COLENEURAMIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C39H68N2O8
Molecular Weight	692.9658
Optical Activity	UNSPECIFIED
Defined Stereocenters	15 / 15
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])C[C@@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)NC(=O)[C@]5(C[C@H](O)[C@@H](NC(C)=O)[C@@]([H])(O5)[C@H](O)[C@H](O)CO)OC)[C@H](C)CCCC(C)C

InChI

InChIKey=CHMRTBYTCBDIRG-JQZMMWJVSA-N

InChI=1S/C39H68N2O8/c1-22(2)9-8-10-23(3)28-13-14-29-27-12-11-25-19-26(15-17-37(25,5)30(27)16-18-38(28,29)6)41-36(47)39(48-7)20-31(44)33(40-24(4)43)35(49-39)34(46)32(45)21-42/h22-23,25-35,42,44-46H,8-21H2,1-7H3,(H,40,43)(H,41,47)/t23-,25+,26-,27+,28-,29+,30+,31+,32-,33-,34-,35-,37+,38-,39-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C39H68N2O8
Molecular Weight	692.9658
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	15 / 15
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://clinicaltrials.gov/ct2/show/NCT00307749 | https://www.ncbi.nlm.nih.gov/pubmed/18758136 | https://www.ncbi.nlm.nih.gov/pubmed/16505223 | https://www.ncbi.nlm.nih.gov/pubmed/25545984

Coleneuramide (MCC-257) is a cholestane amide conjugate originated in Mitsubishi Pharma Corporation. It has been shown to enhance the effect of nerve growth factor (NGF) on cell survival and on tyrosine phosphorylation in PC12 cells. Coleneuramide is believed to act directly on TrkA receptor. In preclinical models, MCC-257 rescued clinical sign and pathological changes in rats after exposure to environmental neurotoxin methylmercury and protected against dysfunction of the peripheral nervers in hyperglycemic animals. The compound was investigated in phase 2 clinical study for the treatment of diabetic polyneuropathy, but no results were reported.

Approval Year

PubMed

Title	Date	PubMed
Methylmercury causes neuronal cell death through the suppression of the TrkA pathway: in vitro and in vivo effects of TrkA pathway activators.	2015 Feb 1	25545984

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:51:45 GMT 2023` Edited by `admin` on `Fri Dec 15 18:51:45 GMT 2023`
Record UNII	G2D52T65LR
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

COLENEURAMIDE

Official Name

English

MCC-257

Code

English

Coleneuramide [WHO-DD]

Common Name

English

COLENEURAMIDE [USAN]

Common Name

English

.ALPHA.-NEURAMINAMIDE, N(SUP 5)-ACETYL-N(SUP 1)-((3.ALPHA.,5.ALPHA.)-CHOLESTAN-3-YL)-2-O-METHYL-

Common Name

English

coleneuramide [INN]

Common Name

English

5-ACETAMIDO-N-(5.ALPHA.-CHOLESTAN-3.ALPHA.-YL)-3,5-DIDEOXY-2-O-METHYL-D-GLYCERO-.ALPHA.-D-GALACTO-NON-2-ULOPYRANOSONAMIDE

Common Name

English

Code System Code Type Description

CAS

204200-47-5