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+
| 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 |
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 |
|---|---|---|
| Synergistic effects of acyclic retinoid and OSI-461 on growth inhibition and gene expression in human hepatoma cells. | 2004 Oct 1 |
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| 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 Mar |
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| 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 |
|
| Synergistic growth inhibition by acyclic retinoid and vitamin K2 in human hepatocellular carcinoma cells. | 2007 Mar |
|
| An antioxidant effect by acyclic retinoid suppresses liver tumor in mice. | 2007 May 1 |
|
| Acyclic retinoid inhibits diethylnitrosamine-induced liver tumorigenesis in obese and diabetic C57BLKS/J- +(db)/+Lepr(db) mice. | 2011 Jan |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:36:33 GMT 2023
by
admin
on
Fri Dec 15 16:36:33 GMT 2023
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| Record UNII |
11ALM7A4RV
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| Record Status |
Validated (UNII)
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| Record Version |
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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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