2-({2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetyl}oxy)acetic acid

• ChemBase ID: 73256
• Molecular Formular: C21H18ClNO6
• Molecular Mass: 415.82372
• Monoisotopic Mass: 415.08226498
• SMILES: Cc1n(c2c(c1CC(=O)OCC(=O)O)cc(cc2)OC)C(=O)c1ccc(cc1)Cl
• Canonical SMILES: COc1ccc2c(c1)c(CC(=O)OCC(=O)O)c(n2C(=O)c1ccc(cc1)Cl)C
• InChI: InChI=1S/C21H18ClNO6/c1-12-16(10-20(26)29-11-19(24)25)17-9-15(28-2)7-8-18(17)23(12)21(27)13-3-5-14(22)6-4-13/h3-9H,10-11H2,1-2H3,(H,24,25)
• InChIKey: FSQKKOOTNAMONP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-({2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetyl}oxy)acetic acid
• IUPAC Traditional name: ({2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetyl}oxy)acetic acid; acemetacin
• Synonyms: Emflex; Acemetacin; 1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetic Acid Carboxymethyl Ester; TV-1322; Acemix; Rantudil; Solart; 1-[p-Chlorobenzoyl]-5-methoxy-2-methylindole-3-acetic acid carboxymethyl ester; Acemetacin; 1-(对氯苯甲酰基)-5-甲氧基-2-甲基吲哚-3-乙酸羧甲酯; 阿西美辛

Database IDs

• CAS Number: 53164-05-9
• EC Number: 258-403-4
• MDL Number: MFCD00151473
• PubChem SID: 24890474; 162038176
• PubChem CID: 1981

CALCULATED PROPERTIES

• Acid pKa: 3.2567155
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 0.9297007
• LogD (pH = 7.4): -0.2813634
• Log P: 3.1535518
• Molar Refractivity: 105.6643 cm^3
• Polarizability: 41.825348 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Light Yellow Solid
• Melting Point: 150-153°C; 150-153°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer; Room Temperature (15-30°C)
• RTECS: NL3521400
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2; II
• Australian Hazchem: 2XE
• Risk Statements: 26/27/28; R:28
• Safety Statements: 22-25-36/37/39-45; S:28-29-36/37/39-45
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H330
• GHS Precautionary statements: P260-P264-P280-P284-P302 + P350-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2

Product Information

• Grade: analytical standard, for drug analysis
• Salt Data: Free Base

DETAILS

MP Biomedicals - 02154668

(1-[p-Chlorobenzoyl]-5-methoxy- 2-methylindole-3-acetic acid carboxymethyl ester)

Selleck Chemicals - S2602

Research Area: Inflammation
Biological Activity:
Acemetacin (Emflex) is a non-steroidal anti-inflammatory drug and a glycolic acid ester of indometacin that is a cyclooxygenase inhibitor.Acemetacin (Emflex) acts as a prodrug. In the body, acemetacin (Emflex) is metabolized to indometacin, which then acts as an inhibitor of cyclooxygenase, producing the anti-inflammatory effects. An advantage of acemetacin is that it reduces gastric damage when compared to indometacin. Acemetacin (Emflex) is used for the treatment of osteoarthritis, rheumatoid arthritis, lower back pain, and relieving post-operative pain. [1][2][3]References on Acemetacin (Emflex)[1] http://en.wikipedia.org/wiki/Acemetacin, , [2] Cochrane Database Syst Rev. , 2009 Jul 8, (3):CD007589[3] Ann Hepatol., 2009 Apr-Jun, 8(2):141-7

Sigma Aldrich - A1674

Biochem/physiol Actions
该非甾体抗炎药 (NSAID) 专门增强蒽环类药（阿霉素、柔红霉素和 epirubium）的细胞毒性。避免 MRP 介导的多药耐药性。
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. A1674.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - A130700

Anti-inflammatory.

REFERENCES

• Chávez-Pi??a AE et al. Ann Hepatol. 2009 Apr-Jun;8(2):141-7.
• Jacobi, H., et al.: Arzneim.-Forsch., 30, 1398 (1980)