IMN

INDOMETHACIN


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Chemical Component Summary

NameINDOMETHACIN
Identifiers2-[1-(4-chlorophenyl)carbonyl-5-methoxy-2-methyl-indol-3-yl]ethanoic acid
FormulaC19 H16 Cl N O4
Molecular Weight357.788
TypeNON-POLYMER
Isomeric SMILESCc1c(c2cc(ccc2n1C(=O)c3ccc(cc3)Cl)OC)CC(=O)O
InChIInChI=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)
InChIKeyCGIGDMFJXJATDK-UHFFFAOYSA-N

Chemical Details

Formal Charge0
Atom Count41
Chiral Atom Count0
Bond Count43
Aromatic Bond Count16

Drug Info: DrugBank

DrugBank IDDB00328 
NameIndomethacin
Groups
  • investigational
  • approved
DescriptionIndometacin, or indomethacin, is a non-steroidal anti-inflammatory drug (NSAID) with anti-inflammatory, analgesic, and antipyretic properties. NSAIDs consist of agents that are structurally unrelated; the NSAID chemical classification of indometacin is an indole-acetic acid derivative with the chemical name 1- (p-chlorobenzoyl)25-methoxy-2-methylindole-3-acetic acid.[A177871] The pharmacological effect of indometacin is not fully understood, however, it is thought to be mediated through potent and nonselective inhibition of the enzyme cyclooxygenase (COX), which is the main enzyme responsible for catalyzes the rate-limiting step in prostaglandin and thromboxane biosynthesis via the arachidonic acid (AA) pathway. Indometacin was first discovered in 1963 and it was first approved for use in the U.S. by the Food and Drug Administration in 1965, [A486] along with other acetic acid derivatives such as [diclofenac] and [sulindac] that were also developed during the 1960s.[A177871] Since then, indometacin has been extensively studied in clinical trials as one of the most potent NSAIDs in blocking prostaglandin synthesis and was among the first NSAIDs to be used in the symptomatic treatment of migraine and for headaches that eventually became known as “indomethacin-responsive” headache disorders.[A177871] Most commonly used in rheumatoid arthritis, ankylosing spondylitis, osteoarthritis, acute shoulder pains, and acute gouty arthritis, indometacin is currently available as oral capsules as well as other methods of administration, including rectal and intravenous formulations. Intravenous indometacin is administered to close a hemodynamically significant patent ductus arteriosus, as indicated by clinical evidence, in premature infants.[L10553] Ophthalmic indometacin has been studied and used in the symptomatic treatment of postoperative ocular inflammation and pain and/or complications after cataract surgery. Although deemed effective in reducing ocular inflammation in clinical studies, topical NSAIDs were also associated with a potential reduction in corneal sensitivity accompanied by an increased risk of superficial punctate keratitis and subjective symptoms of discomfort, including pain, burning or pricking, or a tingling sensation after instillation into the cul‐de‐sac.[A177949]
Synonyms
  • Indometacina
  • Indometacine
  • Indomethacin sodium
  • {1-[(4-chlorophenyl)carbonyl]-5-methoxy-2-methyl-1H-indol-3-yl}acetic acid
  • 1-(p-chlorobenzoyl)-5-methoxy-2-methylindole-3-acetic acid
Brand Names
  • Tivorbex
  • Indocid Cap 25mg
  • Indocid SR 75mg
  • Novo-methacin - Sup 50mg
  • Apo-indomethacin
IndicationOral indometacin is indicated for symptomatic management of moderate to severe rheumatoid arthritis including acute flares of chronic disease, moderate to severe ankylosing spondylitis, moderate to severe osteoarthritis, acute painful shoulder (bursitis and/or tendinitis) and acute gouty arthritis.[A177871,L6778] Intravenous indometacin is indicated to induce closure of a hemodynamically significant patent ductus arteriosus in premature infants weighing between 500 and 1750 g when after 48 hours usual medical management (e.g., fluid restriction, diuretics, digitalis, respiratory support, etc.) is ineffective.[L10553]
Categories
  • Acetic Acid Derivatives and Related Substances
  • Agents causing hyperkalemia
  • Agents that produce hypertension
  • Analgesics
  • Analgesics, Non-Narcotic
ATC-Code
  • S01CC02
  • M01AB51
  • S01BC01
  • M02AA23
  • M01AB01
CAS number53-86-1

Drug Targets

NameTarget SequencePharmacological ActionActions
Prostaglandin G/H synthase 2MLARALLLCAVLALSHTANPCCSHPCQNRGVCMSVGFDQYKCDCTRTGFY...unknowninhibitor
Phospholipase A2, membrane associatedMKTLLLLAVIMIFGLLQAHGNLVNFHRMIKLTTGKEAALSYGFYGCHCGV...unknowninhibitor
Prostaglandin G/H synthase 1MSRSLLLWFLLFLLLLPPLPVLLADPGAPTPVNPCCYYPCQHQGICVRFG...unknowninhibitor
Prostaglandin reductase 2MIVQRVVLNSRPGKNGNPVAENFRMEEVYLPDNINEGQVQVRTLYLSVDP...unknowninhibitor
Peroxisome proliferator-activated receptor gammaMGETLGDSPIDPESDSFTDTLSANISQEMTMVDTEMPFWPTNFGISSVDL...unknownactivator
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL6
PubChem 3715
ChEMBL CHEMBL6
ChEBI CHEBI:49662
CCDC/CSD SESKUY, SESKUY01, LEZKEI01, INDMET05, BANMOT01, DEWNOJ, LEZKEI, INDMET03, JELJES, UFERED01, BANMUZ, INDMET02, INDMET, UFERED03, UFERED, UFERED05, UFERED04, INDMET04, UFERED06, UFERED02, UFERED07, TERKOT, UHEPOP, INDMET06, LEZKEI02, INDMET07, JAMYUV, JAMZEG, JAMYOP, JAMZAC
COD 4002851, 2202423, 2202430, 7206693, 7209836