Melinamide

Details

Stereochemistry	RACEMIC
Molecular Formula	C26H41NO
Molecular Weight	383.6098
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCC\C=C/C\C=C/CCCCCCCC(=O)NC(C)C1=CC=CC=C1

InChI

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-

HIDE SMILES / InChI

Description
Sources: https://books.google.ru/books?id=RUIC6BGv2GwC&pg=PA206&lpg=PA206&dq=MELINAMIDE+use&source=bl&ots=fAL4VA-cIh&sig=LAXPF4aGyiPK6IgHTLN9IWyUrGQ&hl=en&sa=X&ved=0ahUKEwjw_fyY-NzOAhWBrSwKHbZiCLQ4ChDoAQgdMAA#v=onepage&q=MELINAMIDE%20use&f=false retrieved from Current Medicinal Chemistry, p.206
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/3214468 and http://www.ncbi.nlm.nih.gov/pubmed/3214468

Melinamide is an antilipidemic agent similar to gemfibrozil. It acts to lower elevated serum lipids by reducing the very low-density lipoprotein fraction rich in triglycerides. Serum cholesterol may be decreased, particularly in those patients whose cholesterol elevation is due to the presence of IDL as a result of Type III hyperlipoproteinemia. Melinamide caused a decrease of the enhanced intestinal ACAT activity in diabetic rats, but did not affect intestinal cholesterol esterase activity. 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. Melinamide (Artes®) was the only marketed (in Japan) ACAT inhibitor. 04 Aug 2004 was withdrawn for Hypercholesterolaemia in Japan.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Acyl coenzyme A:cholesterol acyltransferase 15 Target ID: CHEMBL2265 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7887979	Inhibitor 8504		3.2 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypercholesterolemia 51 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3214468	Primary		Withdrawn	Artes Approved Use Hypercholesterolaemia

PubMed

Title	Date	PubMed
N-[2-[N'-pentyl-(6,6-dimethyl-2,4-heptadiynyl)amino]ethyl]- (2-methyl-1-naphthylthio)acetamide (FY-087). A new acyl coenzyme a:cholesterol acyltransferase (ACAT) inhibitor of diet-induced atherosclerosis formation in mice.	1995-03-01	7887979
In vivo evidence that the lipid-regulating activity of the ACAT inhibitor CI-976 in rats is due to inhibition of both intestinal and liver ACAT.	1993-02	8429262
Contribution of peroxisomal beta-oxidation system to the chain-shortening of N-(alpha-methylbenzyl)azelaamic acid in rat liver.	1990-06-15	2353938
Cholesterol-lowering effect of N-(alpha-methylbenzyl)linoleamide (melinamide) in cholesterol-fed diabetic rats.	1988-08	3214468
Influence of 5-tridecylpyrazole-3-carboxylic acid, a new hypolipidaemic agent, on cholesteryl ester formation in rabbit intestinal mucosa.	1988-07	2904986
Inhibitory effect of melinamide on cholesterol solubility in mixed micellar solution of sodium taurocholate.	1986-10	3829159

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Melinamide significantly inhibited ACAT in the range of 20 to 100 uM

Name

Type

Language

Melinamide

Official Name

English

ARTES

Preferred Name

English

DL-N-(.ALPHA.-METHYLBENZYL)LINOLEAMIDE

Common Name

English

AC-223

Code

English

MBLA

Common Name

English

melinamide [INN]

Common Name

English

MELINAMIDE [MART.]

Common Name

English

9,12-OCTADECADIENAMIDE, N-(1-PHENYLETHYL)-, (9Z,12Z)-

Systematic Name

English

DL-.ALPHA.-METHYLBENZYL LINOLEAMIDE

Common Name

English

LINOLEAMIDE, N-(.ALPHA.-METHYLBENZYL)-

Systematic Name

English

9,12-OCTADECADIENAMIDE, N-(1-PHENYLETHYL)-, (Z,Z)-

Systematic Name

English

MELINAMIDE [JAN]

Common Name

English

N-(.ALPHA.-METHYLBENZYL)LINOLEAMIDE

Systematic Name

English

MELINAMIDE [MI]

Common Name

English

Melinamide [WHO-DD]

Common Name

English

N-(DL-.ALPHA.-METHYLBENZYL) LINOLEAMIDE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C471