Tenidap

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 408923737

| IUPAC_name = 5-chloro-2-hydroxy-3-(2-thienylcarbonyl)-1H-indole-1-carboxamide

| image = tenidap.png

| image_class = skin-invert-image

| tradename =

| pregnancy_AU =

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| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| legal_status =

| routes_of_administration =

| bioavailability =

| protein_bound =

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| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 120210-48-2

| ATC_prefix = M01

| ATC_suffix = AX23

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 9K7CJ74ONH

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D06072

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1097558

| PubChem = 60712

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 54717

| C=14 | H=9 | Cl=1 | N=2 | O=3 | S=1

| smiles = c1cc(sc1)C(=O)c2c3cc(ccc3n(c2O)C(=O)N)Cl

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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)

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = IZSFDUMVCVVWKW-UHFFFAOYSA-N

}}

Tenidap was a COX/5-LOX inhibitor and cytokine-modulating anti-inflammatory drug candidate{{cite journal | vauthors = Wylie G, Appelboom T, Bolten W, Breedveld FC, Feely J, Leeming MR, Le Loët X, Manthorpe R, Marcolongo R, Smolen J | display-authors = 6 | title = 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 | journal = British Journal of Rheumatology | volume = 34 | issue = 6 | pages = 554–63 | date = June 1995 | pmid = 7543348 | doi = 10.1093/rheumatology/34.6.554 }} that was under development by Pfizer as a promising potential treatment for rheumatoid arthritis,Staff, American Journal of Nursing. [http://journals.lww.com/ajnonline/fulltext/1996/01000/tenidap_offers_arthritis_therapy_minus_toxicity.41.aspx Drug Watch: Tenidap Offers Arthritis Therapy Minus Toxicity] AJN 1996 96(1):58 but Pfizer halted development after marketing approval was rejected by the FDA in 1996Pfizer. Sept 27, 1996 [http://www.thefreelibrary.com/Pfizer+To+Halt+Plans+For+Commercialization+Of+Tenidap+For+Rheumatoid...-a018716065 Press release: Pfizer To Halt Plans For Commercialization Of Tenidap For Rheumatoid Arthritis] {{Webarchive|url=https://web.archive.org/web/20160305160122/http://www.thefreelibrary.com/Pfizer+To+Halt+Plans+For+Commercialization+Of+Tenidap+For+Rheumatoid...-a018716065 |date=2016-03-05 }} due to liver and kidney toxicity, which was attributed to metabolites of the drug with a thiophene moiety that caused oxidative damage.{{cite journal | vauthors = Hwang SH, Wecksler AT, Wagner K, Hammock BD | title = Rationally designed multitarget agents against inflammation and pain | journal = Current Medicinal Chemistry | volume = 20 | issue = 13 | pages = 1783–99 | date = 2013 | pmid = 23410172 | pmc = 4113248 | doi = 10.2174/0929867311320130013 }}