Melinamide - CAS 14417-88-0
Category: Inhibitor
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Molecular Formula:
C26H41NO
Molecular Weight:
383.61
COA:
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Targets:
Others
Description:
Melinamide, also known as AC-223 or Artes, an amide derivative of an unsaturated long-chain fatty acid, is a new hypocholesterolaemic drug, caused a substantial decrease of the enhanced intestinal ACAT activity in diabetic rats, but did not affect intestinal cholesterol esterase activity. Melinamide is an inhibitor of cholesterol absorption (IC50= 20.9 μM).
Brife Description:
An inhibitor of cholesterol absorption (IC50= 20.9 μM)
Synonyms:
(9Z,12Z)-N-(1-phenylethyl)octadeca-9,12-dienamide; melinamide; N-(2-methylbenzyl)linoleamide; N-(2-methylbenzyl)linoleamide, (+)-isomer; N-(2-methylbenzyl)linoleamide, (S-(Z,Z))-isomer; N-(2-methylbenzyl)linoleamide, (Z,Z)-(+-)-isomer; N-(alpha-methylbenzyl)-cis,cis-octadeca-9,12-dienamide; N-(alpha-methylbenzyl)linoleamide; N-(o-methylbenzyl)linoleamide
Solubility:
DMSO
Storage:
Store in a cool and dry place (or refer to the Certificate of Analysis).
MSDS:
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Boiling Point:
200-215 ℃ at 0.03 Torr
Melting Point:
< 4 ℃
Density:
0.928±0.06 g/cm3
InChIKey:
RWIUTHWKQHRQNP-NQLNTKRDSA-N
InChI:
1S/C26H41NO/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-20-23-26(28)27-24(2)25-21-18-17-19-22-25/h7-8,10-11,17-19,21-22,24H,3-6,9,12-16,20,23H2,1-2H3,(H,27,28)/b8-7-,11-10-
Canonical SMILES:
CCCCCC=CCC=CCCCCCCCC(=O)NC(C)C1=CC=CC=C1
1.Formation of fatty acid ethyl esters in rat liver microsomes. Evidence for a key role for acyl-CoA: ethanol O-acyltransferase.
Diczfalusy MA;Björkhem I;Einarsson C;Alexson SE Eur J Biochem. 1999 Jan;259(1-2):404-11.
Fatty acid ethyl esters have been detected in high concentrations in organs commonly damaged by alcohol abuse and are regarded as being important non-oxidative metabolites of ethanol. The formation of fatty acid ethyl esters (FAEEs) has been ascribed to two enzymic activities, acyl-CoA : ethanol O-acyltransferase (AEAT) and FAEE synthase. In the present study we determined AEAT and FAEE synthase activities in isolated rat liver microsomes and further characterized the microsomal AEAT activity in more detail. The determined AEAT and FAEE synthase activities were found to be similar (about 1.7 nmol.min-1.mg-1). However, the AEAT activity was increased about sixfold by the addition of 250 microm bis-(4-nitrophenyl) phosphate (a serine esterase inhibitor) to the incubation whereas FAEE synthase activity was completely inhibited. p-Hydroxymercuribenzoic acid (a cysteine-reacting compound) also stimulated AEAT activity (about fourfold) but had no effect on FAEE synthase activity. The effects of the inhibitors suggest that the formation of FAEEs by AEAT was severely counteracted by enzymic hydrolysis of the substrate (acyl-CoA) and to a lesser extent the product by serine esterases. dl-Melinamide, a hypocholesterolaemic drug, was found to be a very potent inhibitor of AEAT activity with an IC50 value of about 2.
2.Cholesterol-lowering effect of N-(alpha-methylbenzyl)linoleamide (melinamide) in cholesterol-fed diabetic rats.
Matsubara K;Matsuzawa Y;Jiao S;Kihara S;Takama T;Nakamura T;Tokunaga K;Kubo M;Tarui S Atherosclerosis. 1988 Aug;72(2-3):199-204.
Cholesterol loading of diabetic rats is known to induce marked hyperlipoproteinaemia, and we have reported that enhancement of the activity of intestinal acyl-CoA:cholesterol acyltransferase (ACAT), one of the key enzymes involved in cholesterol absorption, might play an important role in the development of hypercholesterolaemia in these animals. In the present study, we have shown that treatment with N-(alpha-methylbenzyl)linoleamide (melinamide), a new hypocholesterolaemic drug, caused a substantial decrease of the enhanced intestinal ACAT activity in diabetic rats, but did not affect intestinal cholesterol esterase activity. Furthermore, marked improvement of hypercholesterolaemia in cholesterol-fed diabetic rats occurred concomitantly with the drug treatment. These results suggest that intestinal ACAT activity is closely related to the serum cholesterol level in diabetic rats, and show that melinamide lowers intestinal ACAT activity.
3.Mechanism of the inhibition of cholesterol absorption by DL-melinamide: inhibition of cholesterol esterification.
Natori K;Okazaki Y;Nakajima T;Hirohashi T;Aono S Jpn J Pharmacol. 1986 Dec;42(4):517-23.
In order to elucidate the mechanism of action of DL-melinamide [DL-MA, N-(alpha-methylbenzyl)linoleamide], an inhibitor of cholesterol absorption, the effect of DL-MA on esterification of cholesterol in the mucosa of rabbit small intestine was studied. DL-MA inhibited acyl CoA:cholesterol acyltransferase (ACAT, EC 2.3.1.26) activity in the mucosal microsomes, with 50% inhibition occurring at approximately 0.5 microM. On the other hand, DL-MA had no effect on the cholesterol esterase (EC 3.1.1.13) activity in the mucosal cytosol. Kinetic studies indicate that DL-MA is an uncompetitive inhibitor of ACAT. D-MA, one of the two optical isomers of DL-MA, was found to be a more effective inhibitor of ACAT than L-MA, another isomer. This finding indicates that the inhibition of cholesterol absorption by DL-MA depends on the inhibition of ACAT by this compound, in view of the fact that D-MA is a more effective inhibitor of cholesterol absorption than L-MA.
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CAS 14417-88-0 Melinamide

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