valrubicin

Also 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.

In the Vinony graph

Vinony's link graph records 278 inbound references to valrubicin, and connects out to urinary bladder, tiazofurin and disease.

It is catalogued under topics including Acetamides, Anthracyclines and Drugs with non-standard legal status.

Vinony links it to 5 Wikipedia language editions.

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 Å²
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 sections

Contents

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

Excerpted from Wikipedia’s “valrubicin” article, available under the CC BY-SA 4.0 licence.