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	M01AX23 (WHO)
Identifiers
IUPAC name 5-chloro-2-hydroxy-3-(2-thienylcarbonyl)-1H-indole-1-carboxamide
CAS Number	120210-48-2^Y
PubChem CID	60712
ChemSpider	54717^N
UNII	9K7CJ74ONH
KEGG	D06072^Y
ChEMBL	ChEMBL1097558^N
CompTox Dashboard (EPA)	DTXSID9046104
Chemical and physical data
Formula	C14H9ClN2O3S
Molar mass	320.75 g·mol^−1
3D model (JSmol)	Interactive image
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.