Tenidap

Chemical compound
  • M01AX23 (WHO)
Identifiers
  • 5-chloro-2-hydroxy-3-(2-thienylcarbonyl)-1H-indole-1-carboxamide
CAS Number
  • 120210-48-2 checkY
PubChem CID
  • 60712
ChemSpider
  • 54717 ☒N
UNII
  • 9K7CJ74ONH
KEGG
  • D06072 checkY
ChEMBL
  • ChEMBL1097558 ☒N
CompTox Dashboard (EPA)
  • DTXSID9046104 Edit this at Wikidata
Chemical and physical dataFormulaC14H9ClN2O3SMolar mass320.75 g·mol−13D model (JSmol)
  • Interactive image
  • 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 Archived 2016-03-05 at the Wayback Machine
  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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Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)
pyrazolones /
pyrazolidinessalicylatesacetic acid derivatives
and related substancesoxicamspropionic acid
derivatives (profens)n-arylanthranilic
acids (fenamates)COX-2 inhibitors
(coxibs)otherNSAID
combinations
Key: underline indicates initially developed first-in-class compound of specific group; #WHO-Essential Medicines; withdrawn drugs; veterinary use.
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Receptor
(ligands)
DP (D2)Tooltip Prostaglandin D2 receptor
DP1Tooltip Prostaglandin D2 receptor 1
DP2Tooltip Prostaglandin D2 receptor 2
EP (E2)Tooltip Prostaglandin E2 receptor
EP1Tooltip Prostaglandin EP1 receptor
  • Antagonists: AH-6809
  • ONO-8130
  • SC-19220
  • SC-51089
  • SC-51322
EP2Tooltip Prostaglandin EP2 receptor
  • Antagonists: AH-6809
  • PF-04418948
  • TG 4-155
EP3Tooltip Prostaglandin EP3 receptor
  • Antagonists: L-798106
EP4Tooltip Prostaglandin EP4 receptor
  • Antagonists: Grapiprant
  • GW-627368
  • L-161982
  • ONO-AE3-208
Unsorted
  • Agonists: 16,16-Dimethyl Prostaglandin E2
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FP (F)Tooltip Prostaglandin F receptor
IP (I2)Tooltip Prostacyclin receptor
  • Antagonists: RO1138452
TP (TXA2)Tooltip Thromboxane receptor
  • Agonists: Carbocyclic thromboxane A2
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Enzyme
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(PTGS)
PGD2STooltip Prostaglandin D synthase
PGESTooltip Prostaglandin E synthase
HQL-79
PGFSTooltip Prostaglandin F synthase
PGI2STooltip Prostacyclin synthase
TXASTooltip Thromboxane A synthase
Others
See also
Receptor/signaling modulators
Leukotriene signaling modulators
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