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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
Structure of ANTROQUINONOL

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

HIDE SMILES / InChI
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.

Approval Year

PubMed

PubMed

TitleDatePubMed
A phase I multicenter study of antroquinonol in patients with metastatic non-small-cell lung cancer who have received at least two prior systemic treatment regimens, including one platinum-based chemotherapy regimen.
2015 Nov

Sample Use Guides

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
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.
Name Type Language
ANTROQUINONOL
Common Name English
2-CYCLOHEXEN-1-ONE, 4-HYDROXY-2,3-DIMETHOXY-6-METHYL-5-((2E,6E)-3,7,11-TRIMETHYL-2,6,10-DODECATRIEN-1-YL)-, (4R,5R,6R)-
Systematic Name English
(+)-ANTROQUINONOL A
Common Name English
ANTROQUINONOL A
Common Name English
(+)-ANTROQUINONOL
Common Name English
(4R)-2,3-DIMETHOXY-4.ALPHA.-HYDROXY-5.ALPHA.-((2E,6E)-3,7,11-TRIMETHYL-2,6,10-DODECATRIENYL)-6.BETA.-METHYL-2-CYCLOHEXENE-1-ONE
Systematic Name English
Antroquinonol [WHO-DD]
Common Name English
HOCENA
Brand Name English
J3.387.174K
Code English
Classification Tree Code System Code
FDA ORPHAN DRUG 460814
Created by admin on Sat Dec 16 10:18:09 GMT 2023 , Edited by admin on Sat Dec 16 10:18:09 GMT 2023
EU-Orphan Drug EU/3/16/1812
Created by admin on Sat Dec 16 10:18:09 GMT 2023 , Edited by admin on Sat Dec 16 10:18:09 GMT 2023
FDA ORPHAN DRUG 476315
Created by admin on Sat Dec 16 10:18:09 GMT 2023 , Edited by admin on Sat Dec 16 10:18:09 GMT 2023
FDA ORPHAN DRUG 488115
Created by admin on Sat Dec 16 10:18:09 GMT 2023 , Edited by admin on Sat Dec 16 10:18:09 GMT 2023
Code System Code Type Description
DRUG BANK
DB12326
Created by admin on Sat Dec 16 10:18:09 GMT 2023 , Edited by admin on Sat Dec 16 10:18:09 GMT 2023
PRIMARY
SMS_ID
100000177179
Created by admin on Sat Dec 16 10:18:09 GMT 2023 , Edited by admin on Sat Dec 16 10:18:09 GMT 2023
PRIMARY
CAS
1010081-09-0
Created by admin on Sat Dec 16 10:18:09 GMT 2023 , Edited by admin on Sat Dec 16 10:18:09 GMT 2023
PRIMARY
NCI_THESAURUS
C119701
Created by admin on Sat Dec 16 10:18:09 GMT 2023 , Edited by admin on Sat Dec 16 10:18:09 GMT 2023
PRIMARY
FDA UNII
AX9P92T7JZ
Created by admin on Sat Dec 16 10:18:09 GMT 2023 , Edited by admin on Sat Dec 16 10:18:09 GMT 2023
PRIMARY
PUBCHEM
24875259
Created by 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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