Fantofarone | SR 33557 | CAS#114432-13-2

MedKoo Cat#: 326888 | Name: Fantofarone

Description:

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

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.

Chemical Structure

Fantofarone

CAS#114432-13-2

Theoretical Analysis

MedKoo Cat#: 326888

Name: Fantofarone

CAS#: 114432-13-2

Chemical Formula: C31H38N2O5S

Exact Mass: 550.2501

Molecular Weight: 550.71

Elemental Analysis: C, 67.61; H, 6.96; N, 5.09; O, 14.53; S, 5.82

Price and Availability

Size	Price	Availability
50mg	USD 450.00	2 Weeks
100mg	USD 750.00	2 Weeks
200mg	USD 1,350.00	2 Weeks
500mg	USD 2,950.00	2 Weeks

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Related CAS #

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Synonym

SR 33557; SR-33557; SR33557; Fantofarone; Fantofarona; Fantofaronum

IUPAC/Chemical Name

N-(3,4-dimethoxyphenethyl)-3-(4-((2-isopropylindolizin-1-yl)sulfonyl)phenoxy)-N-methylpropan-1-amine

InChi Key

ITAMRBIZWGDOHW-UHFFFAOYSA-N

InChi Code

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

SMILES Code

CC(C1=CN2C=CC=CC2=C1S(=O)(C3=CC=C(OCCCN(CCC4=CC=C(OC)C(OC)=C4)C)C=C3)=O)C

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

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

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 550.71 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: Manning A, Mouton J, Chatelain P. Fantofarone (SR 33557): effect on post- ischaemic functional recovery in perfused rat hearts. Eur J Pharmacol. 1992 Sep 22;220(2-3):249-58. doi: 10.1016/0014-2999(92)90755-s. PMID: 1425996. 2: Barthélémy G, Chatelain P, Manning A. Fantofarone (SR 33557): cardiovascular actions in anesthetized dogs. Arch Int Pharmacodyn Ther. 1994 Mar- Apr;327(2):204-19. PMID: 7979829. 3: Chatelain P, Matteazzi JR, Laruel R. Interaction of the calcium antagonist fantofarone with phospholipids: electrostatic effects. Biochem Pharmacol. 1994 Oct 7;48(7):1393-8. doi: 10.1016/0006-2952(94)90562-2. PMID: 7945438. 4: Hodeige D, Chatelain P, Manning A. Fantofarone (SR33557): effects on myocardial oxygen consumption and coronary blood flow. Pharmacology. 1994 Jan;48(1):49-55. doi: 10.1159/000139161. PMID: 8309987. 5: Dongay B, Dol-Gleizes F, Herbert JM. Effect of fantofarone, a new Ca2+ channel antagonist, on angioplasty-induced vasospasm in an atherosclerotic rabbit model. Biochem Pharmacol. 1998 Jun 15;55(12):2047-50. doi: 10.1016/s0006-2952(98)00026-4. PMID: 9714327. 6: Glasser SP, Singh SN, Humen DP. Safety and efficacy of monotherapy with fantofarone, a novel calcium channel antagonist, in patients with chronic stable angina pectoris. Fantofarone Study Group. J Clin Pharmacol. 1997 Jan;37(1):53-7. doi: 10.1177/009127009703700109. PMID: 9048273. 7: Adovelande J, Delèze J, Schrével J. Synergy between two calcium channel blockers, verapamil and fantofarone (SR33557), in reversing chloroquine resistance in Plasmodium falciparum. Biochem Pharmacol. 1998 Feb 15;55(4):433-40. doi: 10.1016/s0006-2952(97)00482-6. PMID: 9514077. 8: Chatelain P, Matteazzi JR, Laruel R. Binding of fantofarone, a novel Ca2+ antagonist, to serum albumin: a fluorescence study. J Pharm Sci. 1994 May;83(5):674-6. doi: 10.1002/jps.2600830516. PMID: 8071819. 9: Bellissant E, Giudicelli JF. Pharmacokinetic-pharmacodynamic model for fantofarone cardiac and brachial haemodynamic effects in healthy volunteers. Br J Clin Pharmacol. 1999 Dec;48(6):801-10. doi: 10.1046/j.1365-2125.1999.00091.x. PMID: 10594483; PMCID: PMC2014307. 10: Vander Elst L, Chatelain P, Manning AS, Laruel R, Van Haverbeke Y, Muller RN. 31P nuclear magnetic resonance study of the effects of the calcium ion channel antagonist fantofarone on the rat heart. Eur J Pharmacol. 1994 Jan 14;251(2-3):163-72. doi: 10.1016/0014-2999(94)90397-2. PMID: 8149974. 11: Romey G, Bois P, Lazdunski M. Effects of two chemically related new Ca2+ channel antagonists, SR33557 (fantofarone) and SR33805, on the L-type cardiac channel. Eur J Pharmacol. 1994 Sep 22;263(1-2):101-5. doi: 10.1016/0014-2999(94)90529-0. PMID: 7821341. 12: Romey G, Lazdunski M. Effects of a new class of calcium antagonists, SR33557 (fantofarone) and SR33805, on neuronal voltage-activated Ca++ channels. J Pharmacol Exp Ther. 1994 Dec;271(3):1348-52. PMID: 7996445. 13: Spedding M, Kenny B, Chatelain P. New drug binding sites in Ca2+ channels. Trends Pharmacol Sci. 1995 Apr;16(4):139-42. doi: 10.1016/s0165-6147(00)89002-1. PMID: 7610500. 14: Chatelain P, Dewinkeleer P, Beaufort P, Meysmans L, Clinet M. Characterization of the binding of [3H]SR 33805 to the slow Ca2+ channel in rat heart sarcolemmal membrane. Eur J Pharmacol. 1994 Apr 15;267(2):151-60. doi: 10.1016/0922-4106(94)90166-x. PMID: 8050476. 15: Chatelain P, Mouton J, Feys G, Laruel A, Manning AS. Vascular calcium overload produced by vitamin D3, in rats. Effect of treatment with SR 33805, a novel calcium entry blocker. Cardiovasc Res. 1995 Dec;30(6):1038-43. PMID: 8746222. 16: Seumois G, Fillet M, Gillet L, Faccinetto C, Desmet C, François C, Dewals B, Oury C, Vanderplasschen A, Lekeux P, Bureau F. De novo C16- and C24-ceramide generation contributes to spontaneous neutrophil apoptosis. J Leukoc Biol. 2007 Jun;81(6):1477-86. doi: 10.1189/jlb.0806529. Epub 2007 Feb 28. PMID: 17329567. 17: Ertel SI, Clozel JP. Mibefradil (Ro 40-5967): the first selective T-type Ca2+ channel blocker. Expert Opin Investig Drugs. 1997 May;6(5):569-82. doi: 10.1517/13543784.6.5.569. PMID: 15989621. 18: Chatelain P, Clinet M, Polster P, Christophe B, Manning AS. In vitro characterization of a novel Ca2+ entry blocker: SR 33805. Eur J Pharmacol. 1993 Aug 15;246(3):181-93. doi: 10.1016/0922-4106(93)90030-d. PMID: 8223943. 19: Cazorla O, Lacampagne A, Fauconnier J, Vassort G. SR33805, a Ca2+ antagonist with length-dependent Ca2+ -sensitizing properties in cardiac myocytes. Br J Pharmacol. 2003 May;139(1):99-108. doi: 10.1038/sj.bjp.0705221. PMID: 12746228; PMCID: PMC1573823. 20: Dol F, Schaeffer P, Lamarche I, Mares AM, Chatelain P, Herbert JM. Effect of SR 33805 on arterial smooth muscle cell proliferation and neointima formation following vascular injury. Eur J Pharmacol. 1995 Jul 4;280(2):135-42. doi: 10.1016/0014-2999(95)00196-r. PMID: 7589177.