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
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
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 |
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
Doses
AEs
Sourcing
PubMed
Patents
Sample Use Guides
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VALSTAR should then be withdrawn from the four vials and diluted with 55 mL 0.9% Sodium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
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.