Sulindac

  • CAT Number: A000486
  • CAS Number: 38194-50-2
  • Molecular Formula: C20H17FO3S
  • Molecular Weight: 356.4
  • Purity: ≥95%
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Sulindac is a non-steroidal anti-inflammatory drug of the arylalkanoic acid class. 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.

Catalog Number A000486
CAS Number 38194-50-2
Molecular Formula

C20H17FO3S

Purity 95%
Target COX
Solubility >12.1mg/mL in DMSO
Storage -20°C
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-
InChIKey MLKXDPUZXIRXEP-MFOYZWKCSA-N
SMILES CC1=C(C2=C(C1=CC3=CC=C(C=C3)S(=O)C)C=CC(=C2)F)CC(=O)O
Reference

1: Chang WL, Jackson C, Riel S, Cooper HS, Devarajan K, Hensley HH, Zhou Y,
Vanderveer LA, Nguyen MT, Clapper ML. Differential preventive activity of
sulindac and atorvastatin in Apc(+/Min-FCCC)mice with or without colorectal
adenomas. Gut. 2017 Nov 9. pii: gutjnl-2017-313942. doi:
10.1136/gutjnl-2017-313942. [Epub ahead of print] PubMed PMID: 29122850.
<br>

2: Rice PFS, Ehrichs KG, Jones MS, Chen H, Hsu CH, Abril ER, Nagle RB, Besselsen
DG, Barton JK, Ignatenko NA. Does mutated K-RAS oncogene attenuate the effect of
Sulindac in colon cancer chemoprevention? Cancer Prev Res (Phila). 2017 Nov 8.
pii: canprevres.0230.2017. doi: 10.1158/1940-6207.CAPR-17-0230. [Epub ahead of
print] PubMed PMID: 29118162.
<br>

3: Shalash AM, Abu Ali HI. Synthesis, crystallographic, spectroscopic studies and
biological activity of new cobalt(II) complexes with bioactive mixed sulindac and
nitrogen-donor ligands. Chem Cent J. 2017 May 10;11(1):40. doi:
10.1186/s13065-017-0268-2. PubMed PMID: 29086831; PubMed Central PMCID:
PMC5423883.
<br>

4: Mathew B, Hobrath JV, Connelly MC, Kiplin Guy R, Reynolds RC. Diverse amide
analogs of sulindac for cancer treatment and prevention. Bioorg Med Chem Lett.
2017 Oct 15;27(20):4614-4621. doi: 10.1016/j.bmcl.2017.09.022. Epub 2017 Sep 13.
PubMed PMID: 28935266.
<br>

5: Ma H, Brosens LAA, Elias SG, Morsink FHM, Nijman IJ, Hylind LM, Montgomery EA,
Offerhaus GJA, Giardiello FM, de Leng WWJ. Longitudinal analysis of colon crypt
stem cell dynamics in sulindac treated Familial Adenomatous Polyposis patients.
Sci Rep. 2017 Sep 20;7(1):11972. doi: 10.1038/s41598-017-11865-y. PubMed PMID:
28931879; PubMed Central PMCID: PMC5607292.
<br>

6: Chandra S, Nymeyer AC, Rice PF, Gerner EW, Barton JK. Intermittent Dosing with
Sulindac Provides Effective Colorectal Cancer Chemoprevention in the
Azoxymethane-Treated Mouse Model. Cancer Prev Res (Phila). 2017
Aug;10(8):459-466. doi: 10.1158/1940-6207.CAPR-17-0038. Epub 2017 Jun 13. PubMed
PMID: 28611038; PubMed Central PMCID: PMC5544532.
<br>

7: Tang YJ, Hu K, Huang WH, Wang CZ, Liu Z, Chen Y, Ouyang DS, Tan ZR, Zhou HH,
Yuan CS. Effects of FMO3 Polymorphisms on Pharmacokinetics of Sulindac in Chinese
Healthy Male Volunteers. Biomed Res Int. 2017;2017:4189678. doi:
10.1155/2017/4189678. Epub 2017 Feb 26. PubMed PMID: 28331852; PubMed Central
PMCID: PMC5346382.

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8: Whitt JD, Keeton AB, Gary BD, Sklar LA, Sodani K, Chen ZS, Piazza GA. Sulindac
sulfide selectively increases sensitivity of ABCC1 expressing tumor cells to
doxorubicin and glutathione depletion. J Biomed Res. 2016 Mar;30(2):120-133. doi:
10.7555/JBR.30.20150108. Epub 2015 Nov 20. PubMed PMID: 28276667; PubMed Central
PMCID: PMC4820889.

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9: Uehara S, Shimizu M, Uno Y, Inoue T, Sasaki E, Yamazaki H. Marmoset
Flavin-Containing Monooxygenase 3 in the Liver Is a Major Benzydamine and
Sulindac Sulfide Oxygenase. Drug Metab Dispos. 2017 May;45(5):497-500. doi:
10.1124/dmd.117.075184. Epub 2017 Mar 3. PubMed PMID: 28258069.
<br>

10: Shazly GA. Effect of Sulindac Binary System on In Vitro and In Vivo Release
Profiles: An Assessment of Polymer Type and Its Ratio. Biomed Res Int.
2016;2016:3182358. Epub 2016 Oct 20. PubMed PMID: 27840824; PubMed Central PMCID:
PMC5093299.

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