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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
Structure of FENDILINE

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

HIDE SMILES / InChI
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.

CNS Activity

Originator

Curator's Comment: reference retrieved from www.drugfuture.com/chemdata/fendiline.html

Approval Year

PubMed

PubMed

TitleDatePubMed
Fendiline, an anti-anginal drug, increases intracellular Ca2+ in PC3 human prostate cancer cells.
2001 Jul
Arylalkylamines are a novel class of positive allosteric modulators at GABA(B) receptors in rat neocortex.
2002 Sep 6
[Role of apoptosis in the kidney after reperfusion].
2008 Feb 17
LuxR-dependent quorum sensing: computer aided discovery of new inhibitors structurally unrelated to N-acylhomoserine lactones.
2010 Aug 1
Patents

Patents

Sample Use Guides

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
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.
Name Type Language
FENDILINE
INN   MI   WHO-DD  
INN  
Official Name English
Fendiline [WHO-DD]
Common Name English
FENDILINE [MI]
Common Name English
fendiline [INN]
Common Name English
N-(3,3-DIPHENYLPROPYL)-.ALPHA.-METHYLBENZYLAMINE
Systematic Name English
Classification Tree Code System Code
WHO-VATC QC08EA01
Created by admin on Fri Dec 15 16:06:52 GMT 2023 , Edited by admin on Fri Dec 15 16:06:52 GMT 2023
NCI_THESAURUS C333
Created by admin on Fri Dec 15 16:06:52 GMT 2023 , Edited by admin on Fri Dec 15 16:06:52 GMT 2023
WHO-ATC C08EA01
Created by admin on Fri Dec 15 16:06:52 GMT 2023 , Edited by admin on Fri Dec 15 16:06:52 GMT 2023
Code System Code Type Description
INN
2924
Created by admin on Fri Dec 15 16:06:52 GMT 2023 , Edited by admin on Fri Dec 15 16:06:52 GMT 2023
PRIMARY
FDA UNII
S253D559A8
Created by admin on Fri Dec 15 16:06:52 GMT 2023 , Edited by admin on Fri Dec 15 16:06:52 GMT 2023
PRIMARY
ECHA (EC/EINECS)
235-915-6
Created by admin on Fri Dec 15 16:06:52 GMT 2023 , Edited by admin on Fri Dec 15 16:06:52 GMT 2023
PRIMARY
CAS
13042-18-7
Created by admin on Fri Dec 15 16:06:52 GMT 2023 , Edited by admin on Fri Dec 15 16:06:52 GMT 2023
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WIKIPEDIA
FENDILINE
Created by admin on Fri Dec 15 16:06:52 GMT 2023 , Edited by admin on Fri Dec 15 16:06:52 GMT 2023
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DRUG CENTRAL
1148
Created by admin on Fri Dec 15 16:06:52 GMT 2023 , Edited by admin on Fri Dec 15 16:06:52 GMT 2023
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DRUG BANK
DB08980
Created by admin on Fri Dec 15 16:06:52 GMT 2023 , Edited by admin on Fri Dec 15 16:06:52 GMT 2023
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NCI_THESAURUS
C81686
Created by admin on Fri Dec 15 16:06:52 GMT 2023 , Edited by admin on Fri Dec 15 16:06:52 GMT 2023
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RXCUI
4327
Created by admin on Fri Dec 15 16:06:52 GMT 2023 , Edited by admin on Fri Dec 15 16:06:52 GMT 2023
PRIMARY RxNorm
EVMPD
SUB07554MIG
Created by admin on Fri Dec 15 16:06:52 GMT 2023 , Edited by admin on Fri Dec 15 16:06:52 GMT 2023
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MESH
D005275
Created by admin on Fri Dec 15 16:06:52 GMT 2023 , Edited by admin on Fri Dec 15 16:06:52 GMT 2023
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MERCK INDEX
m5272
Created by admin on Fri Dec 15 16:06:52 GMT 2023 , Edited by admin on Fri Dec 15 16:06:52 GMT 2023
PRIMARY Merck Index
SMS_ID
100000081250
Created by admin on Fri Dec 15 16:06:52 GMT 2023 , Edited by admin on Fri Dec 15 16:06:52 GMT 2023
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ChEMBL
CHEMBL254832
Created by admin on Fri Dec 15 16:06:52 GMT 2023 , Edited by admin on Fri Dec 15 16:06:52 GMT 2023
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EPA CompTox
DTXSID5048473
Created by admin on Fri Dec 15 16:06:52 GMT 2023 , Edited by admin on Fri Dec 15 16:06:52 GMT 2023
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PUBCHEM
3336
Created by admin on Fri Dec 15 16:06:52 GMT 2023 , Edited by admin on Fri Dec 15 16:06:52 GMT 2023
PRIMARY