| Identification | Back Directory | [Name]
glucametacin | [CAS]
52443-21-7 | [Synonyms]
glucametacin
glucometacin
2-[[1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetylamino]-2-deoxy-D-glucose
2-[[2-[1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetyl]amino]-2-deoxy-D-glucose
D-Glucose, 2-[[2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetyl]amino]-2-deoxy- | [EINECS(EC#)]
257-923-9 | [Molecular Formula]
C25H27ClN2O8 | [MDL Number]
MFCD01725278 | [MOL File]
52443-21-7.mol | [Molecular Weight]
518.94 |
| Chemical Properties | Back Directory | [Melting point ]
>160°C (dec.) | [Boiling point ]
793.7±60.0 °C(Predicted) | [density ]
1.44 | [storage temp. ]
Refrigerator, under inert atmosphere | [solubility ]
DMSO (Slightly) | [form ]
Solid | [pka]
13.05±0.20(Predicted) | [color ]
White to Pale Yellow |
| Hazard Information | Back Directory | [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. |
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