Indomethacin sodiumProduct ingredient for Indomethacin
- Name
- Indomethacin sodium
- Drug Entry
- Indomethacin
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.1 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, 10 along with other acetic acid derivatives such as diclofenac and sulindac that were also developed during the 1960s.1 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.1
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.14 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.6
- Accession Number
- DBSALT001435
- Structure
- Synonyms
- Not Available
- UNII
- 0IMX38M2GG
- CAS Number
- 74252-25-8
- Weight
- Average: 433.82
Monoisotopic: 433.090424 - Chemical Formula
- C19H21ClNNaO7
- InChI Key
- UHYAQBLOGVNWNT-UHFFFAOYSA-M
- InChI
- InChI=1S/C19H16ClNO4.Na.3H2O/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);;3*1H2/q;+1;;;/p-1
- IUPAC Name
- sodium 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate trihydrate
- SMILES
- O.O.O.[Na+].COC1=CC=C2N(C(=O)C3=CC=C(Cl)C=C3)C(C)=C(CC([O-])=O)C2=C1
- External Links
- ChemSpider
- 137624
- ChEMBL
- CHEMBL3989410
- Wikipedia
- Indometacin
- Predicted Properties
Property Value Source Water Solubility 0.00359 mg/mL ALOGPS logP 4.46 ALOGPS logP 3.53 Chemaxon logS -5 ALOGPS pKa (Strongest Acidic) 3.8 Chemaxon pKa (Strongest Basic) -2.3 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 71.36 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 105.65 m3·mol-1 Chemaxon Polarizability 36.21 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon