Sulindac
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| Systematic (IUPAC) name | |
| {(1Z)-5-fluoro-2-methyl-1-[4-(methylsulfinyl)benzylidene]-1H-indene-3-yl}acetic acid | |
| Clinical data | |
| Trade names | Clinoril |
| AHFS/Drugs.com | monograph |
| MedlinePlus | a681037 |
| Pregnancy cat. | C(AU) C(US) |
| Legal status | POM (UK) ℞-only (US) |
| Routes | Oral |
| Pharmacokinetic data | |
| Bioavailability | Approximately 90% (Oral) |
| Metabolism | ? |
| Half-life | 7.8 hours, metabolites up to 16.4 hours |
| Excretion | Renal (50%) and fecal (25%) |
| Identifiers | |
| CAS number | 38194-50-2  |
| ATC code | M01AB02 |
| PubChem | CID 1548887 |
| DrugBank | APRD01243 |
| ChemSpider | 1265915 |
| UNII | 184SNS8VUH |
| KEGG | D00120  |
| ChEBI | CHEBI:9352 |
| ChEMBL | CHEMBL15770 |
| Chemical data | |
| Formula | C20H17FO3S |
| Mol. mass | 356.412 g/mol |
| SMILES | eMolecules & PubChem |
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Sulindac is a non-steroidal anti-inflammatory drug of the arylalkanoic acid class that is marketed in the UK & U.S. by Merck as Clinoril.
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[edit] Uses
Like other NSAIDs, it is useful in the treatment of acute or chronic inflammatory conditions. Sulindac is a prodrug, derived from sulfinylindene, that is converted in the body to the active NSAID. More specifically, the agent is converted by liver enzymes to a sulfide that is excreted in the bile and then reabsorbed from the intestine. This is thought to help maintain constant blood levels with reduced gastrointestinal side effects. Some studies have shown sulindac to be relatively less irritating to the stomach than other NSAIDs except for drugs of the COX-2 inhibitor class[citation needed]. The exact mechanism of its NSAID properties is unknown, but it is thought to act on enzymes COX-1 and COX-2, inhibiting prostaglandin synthesis.
Its usual dosage is 150-200 milligrams twice per day, with food. It should not be used by persons with a history of major allergic reactions (urticaria or anaphylaxis) to aspirin or other NSAIDs, and should be used with caution by persons having pre-existing peptic ulcer disease. Sulindac is much more likely than other NSAIDs to cause damage to the liver or pancreas.
Sulindac seems to have a property, independent of COX-inhibition, of reducing the growth of polyps and precancerous lesions in the colon, especially in association with familial adenomatous polyposis, and may have other anti-cancer properties.[1][2]
Sulindac is an effective tocolytic and may be used in the treatment of preterm labor. In common with other NSAIDs, sulindac is currently being investigated for its role in the treatment of Alzheimer's disease.
Since it was found that the sulfoxide functional group can be reduced by methionine sulfoxide reductase A (MsrA), a possible anti-oxidative capability is being discussed.
[edit] Litigation
In September 2010 a federal jury in New Hampshire awarded $21 million to a woman blinded and scarred by a generic brand of Sulindac (Clinoril) that she took for shoulder pain. Karen Bartlett said she suffered extreme burns to her skin, mucus membranes and eyes after taking sulindac.
[edit] References
- ^ Scheper MA, Nikitakis NG, Chaisuparat R, Montaner S, Sauk JJ (March 2007). "Sulindac induces apoptosis and inhibits tumor growth in vivo in head and neck squamous cell carcinoma". Neoplasia 9 (3): 192–9. doi:10.1593/neo.06781. PMC 1838577. PMID 17401459. http://www.neoplasia.com/abstract.php?msid=1062.
- ^ Shiff SJ, Qiao L, Tsai LL, Rigas B (July 1995). "Sulindac sulfide, an aspirin-like compound, inhibits proliferation, causes cell cycle quiescence, and induces apoptosis in HT-29 colon adenocarcinoma cells". J. Clin. Invest. 96 (1): 491–503. doi:10.1172/JCI118060. PMC 185223. PMID 7615821. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=185223.
[edit] External links
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