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Tenidap

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Tenidap
Clinical data
ATC code
Identifiers
  • 5-chloro-2-hydroxy-3-(2-thienylcarbonyl)-1H-indole-1-carboxamide
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC14H9ClN2O3S
Molar mass320.75 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 aCOX/5-LOX inhibitor andcytokine-modulatinganti-inflammatory drug candidate[1] that was under development by Pfizer as a promising potential treatment forrheumatoid 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 athiophene 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, 1996Press release: Pfizer To Halt Plans For Commercialization Of Tenidap For Rheumatoid ArthritisArchived 2016-03-05 at theWayback 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.
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Key:underline indicates initially developed first-in-class compound of specific group;#WHO-Essential Medicines;withdrawn drugs;veterinary use.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
DP1Tooltip Prostaglandin D2 receptor 1
DP2Tooltip Prostaglandin D2 receptor 2
EP (E2)Tooltip Prostaglandin E2 receptor
EP1Tooltip Prostaglandin EP1 receptor
EP2Tooltip Prostaglandin EP2 receptor
EP3Tooltip Prostaglandin EP3 receptor
EP4Tooltip Prostaglandin EP4 receptor
Unsorted
FP (F)Tooltip Prostaglandin F receptor
IP (I2)Tooltip Prostacyclin receptor
TP (TXA2)Tooltip Thromboxane receptor
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Enzyme
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PGD2STooltip Prostaglandin D synthase
PGESTooltip Prostaglandin E synthase
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PGI2STooltip Prostacyclin synthase
TXASTooltip Thromboxane A synthase
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