Amtolmetin guacil

Amtolmetin guacil
Systematic (IUPAC) name

(2-methoxyphenyl) 2-[ [2-[1-methyl-5-(4-methylbenzoyl)pyrrol-2-yl]acetyl]ami
Identifiers
CAS Number	87344-06-7^N
ATC code	None
PubChem	CID 65655
ChemSpider	59091^Y
UNII	323A00CRO9^N
KEGG	D07453^Y
ChEMBL	CHEMBL1766570^N
Synonyms	ST-679
Chemical data
Formula	C₂₄H₂₄N₂O₅
Molar mass	420.458 g/mol
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).

Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)

Pyrazolones / Pyrazolidines	Aminophenazone Ampyrone Azapropazone Clofezone Famprofazone Feprazone Kebuzone Metamizole Mofebutazone Morazone Nifenazone Oxyphenbutazone Phenazone Phenylbutazone Propyphenazone Sulfinpyrazone Suxibuzone^‡

Salicylates	Aspirin (acetylsalicylic acid)^# Aloxiprin Benorylate Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Methyl salicylate Salsalate Salicin Salicylamide Salicylic acid (salicylate) Sodium salicylate

Acetic acid derivatives and related substances	Aceclofenac Acemetacin Alclofenac Amfenac Bendazac Bromfenac Bumadizone Bufexamac Diclofenac Difenpiramide Etodolac Felbinac Fentiazac Indomethacin Indomethacin farnesil Ketorolac Lonazolac Oxametacin Proglumetacin Sulindac Tolmetin Zomepirac^†

Oxicams	Ampiroxicam Droxicam Lornoxicam Meloxicam Piroxicam Tenoxicam

Propionic acid derivatives (profens)	Alminoprofen Benoxaprofen^† Carprofen^‡ Dexibuprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen^# Ibuproxam Indoprofen^† Ketoprofen Loxoprofen Miroprofen Naproxen Oxaprozin Pirprofen Suprofen Tarenflurbil Tepoxalin^‡ Tiaprofenic acid Vedaprofen^‡ COX-inhibiting nitric oxide donator: Naproxcinod

N-Arylanthranilic acids (fenamates)	Azapropazone Etofenamate Flufenamic acid Flunixin Meclofenamic acid Mefenamic acid Morniflumate Niflumic acid Tolfenamic acid

Coxibs	Apricoxib Celecoxib Cimicoxib^‡ Deracoxib^‡ Etoricoxib Firocoxib^‡ Lumiracoxib^† Mavacoxib^‡ Parecoxib Robenacoxib^‡ Rofecoxib^† Valdecoxib^†

Other	Aminopropionitrile Benzydamine Chondroitin sulfate Diacerein Fluproquazone Glucosamine Glycosaminoglycan Hyperforin Nabumetone Nimesulide Oxaceprol Proquazone Superoxide dismutase/Orgotein Tenidap

Items listed in bold indicate initially developed compounds of specific groups. ^#WHO-EM ^†Withdrawn drugs. ^‡Veterinary use medications.

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