Diclofenac

Diclofenac
	Structure of diclofenac with ball and stick model
Clinical data
Pronunciation	/daɪˈkloʊfənæk/ or /dɪklɒˈfɛnæk/
Trade names	Voltaren, others
AHFS/Drugs.com	Monograph
MedlinePlus	a689002
License data	US DailyMed: Diclofenac;
Pregnancy; category	AU: C;
Routes of; administration	Orally, rectal, intramuscular, intravenous, topical, ophthalmic
Drug class	Nonsteroidal anti-inflammatory agents
ATC code	D11AX18 (WHO) M01AB05 (WHO), M02AA15 (WHO), S01BC03 (WHO);
Legal status
Legal status	AU: S4 (Prescription only) / S3 / S2; CA: ℞-only; UK: POM (Prescription only) / P / GSL; US: ℞-only / OTC; In general: ℞ (Prescription only);
Pharmacokinetic data
Protein binding	More than 99%
Metabolism	Liver, oxidative, primarily by CYP2C9, also by CYP2C8, CYP3A4, as well as conjugative by glucuronidation (UGT2B7) and sulfation; no active metabolites exist
Onset of action	Within 4 hours (gel), 30 min (non-gel)
Elimination half-life	1.2–2 h (35% of the drug enters enterohepatic recirculation)
Excretion	35% bile, 65% urine
Identifiers
	IUPAC name [2-(2,6-Dichloroanilino)phenyl]acetic acid;
CAS Number	15307-86-5 ;
PubChem CID	3033;
IUPHAR/BPS	2714;
DrugBank	DB00586 ;
ChemSpider	2925 ;
UNII	144O8QL0L1;
KEGG	D07816 ;
ChEBI	CHEBI:47381 ;
ChEMBL	ChEMBL139 ;
PDB ligand	DIF (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID6022923 ;
ECHA InfoCard	100.035.755
Chemical and physical data
Formula	C14H11Cl2NO2
Molar mass	296.15 g·mol−1
3D model (JSmol)	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) ; Key:DCOPUUMXTXDBNB-UHFFFAOYSA-N ;
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Diclofenac, sold under the brand name Voltaren among others, is a nonsteroidal anti-inflammatory drug (NSAID) used to treat pain and inflammatory diseases such as gout. It can be taken orally (swallowed by mouth), inserted rectally as a suppository, injected intramuscularly, injected intravenously, applied to the skin topically, or through eye drops. Improvements in pain last up to eight hours. It is also available as the fixed-dose combination diclofenac/misoprostol (Arthrotec) to help protect the stomach; however, proton pump inhibitors such as omeprazole are typically first-line since they are at least as effective as misoprostol, but with better tolerability.

Common side effects include abdominal pain, gastrointestinal bleeding, nausea, dizziness, headache, and swelling. Serious side effects may include heart disease, stroke, kidney problems, and stomach ulceration. Use is not recommended in the third trimester of pregnancy. It is likely safe during breastfeeding. Diclofenac is believed to work by decreasing the production of prostaglandins, like other drugs in this class.

In 2022, it was the 51st most commonly prescribed medication in the United States, with more than 12 million prescriptions. It is available as its acid or in two salts, as either diclofenac sodium or potassium.