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Details

Stereochemistry ABSOLUTE
Molecular Formula C34H36F3NO13
Molecular Weight 723.6437
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VALRUBICIN

SMILES

[H][C@@]1(C[C@@](O)(CC2=C(O)C3=C(C(=O)C4=C(C=CC=C4OC)C3=O)C(O)=C12)C(=O)COC(=O)CCCC)O[C@H]5C[C@H](NC(=O)C(F)(F)F)[C@H](O)[C@H](C)O5

InChI

InChIKey=ZOCKGBMQLCSHFP-KQRAQHLDSA-N
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

HIDE SMILES / InChI

Molecular Formula C34H36F3NO13
Molecular Weight 723.6437
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Valrubicin is a semisynthetic analog of the anthracycline doxorubicin, and is administered by infusion directly into the bladder. 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. Valrubicin is FDA approved drug, sold under the trade name Valstar.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.85 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Valstar

AUC

ValueDoseCo-administeredAnalytePopulation
78 nM × h
900 mg single, intravesical
VALRUBICIN plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
1%
VALRUBICIN plasma
Homo sapiens

Doses

AEs

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
VALSTAR (Valrubicin) is recommended at a dose of 800 mg administered intravesically once a week for six weeks. Administration should be delayed at least two weeks after transurethral resection and/or fulguration. For each instillation, four 5 mL vials (200 mg valrubicin/5 mL vial) should be allowed to warm slowly to room temperature, but should not be heated. Twenty milliliters of VALSTAR should then be withdrawn from the four vials and diluted with 55 mL 0.9% Sodium Chloride Injection, USP providing 75 mL of a diluted VALSTAR solution. A urethral catheter should then be inserted into the patient's bladder under aseptic conditions, the bladder drained, and the diluted 75 mL VALSTAR solution instilled slowly via gravity flow over a period of several minutes. The catheter should then be withdrawn. The patient should retain the drug for two hours before voiding. At the end of two hours, all patients should void. (Some patients will be unable to retain the drug for the full two hours.) Patients should be instructed to maintain adequate hydration following treatment.
Route of Administration: Other
In Vitro Use Guide
At equimolar concentrations (10 uM), or at concentrations related to their 50% growth-inhibitory values vs CEM (human leukemic lymphoblastic) cells, Valrubicin was consistently found to be more inhibitory than adriamycin of DNA and RNA synthesis, as measured by the incorporation of tritiated thymidine and uridine, respectively, into acid-precipitable fractions relative to untreated controls.
Substance Class Chemical
Record UNII
2C6NUM6878
Record Status Validated (UNII)
Record Version