Indometacin

Indometacin, also known as indomethacin, is a nonsteroidal anti-inflammatory drug (NSAID) commonly used as a prescription medication to reduce fever, pain, stiffness, and swelling from inflammation. It works by inhibiting the production of prostaglandins, endogenous signaling molecules known to cause these symptoms. It does this by inhibiting cyclooxygenase, an enzyme that catalyzes the production of prostaglandins.

Indometacin
Clinical data
Pronunciation/ɪndˈmɛtəsɪn/
Trade namesIndocid, Indocin
Other namesIndomethacin (USAN US)
AHFS/Drugs.comMonograph
License data
Pregnancy
category
  • AU: C
Routes of
administration
By mouth, rectal, intravenous, topical
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: WARNINGRx-only
Pharmacokinetic data
Bioavailability~100% (oral), 80–90% (rectal)
Protein binding99%
MetabolismLiver
Elimination half-life2.6-11.2 hours (adults), 12-28 hours (infants)
ExcretionKidney (60%), fecal (33%)
Identifiers
  • 2-{1-[(4-Chlorophenyl)carbonyl]-5-methoxy-2-methyl-1H-indol-3-yl}acetic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.000.170
Chemical and physical data
FormulaC19H16ClNO4
Molar mass357.79 g·mol−1
3D model (JSmol)
SMILES
  • Cc1c(c2cc(ccc2n1C(=O)c3ccc(cc3)Cl)OC)CC(=O)O
  • InChI=1S/C19H16ClNO4/c1-11-15(10-18(22)23)16-9-14(25-2)7-8-17(16)21(11)19(24)12-3-5-13(20)6-4-12/h3-9H,10H2,1-2H3,(H,22,23) Y
  • Key:CGIGDMFJXJATDK-UHFFFAOYSA-N Y
  (verify)

It was patented in 1961 and approved for medical use in 1963. It is on the World Health Organization's List of Essential Medicines. In 2021, it was the 253rd most commonly prescribed medication in the United States, with more than 1 million prescriptions.

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