sodium 2-{2-[(2,6-dichlorophenyl)amino]phenyl}acetate

• ChemBase ID: 72819
• Molecular Formular: C14H10Cl2NNaO2
• Molecular Mass: 318.13047
• Monoisotopic Mass: 316.99862821
• SMILES: c1c(c(c(cc1)Cl)Nc1c(CC(=O)[O-])cccc1)Cl.[Na+]
• Canonical SMILES: [O-]C(=O)Cc1ccccc1Nc1c(Cl)cccc1Cl.[Na+]
• InChI: InChI=1S/C14H11Cl2NO2.Na/c15-10-5-3-6-11(16)14(10)17-12-7-2-1-4-9(12)8-13(18)19;/h1-7,17H,8H2,(H,18,19);/q;+1/p-1
• InChIKey: KPHWPUGNDIVLNH-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 2-{2-[(2,6-dichlorophenyl)amino]phenyl}acetate
• IUPAC Traditional name: sodium diclofenac(1-); potassium diclofenac(1-)
• Synonyms: Voltaren; Solaraze; Ecofenac; Benfofen; Diclofenac sodium; Diclofenac; 2-[(2,6-Dichlorophenyl)amino]benzeneacetic acid sodium salt; Diclofenac sodium salt; 2-((2,6-Dichlorophenyl)aminobenzeneacetic Acid; [o-(2,6-Dichloroanilino)phenyl]acetic Acid Monosodium Salt; Sodium Diclofenac; Sorelmon; Tsudohmin; Valetan; Voldal; Voltaren Ophtha; Delphimix; Diacron; Naclof; Naclofen; Neriodin; Novapirina; Orthofen; Orthophen; 2-[(2,6-Dichlorophenyl)amino]-benzeneacetic acid monosodium salt; DICLOFENAC SODIUM SALT

Database IDs

• CAS Number: 15307-79-6
• EC Number: 239-346-4
• MDL Number: MFCD00082251
• PubChem SID: 24277712; 162037740
• PubChem CID: 5018304

CALCULATED PROPERTIES

• Acid pKa: 3.995652
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.7453504
• LogD (pH = 7.4): 1.0974493
• Log P: 4.2590094
• Molar Refractivity: 86.2985 cm^3
• Polarizability: 28.92262 Å^3
• Polar Surface Area: 52.16 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol; H2O: soluble50 mg/mL; Methanol; Water
• Apperance: Off-White to Pale Beige Solid
• Melting Point: >262°C (dec.); 280-281°C
• Density: 0.55-0.7 g/ml

Safety Information

• Storage Condition: -20°C; -20°C Freezer; Room Temperature (15-30°C)
• RTECS: AG6330000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3; III
• Australian Hazchem: 2X
• Risk Statements: 25; R:25
• Safety Statements: 22-36/37-45; 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: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: room temp

Pharmacology Properties

• Target: COX
• Gene Information: human ... PTGS1(5742)

Product Information

• Grade: ACS; certified reference material
• Salt Data: sodium salt
• Packaging: pkg of 1 g
• Pharmacopeia Traceability: traceable to BP 619; traceable to PhEur S0765000; traceable to USP 118880
• Empirical Formula (Hill Notation): C14H10Cl2NNaO2

DETAILS

MP Biomedicals - 02157660

Sodium Salt
Cyclooxygenase inhibitor.

Selleck Chemicals - S1903

Research Area: cancer
Biological Activity:
Diclofenac is a non-selective COX inhibitor with IC50 of 60 and 220 nM for ovine COX-1 and -2, respectively. It inhibits human COX-1 and -2 with IC50 values of 0.9-2.7 and 1.5-20 µM, respectively. It is thought that the primary mechanism responsible for its anti-inflammatory, antipyretic, and analgesic action is inhibition of prostaglandin synthesis by inhibition of cyclooxygenase (COX), and it appears to inhibit DNA synthesis. [1][2]

Sigma Aldrich - D6899

Biochem/physiol Actions
Standard NSAID and cyclooxygenase (COX) inhibitor. Major metabolites are 4′-hydroxydiclofenac and 5′-hydroxydiclofenac. Has been used as substrate selective for CYP2C9.

Sigma Aldrich - PHR1144

Biochem/physiol Actions
Standard NSAID and cyclooxygenase (COX) inhibitor. Major metabolites are 4′-hydroxydiclofenac and 5′-hydroxydiclofenac. Has been used as substrate selective for CYP2C9.
General description
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34.
Other Notes
Values of analytes vary lot to lot.

Toronto Research Chemicals - D436450

Diclofenac-13C6 Sodium Salt13C Labelled Diclofenac Sodium Salt is a known nonsteroidal anti-inflammatory compound and cyclooxygenase (COX) inhibitor.

REFERENCES

• http://en.wikipedia.org/wiki/Diclofenac
• Patrignani P et al. J Physiol Pharmacol. 1997 Dec;48(4):623-31.
• Kenny, J. R., et al.: J. Med. Chem., 47, 2816 (2004)
• Sasaki, A., et al.: J. Pharmacol. Sci., 108, 266 (2004)
• Dalvie, D., et al.: Chem. Res. Toxicol., 22, 357 (2004)