WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 529209
CAS#: 110480-13-2
Description: Idremcinal is a motilin receptor agonist potentially for the treatment of gastritis
MedKoo Cat#: 529209
Name: Idremcinal
CAS#: 110480-13-2
Chemical Formula: C39H69NO12
Exact Mass: 743.482
Molecular Weight: 743.97
Elemental Analysis: C, 62.96; H, 9.35; N, 1.88; O, 25.81
Synonym: EM-574; EM574; EM 574;
IUPAC/Chemical Name: (2R,3R,4S,5R,8R,9S,10S,11R,12R)-5-ethyl-3,4-dihydroxy-11-(((2S,3R,4S,6R)-3-hydroxy-4-(isopropyl(methyl)amino)-6-methyltetrahydro-2H-pyran-2-yl)oxy)-9-(((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-2,4,8,10,12,14-hexamethyl-6,15-dioxabicyclo[10.2.1]pentadec-1(14)-en-7-one
InChi Key: FPBKIOZMKHHNLL-CBUZSSJJSA-N
InChi Code: InChI=1S/C39H69NO12/c1-15-27-39(12,45)32(42)22(6)30-20(4)17-38(11,52-30)34(51-36-29(41)26(16-21(5)47-36)40(13)19(2)3)23(7)31(24(8)35(44)49-27)50-28-18-37(10,46-14)33(43)25(9)48-28/h19,21-29,31-34,36,41-43,45H,15-18H2,1-14H3/t21-,22+,23+,24-,25+,26+,27-,28+,29-,31+,32-,33+,34-,36+,37-,38-,39-/m1/s1
SMILES Code: O=C1O[C@H](CC)[C@@](C)(O)[C@H](O)[C@@H](C)C(O2)=C(C)C[C@]2(C)[C@H](O[C@@H]3O[C@H](C)C[C@H](N(C)C(C)C)[C@H]3O)[C@@H](C)[C@H](O[C@@H]4O[C@@H](C)[C@H](O)[C@](C)(OC)C4)[C@H]1C
1: Yogo K, Onoma M, Ozaki K, Koto M, Itoh Z, Omura S, Takanashi H. Effects of oral mitemcinal (GM-611), erythromycin, EM-574 and cisapride on gastric emptying in conscious rhesus monkeys. Dig Dis Sci. 2008 Apr;53(4):912-8. PubMed PMID: 17934842.
2: Ozaki K, Yogo K, Sudo H, Onoma M, Kamei K, Akima M, Koga H, Itoh Z, Omura S, Takanashi H. Effects of mitemcinal (GM-611), an acid-resistant nonpeptide motilin receptor agonist, on the gastrointestinal contractile activity in conscious dogs. Pharmacology. 2007;79(4):223-35. PubMed PMID: 17426410.
3: Takanashi H, Yogo K, Ozaki K, Koga H, Itoh Z, Omura S. 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. 2007;79(3):137-48. PubMed PMID: 17183187.
4: Asakawa A, Akio I, Ohinata K, Fujimiya M, Meguid MM, Yoshikawa M. EM574, a motilide, has an orexigenic activity with affinity for growth-hormone secretagogue receptor. J Gastroenterol Hepatol. 2003 Jul;18(7):881-2. PubMed PMID: 12795766.
5: Asakawa A, Inui A, Ueno N, Makino S, Uemoto M, Fujino MA, Kasuga M. Ob/ob mice as a model of delayed gastric emptying. J Diabetes Complications. 2003 Jan-Feb;17(1):27-8. PubMed PMID: 12505753.
6: Gan G, Cartier LL, Huang Y, Yang Z, Sawchuk RJ. Intestinal absorption and presystemic elimination of the prokinetic agent, EM574, in the rabbit. J Pharm Sci. 2002 Jan;91(1):217-28. PubMed PMID: 11782911.
7: Sato F, Marui S, Inatomi N, Itoh Z, Omura S. EM574, an erythromycin derivative, improves delayed gastric emptying of semi-solid meals in conscious dogs. Eur J Pharmacol. 2000 Apr 28;395(2):165-72. Erratum in: Eur J Pharmacol 2000 Sep 22;404(3):397. PubMed PMID: 10794824.
8: Kondo T, Dote N, Hagimoto T, Yoshimura Y. Application of liquid chromatography-turbo ion spray tandem mass spectrometry for quantitative analysis of a potent motilin receptor agonist, EM574, and its metabolites in human plasma. J Chromatogr B Biomed Sci Appl. 1999 Oct 29;734(1):101-12. PubMed PMID: 10574195.
9: Tanaka T, Mizumoto A, Mochiki E, Suzuki H, Itoh Z, Omura S. Effect of EM574 on postprandial pancreaticobiliary secretion, gastric motor activity, and emptying in conscious dogs. Dig Dis Sci. 1999 Jun;44(6):1100-6. PubMed PMID: 10389679.
10: Tanaka T, Mizumoto A, Mochiki E, Suzuki H, Itoh Z, Omura S. Effects of EM574 and cisapride on gastric contractile and emptying activity in normal and drug-induced gastroparesis in dogs. J Pharmacol Exp Ther. 1998 Nov;287(2):712-9. PubMed PMID: 9808701.
11: Choi MG, Camilleri M, Burton DD, Johnson S, Edmonds A. Dose-related effects of N-demethyl-N-isopropyl-8, 9-anhydroerythromycin A 6,9-hemiacetal on gastric emptying of solids in healthy human volunteers. J Pharmacol Exp Ther. 1998 Apr;285(1):37-40. PubMed PMID: 9535992.
12: Sato F, Sekiguchi M, Marui S, Inatomi N, Shino A, Itoh Z, Omura S. EM574, an erythromycin derivative, is a motilin receptor agonist in the rabbit. Eur J Pharmacol. 1997 Mar 12;322(1):63-71. PubMed PMID: 9088872.
13: Funabashi Y, Maeshiba Y, Inatomi N, Tanayama S, Harada S, Itoh Z, Omura S. Bioactive metabolites of EM574 and EM523, erythromycin derivatives having strong gastrointestinal motor stimulating activity. J Antibiot (Tokyo). 1996 Aug;49(8):794-801. PubMed PMID: 8823513.
14: Itoh Z. Motilin and clinical application. Peptides. 1997;18(4):593-608. Review. PubMed PMID: 9210180.
15: Inatomi N, Sato F, Marui S, Itoh Z, Omura S. Vagus-dependent and vagus-independent mechanisms of action of the erythromycin derivative EM574 and motilin in dogs. Jpn J Pharmacol. 1996 May;71(1):29-38. PubMed PMID: 8791169.
16: Funabashi Y, Hakoda S, Inatomi N, Koyama K, Tanida S, Harada S, Itoh Z, Omura S. Microbial conversion of EM574 and EM523, gastrointestinal motor stimulating agents. J Antibiot (Tokyo). 1996 Aug;49(8):802-10. PubMed PMID: 8823514.
17: Sato M, Sakai T, Sano I, Ito S. [Erythromycin derivative EM574 with motilin agonistic effect on human gastric antrum]. J Smooth Muscle Res. 1995 Dec;31(6):495-8. Japanese. PubMed PMID: 8867985.
18: Satoh M, Sakai T, Sano I, Fujikura K, Koyama H, Ohshima K, Itoh Z, Omura S. EM574, an erythromycin derivative, is a potent motilin receptor agonist in human gastric antrum. J Pharmacol Exp Ther. 1994 Oct;271(1):574-9. PubMed PMID: 7965757.
