Amtolmetin Guacil

• CAT Number: R012597
• CAS Number: 87344-06-7
• Molecular Formula: C24H24N2O5
• Molecular Weight: 420.465
• Purity: ≥95%
• Storage: Room temperature
• IUPAC Name: (2-methoxyphenyl) 2-[[2-[1-methyl-5-(4-methylbenzoyl)pyrrol-2-yl]acetyl]amino]acetate
• InChI: InChI=1S/C24H24N2O5/c1-16-8-10-17(11-9-16)24(29)19-13-12-18(26(19)2)14-22(27)25-15-23(28)31-21-7-5-4-6-20(21)30-3/h4-13H,14-15H2,1-3H3,(H,25,27)
• InChIKey: CWJNMKKMGIAGDK-UHFFFAOYSA-N
• SMILES: CC1=CC=C(C=C1)C(=O)C2=CC=C(N2C)CC(=O)NCC(=O)OC3=CC=CC=C3OC

Amtolmetin guacil, also known ST-679 and MED-15, is a non-acidic prodrug of tolmetin, having similar NSAID properties like tolmetin with additional analgesic, antipyretic, and gastro protective properties. Amtolmetin is formed by amidation of tolmetin by glycine. Amtolmetin guacil stimulates capsaicin receptors present on gastro intestinal walls, because of presence of vanillic moiety and also releases NO which is gastro protective. It also inhibits prostaglandin synthesis and cyclooxygenase (COX).

Reference

1:Species difference in the in vitro and in vivo metabolism of amtolmetin guacil. Hotha KK, Dasari VB, Shaik AN, Syed M, Shivva V, Lakshmanarao RK, Korlakunta JN, Mullangi R.Arzneimittelforschung. 2010;60(11):667-74. doi: 10.1055/s-0031-1296345. PMID: 21175039 2:Validation and clinical application of an LC-ESI-MS/MS method for simultaneous determination of tolmetin and MED5, the metabolites of amtolmetin guacil in human plasma. Hotha KK, Bharathi DV, Kumar SS, Reddy YN, Chatki P, Ravindranath LK, Veera KN, Mullangi R.Biomed Chromatogr. 2010 Oct;24(10):1100-7. doi: 10.1002/bmc.1411. PMID: 20853464 3:Alkenyl C-H insertion of iodonium ylides into pyrroles: studies toward the total syntheses of tolmetin and amtolmetin guacil. Batsila C, Gogonas EP, Kostakis G, Hadjiarapoglou LP.Org Lett. 2003 May 1;5(9):1511-4. PMID: 12713311