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Tenidap

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Tenidap
Clinical data
ATC code
Identifiers
  • 5-chloro-2-hydroxy-3-(2-thienylcarbonyl)-1H-indole-1-carboxamide
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H9ClN2O3S
Molar mass320.75086 g/mol g·mol−1
3D model (JSmol)
  • c1cc(sc1)C(=O)c2c3cc(ccc3n(c2O)C(=O)N)Cl
  • InChI=1S/C14H9ClN2O3S/c15-7-3-4-9-8(6-7)11(13(19)17(9)14(16)20)12(18)10-2-1-5-21-10/h1-6,19H,(H2,16,20) ☒N
  • Key:IZSFDUMVCVVWKW-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Tenidap was a COX/5-LOX inhibitor and cytokine-modulating anti-inflammatory drug candidate[1] that was under development by Pfizer as a promising potential treatment for rheumatoid arthritis,[2] but Pfizer halted development after marketing approval was rejected by the FDA in 1996[3] due to liver and kidney toxicity, which was attributed to metabolites of the drug with a thiophene moiety that caused oxidative damage.[4]

References

  1. ^ Wylie, G.; Appelboom, T.; Bolten, W.; Breedveld, F. C.; Feely, J.; Leeming, M. R.; Le Loët, X.; Manthorpe, R.; Marcolongo, R.; Smolen, J. (1995). "A comparative study of tenidap, a cytokine-modulating anti-rheumatic drug, and diclofenac in rheumatoid arthritis: A 24-week analysis of a 1-year clinical trial". British journal of rheumatology. 34 (6): 554–563. doi:10.1093/rheumatology/34.6.554. PMID 7543348.
  2. ^ Staff, American Journal of Nursing. Drug Watch: Tenidap Offers Arthritis Therapy Minus Toxicity AJN 1996 96(1):58
  3. ^ Pfizer. Sept 27, 1996 Press release: Pfizer To Halt Plans For Commercialization Of Tenidap For Rheumatoid Arthritis
  4. ^ Hwang SH et al. Rationally designed multitarget agents against inflammation and pain. Curr Med Chem. 2013;20(13):1783-99. PMID 23410172 PMC 4113248