PERETINOIN

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H30O2
Molecular Weight	302.451
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	4
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)=CCC\C(C)=C\CC\C(C)=C\C=C\C(C)=C\C(O)=O

InChI

InChIKey=UUBHZHZSIKRVIV-KCXSXWJSSA-N

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+

HIDE SMILES / InChI

Molecular Formula	C20H30O2
Molecular Weight	302.451
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	4
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29208982 | https://www.ncbi.nlm.nih.gov/pubmed/29360739 | https://www.cancer.gov/publications/dictionaries/cancer-drug/def/peretinoin | https://adisinsight.springer.com/drugs/800028422

Peretinoin is an orally available, acyclic retinoid with potential antineoplastic and chemopreventive activities. Peretinoin binds to and activates nuclear retinoic acid receptors (RAR), which in turn recruit coactivator proteins and promote, with other transcriptional complexes, the transcription of target genes. As a result, this agent may modulate the expression of genes involved in the regulation of cell proliferation, cell differentiation, and apoptosis of both normal and tumor cells. Peretinoin inhibits post-therapeutic recurrence of hepatocellular carcinoma via unclear mechanisms. The European Commission granted Orphan Drug designation for Kowa's peretinoin to treat hepatocellular carcinoma (HCC).

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
retinoic acid receptor 1 Target ID: retinoic acid receptor Sources: https://www.ncbi.nlm.nih.gov/pubmed/29208982	Activator 1447
Retinoid X receptor 4 Target ID: CHEMBL2363070 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29208982	Activator 1447

C_max

Value	Dose	Analyte	Population
284 ng/mL EXPERIMENT https://onlinelibrary.wiley.com/doi/epdf/10.1111/j.1872-034X.2011.00800.x	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	PERETINOIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
295.4 ng/mL EXPERIMENT https://onlinelibrary.wiley.com/doi/epdf/10.1111/j.1872-034X.2011.00800.x	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	PERETINOIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
316.1 ng/mL EXPERIMENT https://onlinelibrary.wiley.com/doi/epdf/10.1111/j.1872-034X.2011.00800.x	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	PERETINOIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
694.1 ng/mL EXPERIMENT https://onlinelibrary.wiley.com/doi/epdf/10.1111/j.1872-034X.2011.00800.x	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	PERETINOIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
468.4 ng/mL EXPERIMENT https://onlinelibrary.wiley.com/doi/epdf/10.1111/j.1872-034X.2011.00800.x	600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered:	PERETINOIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
1450.5 ng/mL EXPERIMENT https://onlinelibrary.wiley.com/doi/epdf/10.1111/j.1872-034X.2011.00800.x	600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered:	PERETINOIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
906.9 ng/mL EXPERIMENT https://onlinelibrary.wiley.com/doi/epdf/10.1111/j.1872-034X.2011.00800.x	900 mg single, oral dose: 900 mg route of administration: Oral experiment type: SINGLE co-administered:	PERETINOIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
1239.9 ng/mL EXPERIMENT https://onlinelibrary.wiley.com/doi/epdf/10.1111/j.1872-034X.2011.00800.x	900 mg single, oral dose: 900 mg route of administration: Oral experiment type: SINGLE co-administered:	PERETINOIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

AUC

Value	Dose	Analyte	Population
849.5 ng × h/mL EXPERIMENT https://onlinelibrary.wiley.com/doi/epdf/10.1111/j.1872-034X.2011.00800.x	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	PERETINOIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
3518.3 ng × h/mL EXPERIMENT https://onlinelibrary.wiley.com/doi/epdf/10.1111/j.1872-034X.2011.00800.x	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	PERETINOIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
841.3 ng × h/mL EXPERIMENT https://onlinelibrary.wiley.com/doi/epdf/10.1111/j.1872-034X.2011.00800.x	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	PERETINOIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
6497.7 ng × h/mL EXPERIMENT https://onlinelibrary.wiley.com/doi/epdf/10.1111/j.1872-034X.2011.00800.x	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	PERETINOIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
1873.8 ng × h/mL EXPERIMENT https://onlinelibrary.wiley.com/doi/epdf/10.1111/j.1872-034X.2011.00800.x	600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered:	PERETINOIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
15883.3 ng × h/mL EXPERIMENT https://onlinelibrary.wiley.com/doi/epdf/10.1111/j.1872-034X.2011.00800.x	600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered:	PERETINOIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
4009.7 ng × h/mL EXPERIMENT https://onlinelibrary.wiley.com/doi/epdf/10.1111/j.1872-034X.2011.00800.x	900 mg single, oral dose: 900 mg route of administration: Oral experiment type: SINGLE co-administered:	PERETINOIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
16274 ng × h/mL EXPERIMENT https://onlinelibrary.wiley.com/doi/epdf/10.1111/j.1872-034X.2011.00800.x	900 mg single, oral dose: 900 mg route of administration: Oral experiment type: SINGLE co-administered:	PERETINOIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

T_1/2

Value	Dose	Analyte	Population
1.9 h EXPERIMENT https://onlinelibrary.wiley.com/doi/epdf/10.1111/j.1872-034X.2011.00800.x	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	PERETINOIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
11.2 h EXPERIMENT https://onlinelibrary.wiley.com/doi/epdf/10.1111/j.1872-034X.2011.00800.x	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	PERETINOIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1.3 h EXPERIMENT https://onlinelibrary.wiley.com/doi/epdf/10.1111/j.1872-034X.2011.00800.x	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	PERETINOIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
7.2 h EXPERIMENT https://onlinelibrary.wiley.com/doi/epdf/10.1111/j.1872-034X.2011.00800.x	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	PERETINOIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
3.4 h EXPERIMENT https://onlinelibrary.wiley.com/doi/epdf/10.1111/j.1872-034X.2011.00800.x	600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered:	PERETINOIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
8.3 h EXPERIMENT https://onlinelibrary.wiley.com/doi/epdf/10.1111/j.1872-034X.2011.00800.x	600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered:	PERETINOIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
3.6 h EXPERIMENT https://onlinelibrary.wiley.com/doi/epdf/10.1111/j.1872-034X.2011.00800.x	900 mg single, oral dose: 900 mg route of administration: Oral experiment type: SINGLE co-administered:	PERETINOIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
8.9 h EXPERIMENT https://onlinelibrary.wiley.com/doi/epdf/10.1111/j.1872-034X.2011.00800.x	900 mg single, oral dose: 900 mg route of administration: Oral experiment type: SINGLE co-administered:	PERETINOIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

PubMed

Title	Date	PubMed
Acyclic retinoid inhibits diethylnitrosamine-induced liver tumorigenesis in obese and diabetic C57BLKS/J- +(db)/+Lepr(db) mice.	2011-01	21071580
An antioxidant effect by acyclic retinoid suppresses liver tumor in mice.	2007-05-01	17261273
Synergistic growth inhibition by acyclic retinoid and vitamin K2 in human hepatocellular carcinoma cells.	2007-03	17270033
Acyclic retinoid, a novel synthetic retinoid, induces growth inhibition, apoptosis, and changes in mRNA expression of cell cycle- and differentiation-related molecules in human colon carcinoma cells.	2006-05	16596235
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.	2006-03	16546985
Synergistic effects of acyclic retinoid and OSI-461 on growth inhibition and gene expression in human hepatoma cells.	2004-10-01	15475462

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:32:28 GMT 2025` Edited by `admin` on `Mon Mar 31 18:32:28 GMT 2025`
Record UNII	11ALM7A4RV
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NIK-333

Preferred Name

English

PERETINOIN

Official Name

English

Peretinoin [WHO-DD]

Common Name

English

PERETINOIN [JAN]

Common Name

English

peretinoin [INN]

Common Name

English

(2E,4E,6E,10E)-3,7,11,15-TETRAMETHYLHEXADECA-2,4,6,10,14-PENTAENOIC ACID

Systematic Name

English

PERETINOIN [MART.]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C804