Valrubicin

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.

Valrubicin

Clinical data
AHFS/Drugs.com	Consumer Drug Information
MedlinePlus	a611021
Routes of administration	Intravesical
ATC code	L01DB09 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	Negligible
Protein binding	>99%
Metabolism	Negligible
Excretion	In urine
Identifiers
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
CAS Number	56124-62-0 Y
PubChem CID	454216
DrugBank	DB00385 Y
ChemSpider	399974 Y
UNII	2C6NUM6878
ChEMBL	ChEMBL1096885 Y
CompTox Dashboard (EPA)	DTXSID9046497
ECHA InfoCard	100.205.793
Chemical and physical data
Formula	C34H36F3NO13
Molar mass	723.651 g·mol−1
3D model (JSmol)	Interactive image
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
InChI InChI=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 Y Key:ZOCKGBMQLCSHFP-KQRAQHLDSA-N Y
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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patients in whom cystectomy would be associated with unacceptable morbidity or mortality; however, it was voluntarily withdrawn in 2002 due to manufacturing issues.[1] Valstar was relaunched on September 3, 2009.[2]