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a nonsteroidal anti-inflammatory drug (trade name Clinoril) (同)Clinoril

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/04/27 00:27:37」(JST)

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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^{[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.

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 for her shoulder pain. Ms. Bartlett suffered severe injuries including the loss of over 60% of her surface skin and permanent near-blindness. The case has been appealed to the United States Supreme Court, where the main issue is likely to be whether federal law preempts Ms. Bartlett's claim. ^[3]

Cite to:

Bartlett v. Mut. Pharm. Co., Inc., 678 F.3d 30, 34 (1st Cir. 2012).

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.
^ 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.
^ Thomas, Katie. "Justices to Take Up Case on Generic Drug Markers' Liability". New York Times. Retrieved 4 March 2013.

External links

RxList information on Sulindac
Drug Profile
Jury Awards $21 Million

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UpToDate Contents

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1. 非ステロイド性抗炎症剤（NSAIDs）（アスピリンを含む）：大腸癌の予防における役割 nsaids including aspirin role in prevention of colorectal cancer
2. 羊水過多 polyhydramnios
3. 非選択性非ステロイド性抗炎症剤（NSAIDs）：副作用の概要 nonselective nsaids overview of adverse effects
4. 非ステロイド性抗炎症剤（NSAIDs）：電解質の合併症 nsaids electrolyte complications
5. 非ステロイド性抗炎症剤（NSAIDs）：作用機序 nsaids mechanism of action

English Journal

NOSH-sulindac (AVT-18A) is a novel nitric oxide- and hydrogen sulfide-releasing hybrid that is gastrointestinal safe and has potent anti-inflammatory, analgesic, antipyretic, anti-platelet, and anti-cancer properties.

Kashfi K1, Chattopadhyay M2, Kodela R2.
Redox biology.Redox Biol.2015 Dec;6:287-96. doi: 10.1016/j.redox.2015.08.012. Epub 2015 Aug 14.
Sulindac is chemopreventive and has utility in patients with familial adenomatous polyposis; however, side effects preclude its long-term use. NOSH-sulindac (AVT-18A) releases nitric oxide and hydrogen sulfide, was designed to be a safer alternative. Here we compare the gastrointestinal safety, anti
PMID 26298203

Structural Mechanism of the Interaction of Alzheimer Disease Aβ Fibrils with the Non-steroidal Anti-inflammatory Drug (NSAID) Sulindac Sulfide.

Prade E1, Bittner HJ2, Sarkar R1, Lopez Del Amo JM3, Althoff-Ospelt G4, Multhaup G5, Hildebrand PW2, Reif B6.
The Journal of biological chemistry.J Biol Chem.2015 Nov 27;290(48):28737-45. doi: 10.1074/jbc.M115.675215. Epub 2015 Sep 28.
Alzheimer disease is the most severe neurodegenerative disease worldwide. In the past years, a plethora of small molecules interfering with amyloid-β (Aβ) aggregation has been reported. However, their mode of interaction with amyloid fibers is not understood. Non-steroidal anti-inflammatory drugs
PMID 26416887

Removal of selected NSAIDs (nonsteroidal anti-inflammatory drugs) in aqueous samples by Octolig®.

Martin DF1, Martin JM1, Ward TA1.
Journal of environmental science and health. Part A, Toxic/hazardous substances & environmental engineering.J Environ Sci Health A Tox Hazard Subst Environ Eng.2015 Nov 25:1-6. [Epub ahead of print]
The possibility of removing representative nonsteroidal anti-inflammatory drugs (NSAIDs) from water was tested using Octolig®, a commercially available material with polyethylenediimine moieties covalently attached to high-surface area silica gel. The effectiveness of removal should depend on selec
PMID 26606390

Japanese Journal

Characterization of Sulindac Solid Dispersion with Hydroxypropyl Cellulose Prepared by Hot Melt Extrusion

Osawa Mizuho,Higashi Kenjirou,Yamashita Jun,Moribe Kunikazu,Yamamoto Keiji
薬剤学 74(2), 160-169, 2014
… Solid dispersions were prepared with sulindac, a poorly water-soluble drug, and HPC of three different molecular weights using a hot melt extrusion method. … Permeability of sulindac was evaluated using the Caco-2 cell monolayer model. … The results obtained by PXRD, DSC, and solubility studies showed that sulindac in the extrudate of sulindac/HPC (20/80 w/w) was completely amorphized and demonstrated better solubility than the drug alone. …
NAID 130003398004

NO-NSAIDs. Part 3: Nitric Oxide-Releasing Prodrugs of Non-steroidal Anti-inflammatory Drugs

Borhade Namdev,Pathan Asif Rahimkhan,Halder Somnath [他],Karwa Manoj,Dhiman Mini,Pamidiboina Venu,Gund Machhindra,Deshattiwar Jagannath Janardhan,Mali Sunil Vasantrao,Deshmukh Nitin Janardanrao,Senthilkumar Subrayan Palanisamy,Gaikwad Parikshit,Tipparam Santhosh Goud,Mudgal Jayesh,Dutta Milan Chandra,Burhan Aslam Usmangani,Thakre Gajanan,Sharma Ankur,Deshpande Shubhada,Desai Dattatraya Chandrakant,Dubash Nauzer Pervez,Jain Arun Kumar,Sharma Somesh,Nemmani Kumar Venkata Subrahmanya,Satyam Apparao
Chemical and Pharmaceutical Bulletin 60(4), 465-481, 2012
… In continuation of our efforts to discover novel nitric oxide-releasing non-steroidal anti-inflammatory drugs (NO-NSAIDs) as potentially "Safe NSAIDs," we report herein the design, synthesis and evaluation of 21 new NO-NSAIDs of commonly used NSAIDs such as aspirin, diclofenac, naproxen, flurbiprofen, ketoprofen, sulindac, ibuprofen and indomethacin. …
NAID 130001852438

Randomized Double-Blind Trial of Sulindac and Etodolac to Eradicate Aberrant Crypt Foci and to Prevent Sporadic Colorectal Polyps

Takayama Tetsuji,Nagashima Hiroyuki,Maeda Masahiro,Nojiri Shuichi,Hirayama Michiaki,Nakano Yoichiro,Takahashi Yasuo,Sato Yasushi,Sekikawa Hitoshi,Mori Mitsuru,Sonoda Tomoko,Kimura Tetsuo,Kato Junji,Niitsu Yoshiro
CLINICAL CANCER RESEARCH 17(11), 3803-3811, 2011
NAID 120005207289

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Sulindac
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	Prescription Only (S4) (AU) 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	DB00605
ChemSpider	1265915
UNII	184SNS8VUH
KEGG	D00120
ChEBI	CHEBI:9352
ChEMBL	CHEMBL15770
Chemical data
Formula	C20H17FO3S
Mol. mass	356.412 g/mol
	SMILES O=S(c1ccc(cc1)\C=C3/c2ccc(F)cc2\C(=C3C)CC(=O)O)C;
	InChI InChI=1S/C20H17FO3S/c1-12-17(9-13-3-6-15(7-4-13)25(2)24)16-8-5-14(21)10-19(16)18(12)11-20(22)23/h3-10H,11H2,1-2H3,(H,22,23)/b17-9- ; Key:MLKXDPUZXIRXEP-MFOYZWKCSA-N ;
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　　[★]

英: sulindac
商: クリノリル, Cunoril
関: 非ステロイド性抗炎症薬

[1] 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.

[2] 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.

[3] Thomas, Katie. "Justices to Take Up Case on Generic Drug Markers' Liability". New York Times. Retrieved 4 March 2013.

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sulindac