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Structure via PubChem · Public domain (PubChem)
valrubicin
Sign in to saveAlso known as Valstar, (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 (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.
Chemical data
- Formula
- C34H36F3NO13
- Molecular weight
- 723.6 g/mol
- IUPAC name
- [2-oxo-2-[(2S,4S)-2,5,12-trihydroxy-4-[(2R,4S,5S,6S)-5-hydroxy-6-methyl-4-[(2,2,2-trifluoroacetyl)amino]oxan-2-yl]oxy-7-methoxy-6,11-dioxo-3,4-dihydro-1H-tetracen-2-yl]ethyl] pentanoate
- SMILES
- CCCCC(=O)OCC(=O)[C@]1(C[C@@H](C2=C(C1)C(=C3C(=C2O)C(=O)C4=C(C3=O)C=CC=C4OC)O)O[C@H]5C[C@@H]([C@@H]([C@@H](O5)C)O)NC(=O)C(F)(F)F)O
- InChIKey
- ZOCKGBMQLCSHFP-KQRAQHLDSA-N
- XLogP
- 4
- Polar surface area
- 215 Ų
- H-bond donors
- 5
- H-bond acceptors
- 16
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
149 papers- Valrubicin.Drugs & aging · 1999
- Valrubicin.2006
- Valrubicin in refractory non-muscle invasive bladder cancer.Expert review of anticancer therapy · 2015
- Valrubicin-loaded immunoliposomes for specific vesicle-mediated cell death in the treatment of hematological cancers.Cell death & disease · 2024
- Doxorubicin.2012
via PubMed
Wikidata facts
- Mass
- 723.213875
- Has use
- medication
Show 6 more facts
- chemical formula
- C₃₄H₃₆F₃NO₁₃
- medical condition treated
- bladder cancer
- canonical SMILES
- CCCCC(=O)OCC(=O)C1(CC(C2=C(C3=C(C(=C2C1)O)C(=O)C4=C(C3=O)C(=CC=C4)OC)O)OC5CC(C(C(O5)C)O)NC(=O)C(F)(F)F)O
- isomeric SMILES
- CCCCC(=O)OCC(=O)[C@@]1(O)C[C@H](O[C@H]2C[C@H](NC(=O)C(F)(F)F)[C@H](O)[C@H](C)O2)C3=C(C1)C(O)=C4C(=O)C5=CC=CC(OC)=C5C(=O)C4=C3O
- NCI Thesaurus ID
- C1340
- Commons category
- Valrubicin
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
2 sectionsContents
- Side effects
- References
{{Drugbox | verifiedrevid = 470628311 | 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 | image = Valrubicin.svg | image_class = skin-invert-image
| tradename = | Drugs.com = | MedlinePlus = a611021 | pregnancy_US = C | legal_status = Rx-only | routes_of_administration = Intravesical
Excerpted from Wikipedia’s “valrubicin” article, available under the CC BY-SA 4.0 licence.