Details of the Drug

General Information of Drug (ID: DMDZ6Q3)

Drug Name
Napabucasin
Synonyms
83280-65-3; UNII-Z1HHM49K7O; 2-acetylnaphtho[2,3-b]furan-4,9-dione; Z1HHM49K7O; 2-Acetylnaphtho(2,3-b)furan-4,9-dione; 2-Acetyl-4H,9H-naphtho[2,3-b]furan-4,9-dione; Napabucasin [USAN:INN]; Napabucasin (BBI608); 2-Acetylfuranonaphthoquinone; CHEMBL64130; Napabucasin (JAN/USAN/INN); SCHEMBL1883845; Napabucasin - BBI 608/ FNQ; 2-Acetylfuro-1,4-naphthoquinone; DPHUWDIXHNQOSY-UHFFFAOYSA-N; MolPort-039-101-321; EX-A1314; ZINC13306865; s7977; AKOS027470201; DB12155; CS-1747; ACN-053294; HY-13919
Indication
Disease Entry ICD 11 Status REF
Colorectal cancer 2B91.Z Phase 3 [1]
Pancreatic cancer 2C10 Phase 3 [1]
Solid tumour/cancer 2A00-2F9Z Phase 3 [2]
Advanced malignancy 2A00-2F9Z Phase 1/2 [1]
Gastrointestinal cancer 2C11 Phase 1/2 [1]
Hepatocellular carcinoma 2C12.02 Phase 1/2 [1]
Recurrent glioblastoma 2A00.00 Phase 1/2 [3]
Recurring respiratory infection CA07-CA45 Phase 1/2 [1]
Haematological malignancy 2B33.Y Phase 1 [1]
⏷ Show the Full List of Indication(s)
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 240.21
Logarithm of the Partition Coefficient (xlogp) 2.3
Rotatable Bond Count (rotbonds) 1
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 4
Chemical Identifiers
Formula
C14H8O4
IUPAC Name
2-acetylbenzo[f][1]benzofuran-4,9-dione
Canonical SMILES
CC(=O)C1=CC2=C(O1)C(=O)C3=CC=CC=C3C2=O
InChI
InChI=1S/C14H8O4/c1-7(15)11-6-10-12(16)8-4-2-3-5-9(8)13(17)14(10)18-11/h2-6H,1H3
InChIKey
DPHUWDIXHNQOSY-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
10331844
CAS Number
83280-65-3
DrugBank ID
DB12155
TTD ID
D01IGZ
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
Signal transducer and activator of transcription 3 (STAT3) TTH8FZW STAT3_HUMAN Inhibitor [1]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Actin, cytoplasmic 1 (ACTB) OT1MCP2F ACTB_HUMAN Gene/Protein Processing [4]
Aldehyde dehydrogenase 1A1 (ALDH1A1) OTCUWZKB AL1A1_HUMAN Gene/Protein Processing [4]
Ataxin-1 (ATXN1) OTQF0HNR ATX1_HUMAN Gene/Protein Processing [4]
Baculoviral IAP repeat-containing protein 5 (BIRC5) OTILXZYL BIRC5_HUMAN Gene/Protein Processing [5]
Beta-2-microglobulin (B2M) OTDWN6NX B2MG_HUMAN Gene/Protein Processing [4]
Catenin beta-1 (CTNNB1) OTZ932A3 CTNB1_HUMAN Gene/Protein Processing [4]
CD166 antigen (ALCAM) OTCO4LP7 CD166_HUMAN Gene/Protein Processing [4]
CD44 antigen (CD44) OT9TTJ41 CD44_HUMAN Gene/Protein Processing [4]
Dachshund homolog 1 (DACH1) OTMKNAGG DACH1_HUMAN Gene/Protein Processing [4]
DNA cytosine-5)-methyltransferase 1 (DNMT1) OTM2DGTK DNMT1_HUMAN Gene/Protein Processing [4]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Colorectal cancer
ICD Disease Classification 2B91.Z
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Signal transducer and activator of transcription 3 (STAT3) DTT STAT3 6.50E-03 -0.12 -0.21
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
2 First-in-Class Cancer Stemness Inhibitor Shows Promising Results in Advanced Colorectal Cancer. 2016 ASCO GI Conference. January 26, 2016.
3 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
4 Suppression of cancer relapse and metastasis by inhibiting cancer stemness. Proc Natl Acad Sci U S A. 2015 Feb 10;112(6):1839-44. doi: 10.1073/pnas.1424171112. Epub 2015 Jan 20.
5 Suppression of prostate cancer progression by cancer cell stemness inhibitor napabucasin. Cancer Med. 2016 Jun;5(6):1251-8. doi: 10.1002/cam4.675. Epub 2016 Feb 21.