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Details

Stereochemistry RACEMIC
Molecular Formula C23H25N.ClH
Molecular Weight 351.912
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FENDILINE HYDROCHLORIDE

SMILES

Cl.CC(NCCC(C1=CC=CC=C1)C2=CC=CC=C2)C3=CC=CC=C3

InChI

InChIKey=NJXWZWXCHBNOOG-UHFFFAOYSA-N
InChI=1S/C23H25N.ClH/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;1H

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
Effects of the calmodulin antagonists fendiline and calmidazolium on aggregation, secretion of ATP, and internal calcium in washed human platelets.
1991 Jan
Effects of the antianginal drug fendiline on Ca2+ movement in hepatoma cells.
2001 Jul
Dual effect of the antianginal drug fendiline on bladder female transitional carcinoma cells: mobilization of intracellular CA2+ and induction of cell death.
2001 May
Calcimimetic and calcilytic drugs: just for parathyroid cells?
2004 Mar
Interaction of antagonists with calmodulin: insights from molecular dynamics simulations.
2008 Jun 12
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 HYDROCHLORIDE
MART.   MI   WHO-DD  
Common Name English
FENDILAR
Brand Name English
SENSIT
Brand Name English
BENZENEPROPANAMINE, .GAMMA.-PHENYL-N-(1-PHENYLETHYL)-, HYDROCHLORIDE (1:1)
Systematic Name English
FENDILINE HYDROCHLORIDE [MART.]
Common Name English
NSC-757826
Code English
BENZYLAMINE, N-(3,3-DIPHENYLPROPYL)-.ALPHA.-METHYL-, HYDROCHLORIDE
Systematic Name English
BENZENEPROPANAMINE, .GAMMA.-PHENYL-N-(1-PHENYLETHYL)-, HYDROCHLORIDE
Systematic Name English
FENDILINE HYDROCHLORIDE [MI]
Common Name English
CORDAN
Brand Name English
Fendiline hydrochloride [WHO-DD]
Common Name English
N-(2-BENZHYDRYLETHYL)-.ALPHA.-METHYLBENZYLAMINE HYDROCHLORIDE
Systematic Name English
PHENOXAN
Brand Name English
SENSITE
Brand Name English
FENDILINE HCL
Common Name English
Code System Code Type Description
SMS_ID
100000092346
Created by admin on Fri Dec 15 17:24:16 GMT 2023 , Edited by admin on Fri Dec 15 17:24:16 GMT 2023
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CAS
13636-18-5
Created by admin on Fri Dec 15 17:24:16 GMT 2023 , Edited by admin on Fri Dec 15 17:24:16 GMT 2023
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MERCK INDEX
m5272
Created by admin on Fri Dec 15 17:24:16 GMT 2023 , Edited by admin on Fri Dec 15 17:24:16 GMT 2023
PRIMARY Merck Index
PUBCHEM
26154
Created by admin on Fri Dec 15 17:24:16 GMT 2023 , Edited by admin on Fri Dec 15 17:24:16 GMT 2023
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EVMPD
SUB02113MIG
Created by admin on Fri Dec 15 17:24:16 GMT 2023 , Edited by admin on Fri Dec 15 17:24:16 GMT 2023
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NSC
757826
Created by admin on Fri Dec 15 17:24:16 GMT 2023 , Edited by admin on Fri Dec 15 17:24:16 GMT 2023
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ECHA (EC/EINECS)
237-121-5
Created by admin on Fri Dec 15 17:24:16 GMT 2023 , Edited by admin on Fri Dec 15 17:24:16 GMT 2023
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EPA CompTox
DTXSID2045860
Created by admin on Fri Dec 15 17:24:16 GMT 2023 , Edited by admin on Fri Dec 15 17:24:16 GMT 2023
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RXCUI
236767
Created by admin on Fri Dec 15 17:24:16 GMT 2023 , Edited by admin on Fri Dec 15 17:24:16 GMT 2023
PRIMARY RxNorm
FDA UNII
HEM3Z10IIK
Created by admin on Fri Dec 15 17:24:16 GMT 2023 , Edited by admin on Fri Dec 15 17:24:16 GMT 2023
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