Valrubicin

Valrubicin

Systematic (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
Clinical data
AHFS/Drugs.com	Consumer Drug Information
MedlinePlus	a611021
Pregnancy category	US: C (Risk not ruled out)
Legal status	℞ (Prescription only)
Routes of administration	Intravesical
Pharmacokinetic data
Bioavailability	Negligible
Protein binding	>99%
Metabolism	Negligible
Excretion	In urine
Identifiers
CAS Number	56124-62-0 Y
ATC code	L01DB09 (WHO)
PubChem	CID: 454216
DrugBank	DB00385 Y
ChemSpider	399974 Y
UNII	2C6NUM6878 Y
ChEMBL	CHEMBL1096885 Y
Chemical data
Formula	C34H36F3NO13
Molecular mass	723.644 g/mol
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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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patients in whom cystectomy would be associated with unacceptable morbidity or mortality; however, it was voluntarily withdrawn in 2002 due to manufacturing issues. Valstar was relaunched on September 3, 2009.

Side effects

• Blood in urine
• Incontinence
• painful or difficult urination
• Unusually frequent urination