MITEMCINAL FUMARATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	2C40H69NO12.C4H4O4
Molecular Weight	1628.0229
Optical Activity	UNSPECIFIED
Defined Stereocenters	32 / 32
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)\C=C\C(O)=O.[H][C@@]2(O[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1)[C@@H](C)C(=O)O[C@H](CC)[C@@](C)(OC)C(=O)[C@@H](C)C3=C(C)C[C@@](C)(O3)[C@]([H])(O[C@@H]4O[C@H](C)C[C@@H]([C@H]4O)N(C)C(C)C)[C@H]2C.[H][C@@]6(O[C@H]5C[C@@](C)(OC)[C@@H](O)[C@H](C)O5)[C@@H](C)C(=O)O[C@H](CC)[C@@](C)(OC)C(=O)[C@@H](C)C7=C(C)C[C@@](C)(O7)[C@]([H])(O[C@@H]8O[C@H](C)C[C@@H]([C@H]8O)N(C)C(C)C)[C@H]6C

InChI

InChIKey=KQRXEQGYUDDPNW-QXRSSOOUSA-N

InChI=1S/2C40H69NO12.C4H4O4/c2*1-16-28-40(12,47-15)33(43)23(6)31-21(4)18-39(11,53-31)35(52-37-30(42)27(17-22(5)48-37)41(13)20(2)3)24(7)32(25(8)36(45)50-28)51-29-19-38(10,46-14)34(44)26(9)49-29;5-3(6)1-2-4(7)8/h2*20,22-30,32,34-35,37,42,44H,16-19H2,1-15H3;1-2H,(H,5,6)(H,7,8)/b;;2-1+/t2*22-,23+,24+,25-,26+,27+,28-,29+,30-,32+,34+,35-,37+,38-,39-,40-;/m11./s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17785940 | https://www.ncbi.nlm.nih.gov/pubmed/17894654 | https://www.ncbi.nlm.nih.gov/pubmed/11566017

Mitemcinal (GM-611), an erythromycin-derived prokinetic agent, was developed by Chuga as an agonist of the motilin receptor. Mitemcinal acts by a novel mechanism whereby it stimulates and promotes peristalsis in the stomach and other segments of the gastrointestinal tract. This drug was studied as a potential treatment for gastric motility disorder, as well as reflux esophagitis, non-ulcer dyspepsia, and diabetic gastroparesis. Mitemcinal was involved in phase II clinical trials in Patients with diabetic gastroparesis. Although gastroparetic symptoms improved with both mitemcinal and placebo, the prominent placebo effect was not statistically exceeded by mitemcinal. That is why the development of this drug has stalled. In addition, mitemcinal has been studied in phase II for the treatment of irritable bowel syndrome, but this study was also discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Motilin receptor 3 Target ID: O43193 Gene ID: 2862.0 Gene Symbol: MLNR Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/17785940	Agonist 2678

PubMed

Title	Date	PubMed
Hemodynamic and electrophysiological effects of mitemcinal (GM-611), a novel prokinetic agent derived from erythromycin in a halothane-anesthetized canine model.	2007 Aug	17785940
Preclinical electrophysiology assays of mitemcinal (GM-611), a novel prokinetic agent derived from erythromycin.	2007 Aug	17785939
Clinical trial: effect of mitemcinal (a motilin agonist) on gastric emptying in patients with gastroparesis - a randomized, multicentre, placebo-controlled study.	2007 Oct 15	17894654
Phase II drugs under clinical investigation for the treatment of chronic constipation.	2014 Nov	24960333

Patents

Sample Use Guides

In Vivo Use Guide

12 weeks of treatment with oral tablets given twice a day of GM-611 (Mitemcinal) 5mg, 10mg

Route of Administration: Oral

Name

Type

Language

MITEMCINAL FUMARATE

Official Name

English

ERYTHROMYCIN, 8,9-DIDEHYDRO-N-DEMETHYL-9-DEOXO-6,11-DIDEOXY-6,9-EPOXY-12-O-METHYL N-(1-METHYLETHYL)-11-OXO-, (2E)-2-BUTENEDIOATE (2:1)

Common Name

English

MITEMCINAL FUMARATE [USAN]

Common Name

English

5-1 UKIMA 5 CHOME

Code

English

5-1-UKIMA-5-CHOME

Code

English

115-8543 JAPAN

Code

English

Mitemcinal fumarate [WHO-DD]

Common Name

English

115-8543-JAPAN

Code

English

KITA-KU TOYKO

Code

English

GM-611

Code

English

8,9-Didehydro-N-demethyl-9-deoxo-6,11-dideoxy-6,9-epoxy-N-isopropyl-12-O-methyl-11-oxoerythromycin fumarate (2:1) (salt)

Common Name

English

Code System Code Type Description

SMS_ID

300000044523