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Valrubicin
Identification
- Name
- Valrubicin
- Accession Number
- DB00385
- Description
Valrubicin (N-trifluoroacetyladriamycin-14-valerate) is a chemotherapy drug commonly marketed under the trade name VALSTAR. It is a semisynthetic analog of the doxorubicin, which is an anthracycline drug. Used in the treatment of the bladder cancer, valrubicin is administered by direct infusion into the bladder.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Valrubicin (DB00385)
- Weight
- Average: 723.651
Monoisotopic: 723.213874712 - Chemical Formula
- C34H36F3NO13
- Synonyms
- (8S, 10S)-8-glycoloyl-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-10-[[2,3,6-trideoxy-3-(2,2,2-trifluoroacetamido)-α-L-lyxo-hexopyranosyl]oxy]-5,12-naphthacenedione 8²-valerate
- 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
- Valrubicin
- Valrubicina
- Valrubicine
- Valrubicinum
- External IDs
- AD 32
- AD-32
- NSC 246131
- NSC-246131
Pharmacology
- Indication
For the treatment of cancer of the bladder.
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
Valrubicin is an anticancer agent.
- 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.
Target Actions Organism ADNA intercalationHumans ADNA topoisomerase 2-alpha inhibitorHumans - Absorption
- Not Available
- Volume of distribution
- Not Available
- Protein binding
>99%
- Metabolism
Valrubicin is metabolized to two primary metabolites: N-trifluoroacetyladriamycin and N-trifluoroacetyladriamycinol.
Hover over products below to view reaction partners
- Route of elimination
- Not Available
- Half-life
- Not Available
- Clearance
- Not Available
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- 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
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional DataDarbepoetin alfa The risk or severity of Thrombosis can be increased when Darbepoetin alfa is combined with Valrubicin. Erythropoietin The risk or severity of Thrombosis can be increased when Erythropoietin is combined with Valrubicin. Methoxy polyethylene glycol-epoetin beta The risk or severity of Thrombosis can be increased when Methoxy polyethylene glycol-epoetin beta is combined with Valrubicin. Peginesatide The risk or severity of Thrombosis can be increased when Peginesatide is combined with Valrubicin. Trastuzumab The risk or severity of cardiotoxicity can be increased when Trastuzumab is combined with Valrubicin. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- No interactions found.
Products
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataValstar Solution, concentrate 40 mg/1mL Intravesical Endo Pharmaceuticals Inc. 1998-10-01 Not applicable US 
Valtaxin Solution Intravesical Endo Pharmaceuticals Solutions Inc. 2001-04-23 2017-08-01 Canada 
Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataValrubicin Intravesical Solution Solution, concentrate 40 mg/1mL Intravesical Leucadia Pharmaceuticals 2019-04-23 Not applicable US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
Categories
- ATC Codes
- L01DB09 — Valrubicin
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage.
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Anthracyclines
- Sub Class
- Not Available
- Direct Parent
- Anthracyclines
- Alternative Parents
- Tetracenequinones / Anthraquinones / O-glycosyl compounds / Tetralins / Anisoles / Aryl ketones / Alkyl aryl ethers / Alpha-acyloxy ketones / Fatty acid esters / Oxanes show 17 more
- Substituents
- 1,4-anthraquinone / 9,10-anthraquinone / Acetal / Alcohol / Alkyl aryl ether / Alkyl fluoride / Alkyl halide / Alpha-acyloxy ketone / Alpha-hydroxy ketone / Anisole show 37 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
Chemical Identifiers
- UNII
- 2C6NUM6878
- CAS number
- 56124-62-0
- InChI Key
- ZOCKGBMQLCSHFP-KQRAQHLDSA-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
- IUPAC Name
- 2-oxo-2-[(2S,4S)-2,5,12-trihydroxy-4-{[(2R,4S,5S,6S)-5-hydroxy-6-methyl-4-(2,2,2-trifluoroacetamido)oxan-2-yl]oxy}-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-2-yl]ethyl pentanoate
- SMILES
- [H][[email protected]@]1(C[[email protected]@](O)(CC2=C(O)C3=C(C(O)=C12)C(=O)C1=C(OC)C=CC=C1C3=O)C(=O)COC(=O)CCCC)O[[email protected]]1C[[email protected]](NC(=O)C(F)(F)F)[[email protected]](O)[[email protected]](C)O1
References
- Synthesis Reference
Francesca Scarpitta, Csilla Nemethne Racz, "Crystalline forms of valrubicin and processes for their preparation." U.S. Patent US20080139490, issued June 12, 2008.
US20080139490- General References
- Not Available
- External Links
- PubChem Compound
- 454216
- PubChem Substance
- 46506642
- ChemSpider
- 399974
- 31435
- ChEBI
- 135876
- ChEMBL
- CHEMBL1096885
- ZINC
- ZINC000049783788
- Therapeutic Targets Database
- DAP000650
- PharmGKB
- PA164748616
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Valrubicin
- AHFS Codes
- 10:00.00 — Antineoplastic Agents
- FDA label
- Download (80 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Terminated Treatment Carcinoma in Situ / Non-muscle Invasive Bladder Cancer (NMIBC) / Transitional Cell Carcinoma 1 3 Unknown Status Treatment Cancer, Bladder 1 2 Completed Treatment Cancer, Bladder 2 2, 3 Completed Treatment Cancer, Bladder / Carcinoma in Situ 1 1 Completed Treatment Transitional Cell Carcinoma 1
Pharmacoeconomics
- Manufacturers
- Endo pharmaceutical solutions inc
- Packagers
- Endo Pharmaceuticals Inc.
- Primapharm Inc.
- Dosage Forms
Form Route Strength Solution, concentrate Intravesical 40 mg/1mL Solution Intravesical - Prices
Unit description Cost Unit Valstar 40 mg/ml vial 219.96USD 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 (°C) 116-117 °C Not Available water solubility insoluble Not Available logP 2.2 Not Available - Predicted Properties
Property Value Source Water Solubility 0.0325 mg/mL ALOGPS logP 2.67 ALOGPS logP 4.49 ChemAxon logS -4.4 ALOGPS pKa (Strongest Acidic) 8 ChemAxon pKa (Strongest Basic) -3.4 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 12 ChemAxon Hydrogen Donor Count 5 ChemAxon Polar Surface Area 215.22 Å2 ChemAxon Rotatable Bond Count 12 ChemAxon Refractivity 168.03 m3·mol-1 ChemAxon Polarizability 69.2 Å3 ChemAxon Number of Rings 5 ChemAxon Bioavailability 0 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule Yes ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.8596 Blood Brain Barrier - 0.8907 Caco-2 permeable - 0.6894 P-glycoprotein substrate Substrate 0.8165 P-glycoprotein inhibitor I Non-inhibitor 0.5747 P-glycoprotein inhibitor II Non-inhibitor 0.5584 Renal organic cation transporter Non-inhibitor 0.9348 CYP450 2C9 substrate Non-substrate 0.8061 CYP450 2D6 substrate Non-substrate 0.7947 CYP450 3A4 substrate Substrate 0.7203 CYP450 1A2 substrate Non-inhibitor 0.7239 CYP450 2C9 inhibitor Non-inhibitor 0.8228 CYP450 2D6 inhibitor Non-inhibitor 0.9016 CYP450 2C19 inhibitor Non-inhibitor 0.7565 CYP450 3A4 inhibitor Non-inhibitor 0.6895 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7154 Ames test Non AMES toxic 0.5421 Carcinogenicity Non-carcinogens 0.9272 Biodegradation Not ready biodegradable 0.9972 Rat acute toxicity 2.8652 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9846 hERG inhibition (predictor II) Inhibitor 0.5129
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
Yes
Intercalation
References
- 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:7006761]
- Perabo FG, Muller SC: New agents in intravesical chemotherapy of superficial bladder cancer. Scand J Urol Nephrol. 2005;39(2):108-16. [PubMed:16019763]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Ubiquitin binding
- Specific Function
- Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks. Essential during mitosis and meiosis for proper segr...
- Gene Name
- TOP2A
- Uniprot ID
- P11388
- Uniprot Name
- DNA topoisomerase 2-alpha
- Molecular Weight
- 174383.88 Da
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- Perabo FG, Muller SC: New agents in intravesical chemotherapy of superficial bladder cancer. Scand J Urol Nephrol. 2005;39(2):108-16. [PubMed:16019763]
Drug created on June 13, 2005 07:24 / Updated on September 20, 2020 08:50
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