Details of the Drug

General Information of Drug (ID: DMESAZK)

Drug Name
Peretinoin
Synonyms Polyprenoic acid; E-5166; NIK-333; Peretinoin (oral); Peretinoin (oral), Kowa; Peretinoin (oral formulation, hepatocellular carcinoma), Kowa Pharmaceutical
Indication
Disease Entry ICD 11 Status REF
Hepatocellular carcinoma 2C12.02 Phase 3 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 302.5
Logarithm of the Partition Coefficient (xlogp) 6.9
Rotatable Bond Count (rotbonds) 9
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 2
Chemical Identifiers
Formula
C20H30O2
IUPAC Name
(2E,4E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,4,6,10,14-pentaenoic acid
Canonical SMILES
CC(=CCC/C(=C/CC/C(=C/C=C/C(=C/C(=O)O)/C)/C)/C)C
InChI
InChI=1S/C20H30O2/c1-16(2)9-6-10-17(3)11-7-12-18(4)13-8-14-19(5)15-20(21)22/h8-9,11,13-15H,6-7,10,12H2,1-5H3,(H,21,22)/b14-8+,17-11+,18-13+,19-15+
InChIKey
UUBHZHZSIKRVIV-KCXSXWJSSA-N
Cross-matching ID
PubChem CID
6437836
CAS Number
81485-25-8
UNII
11ALM7A4RV
DrugBank ID
DB16291
TTD ID
D05TOJ

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Retinoic acid receptor (RAR) TTOD7B3 NOUNIPROTAC Modulator [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Baculoviral IAP repeat-containing protein 3 (BIRC3) OT3E95KB BIRC3_HUMAN Gene/Protein Processing [3]
Cyclin-dependent kinase inhibitor 1 (CDKN1A) OTQWHCZE CDN1A_HUMAN Gene/Protein Processing [4]
E3 ubiquitin-protein ligase XIAP OT24GP9B XIAP_HUMAN Gene/Protein Processing [3]
G1/S-specific cyclin-D2 (CCND2) OTDULQF9 CCND2_HUMAN Gene/Protein Processing [3]
Retinoblastoma-associated protein (RB1) OTQJUJMZ RB_HUMAN Post-Translational Modifications [4]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 ClinicalTrials.gov (NCT01640808) Study of Peretinoin for Suppressing Recurrence of HCV-positive HCC. U.S. National Institutes of Health.
2 Peretinoin, an acyclic retinoid, improves the hepatic gene signature of chronic hepatitis C following curative therapy of hepatocellular carcinoma. BMC Cancer. 2013 Apr 15;13:191.
3 NIK-333 inhibits growth of human T-cell leukemia virus type I-infected T-cell lines and adult T-cell leukemia cells in association with blockade of nuclear factor-kappaB signal pathway. Mol Cancer Ther. 2006 Mar;5(3):704-12. doi: 10.1158/1535-7163.MCT-05-0434.
4 Synergistic effects of acyclic retinoid and OSI-461 on growth inhibition and gene expression in human hepatoma cells. Clin Cancer Res. 2004 Oct 1;10(19):6710-21. doi: 10.1158/1078-0432.CCR-04-0659.