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FENDILINE HYDROCHLORIDE

FENDILINE HYDROCHLORIDE structure

CAS No:
13636-18-5
Formula:
C23H26ClN
Chemical Name:
FENDILINE HYDROCHLORIDE
Synonyms:
FENDILINE HYDROCHLORIDE;N-[3,3-DIPHENYLPROPYL]-ALPHA-METHYLBENZYLAMINE HYDROCHLORIDE;difmecor;gamma-phenyl-n-(1-phenylethyl)benzenepropanaminehydrochloride;3,3-diphenyl-N-(1-phenylethyl)-1-propanamine hydrochloride;N-(3,3-Diphenylpropyl)-α-methylbenzylamine hydrochloride;gamma-phenyl-n-(1-phenylethyl)-benzenepropanaminhydrochloride;hk137
Categories:
Organic Chemistry > Amides

Description

Coronary vasodilator; inhibits calcium function in muscle cells in excitation-contraction coupling; proposed as antiarrhythmic and antianginal agents.

FENDILINE HYDROCHLORIDE Basic Attributes

Molecular Weight：

351.91

Exact Mass：

351.1753775 g/mol

EC Number：

237-121-5

Color/Form：

White to off-white

Characteristics

PSA：

16.6 Å²

Melting Point：

204-205℃

Toxicity：

LD50 in mice (mg/kg): 14.5 i.v.; 950 orally (Harsányi)

Safety Information

wgk germany：

hazard class code：

safety instructions：

RTECS Number：

DP4790000

Marks：

Storage features：

Store at +4°C

Hazard Statements：

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory.

Drug Information

MeSH：

A class of drugs that act by selective inhibition of calcium influx through cellular membranes. (See all compounds classified as Calcium Channel Blockers.)

MeSH Entry Terms：

Fendilin

FENDILINE HYDROCHLORIDE Use and Manufacturing

Methods of Manufacturing

21.13 grams of γ,γ-diphenyl-propylamine and 12.01 grams of acetophenone are hydrogenated in 200 ml of methanol at 55°C and a pressure of 10 atmospheres in the presence of palladium charcoal. On filtration of the catalyst the solution is concentrated and the remainder is distilled in vacuo at a pressure of 0.3 Hg mm. The main distillate is collected at 206° to 210°C. 25.38 grams of N-[1'-phenylethyl-(1')]-1,1-diphenyl-propyl-(3)-amine are obtained. The product is dissolved in 134 ml of 96% ethanol whereupon 26.8 ml of concentrated hydrochloric acid and 201 ml of water are added while cooling with ice-water. The precipitate is filtered off and dried in vacuo at 100°C. 22.98 grams of N-[1'-phenylethyl)-(1')]-1,1-diphenyl-propyl-(3)-amine hydrochloride are obtained. MP 200° to 201°C. On recrystallization from 285 ml of a 2:1 mixture of water and 96% ethanol the melting point remains unchanged.

Uses

Fendiline is an α2-adrenergic receptor antagonist (Kd = 2.6 μM) and an L-type calcium channel blocker (IC50 = 17 μM) well-known for its coronary vasodilator effects. Fendiline has recently been reported to inhibit K-Ras plasma membrane localization (IC50 = 9.64 μM), which prevents K-Ras signal transduction and blocks the proliferation of K-Ras-transformed tumor cells.

Antianginal;Ca++ channel activator

Fendiline hydrochloride is used as a calcium channel blocker.

Computed Properties

Molecular Weight:351.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:7
Exact Mass:351.1753775
Monoisotopic Mass:351.1753775
Topological Polar Surface Area:16.6
Heavy Atom Count:25
Complexity:303
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes