Diclofenac

Diclofenac

Clinical data
Trade names	Aclonac, Cataflam, Voltaren, see trade names
AHFS/Drugs.com	Monograph
MedlinePlus	a689002
Pregnancy category	AU: C US: C (Risk not ruled out) in 1st and 2nd trimester, D in 3rd trimester
Routes of administration	oral, rectal, intramuscular, intravenous (renal- and gallstones), topical
ATC code	D11AX18 (WHO) M01AB05 (WHO), M02AA15 (WHO), S01BC03 (WHO)
Legal status
Legal status	AU: S2 (Pharmacy only) – S4 UK: POM (Prescription only) (P for topical formulation) ℞-only in 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
Pharmacokinetic data
Protein binding	More than 99%
Metabolism	hepatic, oxidative, primarily by CYP2C9, also by CYP2C8, CYP3A4, as well as conjugative by glucuronidation (UGT2B7) and sulfation; no active metabolites exist
Biological half-life	1.2-2 hr (35% of the drug enters enterohepatic recirculation)
Excretion	40% biliary 60% urine
Identifiers
IUPAC name [2-(2,6-Dichloroanilino)phenyl]acetic acid
CAS Number	15307-86-5 Y
PubChem (CID)	3033
IUPHAR/BPS	2714
DrugBank	DB00586 N
ChemSpider	2925 Y
UNII	144O8QL0L1 Y
KEGG	D07816 Y
ChEBI	CHEBI:47381 Y
ChEMBL	CHEMBL139 Y
PDB ligand ID	DIF (PDBe, RCSB PDB)
ECHA InfoCard	100.035.755
Chemical and physical data
Formula	C14H11Cl2NO2
Molar mass	296.148 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(O)Cc1ccccc1Nc2c(Cl)cccc2Cl
InChI InChI=1S/C14H11Cl2NO2/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) Y Key:DCOPUUMXTXDBNB-UHFFFAOYSA-N Y
NY (what is this?)

Diclofenac (sold under a number of trade names) 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 first synthesized by Alfred Sallmann and Rudolf Pfister and introduced as Voltaren by Ciba-Geigy (now Novartis) in 1973.

In the United Kingdom, United States, India, and Brazil 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. It 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. As of 2015 the cost for a typical month of medication in the United States is 50 to 100 USD.

The drug's use in animals is controversial due to its toxicity which can rapidly kill scavenging birds that may eat dead animals. It has been banned for veterinary use in many countries.

Diclofenac is used to treat pain, inflammatory disorders, and dysmenorrhea.

Inflammatory disorders may include musculoskeletal complaints, especially arthritis, rheumatoid arthritis, polymyositis, dermatomyositis, osteoarthritis, dental pain, temporomandibular joint (TMJ) pain, spondylarthritis, ankylosing spondylitis, gout attacks, and pain management in cases of kidney stones and gallstones. An additional indication is the treatment of acute migraines. Diclofenac is used commonly to treat mild to moderate postoperative or post-traumatic pain, in particular when inflammation is also present, and is effective against menstrual pain and endometriosis.