Chemical Component Summary | |
|---|---|
| Name | INDOMETHACIN |
| Identifiers | 2-[1-(4-chlorophenyl)carbonyl-5-methoxy-2-methyl-indol-3-yl]ethanoic acid |
| Formula | C19 H16 Cl N O4 |
| Molecular Weight | 357.788 |
| Type | NON-POLYMER |
| Isomeric 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) |
| InChIKey | CGIGDMFJXJATDK-UHFFFAOYSA-N |
Chemical Details | |
|---|---|
| Formal Charge | 0 |
| Atom Count | 41 |
| Chiral Atom Count | 0 |
| Bond Count | 43 |
| Aromatic Bond Count | 16 |
Drug Info: DrugBank
| DrugBank ID | DB00328? |
|---|---|
| Name | Indomethacin |
| Groups |
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| Description | Indometacin, 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 ˇ°indomethacin-responsiveˇ± 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 |
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| Brand Names |
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| Indication | Oral 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 |
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| ATC-Code |
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| CAS number | 53-86-1 |
Drug Targets
| Name | Target Sequence | Pharmacological Action | Actions |
|---|---|---|---|
| Prostaglandin G/H synthase 2 | MLARALLLCAVLALSHTANPCCSHPCQNRGVCMSVGFDQYKCDCTRTGFY... | unknown | inhibitor |
| Phospholipase A2, membrane associated | MKTLLLLAVIMIFGLLQAHGNLVNFHRMIKLTTGKEAALSYGFYGCHCGV... | unknown | inhibitor |
| Prostaglandin G/H synthase 1 | MSRSLLLWFLLFLLLLPPLPVLLADPGAPTPVNPCCYYPCQHQGICVRFG... | unknown | inhibitor |
| Prostaglandin reductase 2 | MIVQRVVLNSRPGKNGNPVAENFRMEEVYLPDNINEGQVQVRTLYLSVDP... | unknown | inhibitor |
| Peroxisome proliferator-activated receptor gamma | MGETLGDSPIDPESDSFTDTLSANISQEMTMVDTEMPFWPTNFGISSVDL... | unknown | activator |
| 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 Name | Reference |
|---|---|
| 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 |
