Bicyclol

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Cat Number

API118159481

CAS Number

118159-48-1

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Product Detail Description Scientific Support Advanced Innovations Customer Q&A

CAS Number

118159-48-1

EINECS

633-021-4

Storage

Store at room temperature

Synonyms

methyl 4-[5-(hydroxymethyl)-7-methoxy-1,3-benzodioxol-4-yl]-7-methoxy-1,3-benzodioxole-5-carboxylate; 9734122TH2; DTXSID30152026; 4,4'-Bi-1,3-benzodioxole)-5-carboxylic acid, 5'-(hydroxymethyl)-7,7'-dimethoxy-, methyl ester

Molecular Formula

C19H18O9

Molecular Weight

390.3

Smiles

COC1=C2C(=C(C(=C1)CO)C3=C4C(=C(C=C3C(=O)OC)OC)OCO4)OCO2

General Description

Bicyclol is a synthetic biphenyl derivative developed as a hepatoprotective agent. It is a small-molecule pharmaceutical with established liver-protective properties.

Mechanism of Action

Bicyclol exerts its protective effects primarily through the clearance of reactive oxygen species (ROS) and the inhibition of free radical-induced damage to hepatocytes. It also regulates cytokine secretion, inhibits apoptosis from immunological injury, and modulates the disturbance of the PPARα pathway, thereby improving mitochondrial function and lipid metabolism.

Application

Bicyclol is indicated for the improvement of liver function in patients with viral hepatitis and for the management of drug-induced liver injury. It has demonstrated efficacy in reducing serum alanine aminotransferase (ALT) and aspartate aminotransferase (AST) levels, as well as protecting against fatty liver by enhancing lipid oxidation.

In a rat model of cholestatic liver fibrosis induced by bile duct ligation (BDL), oral bicyclol (100 mg/kg/day for 2 weeks) significantly reduced liver fibrosis, bile duct proliferation, and serum transaminases. Microarray analysis showed that bicyclol reversed the expression of 45 fibrogenic genes and pathways, including collagen 1a1, MMP‑2, TNF‑α, TIMP‑2, TGF‑β1, and α‑SMA. The authors conclude that bicyclol attenuates BDL‑induced hepatic fibrosis and may be an effective anti‑fibrotic drug for cholestatic liver disease.

Fig. 1 Microarray analysis of rat liver tissues. (Zhen YZ, et al., 2015)

References

Zhen YZ, et al. Protective effect of bicyclol against bile duct ligation-induced hepatic fibrosis in rats. World J Gastroenterol. 2015;21(23):7155-7164.

In HepG2 hepatocellular carcinoma cells, bicyclol inhibited proliferation in a dose‑ and time‑dependent manner, induced G1 phase arrest, and promoted autophagy. It suppressed phosphorylation of Akt and ERK, downregulated cyclin D1, cyclin E2, CDK2, CDK4, p‑Rb, and p‑mTOR. Knockdown of AKT or ERK enhanced bicyclol’s anti‑proliferative and pro‑autophagic effects. Bicyclol acts via PI3K/AKT and Ras/Raf/MEK/ERK pathways, suggesting it is a potential liver cancer drug worthy of further development.

Fig. 2 The effect of bicyclol on the living cell number of cancer cell lines and normal liver cells. (Wang Y, et al., 2016)

References

Wang Y, et al. Bicyclol induces cell cycle arrest and autophagy in HepG2 human hepatocellular carcinoma cells through the PI3K/AKT and Ras/Raf/MEK/ERK pathways. BMC Cancer. 2016;16(1):742.

Does Bicyclol require protection from light during long-term storage?

Yes, it is photosensitive. UV light can cause photodegradation of the biphenyl structure. Store in light-resistant containers, preferably amber glass or foil-lined bags.

What is the recommended storage temperature for Bicyclol?

Store at controlled room temperature (15-25°C). Avoid temperatures above 30°C, which can accelerate oxidative degradation and discoloration.

Is Bicyclol hygroscopic, and how is this managed?

It is slightly hygroscopic. Under high humidity (>70% RH), it may absorb moisture and clump. Storage in tightly sealed containers with desiccant is recommended.

How is the impurity bicyclol methyl ester (a process-related impurity) monitored?

This impurity is quantified using a stability-indicating HPLC method, ensuring it remains below ICH qualification thresholds.