Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C24H38O4 |
Molecular Weight | 390.5561 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 2 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C(OC)C(=O)[C@H](C)[C@@H](C\C=C(/C)CC\C=C(/C)CCC=C(C)C)[C@H]1O
InChI
InChIKey=LJTSIMVOOOLKOL-FNRDIUJOSA-N
InChI=1S/C24H38O4/c1-16(2)10-8-11-17(3)12-9-13-18(4)14-15-20-19(5)21(25)23(27-6)24(28-7)22(20)26/h10,12,14,19-20,22,26H,8-9,11,13,15H2,1-7H3/b17-12+,18-14+/t19-,20-,22-/m1/s1
Antroquinonol is isolated from Antrodia camphorata, a camphor tree mushroom, and is a valuable traditional Chinese herbal medicine that exhibits pharmacological activities against several diseases, including cancer. Antroquinonol displayed anticancer activity against hepatocellular carcinoma cell lines through activation of 5′ adenosine-monophosphate-activated protein kinase and inhibition of the mammalian target of rapamycin (mTOR) pathway. Antroquinonol also exhibits anticancer activity in human pancreatic cancers through inhibition of the phosphoinositide-3 kinase (PI3K)/Akt/mTOR pathway, which in turn downregulates the expression of cell cycle regulators. The translational inhibition causes a G1 arrest of the cell cycle and ultimately mitochondria-dependent apoptosis. A study on the A549 pulmonary adenocarcinoma cell line demonstrated that antroquinonol-induced apoptosis was associated with disrupted mitochondrial membrane potential and activation of caspase-3 and poly ADP ribose polymerase cleavage. Moreover, antroquinonol treatment downregulated the expression of B-cell lymphoma 2 proteins, which was correlated with decreased PI3K and mTOR protein levels, without altering the levels of pro- or antiapoptotic proteins. Antroquinonol is currently in phase II trials (USA and Taiwan) for the treatment of non-small-cell lung carcinoma (NSCLC), atopic dermatitis; colorectal cancer; hepatitis B; hyperlipidaemia; pancreatic cancer. Antroquinonol was also approved for drug clinical trials by the Russian Ministry of Health (MoH). The MoH gave permission to test the efficacy and safety of Phase II clinical trials in patients with acute myeloid leukemia in Russia. Antroquinonol received the Orphan Drug Designation by the FDA in treatment of pancreatic cancer, liver cancer and acute myeloid leukaemia.
Originator
Approval Year
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26807250
The patients received escalating doses of once-daily antroquinonol in 4-week cycles (up to 3 cycles). The escalated doses were 50-600 mg. PKs were evaluated on day 1 and 28 of cycle 1. The recommended dose level for a phase II study is ≥600 mg daily.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26517117
Curator's Comment: Incubation of cells with the desired concentrations of antroquinonol for 24 h to determine the cytotoxic effects of antroquinonol on both the C6 and N18 cell lines, and an MTT assay was performed to analyze cell viability.
After 24 h of treatment, the cell viability was significantly decreased with an increasing concentration of antroquinonol. Antroquinonol reached the IC50 value at a concentration of 10 uM.
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Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
460814
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EU-Orphan Drug |
EU/3/16/1812
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FDA ORPHAN DRUG |
476315
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admin on Sat Dec 16 10:18:09 GMT 2023 , Edited by admin on Sat Dec 16 10:18:09 GMT 2023
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FDA ORPHAN DRUG |
488115
Created by
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DB12326
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100000177179
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1010081-09-0
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C119701
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AX9P92T7JZ
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24875259
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ACTIVE MOIETY