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]
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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
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]

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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-D1 (CCND1)	OT8HPTKJ	CCND1_HUMAN	Gene/Protein Processing	[4]
G1/S-specific cyclin-D2 (CCND2)	OTDULQF9	CCND2_HUMAN	Gene/Protein Processing	[3]
NF-kappa-B inhibitor alpha (NFKBIA)	OTFT924M	IKBA_HUMAN	Post-Translational Modifications	[3]
Retinoblastoma-associated protein (RB1)	OTQJUJMZ	RB_HUMAN	Post-Translational Modifications	[4]
Retinoic acid receptor beta (RARB)	OT367U3E	RARB_HUMAN	Gene/Protein Processing	[4]

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Molecular Interaction Atlas (MIA)

MIA Detail

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.