Diclofenac

Title: Diclofenac
CAS Registry Number: 15307-86-5
CAS Name: 2-[(2,6-Dichlorophenyl)amino]benzeneacetic acid
Additional Names: [o-(2,6-dichloroanilino)phenyl]acetic acid
Trademarks: Motifene (Sankyo)
Molecular Formula: C14H11Cl2NO2
Molecular Weight: 296.15
Percent Composition: C 56.78%, H 3.74%, Cl 23.94%, N 4.73%, O 10.80%
Literature 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).
Properties: Crystals from ether-petr ether, mp 156-158°.
Melting point: mp 156-158°
Derivative Type: Diethylammonium salt
CAS Registry Number: 78213-16-8
Trademarks: Voltarol (Novartis)
Molecular Formula: C14H11Cl2NO2.C4H11N
Molecular Weight: 369.29
Percent Composition: C 58.54%, H 6.00%, Cl 19.20%, N 7.59%, O 8.66%
Derivative Type: Sodium salt
CAS Registry Number: 15307-79-6
Manufacturers' Codes: GP-45840
Trademarks: 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)
Molecular Formula: C14H10Cl2NNaO2
Molecular Weight: 318.13
Percent Composition: 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 (e 1.05 ´ 105); (phosphate buffer, pH 7.2) 276 nm (e 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).
Melting point: mp 283-285°
pKa: pKa 4
Log P: Partition coefficient (N-octanol/aq. buffer): 13.4
Absorption maximum: uv max (methanol) 283 nm (e 1.05 ´ 105); (phosphate buffer, pH 7.2) 276 nm (e 1.01 ´ 105)
Toxicity data: LD50 in mice, rats (mg/kg): ~390, 150 orally (Krupp)
Derivative Type: Potassium salt
CAS Registry Number: 15307-81-0
Manufacturers' Codes: CGP-45840B
Trademarks: Cataflam (Novartis)
Molecular Formula: C14H10Cl2KNO2
Molecular Weight: 334.24
Percent Composition: C 50.31%, H 3.02%, Cl 21.21%, K 11.70%, N 4.19%, O 9.57%
Therap-Cat: Anti-inflammatory.
Keywords: Anti-inflammatory (Nonsteroidal); Arylacetic Acid Derivatives.
Diclofop-methyl Diclosulam Dicloxacillin Dicobalt Octacarbonyl Dicofol

Diclofenac
Diclofenac.svg
Diclofenac 3D 2ek.png
Systematic (IUPAC) name
2-(2-(2,6-dichlorophenylamino)phenyl)acetic acid
Clinical data
Trade names Aclonac, Cataflam, Voltaren
AHFS/Drugs.com monograph
MedlinePlus a689002
Pregnancy cat. C (AU) C (1st. and 2nd. trimenon), D (third trimenon)
Legal status Prescription Only (S4) (AU) P (UK) Rx-only most preparations/countries, limited OTC in some countries, manufacture and veterinary use is banned in India, Nepal, and Pakistan due to imminent extinction of local vultures
Routes oral, rectal, intramuscular, intravenous (renal- and gallstones), topical
Pharmacokinetic data
Protein binding more than 99%
Metabolism hepatic, no active metabolites exist
Half-life 1.2-2 hr (35% of the drug enters enterohepatic recirculation)
Excretion 40% biliary 60% urine
Identifiers
CAS number 15307-86-5 YesY
ATC code D11AX18 M01AB05, M02AA15, S01BC03
PubChem CID 3033
IUPHAR ligand 2714
DrugBank DB00586
ChemSpider 2925 YesY
UNII 144O8QL0L1 YesY
KEGG D07816 YesY
ChEBI CHEBI:47381 YesY
ChEMBL CHEMBL139 YesY
PDB ligand ID DIF (PDBe, RCSB PDB)
Chemical data
Formula C14H11Cl2NO2 
Mol. mass 296.148 g/mol
 N (what is this?)  (verify)

Diclofenac (INN; see trade names below) is a nonsteroidal anti-inflammatory drug (NSAID) taken or applied to reduce inflammation and as an analgesic reducing pain in certain conditions. It is supplied as or contained in medications under a variety of trade names.

The name "diclofenac" derives from its chemical name: 2-(2,6-dichloranilino) phenylacetic acid. Diclofenac was originally developed by Ciba-Geigy (now Novartis) in 1973.[1] It was first introduced in the UK in 1979.[2][3]

In the United Kingdom, India, Brazil, and the United States, diclofenac may be supplied as either the sodium or potassium salt; in China, it is most often supplied as the sodium salt, while in some other countries it is only available as the potassium salt. Diclofenac is available as a generic drug in a number of formulations, including diclofenac diethylamine, which is applied topically. Over-the-counter (OTC) use is approved in some countries for minor aches and pains and fever associated with common infections.