valrubicin

{{Short description|Pharmaceutical drug}}

{{Drugbox

| verifiedrevid = 470628311

| IUPAC_name = 2-oxo-2-[(2S,4S)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-4-({2,3,6-trideoxy-3-[(trifluoroacetyl)amino]hexopyranosyl}oxy)-1,2,3,4,6,11-hexahydrotetracen-2-yl]ethyl pentanoate

| image = Valrubicin.svg

| tradename =

| Drugs.com = {{drugs.com|CDI|valrubicin}}

| MedlinePlus = a611021

| pregnancy_US = C

| legal_status = Rx-only

| routes_of_administration = Intravesical

| bioavailability = Negligible

| protein_bound = >99%

| metabolism = Negligible

| excretion = In urine

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 56124-62-0

| ATC_prefix = L01

| ATC_suffix = DB09

| PubChem = 454216

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

| DrugBank = DB00385

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 399974

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

| UNII = 2C6NUM6878

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 1096885

| C=34 | H=36 | F=3 | N=1 | O=13

| smiles = FC(F)(F)C(=O)N[C@@H]5[C@H](O)[C@@H](O[C@@H](O[C@@H]4c3c(O)c2C(=O)c1c(OC)cccc1C(=O)c2c(O)c3C[C@@](O)(C(=O)COC(=O)CCCC)C4)C5)C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C34H36F3NO13/c1-4-5-9-21(40)49-13-20(39)33(47)11-16-24(19(12-33)51-22-10-17(27(41)14(2)50-22)38-32(46)34(35,36)37)31(45)26-25(29(16)43)28(42)15-7-6-8-18(48-3)23(15)30(26)44/h6-8,14,17,19,22,27,41,43,45,47H,4-5,9-13H2,1-3H3,(H,38,46)/t14-,17-,19-,22-,27+,33-/m0/s1

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = ZOCKGBMQLCSHFP-KQRAQHLDSA-N

}}

Valrubicin (N-trifluoroacetyladriamycin-14-valerate, trade name Valstar) is a chemotherapy drug used to treat bladder cancer. Valrubicin is a semisynthetic analog of the anthracycline doxorubicin, and is administered by infusion directly into the bladder.

It was originally launched as Valstar in the U.S. in 1999 for intravesical therapy of Bacille Calmette-Guérin (BCG)-refractory carcinoma in situ of the urinary bladder in patients in whom cystectomy would be associated with unacceptable morbidity or mortality; however, it was voluntarily withdrawn in 2002 due to manufacturing issues.[http://www.fdanews.com/newsletter/article?articleId=103010&issueId=11203 "Manufacturing Issues Remain for Indevus' Valstar"], U.S. Food and Drug Administration News. The MQN Weekly Bulletin, Jan. 11, 2008 Valstar was relaunched on September 3, 2009.{{cite press release |url=http://www.news-medical.net/news/20090903/Endo-Pharmaceuticals-launches-VALSTAR-for-treating-recurrent-carcinoma-in-situ-bladder-tumors.aspx |title=Endo Pharmaceuticals launches VALSTAR for treating recurrent carcinoma in situ bladder tumors |date=2009-09-03 |access-date=2009-11-26}}