Details of the Drug

General Information of Drug (ID: DMOYJFK)

Drug Name
Valrubicin
Synonyms
Valstar; Valrubicin [USAN]; Valstar Preservative Free; AD 32; Antibiotic AD 32; Valstar (TN); N-Trifluoroacetyladriamycin 14-valerate; N-Trifluoroacetyldoxorubicin 14-valerate; Trifluoroacetyladriamycin-14-valerate; Valrubicin (USP/INN); N-Trifluoroacetyladriamycin-14-valerate; Adriamycin, trifluoroacetyl-, 14-valerate; [2-oxo-2-[(2S,4S)-2,5,12-trihydroxy-4-[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; (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; (2S-cis)-Pentanoic acid, 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-naphth acenyl)-2-oxoethyl ester; (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; Pentanoic acid, 2-((2S,4S)-1,2,3,4,6,11-hexahydro-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-4-((2,3,6-trideoxy-3-((trifluoroacetylamino)-, alpha-L-lysohexopyranoxyl)oxy)-2-naphthacenyl)-2-oxoethyl ester
Indication
Disease Entry ICD 11 Status REF
Bladder cancer 2C94 Approved [1]
In situ carcinoma N.A. Approved [2]
Urinary bladder cancer N.A. Approved [2]
Psoriasis vulgaris EA90 Phase 2 [3]
Therapeutic Class
Anticancer Agents
Affected Organisms
Humans and other mammals
ATC Code
L01DB09: Valrubicin
L01DB: Anthracyclines and related substances
L01D: CYTOTOXIC ANTIBIOTICS AND RELATED SUBSTANCES
L01: ANTINEOPLASTIC AGENTS
L: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Drug Type
Small molecular drug
Structure
3D MOL is unavailable 2D MOL
#Ro5 Violations (Lipinski): 3 Molecular Weight (mw) 723.6
Logarithm of the Partition Coefficient (xlogp) 4
Rotatable Bond Count (rotbonds) 11
Hydrogen Bond Donor Count (hbonddonor) 5
Hydrogen Bond Acceptor Count (hbondacc) 16
Chemical Identifiers
Formula
C34H36F3NO13
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
Canonical 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
InChI
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
InChIKey
ZOCKGBMQLCSHFP-KQRAQHLDSA-N
Cross-matching ID
PubChem CID
454216
ChEBI ID
CHEBI:135876
CAS Number
56124-62-0
UNII
2C6NUM6878
DrugBank ID
DB00385
TTD ID
D07IPB
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
DNA topoisomerase II (TOP2) TT0IHXV TOP2A_HUMAN ; TOP2B_HUMAN Inhibitor [4]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Bile salt export pump (ABCB11) OTRU7THO ABCBB_HUMAN Gene/Protein Processing [5]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Valrubicin (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Omacetaxine mepesuccinate DMPU2WX Moderate Additive myelosuppressive effects by the combination of Valrubicin and Omacetaxine mepesuccinate. Myeloproliferative neoplasm [2A20] [6]

References

1 Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77.
2 Valrubicin FDA Label
3 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
4 Metabolic activation of N-acylanthracyclines precedes their interaction with DNA topoisomerase II. NCI Monogr. 1987;(4):111-5.
5 A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development. Toxicol Sci. 2013 Nov;136(1):216-41.
6 Product Information. Synribo (omacetaxine). Teva Pharmaceuticals USA, North Wales, PA.