glucametacin

Description

Glucametacin is used to treat inflammatory and degenerative arthropathy. The compound is well tolerated with significantly less gastrointestinal distress than indomethacin. Glucametacin does not appear to be metabolized to indomethacin.

Originator

Glucametacin,Shanghai Lansheng Corporation

Uses

A nonsteroidal antiinflammatory analgesic. An indomethacin conjugates with D-glucosamine was prepared for reducing ulcerogenic potency, increasing the bioavailability of indomethacin and exerting the coordinative effects on osteoarthritis.

Manufacturing Process

125 g (75 ml) thionyl chloride were added to 30 g 1-(p-chlorobenzoyl)-2- methyl-5-methoxy-indolyl-3-acetic acid (indometacine) in 200 ml of dry chloroform and heated to reflux for 15 min. The solvent was distilled off and the residue was recrystallized from benzene to give 23 g 1-(p-chlorobenzoyl)- 2-methyl-5-methoxy-indolyl-3-acetyl chloride. MP: 126°-129°C.
43 g d-(+)-glucosamine hydrochloride in 140 ml of cold water, 20 g above prepared acetyl chloride in any inert solvent (chloroform, ethyl acetate, dioxane) and 35 ml 12% NaOH was mixed and stirred for 1hour at a room temperature. Then it was diluted with water and a solid was filtered off, washed and dried in vacuum. 10 volumes (by weight) methanol was added to the obtained dry product, filtered off and dried in vacuum. Yield of 1-(pchlorobenzoyl)-5-methoxy-2-methylindole-3-acetic acid monohydrate glucosamide 20 g. Glucametacine was obtained as a powder. MP: about 218°C (with decomposition).

Therapeutic Function

Antiinflammatory, Analgesic, Antipyretic

Trade name

Euminex (Asta Medica, Spain), Teoremin (Labofarma/Degussa, Brazil).

Synthesis

glucametacin is prepared by acylation of d-glucosamine with indomethacin acid chloride (prepared from indomethacin and thionyl chloride) in the presence of sodium hydroxide.

Raw materials

Preparation Products