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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2D Structure
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Physico-chemical Properties
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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
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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
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]