E, Giudicelli JF.Br J Clin Pharmacol. 1999 Dec;48(6):801-10. PMID: 10594483 Free PMC Article2:Effect of fantofarone, a new Ca2+ channel antagonist, on angioplasty-induced vasospasm in an atherosclerotic rabbit model. Dongay B, Dol-Gleizes F, Herbert JM.Biochem Pharmacol. 1998 Jun 15;55(12):2047-50. PMID: 9714327 3:Synergy between two calcium channel blockers, verapamil and fantofarone (SR33557), in reversing chloroquine resistance in Plasmodium falciparum. Adovelande J, Delèze J, Schrével J.Biochem Pharmacol. 1998 Feb 15;55(4):433-40. PMID: 9514077 4:Safety and efficacy of monotherapy with fantofarone, a novel calcium channel antagonist, in patients with chronic stable angina pectoris. Fantofarone Study Group. Glasser SP, Singh SN, Humen DP.J Clin Pharmacol. 1997 Jan;37(1):53-7. PMID: 9048273 5:Effects of a new class of calcium antagonists, SR33557 (fantofarone) and SR33805, on neuronal voltage-activated Ca++ channels. Romey G, Lazdunski M.J Pharmacol Exp Ther. 1994 Dec;271(3):1348-52. PMID: 7996445 6:Interaction of the calcium antagonist fantofarone with phospholipids: electrostatic effects. Chatelain P, Matteazzi JR, Laruel R.Biochem Pharmacol. 1994 Oct 7;48(7):1393-8. PMID: 7945438 7:Effects of two chemically related new Ca2+ channel antagonists, SR33557 (fantofarone) and SR33805, on the L-type cardiac channel. Romey G, Bois P, Lazdunski M.Eur J Pharmacol. 1994 Sep 22;263(1-2):101-5. PMID: 7821341 8:Binding of fantofarone, a novel Ca2+ antagonist, to serum albumin: a fluorescence study. Chatelain P, Matteazzi JR, Laruel R.J Pharm Sci. 1994 May;83(5):674-6. PMID: 8071819 9:Fantofarone (SR 33557): cardiovascular actions in anesthetized dogs. Barthélémy G, Chatelain P, Manning A.Arch Int Pharmacodyn Ther. 1994 Mar-Apr;327(2):204-19. PMID: 7979829 10:31P nuclear magnetic resonance study of the effects of the calcium ion channel antagonist fantofarone on the rat heart. Vander Elst L, Chatelain P, Manning AS, Laruel R, Van Haverbeke Y, Muller RN.Eur J Pharmacol. 1994 Jan 14;251(2-3):163-72. PMID: 8149974