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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 of MITEMCINAL FUMARATE

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

Molecular Formula C40H69NO12
Molecular Weight 755.9754
Charge 0
Count
MOL RATIO 2 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 16 / 16
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

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 TargetPharmacologyConditionPotency

PubMed

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
Substance Class Chemical
Record UNII
XU63LQ260J
Record Status Validated (UNII)
Record Version