Amtolmetin guacil

Amtolmetin guacil

Clinical data
Synonyms	ST-679
ATC code	none
Identifiers
IUPAC name (2-methoxyphenyl) 2-[ [2-[1-methyl-5-(4-methylbenzoyl)pyrrol-2-yl]acetyl]ami
CAS Number	87344-06-7 N
PubChem CID	65655
ChemSpider	59091 Y
UNII	323A00CRO9
KEGG	D07453 Y
ChEMBL	CHEMBL1766570 N
ECHA InfoCard	100.207.038
Chemical and physical data
Formula	C24H24N2O5
Molar mass	420.458 g/mol
3D model (JSmol)	Interactive image
SMILES O=C(c1ccc(n1C)CC(=O)NCC(=O)Oc2ccccc2OC)c3ccc(cc3)C
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) Y Key:CWJNMKKMGIAGDK-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Amtolmetin guacil is a NSAID which is a prodrug of tolmetin sodium.

Background

Tolmetin sodium is an effective NSAID approved and marketed for the treatment of rheumatoid arthritis, osteoarthritis and juvenile rheumatoid arthritis. In humans, tolmetin sodium is absorbed rapidly with peak plasma levels observed 30 min after p.o. administration, but it is also eliminated rapidly with a mean plasma elimination t½ of approximately 1 hr. The preparation of slow release formulations or chemical modification of NSAIDs to form prodrugs has been suggested as a method to reduce the gastrotoxicity of these agents.

Amtolmetin guacil 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

Pharmacology

• Almost is absorbed on oral administration. It is concentrated maximum in internal the gastric wall, and highest concentration reached in 2 hours after administration.
• Amtolmetin guacil hydrolysed in to following metabolites Tolmetin, MED5 and Guiacol.
• Elimination will complete in 24 hours. Happens mostly with urine in shape of gluconides products (77%), faecal (7.5%).
• It is advised to take the drug on empty stomach.
• Permanent anti-inflammatory action is continued up to 72 hours, with single administration.

Mechanism of action

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).