mitemcinal   Click here for help

GtoPdb Ligand ID: 3511

Synonyms: GM-611 | GM611
Compound class: Synthetic organic
Comment: Mitemcinal is a non-peptide, orally active motilin receptor agonist that was developed by Chugai Pharmaceutical [6] as a prokinetic agent for the treatment of gastroparesis [5,7].
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 13
Hydrogen bond donors 2
Rotatable bonds 9
Topological polar surface area 151.68
Molecular weight 755.48
XLogP 2.66
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES CCC1OC(=O)C(C)C(OC2OC(C)C(C(C2)(C)OC)O)C(C)C(C2(OC(=C(C)C2)C(C(=O)C1(C)OC)C)C)OC1OC(C)CC(C1O)N(C(C)C)C
Isomeric SMILES CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@@H]2O[C@@H](C)[C@@H]([C@](C2)(C)OC)O)[C@H](C)[C@H]([C@]2(OC(=C(C)C2)[C@@H](C(=O)[C@]1(C)OC)C)C)O[C@@H]1O[C@H](C)C[C@@H]([C@H]1O)N(C(C)C)C
InChI InChI=1S/C40H69NO12/c1-16-28-40(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/h20,22-30,32,34-35,37,42,44H,16-19H2,1-15H3/t22-,23+,24+,25-,26+,27+,28-,29+,30-,32+,34+,35-,37+,38-,39+,40-/m1/s1
InChI Key BELMMAAWNYFCGF-AQBNEDITSA-N
References
1. Clark MJ, Wright T, Bertrand PP, Bornstein JC, Jenkinson KM, Verlinden M, Furness JB. (1999)
Erythromycin derivatives ABT 229 and GM 611 act on motilin receptors in the rabbit duodenum.
Clin Exp Pharmacol Physiol, 26 (3): 242-5. [PMID:10081621]
2. Koga H, Sato T, Tsuzuki K, Onoda H, Kuboniwa H, Takanashi H. (1994)
Potent, acid-stable and orally active macrolide-type motilin receptor agonists, GM-611 and the derivatives.
Bioorg Med Chem Lett, 4 (11): 1347-1352.
3. McCallum RW, Cynshi O, Investigative Team. (2007)
Clinical trial: effect of mitemcinal (a motilin agonist) on gastric emptying in patients with gastroparesis - a randomized, multicentre, placebo-controlled study.
Aliment Pharmacol Ther, 26 (8): 1121-30. [PMID:17894654]
4. McCallum RW, Cynshi O, US INVESTIGATIVE TEAM. (2007)
Efficacy of mitemcinal, a motilin agonist, on gastrointestinal symptoms in patients with symptoms suggesting diabetic gastropathy: a randomized, multi-center, placebo-controlled trial.
Aliment Pharmacol Ther, 26 (1): 107-16. [PMID:17555427]
5. Onoma M, Ozaki K, Yogo K, Monnai M, Muramatsu H, Kamei K, Kawabe Y, Hayashi S, Shiga T, Matsuo S et al.. (2008)
Mitemcinal (GM-611), an orally active motilin receptor agonist, improves delayed gastric emptying in a canine model of diabetic gastroparesis.
Clin Exp Pharmacol Physiol, 35 (7): 788-96. [PMID:18346169]
6. Peeters TL. (2001)
GM-611 (Chugai Pharmaceutical).
Curr Opin Investig Drugs, 2 (4): 555-7. [PMID:11566017]
7. Takanashi H, Cynshi O. (2009)
Motilides: a long and winding road: lessons from mitemcinal (GM-611) on diabetic gastroparesis.
Regul Pept, 155 (1-3): 18-23. [PMID:19345243]
8. Takanashi H, Yogo K, Ozaki K, Koga H, Itoh Z, Omura S. (2007)
In vitro pharmacological characterization of mitemcinal (GM-611), the first acid-resistant non-peptide motilin receptor agonist, in smooth muscle of rabbit small intestine.
Pharmacology, 79 (3): 137-48. [PMID:17183187]