Sulindac Chemical Properties
- Melting point:
- Boiling point:
- 581.6±50.0 °C(Predicted)
- 1.2581 (estimate)
- storage temp.
- Store at RT
- Very slightly soluble in water, soluble in methylene chloride, sparingly soluble in ethanol (96 per cent). It dissolves in dilute solutions of alkali hydroxides.
- pKa (25°) 4.7
- Water Solubility
- Soluble in water, methanol, ethanol.
- 327nm(0.05mol/L methanolic HCl)(lit.)
- CAS DataBase Reference
- 38194-50-2(CAS DataBase Reference)
- NIST Chemistry Reference
- EPA Substance Registry System
- 1H-Indene-3-acetic acid, 5-fluoro-2-methyl-1-[[4-(methylsulfinyl)phenyl]methylene]-, (1Z)- (38194-50-2)
Sulindac Usage And Synthesis
Used in Particular Diseases
Acute Gouty Arthritis:
Dosage and Frequency: 200 mg twice daily for 7–10 days
Yellow Crystalline Solid
A non-steroidal anti-inflammatory agent. An anti-inflammatory
Sulindac is a non-steroidal anti-inflammatory drug.
ChEBI: A monocarboxylic acid that is 1-benzylidene-1H-indene which is substituted at positions 2, 3, and 5 by methyl, carboxymethyl, and fluorine respectively, and in which the phenyl group of the benzylidene moiety is substituted at the ara position by a methylsulfinyl group. It is a prodrug for the corresponding sulfide, a non-steroidal anti-inflammatory drug, used particularly in the treatment of acute and chronic inflammatory conditions.
Sulindac (Clinoril) is chemically related to indomethacin and is generally used for the same indications. It is a prodrug that is metabolized to an active sulfide metabolite and an inactive metabolite. The most frequently reported side effects are GI pain, nausea, diarrhea, and constipation. The incidence of these effects is lower than for indomethacin, presumably because sulindac is a prodrug and thus the active metabolite is not highly concentrated at the gastric mucosa. As with indomethacin, a rather high incidence of CNS side effects (dizziness, headache) also occurs.
Sulindac, (Z)-5-fluoro-2-methyl-1-([p-(methylsulfinyl)phenyl]methylene)-1H-indene-3-acetic acid (Clinoril), isan NSAID prodrug that contains a chiral sulfoxide moietybut is marketed as the racemate because it undergoes invivo reduction by the hepatic enzymes into its achiral, activemetabolite, methyl sulfide that exhibits potent andnonselective COX inhibition similar to indomethacin.
The parent sulfoxide has a plasma half-life of 8 hours, andthe active methyl sulfide metabolite is 16.4 hours. The morepolar and inactive sulfoxide is virtually the only form excretedinto the renal tubules, thus sulindac is believed to haveminimal nephrotoxicity associated with indomethacin. Thelong half-life of sulindac is caused by the extensive enterohepaticcirculation and reactivation of the inactive sulfoxideexcreted. Coadministration of aspirin is contraindicated becauseit considerably reduces the sulfide blood levels. Carefulmonitoring of patients with a history of ulcers is recommended.Gastric bleeding, nausea, diarrhea, dizziness, andother adverse effects have been noted with sulindac, but witha lower frequency than with aspirin. Sulindac is recommendedfor RA, OA, and ankylosing spondylitis.
Prodrug. Metabolizes to sulindac sulfide, a cyclooxgenase inhibitor that represses ras signaling, and sulindac sulfone, an antitumor agent, following oral administration in vivo . Widely used anti-inflammatory agent.
- (5-Fluoro-2-methyl-1H-inden-3-yl)acetic acid
- trans-3-Hexenoic acid
- Trimethylphenylammonium chloride
- Ethyl 2-(Chlorosulfonyl)acetate
- fluoro jade
- Dimethyl sulfone
- Chloroacetic acid
- Acetic anhydride
- Methyltriphenylphosphonium bromide
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