Sulindac

Overview

Sulindac is a nonsteroidal anti-inflammatory drug (NSAID) of the arylalkanoic acid class that is marketed as Clinoril. Imbaral is another name for this drug. Its name is derived from sul(finyl)+ ind(ene)+ ac(etic acid) It was patented in 1969 and approved for medical use in 1976.[1] WP

Uses, dosage and effects

Medical 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.[2] WP

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, though it is less likely to cause kidney damage than other NSAIDs. WP

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.[3][4] WP

Risks and side effects

Adverse effects

In October 2020, the U.S. Food and Drug Administration (FDA) required the prescribing information to be updated for all nonsteroidal anti-inflammatory medications to describe the risk of kidney problems in unborn babies that result in low amniotic fluid. They recommend avoiding NSAIDs in pregnant women at 20 weeks or later in pregnancy.[5][6] WP

Legal status

Litigation

In September 2010, a federal jury in New Hampshire awarded $21 million to Karen Bartlett, a woman who developed Stevens–Johnson syndrome/toxic epidermal necrolysis as a result of taking a generic brand of sulindac manufactured by Mutual Pharmaceuticals for her shoulder pain. Bartlett sustained severe injuries including the loss of over 60% of her surface skin and permanent near-blindness. The case had been appealed to the United States Supreme Court, where the main issue was whether federal law preempts Bartlett's claim. On June 24, 2013, the Supreme Court ruled 5–4 in favor of Mutual Pharmaceuticals, throwing out the earlier $21 million jury verdict.[7][8][9] WP

Chemistry

Formula

C20H17FO3S PC

CAS number

38194-50-2 PC

Molar mass (g/mol)

356.4 PC

IUPAC name (computed by PubChem)

2-[(3Z)-6-fluoro-2-methyl-3-[(4-methylsulfinylphenyl)methylidene]inden-1-yl]acetic acid PC

SMILES

CC\1=C(C2=C(/C1=C\C3=CC=C(C=C3)S(=O)C)C=CC(=C2)F)CC(=O)O PC

InChIKey

MLKXDPUZXIRXEP-MFOYZWKCSA-N PC

PubChem CID

1548887

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Other Fischer J, Ganellin CR. Analogue-based Drug Discovery. 2006
2. Journal / agency LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. 2012. PMID 31643638
3. Journal / agency Scheper MA, Nikitakis NG, Chaisuparat R, Montaner S, Sauk JJ. Sulindac induces apoptosis and inhibits tumor growth in vivo in head and neck squamous cell carcinoma. Neoplasia. March 2007. doi:10.1593/neo.06781 · PMID 17401459 · PMC1838577
4. Journal / agency Shiff SJ, Qiao L, Tsai LL, Rigas B. Sulindac sulfide, an aspirin-like compound, inhibits proliferation, causes cell cycle quiescence, and induces apoptosis in HT-29 colon adenocarcinoma cells. The Journal of Clinical Investigation. July 1995. doi:10.1172/JCI118060 · PMID 7615821 · PMC185223
5. Journal / agency FDA Warns that Using a Type of Pain and Fever Medication in Second Half of Pregnancy Could Lead to Complications. 15 October 2020
6. Journal / agency NSAIDs may cause rare kidney problems in unborn babies. 21 July 2017
7. Other Thomas K. Justices to Take Up Case on Generic Drug Markers' Liability. 2013-03-04
8. Other Kendall B. Supreme Court Again Limits Product-Liability Suits on Generic Drugs
9. Other https://www.law.cornell.edu/supct/cert/12-142. March 19, 2013

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.