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 ;
PubChem CID	454216;
DrugBank	DB00385 ;
ChemSpider	399974 ;
UNII	2C6NUM6878;
ChEMBL	ChEMBL1096885 ;
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 ; Key:ZOCKGBMQLCSHFP-KQRAQHLDSA-N ;
	(verify)

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patients in whom cystectomy would be associated with unacceptable morbidity or mortality; however, it was voluntarily withdrawn in 2002 due to manufacturing issues.^[2] Valstar was relaunched on September 3, 2009.^[3]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

^ 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.
^ "Manufacturing Issues Remain for Indevus' Valstar", U.S. Food and Drug Administration News. The MQN Weekly Bulletin, Jan. 11, 2008
^ "Endo Pharmaceuticals launches VALSTAR for treating recurrent carcinoma in situ bladder tumors" (Press release). 2009-09-03. Retrieved 2009-11-26.

[Sharma_2015-1] 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.

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