Fantofarone
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MedKoo CAT#: 326888

CAS#: 114432-13-2

Description: 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

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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: 550.714
Elemental Analysis: C, 67.61; H, 6.96; N, 5.09; O, 14.53; S, 5.82

Price and Availability

Size Price Availability Quantity
100.0mg USD 650.0 2 weeks
200.0mg USD 1050.0 2 weeks
500.0mg USD 1950.0 2 weeks
1.0g USD 2950.0 2 weeks
2.0g USD 5450.0 2 weeks
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Synonym: SR 33557; SR-33557; SR33557; Fantofarone

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

Preparing Stock Solutions

The following data is based on the product molecular weight 550.714 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.

Recalculate based on batch purity %
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

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1: 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. PubMed PMID: 10594483; PubMed Central PMCID: PMC2014307.

2: 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. PubMed PMID: 9714327.

3: 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. PubMed PMID: 9514077.

4: 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. PubMed PMID: 9048273.

5: 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. PubMed PMID: 7996445.

6: 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. PubMed PMID: 7945438.

7: 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. PubMed PMID: 7821341.

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. PubMed PMID: 8071819.

9: 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. PubMed PMID: 7979829.

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. PubMed PMID: 8149974.

11: Hodeige D, Chatelain P, Manning A. Fantofarone (SR33557): effects on myocardial oxygen consumption and coronary blood flow. Pharmacology. 1994 Jan;48(1):49-55. PubMed PMID: 8309987.

12: 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. PubMed PMID: 1425996.