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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
Molecular Formula C23H25N
Molecular Weight 315.4513
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

Chinoin
5
Curator's Comment: reference retrieved from www.drugfuture.com/chemdata/fendiline.html

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Blocker
537
 17.0 µM [IC50]
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
Sensit

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
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
Inhibitors of calmodulin impair the constitutive but not the inducible nitric oxide synthase activity in the rat aorta.
1992 May
Effects of the antianginal drug fendiline on Ca2+ movement in hepatoma cells.
2001 Jul
Fendiline, an anti-anginal drug, increases intracellular Ca2+ in PC3 human prostate cancer cells.
2001 Jul
Determination of fendiline and gallopamil by capillary isotachophoresis.
2001 Jun 15
Fendiline-Induced Ca2+ movement in A10 smooth muscle cells.
2001 Mar 31
The anti-anginal drug fendiline increases intracellular Ca(2+) levels in MG63 human osteosarcoma cells.
2001 Mar 8
Dual effect of the antianginal drug fendiline on bladder female transitional carcinoma cells: mobilization of intracellular CA2+ and induction of cell death.
2001 May
Fendiline mobilizes intracellular Ca2+ in Chang liver cells.
2001 Sep
The anti-anginal drug fendiline elevates cytosolic Ca(2+) in rabbit corneal epithelial cells.
2002 Jul 19
Arylalkylamines are a novel class of positive allosteric modulators at GABA(B) receptors in rat neocortex.
2002 Sep 6
Allosteric modulators of GABA(B) receptors: mechanism of action and therapeutic perspective.
2007 Sep
Allosteric modulation of the calcium-sensing receptor.
2007 Sep
[Role of apoptosis in the kidney after reperfusion].
2008 Feb 17
Fendiline-evoked [Ca2+]i rises and non-Ca2+-triggered cell death in human oral cancer cells.
2009 Jan
LuxR-dependent quorum sensing: computer aided discovery of new inhibitors structurally unrelated to N-acylhomoserine lactones.
2010 Aug 1
Contractile actions of L-type Ca2+ agonists in human vas deferens and effects of structurally different Ca2+ antagonists.
2010 Feb 10
Patents

Patents

US3262977
2

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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:24:16 GMT 2023
Edited
by admin
on Fri Dec 15 17:24:16 GMT 2023
Record UNII
HEM3Z10IIK
Record Status Validated (UNII)
Record Version
  • Download
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
Related Record Type Details
Structure of FENDILINE HYDROCHLORIDE, (S)-
ENANTIOMER -> RACEMATE
Structure of FENDILINE HYDROCHLORIDE, (R)-
ENANTIOMER -> RACEMATE
Structure of FENDILINE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of FENDILINE
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