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ChemicalBook--->CAS DataBase List--->13636-18-5

13636-18-5

13636-18-5 Structure

13636-18-5 Structure
IdentificationBack Directory
[Name]

FENDILINE HYDROCHLORIDE
[CAS]

13636-18-5
[Synonyms]

hk137
Sensit
Fendilar
difmecor
Fendiline HCl
FENDILINE HYDROCHLORIDE
N-(3,3-Diphenylpropyl)-α-methylbenzylamine
(3,3-diphenylpropyl)(1-phenylethyl)ammonium chloride
n-(1-phenylethyl)-3,3-diphenylpropylaminehydrochloride
N-(3,3-Diphenylpropyl)-α-methylbenzylamine hydrochloride
3,3-diphenyl-N-(1-phenylethyl)-1-propanamine hydrochloride
n-(3,3-diphenylpropyl)-alpha-methyl-benzylaminhydrochloride
N-[3,3-DIPHENYLPROPYL]-ALPHA-METHYLBENZYLAMINE HYDROCHLORIDE
gamma-phenyl-n-(1-phenylethyl)benzenepropanaminehydrochloride
gamma-phenyl-n-(1-phenylethyl)-benzenepropanaminhydrochloride
[EINECS(EC#)]

237-121-5
[Molecular Formula]

C23H26ClN
[MDL Number]

MFCD00079301
[MOL File]

13636-18-5.mol
[Molecular Weight]

351.91
Chemical PropertiesBack Directory
[Melting point ]

204-205℃
[solubility ]

Soluble in ethanol.
[form ]

Powder
[color ]

White to off-white
Safety DataBack Directory
[Hazard Codes ]

Xn
[Risk Statements ]

22
[Safety Statements ]

36
[WGK Germany ]

3
[RTECS ]

DP4790000
[Toxicity]

LD50 in mice (mg/kg): 14.5 i.v.; 950 orally (Harsányi)
Hazard InformationBack Directory
[Originator]

Sensit,Thiemann,W. Germany,1974
[Uses]

Antianginal;Ca++ channel activator
[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.
[Manufacturing Process]

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.
[Therapeutic Function]

Coronary vasodilator
[Biological Activity]

fendiline is an α2-adrenergic receptor antagonist and l-type calcium channel blocker [1,2].the α2 adrenergic receptor is a g protein-coupled receptor (gpcr). until now, three different α2-receptor subtypes have been identified: α2a, α2b, and α2c. the α2-adrenergic receptor exists in vascular prejunctional terminals and inhibits the release of norepinephrine in a form of negative feedback. the α2 adrenergic receptor agonists produce diverse responses, including analgesia, sedation, anxiolysis, and sympatholysis [3]. l-type calcium channels are responsible for the excitation-contraction coupling of skeletal, cardiac muscle, smooth, and for aldosterone secretion in endocrine cells of the adrenal cortex [4].fendiline inhibited the activity of l-type ca2+ channel blocker with the ic50 value of 17 μm [1]. fendiline inhibited the activity of α2-adrenergic receptor with the kd of 2.6 μm [2]. fendiline significantly reduced nanoclustering of k-ras and redistributed k-ras from the plasma membrane to the endoplasmic reticulum (er), golgi apparatus, endosomes, and cytosol. fendiline significantly inhibited signaling downstream of constitutively active k-ras and endogenous k-ras signaling in cells transformed by oncogenic h-ras. fendiline blocked the proliferation of pancreatic, colon, lung, and endometrial cancer cell lines expressing oncogenic mutant k-ras [5]. fendiline inhibited k-ras plasma membrane localization with an ic50 of 9.64 μm [5]. fendiline is an anti-anginal agent for the treatment of coronary heart disease. the anti-anginal and anti-ischaemic efficacy of fendiline has been proven in several placebo-controlled, double-blind trials [6].
[storage]

Store at +4°C
[References]

[1] tripathi, o. ,schreibayer, w., and tritthart, h.a. fendiline inhibits l-type calcium channels in guinea-pig ventricular myocytes: a whole-cell patch-clamp study. british journal of pharmacology 108(4), 865-869 (1993).
[2] motulsky, h. j.,snavely, m.d.,hughes, r.j., et al. interaction of verapamil and other calcium channel blockers with α1- and α2-adrenergic receptors. circulation research 52(2), 226-231 (1983).
[3] kamibayashi t, maze m. clinical uses of α2-adrenergic agonists[j]. the journal of the american society of anesthesiologists, 2000, 93(5): 1345-1349.
[4] lipscombe d. l-type calcium channels[j]. 2002.
[5] van der hoeven d, cho k, ma x, et al. fendiline inhibits k-ras plasma membrane localization and blocks k-ras signal transmission[j]. molecular and cellular biology, 2013, 33(2): 237-251.
[6] bayer r, mannhold r. fendiline: a review of its basic pharmacological and clinical properties[j]. pharmatherapeutica, 1986, 5(2): 103-136.
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