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Tenidap

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Chemical compound
Pharmaceutical compound
Tenidap
Clinical data
ATC code
Identifiers
  • 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
Formula C14H9ClN2O3S
Molar mass 320.75 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

[edit ]
  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年03月05日 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.
Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)
pyrazolones /
pyrazolidines
salicylates
acetic acid derivatives
and related substances
oxicams
propionic acid
derivatives (profens)
n-arylanthranilic
acids (fenamates)
COX-2 inhibitors
(coxibs)
other
NSAID
combinations
Key: underline indicates initially developed first-in-class compound of specific group; #WHO-Essential Medicines; withdrawn drugs; veterinary use.
Receptor
(ligands)
DP (D2) Tooltip Prostaglandin D2 receptor
DP1 Tooltip Prostaglandin D2 receptor 1
DP2 Tooltip Prostaglandin D2 receptor 2
EP (E2) Tooltip Prostaglandin E2 receptor
EP1 Tooltip Prostaglandin EP1 receptor
EP2 Tooltip Prostaglandin EP2 receptor
EP3 Tooltip Prostaglandin EP3 receptor
EP4 Tooltip Prostaglandin EP4 receptor
Unsorted
FP (F) Tooltip Prostaglandin F receptor
IP (I2) Tooltip Prostacyclin receptor
TP (TXA2) Tooltip Thromboxane receptor
Unsorted
Enzyme
(inhibitors)
COX
(PTGS)
PGD2S Tooltip Prostaglandin D synthase
PGES Tooltip Prostaglandin E synthase
PGFS Tooltip Prostaglandin F synthase
PGI2S Tooltip Prostacyclin synthase
TXAS Tooltip Thromboxane A synthase
Others
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