3081. Diclofenac

Nomenclature

CAS number: 15307-86-5
2-[(2,6-Dichlorophenyl)amino]benzeneacetic acid; [o-(2,6-dichloroanilino)phenyl]acetic acid; Motifene (Sankyo).
C14H11Cl2NO2; mol wt 296.15.
C 56.78%, H 3.74%, Cl 23.94%, N 4.73%, O 10.80%.

Description and references

Prepn: NL 6604752; A. Sallmann, R. Pfister, US 3558690 (1966, 1971 both to Geigy). Pharmacology: Renaud, Lecompte, Thromb. Diath. Haemorrh. 24, 577 (1970), C.A. 74, 86215m (1971); Krupp et al., Experientia 29, 450 (1973). HPLC determn in plasma and urine: J. Godbillon et al., J. Chromatogr. 338, 151 (1985). Symposium on pharmacology and clinical experience: Semin. Arthritis Rheum. 15, Suppl. 1, 57-110 (1985); on pharmacology, efficacy and safety: Am. J. Med. 80, Suppl. 4B, 1-87 (1986). Comprehensive description: C. M. Adeyeye, P-K. Li, Anal. Profiles Drug Subs. 19, 123-144 (1990). Review of clinical trials in actinic keratosis: D. C. Peters, R. H. Foster, Drugs Aging 14, 313-319 (1999).

Chemical structure

Properties

Crystals from ether-petr ether, mp 156-158°.

Derivative

Diethylammonium salt.

Nomenclature

CAS number: 78213-16-8
Voltarol (Novartis).
C14H11Cl2NO2.C4H11N; mol wt 369.29.
C 58.54%, H 6.00%, Cl 19.20%, N 7.59%, O 8.66%.

Derivative

Sodium salt.

Nomenclature

CAS number: 15307-79-6
GP-45840; Allvoran (TAD); Benfofen (Sanofi-Synthelabo); Dealgic (Pharmacia); Deflamat (Sankyo); Delphinac (Riemser); Dicloflex (Dexcel); Diclomax (Provalis); Diclophlogont (Azupharma); Dicloreum (Alfa); Duravolten (Dura); Ecofenac (Ecosol); Effekton (Teofarma); Lexobene (Merckle); Neriodin (Nagase); Novapirina (Novartis); Primofenac (Streuli); Prophenatin (Nipro); Rewodina (AWD); Rhumalgan (Sandoz); Voldal (Novartis); Voltaren (Novartis); Xenid (RPG).
C14H10Cl2NNaO2; mol wt 318.13.
C 52.86%, H 3.17%, Cl 22.29%, N 4.40%, Na 7.23%, O 10.06%.

Properties

Crystals from water, mp 283-285°. uv max (methanol) 283 nm (ε 1.05 × 105); (phosphate buffer, pH 7.2) 276 nm (ε 1.01 × 105). Soly at 25°C (mg/ml): deionized water (pH 5.2) >9; methanol >24; acetone 6; acetonitrile <1; cyclohexane <1; HCl (pH 1.1) <1; phosphate buffer (pH 7.2) 6. pKa 4. Partition coefficient (N-octanol/aq. buffer): 13.4. LD50 in mice, rats (mg/kg): ≈390, 150 orally (Krupp).

Derivative

Potassium salt.

Nomenclature

CAS number: 15307-81-0
CGP-45840B; Cataflam (Novartis).
C14H10Cl2KNO2; mol wt 334.24.
C 50.31%, H 3.02%, Cl 21.21%, K 11.70%, N 4.19%, O 9.57%.

Therapeutic Category

Anti-inflammatory.

Keywords

Anti-inflammatory (Nonsteroidal); Arylacetic Acid Derivatives