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
ChemSpider
137624
ChEMBL
CHEMBL3989410
Wikipedia
Indometacin
Predicted Properties
PropertyValueSource
Water Solubility0.00359 mg/mLALOGPS
logP4.46ALOGPS
logP3.53Chemaxon
logS-5ALOGPS
pKa (Strongest Acidic)3.8Chemaxon
pKa (Strongest Basic)-2.3Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area71.36 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity105.65 m3·mol-1Chemaxon
Polarizability36.21 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon