Tenidap

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]

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
 NY (what is this?)  (verify)

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.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.