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Details

Stereochemistry ABSOLUTE
Molecular Formula C34H36F3NO13
Molecular Weight 723.6451
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(Cc2c([C@]([H])(C1)O[C@@]3([H])C[C@@]([H])([C@@]([H])([C@]([H])(C)O3)O)N=C(C(F)(F)F)O)c(c4c(C(=O)c5cccc(c5C4=O)OC)c2O)O)O

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 723.6451
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: Description was created based on several sources including http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020892s013lbl.pdf

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

Approved Use

VALSTAR is indicated for intravesical therapy of BCG-refractory carcinoma in situ (CIS) of the urinary bladder in patients for whom immediate cystectomy would be associated with unacceptable morbidity or mortality.

Launch Date

906595200000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
5.2 μg/g
80 mg/kg single, intravenous
dose: 80 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
VALRUBICIN unknown
Mus musculus
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
78 nM × h
900 mg single, intravesical
dose: 900 mg
route of administration: Intravesical
experiment type: SINGLE
co-administered:
VALRUBICIN plasma
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
161 μg × min/g
80 mg/kg single, intravenous
dose: 80 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
VALRUBICIN unknown
Mus musculus
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
10 h
50 mg/kg single, intravenous
dose: 50 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
VALRUBICIN plasma
Mus musculus
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
0.34 h
80 mg/kg single, intravenous
dose: 80 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
VALRUBICIN unknown
Mus musculus
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
1%
VALRUBICIN plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
900 mg 1 times / week multiple, intravesical
Highest studied dose
Dose: 900 mg, 1 times / week
Route: intravesical
Route: multiple
Dose: 900 mg, 1 times / week
Sources:
unhealthy, 66.2 +/- 8.7
Health Status: unhealthy
Age Group: 66.2 +/- 8.7
Sex: M+F
Sources:
Other AEs: Vaginitis, Skin irritation...
Other AEs:
Vaginitis (11%)
Skin irritation (11%)
Sources:
800 mg 1 times / week multiple, intravesical
MTD
Dose: 800 mg, 1 times / week
Route: intravesical
Route: multiple
Dose: 800 mg, 1 times / week
Sources:
unhealthy, 66.2 +/- 8.7
Health Status: unhealthy
Age Group: 66.2 +/- 8.7
Sex: M+F
Sources:
800 mg 1 times / week multiple, intravesical
MTD
Dose: 800 mg, 1 times / week
Route: intravesical
Route: multiple
Dose: 800 mg, 1 times / week
Sources:
unhealthy, 67
Health Status: unhealthy
Age Group: 67
Sex: M+F
Sources:
AEs

AEs

AESignificanceDosePopulation
Skin irritation 11%
900 mg 1 times / week multiple, intravesical
Highest studied dose
Dose: 900 mg, 1 times / week
Route: intravesical
Route: multiple
Dose: 900 mg, 1 times / week
Sources:
unhealthy, 66.2 +/- 8.7
Health Status: unhealthy
Age Group: 66.2 +/- 8.7
Sex: M+F
Sources:
Vaginitis 11%
900 mg 1 times / week multiple, intravesical
Highest studied dose
Dose: 900 mg, 1 times / week
Route: intravesical
Route: multiple
Dose: 900 mg, 1 times / week
Sources:
unhealthy, 66.2 +/- 8.7
Health Status: unhealthy
Age Group: 66.2 +/- 8.7
Sex: M+F
Sources:
PubMed

PubMed

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

Patents

Sample Use Guides

VALSTAR (Valrubicin) is recommended at a dose of 800 mg administered intravesically once a week for six
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
Created
by admin
on Fri Jun 25 21:00:00 UTC 2021
Edited
by admin
on Fri Jun 25 21:00:00 UTC 2021
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
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
VALRUBICIN [USP MONOGRAPH]
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 Fri Jun 25 21:00:00 UTC 2021 , Edited by admin on Fri Jun 25 21:00:00 UTC 2021
LIVERTOX 1018
Created by admin on Fri Jun 25 21:00:00 UTC 2021 , Edited by admin on Fri Jun 25 21:00:00 UTC 2021
WHO-VATC QL01DB09
Created by admin on Fri Jun 25 21:00:00 UTC 2021 , Edited by admin on Fri Jun 25 21:00:00 UTC 2021
NCI_THESAURUS C1594
Created by admin on Fri Jun 25 21:00:00 UTC 2021 , Edited by admin on Fri Jun 25 21:00:00 UTC 2021
WHO-ATC L01DB09
Created by admin on Fri Jun 25 21:00:00 UTC 2021 , Edited by admin on Fri Jun 25 21:00:00 UTC 2021
Code System Code Type Description
FDA UNII
2C6NUM6878
Created by admin on Fri Jun 25 21:00:00 UTC 2021 , Edited by admin on Fri Jun 25 21:00:00 UTC 2021
PRIMARY
RXCUI
31435
Created by admin on Fri Jun 25 21:00:00 UTC 2021 , Edited by admin on Fri Jun 25 21:00:00 UTC 2021
PRIMARY RxNorm
DRUG CENTRAL
2805
Created by admin on Fri Jun 25 21:00:00 UTC 2021 , Edited by admin on Fri Jun 25 21:00:00 UTC 2021
PRIMARY
MESH
C016163
Created by admin on Fri Jun 25 21:00:00 UTC 2021 , Edited by admin on Fri Jun 25 21:00:00 UTC 2021
PRIMARY
EVMPD
SUB05075MIG
Created by admin on Fri Jun 25 21:00:00 UTC 2021 , Edited by admin on Fri Jun 25 21:00:00 UTC 2021
PRIMARY
ChEMBL
CHEMBL1096885
Created by admin on Fri Jun 25 21:00:00 UTC 2021 , Edited by admin on Fri Jun 25 21:00:00 UTC 2021
PRIMARY
USP_CATALOG
1708730
Created by admin on Fri Jun 25 21:00:00 UTC 2021 , Edited by admin on Fri Jun 25 21:00:00 UTC 2021
PRIMARY USP-RS
DRUG BANK
DB00385
Created by admin on Fri Jun 25 21:00:00 UTC 2021 , Edited by admin on Fri Jun 25 21:00:00 UTC 2021
PRIMARY
MERCK INDEX
M11371
Created by admin on Fri Jun 25 21:00:00 UTC 2021 , Edited by admin on Fri Jun 25 21:00:00 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C1340
Created by admin on Fri Jun 25 21:00:00 UTC 2021 , Edited by admin on Fri Jun 25 21:00:00 UTC 2021
PRIMARY
CAS
56124-62-0
Created by admin on Fri Jun 25 21:00:00 UTC 2021 , Edited by admin on Fri Jun 25 21:00:00 UTC 2021
PRIMARY
PUBCHEM
454216
Created by admin on Fri Jun 25 21:00:00 UTC 2021 , Edited by admin on Fri Jun 25 21:00:00 UTC 2021
PRIMARY
EPA CompTox
56124-62-0
Created by admin on Fri Jun 25 21:00:00 UTC 2021 , Edited by admin on Fri Jun 25 21:00:00 UTC 2021
PRIMARY
HSDB
7288
Created by admin on Fri Jun 25 21:00:00 UTC 2021 , Edited by admin on Fri Jun 25 21:00:00 UTC 2021
PRIMARY
WIKIPEDIA
VALRUBICIN
Created by admin on Fri Jun 25 21:00:00 UTC 2021 , Edited by admin on Fri Jun 25 21:00:00 UTC 2021
PRIMARY
INN
7750
Created by admin on Fri Jun 25 21:00:00 UTC 2021 , Edited by admin on Fri Jun 25 21:00:00 UTC 2021
PRIMARY
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