mitemcinal

Also known as GM-611

Mitemcinal (GM-611 or 3'-N-dimethyl-11-deoxy-3'-N-isopropyl-12-O-methyl-11-oxo-8,9-didehydroerythromycin) is a motilin agonist derived from the macrolide antibiotic, erythromycin. It was discovered in the labs of Chugai Pharma. Mitemcinal is orally administered and it is believed to have strong promotility (or prokinetic) effects. Promotility drugs relieve symptoms of reflux by speeding the clearance of acid from the oesophagus and stomach. The parent compound, erythromycin, has these characteristics, but mitemcinal lacks the antibiotic properties of erythromycin.

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Vinony's link graph records 2 inbound references to mitemcinal, and connects out to digital object identifier, chemical formula and molar mass.

Vinony files it under Chembox image size set and Macrolides.

Vinony links it to 5 Wikipedia language editions.

Chemical data

Formula: C40H69NO12
Molecular weight: 756 g/mol
IUPAC name: (2S,4R,5R,8R,9S,10S,11R,12R)-5-ethyl-9-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-11-[(2S,3R,4S,6R)-3-hydroxy-6-methyl-4-[methyl(propan-2-yl)amino]oxan-2-yl]oxy-4-methoxy-2,4,8,10,12,14-hexamethyl-6,15-dioxabicyclo[10.2.1]pentadec-1(14)-ene-3,7-dione
SMILES: CC[C@@H]1[C@@](C(=O)[C@H](C2=C(C[C@@](O2)([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]3C[C@@]([C@H]([C@@H](O3)C)O)(C)OC)C)O[C@H]4[C@@H]([C@H](C[C@H](O4)C)N(C)C(C)C)O)C)C)C)(C)OC
InChIKey: BELMMAAWNYFCGF-PZXAHSFZSA-N
XLogP: 4.1
Polar surface area: 152 Å²
H-bond donors: 2
H-bond acceptors: 13
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Phase 2
Molecule type: Small molecule

via ChEMBL · EBI

Wikidata facts

Subclass of: chemical compound
Mass: 755.482

Show 3 more facts

chemical formula: C₄₀H₆₉NO₁₂
canonical SMILES: CCC1C(C(=O)C(C2=C(CC(O2)(C(C(C(C(C(=O)O1)C)OC3CC(C(C(O3)C)O)(C)OC)C)OC4C(C(CC(O4)C)N(C)C(C)C)O)C)C)C)(C)OC
isomeric SMILES: CC[C@@H]1[C@@](C(=O)[C@H](C2=C(C[C@@](O2)([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]3C[C@@]([C@H]([C@@H](O3)C)O)(C)OC)C)O[C@H]4[C@@H]([C@H](C[C@H](O4)C)N(C)C(C)C)O)C)C)C)(C)OC

Sources (4)

via Wikidata · CC0

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Encyclopedic overview

1 sections

Contents

Notes and references

Presently, erythromycin is commonly used off-label for gastric motility indications such as gastroparesis. If mitemcinal can be shown to be as effective a promotility agent, it would represent a significant advance in the GI field as treatment with this drug would not carry the risk of unintentional selection of antibiotic-resistant bacteria. This concept greatly intrigued Chugai, and the company pursued it as an ideal candidate for a long-term prokinetic agent to treat lower gastrointestinal deficiencies including gastroparesis.

Excerpted from Wikipedia’s “mitemcinal” article, available under the CC BY-SA 4.0 licence.