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Revision as of 03:17, 17 December 2011 by 184.59.173.242 (talk) (→Uses)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff) Pharmaceutical compound | |
| Clinical data | |
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| Trade names | Clinoril |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a681037 |
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| Routes of administration | Oral |
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| Legal status | |
| Legal status | |
| Pharmacokinetic data | |
| Bioavailability | Approximately 90% (Oral) |
| Metabolism | ? |
| Elimination half-life | 7.8 hours, metabolites up to 16.4 hours |
| Excretion | Renal (50%) and fecal (25%) |
| Identifiers | |
IUPAC name
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| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.048.909  |
| Chemical and physical data | |
| Formula | C20H17FO3S |
| Molar mass | 356.412 g/mol g·mol |
| 3D model (JSmol) | |
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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.
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 . 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.
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.
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.
References
- Scheper MA, Nikitakis NG, Chaisuparat R, Montaner S, Sauk JJ (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.
{{cite journal}}: Unknown parameter|month=ignored (help)CS1 maint: multiple names: authors list (link) - Shiff SJ, Qiao L, Tsai LL, Rigas B (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.
{{cite journal}}: Unknown parameter|month=ignored (help)CS1 maint: multiple names: authors list (link)
External links
| Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA) | |
|---|---|
| pyrazolones / pyrazolidines | |
| salicylates | |
| acetic acid derivatives and related substances | |
| oxicams | |
| propionic acid derivatives (profens) |
|
| n-arylanthranilic acids (fenamates) | |
| COX-2 inhibitors (coxibs) | |
| other | |
| NSAID combinations | |
| Key: underline indicates initially developed first-in-class compound of specific group; WHO-Essential Medicines; withdrawn drugs; veterinary use. | |
| Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA) | |
|---|---|
| pyrazolones / pyrazolidines | |
| salicylates | |
| acetic acid derivatives and related substances | |
| oxicams | |
| propionic acid derivatives (profens) |
|
| n-arylanthranilic acids (fenamates) | |
| COX-2 inhibitors (coxibs) | |
| other | |
| NSAID combinations | |
| Key: underline indicates initially developed first-in-class compound of specific group; WHO-Essential Medicines; withdrawn drugs; veterinary use. | |
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