Tenidap

Tenidap
Clinical data
ATC code
Identifiers
IUPAC name
  • 5-chloro-2-hydroxy-3-(2-thienylcarbonyl)-1H-indole-1-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H9ClN2O3S
Molar mass320.75 g·mol−1
3D model (JSmol)
SMILES
  • c1cc(sc1)C(=O)c2c3cc(ccc3n(c2O)C(=O)N)Cl
InChI
  • 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 FC, Feely J, Leeming MR, et al. (June 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): 554–63. 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, Wecksler AT, Wagner K, Hammock BD (2013). "Rationally designed multitarget agents against inflammation and pain". Current Medicinal Chemistry. 20 (13): 1783–99. doi:10.2174/0929867311320130013. PMC 4113248. PMID 23410172.
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