U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

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

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
Stereochemistry ABSOLUTE
Additional Stereochemistry
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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Valstar
PubMed

PubMed

TitleDatePubMed
Evaluation of anti-SIV potential of anti-neoplastic anthracyclines.
1992
Patents

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 Twenty milliliters of VALSTAR should then be withdrawn from the four vials and diluted with 55 mL 0.9% Sodium Chloride Injection, USP providing 75 mL of a diluted VALSTAR solution.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: intravesically
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
Created
by admin
on Tue Oct 22 00:07:42 UTC 2019
Edited
by admin
on Tue Oct 22 00:07:42 UTC 2019
Record UNII
2C6NUM6878
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VALRUBICIN
HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
NSC-246131
Code English
VALSTAR
Brand Name English
AD 32
Code English
VALRUBICIN [USAN]
Common Name English
VALRUBICIN [USP-RS]
Common Name English
VALRUBICIN [ORANGE BOOK]
Common Name English
VALRUBICIN [USP]
Common Name English
VALRUBICIN [MI]
Common Name English
VALRUBICIN [HSDB]
Common Name English
VALRUBICIN [VANDF]
Common Name English
(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)-.ALPHA.-L-LYXO-HEXOPYRANOSYL)OXY)-5,12-NAPHTHACENEDIONE 8(SUP 2)-VALERATE
Common Name English
VALRUBICIN [INN]
Common Name English
VALRUBICIN [WHO-DD]
Common Name English
(2S-CIS)-2-(1,2,3,4,6,11-HEXAHYDRO-2,5,12-TRIHYDROXY-7-METHOXY-6,11-DIOXO-4-((2,3,6-TRIDEOXY-3-((TRIFLUOROACETYL)AMINO)-.ALPHA.-L-LYXO-HEXOPYRANOSYL)OXY)-2-NAPHTHACENYL)-2-OXOETHYL PENTANOATE
Common Name English
VALRUBICIN [MART.]
Common Name English
AD-32
Code English
Classification Tree Code System Code
FDA ORPHAN DRUG 82194
Created by admin on Tue Oct 22 00:07:42 UTC 2019 , Edited by admin on Tue Oct 22 00:07:42 UTC 2019
LIVERTOX 1018
Created by admin on Tue Oct 22 00:07:42 UTC 2019 , Edited by admin on Tue Oct 22 00:07:42 UTC 2019
WHO-VATC QL01DB09
Created by admin on Tue Oct 22 00:07:42 UTC 2019 , Edited by admin on Tue Oct 22 00:07:42 UTC 2019
NCI_THESAURUS C1594
Created by admin on Tue Oct 22 00:07:42 UTC 2019 , Edited by admin on Tue Oct 22 00:07:42 UTC 2019
WHO-ATC L01DB09
Created by admin on Tue Oct 22 00:07:42 UTC 2019 , Edited by admin on Tue Oct 22 00:07:42 UTC 2019
Code System Code Type Description
RXCUI
31435
Created by admin on Tue Oct 22 00:07:42 UTC 2019 , Edited by admin on Tue Oct 22 00:07:42 UTC 2019
PRIMARY RxNorm
MESH
C016163
Created by admin on Tue Oct 22 00:07:42 UTC 2019 , Edited by admin on Tue Oct 22 00:07:42 UTC 2019
PRIMARY
EVMPD
SUB05075MIG
Created by admin on Tue Oct 22 00:07:42 UTC 2019 , Edited by admin on Tue Oct 22 00:07:42 UTC 2019
PRIMARY
ChEMBL
CHEMBL1096885
Created by admin on Tue Oct 22 00:07:42 UTC 2019 , Edited by admin on Tue Oct 22 00:07:42 UTC 2019
PRIMARY
DRUG BANK
DB00385
Created by admin on Tue Oct 22 00:07:42 UTC 2019 , Edited by admin on Tue Oct 22 00:07:42 UTC 2019
PRIMARY
MERCK INDEX
M11371
Created by admin on Tue Oct 22 00:07:42 UTC 2019 , Edited by admin on Tue Oct 22 00:07:42 UTC 2019
PRIMARY Merck Index
NCI_THESAURUS
C1340
Created by admin on Tue Oct 22 00:07:42 UTC 2019 , Edited by admin on Tue Oct 22 00:07:42 UTC 2019
PRIMARY
CAS
56124-62-0
Created by admin on Tue Oct 22 00:07:42 UTC 2019 , Edited by admin on Tue Oct 22 00:07:42 UTC 2019
PRIMARY
PUBCHEM
454216
Created by admin on Tue Oct 22 00:07:42 UTC 2019 , Edited by admin on Tue Oct 22 00:07:42 UTC 2019
PRIMARY
EPA CompTox
56124-62-0
Created by admin on Tue Oct 22 00:07:42 UTC 2019 , Edited by admin on Tue Oct 22 00:07:42 UTC 2019
PRIMARY
HSDB
56124-62-0
Created by admin on Tue Oct 22 00:07:42 UTC 2019 , Edited by admin on Tue Oct 22 00:07:42 UTC 2019
PRIMARY
WIKIPEDIA
VALRUBICIN
Created by admin on Tue Oct 22 00:07:42 UTC 2019 , Edited by admin on Tue Oct 22 00:07:42 UTC 2019
PRIMARY
INN
7750
Created by admin on Tue Oct 22 00:07:42 UTC 2019 , Edited by admin on Tue Oct 22 00:07:42 UTC 2019
PRIMARY
Related Record Type Details
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
TARGET -> INHIBITOR
Related Record Type Details
METABOLITE -> PARENT
METABOLITE -> PARENT
MAJOR
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY