Valrubicin

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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Valrubicin (N-trifluoroacetyladriamycin-14-valerate, trade name Valstar) is a chemotherapy drug used to treat bladder cancer. ^[1] 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patients in whom cystectomy would be associated with unacceptable morbidity or mortality; however, it was voluntarily withdrawn in 2002 due to manufacturing issues. ^[2] Valstar was relaunched on September 3, 2009. ^[3]

Side effects

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

References

1. Sharma P, Zargar-Shoshtari K, Sexton WJ (2015). "Valrubicin in refractory non-muscle invasive bladder cancer". Expert Review of Anticancer Therapy. 15 (12): 1379–1387. doi:10.1586/14737140.2015.1115350. PMID   26569509.
2. "Manufacturing Issues Remain for Indevus' Valstar", U.S. Food and Drug Administration News. The MQN Weekly Bulletin, Jan. 11, 2008
3. "Endo Pharmaceuticals launches VALSTAR for treating recurrent carcinoma in situ bladder tumors" (Press release). 2009-09-03. Retrieved 2009-11-26.