FANTOFARONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C31H38N2O5S
Molecular Weight	550.709
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C(OC)C=C(CCN(C)CCCOC2=CC=C(C=C2)S(=O)(=O)C3=C4C=CC=CN4C=C3C(C)C)C=C1

InChI

InChIKey=ITAMRBIZWGDOHW-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C31H38N2O5S
Molecular Weight	550.709
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://adisinsight.springer.com/drugs/800000155 | https://www.ncbi.nlm.nih.gov/pubmed/7610500 | https://www.ncbi.nlm.nih.gov/pubmed/7979829

Fantofarone (SR 33557) is a non-dihydropyridine calcium antagonist with a novel site of action in the L-type Ca2+ channel. Fantofarone is capable of significantly modifying the cardiovascular function without increasing heart rate. Fantofarone was being developed for the treatment of angina pectoris, arrhythmias and hypertension.

Originator

Approval Year

PubMed

Title	Date	PubMed
(7R,8S,8aS)-8-Hydr-oxy-7-phenyl-perhydro-indolizin-3-one.	2009-05-23	21583218
Potential roles of membrane fluidity and ceramide in hyperthermia and alcohol stimulation of TRAIL apoptosis.	2007-09	17610065
Acidic extracellular pH increases calcium influx-triggered phospholipase D activity along with acidic sphingomyelinase activation to induce matrix metalloproteinase-9 expression in mouse metastatic melanoma.	2007-06	17540003
De novo C16- and C24-ceramide generation contributes to spontaneous neutrophil apoptosis.	2007-06	17329567
SR33805, a Ca2+ antagonist with length-dependent Ca2+ -sensitizing properties in cardiac myocytes.	2003-05	12746228
Acid sphingomyelinase activation requires caspase-8 but not p53 nor reactive oxygen species during Fas-induced apoptosis in human glioma cells.	2002-02-15	11822871

Sample Use Guides

In Vivo Use Guide

In doses of 100 mg to 150 mg twice daily, monotherapy fantofarone was effective and safe in the treatment of patients with chronic, stable angina pectoris.

Route of Administration: Oral

In Vitro Use Guide

SR 33557 potently antagonized calcium-induced contraction of potassium-depolarized rat aorta in vitro with an IC50 value of 5.6 +/- 0.9 nM, but was a much weaker inhibitor of noradrenaline-induced contraction of the same tissue (IC50 = 96 +/- 22 nM).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:32:40 GMT 2025` Edited by `admin` on `Mon Mar 31 21:32:40 GMT 2025`
Record UNII	KU213XYO69
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FANTOFARONE

Official Name

English

SR 33557

Preferred Name

English

1-((P-(3-((3,4-DIMETHOXYPHENETHYL)METHYLAMINO)PROPOXY)PHENYL)SULFONYL)-2-ISOPROPYLINDOLIZINE

Common Name

English

SR-33557

Code

English

FANTOFARONE [MI]

Common Name

English

fantofarone [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C471