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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
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
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: O43193
Gene ID: 2862.0
Gene Symbol: MLNR
Target Organism: Homo sapiens (Human)
PubMed

PubMed

TitleDatePubMed
Patents

Patents

Sample Use Guides

12 weeks of treatment with oral tablets given twice a day of GM-611 (Mitemcinal) 5mg, 10mg
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:55:38 GMT 2023
Edited
by admin
on Fri Dec 15 15:55:38 GMT 2023
Record UNII
XU63LQ260J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MITEMCINAL FUMARATE
USAN   WHO-DD  
USAN  
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
Created by admin on Fri Dec 15 15:55:38 GMT 2023 , Edited by admin on Fri Dec 15 15:55:38 GMT 2023
PRIMARY
DRUG BANK
DBSALT002825
Created by admin on Fri Dec 15 15:55:38 GMT 2023 , Edited by admin on Fri Dec 15 15:55:38 GMT 2023
PRIMARY
USAN
MM-18
Created by admin on Fri Dec 15 15:55:38 GMT 2023 , Edited by admin on Fri Dec 15 15:55:38 GMT 2023
PRIMARY
ChEMBL
CHEMBL2110756
Created by admin on Fri Dec 15 15:55:38 GMT 2023 , Edited by admin on Fri Dec 15 15:55:38 GMT 2023
PRIMARY
CAS
154802-96-7
Created by admin on Fri Dec 15 15:55:38 GMT 2023 , Edited by admin on Fri Dec 15 15:55:38 GMT 2023
PRIMARY
NCI_THESAURUS
C170187
Created by admin on Fri Dec 15 15:55:38 GMT 2023 , Edited by admin on Fri Dec 15 15:55:38 GMT 2023
PRIMARY
FDA UNII
XU63LQ260J
Created by admin on Fri Dec 15 15:55:38 GMT 2023 , Edited by admin on Fri Dec 15 15:55:38 GMT 2023
PRIMARY
EPA CompTox
DTXSID101027165
Created by admin on Fri Dec 15 15:55:38 GMT 2023 , Edited by admin on Fri Dec 15 15:55:38 GMT 2023
PRIMARY
PUBCHEM
11513721
Created by admin on Fri Dec 15 15:55:38 GMT 2023 , Edited by admin on Fri Dec 15 15:55:38 GMT 2023
PRIMARY
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ACTIVE MOIETY