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Identification
Name Valrubicin
Accession Number DB00385 (APRD00662)
Type small molecule
Groups approved
Description

Valrubicin (N-trifluoroacetyladriamycin-14-valerate, 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. [Wikipedia]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Antibiotic Ad 32
Salts Not Available
Brand names
Name Company
Valstar
Valstar Preservative Free
Brand mixtures Not Available
Categories
  • Antineoplastic Agents
CAS number 56124-62-0
Weight Average: 723.6437
Monoisotopic: 723.213874858
Chemical Formula C34H36F3NO13
InChI Key InChIKey=ZOCKGBMQLCSHFP-ZQUOIQDWSA-N
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
Plain Text
IUPAC Name
2-oxo-2-[(2S,4S)-2,5,12-trihydroxy-4-{[5-hydroxy-6-methyl-4-(trifluoroacetamido)oxan-2-yl]oxy}-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-2-yl]ethyl pentanoate
SMILES
CCCCC(=O)OCC(=O)[C@@]1(O)C[C@H](OC2CC(NC(=O)C(F)(F)F)C(O)C(C)O2)C2=C(C1)C(O)=C1C(=O)C3=C(C(=O)C1=C2O)C(OC)=CC=C3
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Anthracyclines
Substructures
  • Anthracyclines
  • Carboxylic Acids and Derivatives
  • Hydroxy Compounds
  • Pyrans
  • Benzyl Alcohols and Derivatives
  • Naphthalenes
  • Acetates
  • Acetals and Derivatives
  • Phenols and Derivatives
  • Amino Ketones
  • Benzoquinones
  • Ethers
  • Halogen Derivatives
  • Benzene and Derivatives
  • Naphthoquinones
  • Anthraquinones
  • Anthracenes
  • Hydroquinones
  • Alcohols and Polyols
  • Heterocyclic compounds
  • Aromatic compounds
  • Anisoles
  • Carboxamides and Derivatives
  • Benzoyl Derivatives
  • Cyclohexenes and Derivatives
  • Phenyl Esters
  • Ketones
Pharmacology
Indication For the treatment of cancer of the bladder.
Pharmacodynamics Valrubicin is a semisynthetic analog of the anthracycline doxorubicin, and is administered by infusion directly into the bladder.
Mechanism of action Valrubicin is an anthracycline that affects a variety of inter-related biological functions, most of which involve nucleic acid metabolism. It readily penetrates into cells, where after DNA intercalation, it inhibits the incorporation of nucleosides into nucleic acids, causes extensive chromosomal damage, and arrests cell cycle in G2. Although valrubicin does not bind strongly to DNA, a principal mechanism of its action, mediated by valrubicin metabolites, is interference with the normal DNA breaking-resealing action of DNA topoisomerase II.
Absorption Not Available
Volume of distribution Not Available
Protein binding >99%
Metabolism Valrubicin is metabolized to two primary metabolites: N-trifluoroacetyladriamycin and N-trifluoroacetyladriamycinol.
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity The primary anticipated complications of overdosage associated with intravesical administration would be consistent with irritable bladder symptoms. Myelosuppression is possible if valrubicin is inadvertently administered systemically or if significant systemic exposure occurs following intravesical administration (e.g., in patients with bladder/rupture perforation). The maximum tolerated dose in humans by either intraperitoneal or intravenous administration is 600 mg/m2.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Endo pharmaceutical solutions inc
Packagers
Dosage forms
Form Route Strength
Liquid Intravesical
Prices
Unit description Cost Unit
Valstar 40 mg/ml vial 219.96 USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 116-117 °C Not Available
water solubility insoluble Not Available
logP 2.2 Not Available
Predicted Properties
Property Value Source
water solubility 3.25e-02 g/l ALOGPS
logP 2.67 ALOGPS
logP 4.49 ChemAxon
logS -4.3 ALOGPS
pKa (strongest acidic) 5.39 ChemAxon
pKa (strongest basic) -3.4 ChemAxon
physiological charge -1 ChemAxon
hydrogen acceptor count 12 ChemAxon
hydrogen donor count 5 ChemAxon
polar surface area 215.22 ChemAxon
rotatable bond count 12 ChemAxon
refractivity 168.03 ChemAxon
polarizability 68.86 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
PubChem Compound 41744 Link_out
PubChem Substance 46506642 Link_out
ChemSpider 38088 Link_out
Therapeutic Targets Database DAP000650 Link_out
PharmGKB PA164748616 Link_out
Drug Product Database 2242466 Link_out
RxList http://www.rxlist.com/cgi/generic2/rubicin.htm Link_out
Drugs.com http://www.drugs.com/cdi/valrubicin.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Valrubicin Link_out
ATC Codes
  • L01DB09
AHFS Codes
  • 10:00.00
PDB Entries Not Available
FDA label show (80 KB)
MSDS Not Available
Interactions
Drug Interactions
Drug Interaction
Docetaxel The taxane derivative, Docetaxel, may increase Valrubicin toxicity. Consider alternate therapy or monitor for toxic effects.
Natalizumab Valrubicin may increase Natalizumab toxicity. Concurrent therapy should be avoided.
Paclitaxel The taxane derivative, Paclitaxel, may increase Valrubicin toxicity. Consider alternate therapy or monitor for toxic effects.
Trastuzumab Trastuzumab may increase the cardiotoxicity of Valrubicin. Signs and symptoms of cardiac dysfunction should be monitored for frequently. Increased risk of heart failure. Trastuzumab may increase the risk of neutropenia and anemia. Monitor closely for signs and symptoms of adverse events.
Food Interactions Not Available
Targets

1. DNA

Pharmacological action: yes
Actions: intercalation

DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes.

Gene Sequence: FASTA

References:
  1. Brox L, Gowans B, Belch A: N-trifluoroacetyladriamycin-14-valerate and adriamycin induced DNA damage in the RPMI-6410 human lymphoblastoid cell line. Can J Biochem. 1980 Sep;58(9):720-5. Pubmed
  2. Perabo FG, Muller SC: New agents in intravesical chemotherapy of superficial bladder cancer. Scand J Urol Nephrol. 2005;39(2):108-16. Pubmed

2. DNA topoisomerase 2-alpha

Pharmacological action: yes
Actions: inhibitor

Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks

Organism class: human
UniProt ID: P11388 Link_out
Gene: TOP2A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  2. Perabo FG, Muller SC: New agents in intravesical chemotherapy of superficial bladder cancer. Scand J Urol Nephrol. 2005;39(2):108-16. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19