Indometacin

Indometacin

Systematic (IUPAC) name
2-{1-[(4-Chlorophenyl)carbonyl]-5-methoxy-2-methyl-1H-indol-3-yl}acetic acid
Clinical data
Pronunciation	/ɪndoʊˈmɛtəsᵻn/
Trade names	Indocid, Indocin
AHFS/Drugs.com	Monograph
License data	US FDA: Indomethacin
Pregnancy category	AU: C C/D (US)
Routes of administration	Oral, rectal, IV, topical
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	~100% (oral), 80–90% (rectal)
Protein binding	99%
Metabolism	Hepatic
Biological half-life	2.6-11.2 hours (adults), 12-28 hours (infants)
Excretion	Renal (60%), fecal (33%)
Identifiers
CAS Number	53-86-1 Y
ATC code	C01EB03 (WHO) M01AB01 (WHO), M02AA23 (WHO), S01BC01 (WHO)
PubChem	CID 3715
IUPHAR/BPS	1909
DrugBank	DB00328 Y
ChemSpider	3584 Y
UNII	XXE1CET956 Y
KEGG	D00141 Y
ChEBI	CHEBI:49662 Y
ChEMBL	CHEMBL6 Y
PDB ligand ID	IMN (PDBe, RCSB PDB)
Chemical data
Formula	C19H16ClNO4
Molar mass	357.787 g.mol−1
3D model (Jmol)	Interactive image
SMILES Cc1c(c2cc(ccc2n1C(=O)c3ccc(cc3)Cl)OC)CC(=O)O
InChI 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

Indometacin (INN and BAN) or indomethacin (AAN, USAN and former BAN) 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, molecules known to cause these symptoms.

It is marketed under more than twelve different trade names. As of 2015 the cost for a typical month of medication in the United States is less than 25 USD.

Clinical indications for indometacin include:

Indometacin has also been used clinically to delay premature labor, reduce amniotic fluid in polyhydramnios, and to close patent ductus arteriosus.

Indometacin is a potent drug with many serious side effects and should not be considered an analgesic for minor aches and pains or fever. The medication is better described as an anti-inflammatory, rather than an analgesic. Indometacin can also affect warfarin and subsequently raise INR.

Since indometacin inhibits both cyclooxygenase-1 and cyclooxygenase-2, it inhibits the production of prostaglandins in the stomach and intestines, which maintain the mucous lining of the gastrointestinal tract. Indometacin, therefore, like other non-selective COX inhibitors can cause peptic ulcers. These ulcers can result in serious bleeding and/or perforation requiring hospitalization of the patient.