52443-21-7, Glucametacin,
CAS:52443-21-7
C25H27ClN2O8 / 518.94
MFCD01725278
Glucametacin is a non-steroidal anti-inflammatory drug that has been shown to be effective in the treatment of inflammatory diseases such as arthritis. Glucametacin is an amide, which means it contains both an amine group and a carboxylic acid group. It has been shown to have a chemical stability in the gastrointestinal tract, so it can be taken orally. This drug binds to insulin receptors on target tissues, resulting in increased insulin sensitivity and decreased insulin resistance. It also inhibits choroidal neovascularization by reducing vascular permeability and inhibiting angiogenesis. One possible mechanism for these effects may be due to glucametacin's ability to inhibit tumor growth by covalently binding to DNA and RNA molecules or by preventing protein synthesis.
Title: Glucametacin
CAS Registry Number: 52443-21-7
CAS Name: 2-[[[1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetyl]amino]-2-deoxy-D-glucose
Additional Names: 2-[2-[1-(p-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetamido]-2-deoxy-D-glucose; glucametacine; glucamethacin; indomethacin glucosamide
Molecular Formula: C25H27ClN2O8
Molecular Weight: 518.94
Percent Composition: C 57.86%, H 5.24%, Cl 6.83%, N 5.40%, O 24.66%
Literature References: Deriv of indomethacin, q.v. Prepn: A. Demetrio et al., DE 2223051 (1973 to SIR Lab. Chem. Biol. SpA), C.A. 80, 83529e (1974). Pharmacological study: E. Paroli et al., Arzneim.-Forsch. 28, 819 (1978). Clinical studies: P. Petera et al., Int. J. Clin. Pharmacol. Biopharm. 15, 581 (1977); L. Capelli et al., Curr. Med. Res. Opin. 7, 227 (1981).
Derivative Type: Monohydrate
Trademarks: Euminex (Lacer); Teorema (Panchemie); Teoremac (Farmades)
Molecular Formula: C25H27ClN2O8.H2O
Molecular Weight: 536.96
Percent Composition: C 55.92%, H 5.44%, Cl 6.60%, N 5.22%, O 26.82%
Therap-Cat: Anti-inflammatory.
Keywords: Anti-inflammatory (Nonsteroidal); Arylacetic Acid Derivatives.
CAS Number | 52443-21-7 |
Product Name | Glucametacin |
IUPAC Name | 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]-N-[(2R,3R,4S,5R)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl]acetamide |
Molecular Formula | C25H27ClN2O8 |
Molecular Weight | 518.94 g/mol |
InChI | InChI=1S/C25H27ClN2O8/c1-13-17(10-22(32)27-19(11-29)23(33)24(34)21(31)12-30)18-9-16(36-2)7-8-20(18)28(13)25(35)14-3-5-15(26)6-4-14/h3-9,11,19,21,23-24,30-31,33-34H,10,12H2,1-2H3,(H,27,32)/t19-,21+,23+,24+/m0/s1 |
InChI Key | XLVXAUNDHWERBM-IVGWJTKZSA-N |
SMILES | CC1=C(C2=C(N1C(=O)C3=CC=C(C=C3)Cl)C=CC(=C2)OC)CC(=O)NC(C=O)C(C(C(CO)O)O)O |
Synonyms | glucametacin, glucametacine, glucamethacin1-(p-chlorobenzoyl)-5-methoxy-2-methylindole-3-acetic acid monohydrate glucosamide, glucometacin, glucometacine, Teorema, Teoremac |
Canonical SMILES | CC1=C(C2=C(N1C(=O)C3=CC=C(C=C3)Cl)C=CC(=C2)OC)CC(=O)NC(C=O)C(C(C(CO)O)O)O |
Isomeric SMILES | CC1=C(C2=C(N1C(=O)C3=CC=C(C=C3)Cl)C=CC(=C2)OC)CC(=O)N[C@@H](C=O)[C@H]([C@@H]([C@@H](CO)O)O)O |
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