FENDILINE HYDROCHLORIDE

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3310016 | https://www.ncbi.nlm.nih.gov/pubmed/23129805

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Voltage-gated L-type calcium channel 92 Target ID: CHEMBL2095229 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8485628 \| https://www.ncbi.nlm.nih.gov/pubmed/9580596	Blocker 537		17.0 µM [IC50]
GTPase KRas 3 Target ID: CHEMBL2189121 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23129805	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Angina pectoris 106 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7188139 https://www.ncbi.nlm.nih.gov/pubmed/3449975 https://www.ncbi.nlm.nih.gov/pubmed/1764956 https://www.ncbi.nlm.nih.gov/pubmed/3310016	Primary	Approved 8429	Sensit Approved Use Unknown
Anxiety 267 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9162271	Primary	Preclinical	Unknown Approved Use Unknown
Drug addiction 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24264565 https://www.ncbi.nlm.nih.gov/pubmed/26345344	Primary	Preclinical	Unknown Approved Use Unknown
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23129805	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Effects of the calmodulin antagonists fendiline and calmidazolium on aggregation, secretion of ATP, and internal calcium in washed human platelets.	1991 Jan	2030746
Effects of the antianginal drug fendiline on Ca2+ movement in hepatoma cells.	2001 Jul	11530834
Fendiline, an anti-anginal drug, increases intracellular Ca2+ in PC3 human prostate cancer cells.	2001 Jul	11488522
The anti-anginal drug fendiline increases intracellular Ca(2+) levels in MG63 human osteosarcoma cells.	2001 Mar 8	11246176
Clinical potential of GABAB receptor modulators.	2005 Autumn	16389296
Quantitative structure-pharmacokinetic relationships for drug clearance by using statistical learning methods.	2006 Mar	16290201
2'-hydroxy-fendiline analogues as potent relaxers of isolated arteries.	2007 Apr 30	17331497
[Role of apoptosis in the kidney after reperfusion].	2008 Feb 17	18258561
LuxR-dependent quorum sensing: computer aided discovery of new inhibitors structurally unrelated to N-acylhomoserine lactones.	2010 Aug 1	20615699
Contractile actions of L-type Ca2+ agonists in human vas deferens and effects of structurally different Ca2+ antagonists.	2010 Feb 10	19878664

Patents

Sample Use Guides

In Vivo Use Guide

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

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