Details
Stereochemistry | RACEMIC |
Molecular Formula | C23H25N |
Molecular Weight | 315.4513 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(NCCC(C1=CC=CC=C1)C2=CC=CC=C2)C3=CC=CC=C3
InChI
InChIKey=NMKSAYKQLCHXDK-UHFFFAOYSA-N
InChI=1S/C23H25N/c1-19(20-11-5-2-6-12-20)24-18-17-23(21-13-7-3-8-14-21)22-15-9-4-10-16-22/h2-16,19,23-24H,17-18H2,1H3
Fendiline or Sensit (N-(3,3-diphenylpropyl)-(1-phenylethyl)-amine), is a diphenylalkylamine blocker of L-type calcium channels. Fendiline is an anti-anginal agent for the treatment of coronary heart disease. Pharmaco-dynamically, it exerts the typical calcium as well as calmodulin antagonistic actions: inhibition of the transmembrane calcium current, smooth muscle relaxation, negative inotropism, cardioprotection, inhibition of calmodulin-activated myosin light-chain kinase and phosphodiesterase. Pharmacokinetics reveal slow onset of action and a long half-life. The anti-anginal and anti-ischaemic efficacy of fendiline has been proven in several placebo-controlled, double-blind trials. Fendiline is an FDA-approved, albeit now clinically obsolete. Additionally, fendiline is a specific inhibitor of K-Ras plasma membrane localization that also inhibits K-Ras signal output and blocks the proliferation of K-Ras-transformed tumor cells.
Originator
Sources: http://pubs.acs.org/doi/abs/10.1021/jm00335a011 | https://www.google.com/patents/US3262977
Curator's Comment: reference retrieved from www.drugfuture.com/chemdata/fendiline.html
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2095229 |
17.0 µM [IC50] | ||
Target ID: CHEMBL2189121 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23129805 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Sensit Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Fendiline, an anti-anginal drug, increases intracellular Ca2+ in PC3 human prostate cancer cells. | 2001 Jul |
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Arylalkylamines are a novel class of positive allosteric modulators at GABA(B) receptors in rat neocortex. | 2002 Sep 6 |
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[Role of apoptosis in the kidney after reperfusion]. | 2008 Feb 17 |
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LuxR-dependent quorum sensing: computer aided discovery of new inhibitors structurally unrelated to N-acylhomoserine lactones. | 2010 Aug 1 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3566858
Pharmacokinetics in healthy volunteers: single doses of 200, 400, 600, 800, 1000, and 1200 mg; or 400 mg twice daily
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2441812
Fendiline (100-200 microM) reduced the postsynaptic influx of calcium but did not alter calcium loss from the extracellular space into presynaptic terminals in the rat hippocampus in vitro.
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QC08EA01
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C333
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C08EA01
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S253D559A8
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13042-18-7
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FENDILINE
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DB08980
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C81686
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4327
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SUB07554MIG
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D005275
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m5272
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100000081250
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CHEMBL254832
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DTXSID5048473
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3336
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)