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
• Drug Type: Small molecular drug
• #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
  DrugBank ID: DB00385
  TTD ID: D07IPB
• 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]

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.