N-(2-phenylethyl)-Indomethacin amide - CAS 261766-32-9
Catalog number: 261766-32-9
Category: Inhibitor
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Molecular Formula:
C27H25ClN2O3
Molecular Weight:
461
COA:
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Targets:
Cox-2
Description:
A potent elective reversible inhibitors of COX-2
Brife Description:
A potent elective reversible inhibitors of COX-2
Appearance:
A crystalline solid
Synonyms:
N-(2-phenylethyl)-1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetamide; N-2PIA
Storage:
Store at -20°C
MSDS:
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Quality Standard:
In-house
Quantity:
Grams-Kilos
InChIKey:
VYDBTNADENXYSN-UHFFFAOYSA-N
InChI:
1S/C27H25ClN2O3/c1-18-23(17-26(31)29-15-14-19-6-4-3-5-7-19)24-16-22(33-2)12-13-25(24)30(18)27(32)20-8-10-21(28)11-9-20/h3-13,16H,14-15,17H2,1-2H3,(H,29,31)
Canonical SMILES:
O=C(CC1=C(C)N(C(C2=CC=C(Cl)C=C2)=O)C3=C1C=C(OC)C=C3)N([H])CCC4=CC=CC=C4
1.Methyl 3'-benzyl-4'-(2-chloro-phen-yl)-1'-methyl-2-oxo-spiro-[indoline-3,2'-pyrrolidine]-3'-carboxyl-ate.
Anuradha T;Devaraj A;Seshadri PR;Bakthadoss M Acta Crystallogr Sect E Struct Rep Online. 2013 Jul 6;69(Pt 8):o1214. doi: 10.1107/S1600536813018424. eCollection 2013.
In the title compound, C27H25ClN2O3, the methyl-pyrrolidine ring adopts an envelope conformation with the N atom at the flap. The mean plane of the pyrrolidine ring makes dihedral angles of 82.1 (1), 84.4 (1) and 79.8 (1)°, respectively, with the adjacent benzene ring, the mean plane of the indoline ring system and the phenyl ring. The mol-ecular structure is stabilized by intra-molecular C-H⋯O hydrogen bonds. In the crystal, mol-ecules are linked into chains along [101] by N-H⋯O hydrogen bonds. C-H⋯π inter-actions are observed between the chains.
2.Studies on the metabolism of the novel, selective cyclooxygenase-2 inhibitor indomethacin phenethylamide in rat, mouse, and human liver microsomes: identification of active metabolites.
Remmel RP;Crews BC;Kozak KR;Kalgutkar AS;Marnett LJ Drug Metab Dispos. 2004 Jan;32(1):113-22.
The metabolism of 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-N-phenethyl-acetamide (indomethacin phenethylamide, LM-4108), a highly selective cyclooxygenase-2 inhibitor, was studied in rat, mouse, and human liver microsomes. The primary site of oxidation in all species examined was on the methylene carbons of the phenethyl side chain to form the 1'- and 2'-hydroxy and 2'-oxo metabolites as determined by electrospray ionization liquid chromatography-tandem mass spectrometry. Half-lives for the disappearance of 10 microM LM-4108 in rat, human, and mouse liver microsomes (0.15 pmol P450/ml) were 11 min, 21 min, and 51 min, respectively. Indomethacin formation was not observed in incubations with rat, mouse, or human liver microsomes. Both the 2'-hydroxy-LM-4108 and 2'-oxo-LM-4108 metabolites were synthesized and found to be equipotent to the parent compound with regard to COX-2 inhibitory potency and selectivity [2'-hydroxy-LM-4108: IC(50)(COX-2) = 0.06 microM, IC(50)(COX-1) >66 microM; 2'-oxo-LM-4108: IC(50)(COX-2) = 0.05 microM, IC(50)(COX-1) >66 microM]. The formation of the metabolites was strongly inhibited by specific CYP3A4 inhibitors ketoconazole and troleandomycin but not by other isoform-selective inhibitors.
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CAS 261766-32-9 N-(2-phenylethyl)-Indomethacin amide

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