CAS No 53-86-1 , 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Title: Indomethacin
CAS Registry Number: 53-86-1
CAS Name: 1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid
Synonyms: 1-(p-chlorobenzoyl)-5-methoxy-2-methyl-3-indolylacetic acid; indometacin
Trademarks: Bonidon (Mepha); Catlep (Sumitomo); Chrono-Indocid (Merck & Co.); Confortid (Alpharma); Dolcidium (Galephar); Elmetacin (Sankyo); Idomethine (Kowa); Inacid (Merck & Co.); Indacin (Merck & Co.); Indocid (Merck & Co.); Indocin (Merck & Co.); Indomed (Merck & Co.); Indomee (Merck & Co.); Indomod (Pfizer); Indoptic (Merck & Co.); Indoptol (Merck & Co.); Indoxen (Sigma-Tau); Inflazon (Taisho); Inteban (Sumitomo); Mikametan (Mikasa); Rheumacin LA (CP Pharm.); Serastar (Yamanouchi); Vonum (Sanofi-Synthelabo)
Molecular Formula: C19H16ClNO4
Molecular Weight: 357.79
Percent Composition: C 63.78%, H 4.51%, Cl 9.91%, N 3.91%, O 17.89%
Literature References: Nonsteroidal anti-inflammatory agent (NSAID); inhibits prostaglandin synthesis. Prepn: T. Y. Shen et al., J. Am. Chem. Soc. 85, 488 (1963); T. Y. Shen, US 3161654 (1964 to Merck & Co.). Alternate process: BE 679678 (1966 to Sumitomo). Anti-inflammatory and antipyretic activity: C. A. Winter et al., J. Pharmacol. Exp. Ther. 141, 369 (1963). Metabolic studies: D. W. Yesair et al., Biochem. Pharmacol. 19, 1579 (1970). Toxicity: C. D. Klaassen, Toxicol. Appl. Pharmacol. 38, 127 (1976). Review of discovery, pharmacology and mechanism of action: T. Y. Shen, C. A. Winter in Advances in Drug Research vol. 12, A. B. Simmons, Ed. (Academic Press, New York, 1977) pp 89-245; of clinical trials in osteoarthritis: W. M. O'Brien, Clin. Pharmacol. Ther. 9, 94-107 (1968); of role in ductus closure: S. M. Douidar et al., Dev. Pharmacol. Ther. 11, 196-212 (1988).
Properties: Crystals exhibiting polymorphism, mp for one form ~155°, for the other ~162°. uv max (ethanol): 230, 260, 319 nm (e 20800, 16200, 6290). pKa 4.5. Sol in ethanol, ether, acetone, castor oil. Practically insol in water. Stable in neutral or slightly acidic media; dec by strong alkali. LD50 i.p. in rats: 13 mg/kg (Klaassen).
Melting point: mp for one form ~155°, for the other ~162°
pKa: pKa 4.5
Absorption maximum: uv max (ethanol): 230, 260, 319 nm (e 20800, 16200, 6290)
Toxicity data: LD50 i.p. in rats: 13 mg/kg (Klaassen)
 
Derivative Type: Sodium salt trihydrate
CAS Registry Number: 74252-25-8
Trademarks: Indocin I.V. (Merck & Co.); Indocid PDA (Merck & Co.)
Molecular Formula: C19H15ClNNaO4.3H2O
Molecular Weight: 433.82
Percent Composition: C 52.60%, H 4.88%, Cl 8.17%, N 3.23%, Na 5.30%, O 25.82%
Properties: Pale yellow crystalline powder. pH of 1% soln: 8.4. Very sol in methanol; sol in water, ethanol. Very slightly sol in chloroform, acetone.
 
Derivative Type: Meglumine salt
Trademarks: Liometacen (Chiesi)
 
Therap-Cat: Anti-inflammatory; analgesic. For closure of patent ductus arteriosus in preterm infants.
Keywords: Analgesic (Non-Narcotic); Anti-inflammatory (Nonsteroidal); Arylacetic Acid Derivatives.