2-[(2-{2-[(2,6-dichlorophenyl)amino]phenyl}acetyl)oxy]acetic acid

• ChemBase ID: 121642
• Molecular Formular: C16H13Cl2NO4
• Molecular Mass: 354.18472
• Monoisotopic Mass: 353.02216326
• SMILES: N(c1c(Cl)cccc1Cl)c1c(CC(=O)OCC(=O)O)cccc1
• Canonical SMILES: OC(=O)COC(=O)Cc1ccccc1Nc1c(Cl)cccc1Cl
• InChI: InChI=1S/C16H13Cl2NO4/c17-11-5-3-6-12(18)16(11)19-13-7-2-1-4-10(13)8-15(22)23-9-14(20)21/h1-7,19H,8-9H2,(H,20,21)
• InChIKey: MNIPYSSQXLZQLJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2-{2-[(2,6-dichlorophenyl)amino]phenyl}acetyl)oxy]acetic acid
• IUPAC Traditional name: aceclofenac; 2-[(2-{2-[(2,6-dichlorophenyl)amino]phenyl}acetyl)oxy]acetic acid
• Synonyms: 2-(2-(2-((2,6-dichlorophenyl)amino)phenyl)acetoxy)acetic acid; 2-[(2,6-Dichlorophenyl)amino]benzeneacetic acid carboxymethyl ester;; Aceclofenac; 2-[(2,6-Dichlorophenyl)-amino]benzeneacetic Acid Carboxymethyl Ester; Glycolic Acid [o-(2,6-Dichloroanilino)phenyl]acetate Ester; PR-82/3; Airtal; Aceclofar; Falcol; Gerbin; Preservex; Tresquim; Zerodol; Aceclofenac; More...

Database IDs

• CAS Number: 89796-99-6
• MDL Number: MFCD00864296
• PubChem SID: 162215995
• PubChem CID: 71771

CALCULATED PROPERTIES

• Molar Refractivity: 86.3151 cm^3
• Polarizability: 33.552105 Å^3
• Polar Surface Area: 75.63 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true
• Acid pKa: 3.4446704
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.8380795
• LogD (pH = 7.4): 0.49170047
• Log P: 3.8828866

PROPERTIES

Physical Property

• Solubility: DMSO: ≥20 mg/mL; Ethanol
• Apperance: off-white to light tan powder; White Crystalline Solid
• Melting Point: 149-150°C

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Nature polluting (N); Toxic (T)
• German water hazard class: 3
• Risk Statements: 25-36-50/53
• Safety Statements: 26-45-60-61
• GHS Pictograms: GHS06; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H319-H410
• GHS Precautionary statements: P273-P301 + P310-P305 + P351 + P338-P501
• Storage Temperature: room temp

Pharmacology Properties

• Mechanism of Action: Cyclooxygenase-Inhibitor-1; Cyclooxygenase-Inhibitor-2; Prostaglandin-Antagonist-E2

Product Information

• Purity: ≥98% (HPLC)
• Application(s): Analgesic; Antiinflammatory agent
• Empirical Formula (Hill Notation): C16H13Cl2NO4

DETAILS

Sigma Aldrich - A8861

Biochem/physiol Actions
Non-steroidal, anti-inflammatory drug (NSAID), with selectivity for COX-2 over COX-1.

Toronto Research Chemicals - A130400

Aceclofenac is an anti-inflammatory and analgesic drug.

REFERENCES

• Yscla, A., et al.: Drugs Exp. Clin. Res., 14, 491 (1988)
• Ballesteros, R., et al.: Clin. Trials J., 27, 12 (1990)
• Ger. Pat., 1969, 1 815 802; CA, 72, 12385d, (synth)
• Menasse-Gdynia, R. et al., Experientia, 1973, 29, 450, (pharmacol)
• Kracmar, J. et al., Pharmazie, 1976, 31, 614, (uv)
• Tamura, Y. et al., Chem. Pharm. Bull., 1984, 32, 1995, (synth)
• Spanish Pat., 1984, 520 813; CA, 104, 88301, (Aceclofenac)
• Sallman, A.R. et al., Am. J. Med., 1986, 80, 1, (revs)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 3010, (synonyms)
• Todd, P.A. et al., Drugs, 1988, 35, 244, (rev)
• Adeyeye, C.M. et al., Anal. Profiles Drug Subst., 1990, 19, 123, (rev)
• Grau, M. et al., Arzneim.-Forsch., 1991, 41, 1265, (Aceclofenac, rev)
• Castellari, C. et al., Acta Cryst. C, 1994, 50, 1723; 1997, 53, 794-797, (cryst struct)
• Hanses, A. et al., Arch. Pharm. (Weinheim, Ger.), 1995, 328, 257, (hplc)
• Brogden, R.N. et al., Drugs, 1996, 52, 113, (Aceclofenac, rev, pharmacol)
• McNeely, W. et al., Drugs, 1999, 57, 991-1003, (rev)
• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 12; 31
• Dooley, M. et al., Drugs, 2001, 61, 1351-1378, (rev)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, DEO600