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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

Molecular Formula C23H25N
Molecular Weight 315.4513
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
17.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Sensit
Primary
Unknown
Primary
Unknown
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
4.2 ng/mL
3 mg single, oral
FENDILINE plasma
Homo sapiens
7.2 ng/mL
50 mg single, oral
FENDILINE plasma
Homo sapiens
8.8 ng/mL
75 mg single, oral
FENDILINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
39.8 ng × h/mL
3 mg single, oral
FENDILINE plasma
Homo sapiens
111.2 ng × h/mL
50 mg single, oral
FENDILINE plasma
Homo sapiens
219.6 ng × h/mL
75 mg single, oral
FENDILINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
20 h
1200 mg single, oral
FENDILINE plasma
Homo sapiens
19.4 h
3 mg single, oral
FENDILINE plasma
Homo sapiens
22 h
50 mg single, oral
FENDILINE plasma
Homo sapiens
35.6 h
75 mg single, oral
FENDILINE plasma
Homo sapiens

Doses

AEs

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

PubMed

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.
Substance Class Chemical
Record UNII
S253D559A8
Record Status Validated (UNII)
Record Version