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
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+
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
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 May |
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| An antioxidant effect by acyclic retinoid suppresses liver tumor in mice. | 2007 May 1 |
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| Acyclic retinoid inhibits diethylnitrosamine-induced liver tumorigenesis in obese and diabetic C57BLKS/J- +(db)/+Lepr(db) mice. | 2011 Jan |
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| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C804
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FDA ORPHAN DRUG |
352011
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EU-Orphan Drug |
EU/3/11/890
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81485-25-8
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DTXSID801316826
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100000139943
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SUB89120
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C87202
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6437836
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11ALM7A4RV
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8838
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ACTIVE MOIETY
