Bicyclol
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MedKoo CAT#: 329867

CAS#: 118159-48-1

Description: Bicyclol, also known as SY 801, is a hepatoprotective agent. Bicyclol upregulates transcription factor Nrf2, HO-1 expression and protects rat brains against focal ischemia. Bicyclol induces cell cycle arrest and autophagy in HepG2 human hepatocellular carcinoma cells through the PI3K/AKT and Ras/Raf/MEK/ERK pathways. Bicyclol attenuates tetracycline-induced fatty liver associated with inhibition of hepatic ER stress and apoptosis in mice. Bicyclol promotes toll-like 2 receptor recruiting inosine 5'-monophosphate dehydrogenase II to exert its anti-inflammatory effect.

Chemical Structure

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Bicyclol
CAS# 118159-48-1
Instruction

Theoretical Analysis

MedKoo Cat#: 329867
Name: Bicyclol
CAS#: 118159-48-1
Chemical Formula: C19H18O9
Exact Mass: 390.10
Molecular Weight: 390.344
Elemental Analysis: C, 58.46; H, 4.65; O, 36.89

Price and Availability

Size Price Availability Quantity
5mg USD 190 2 weeks
10mg USD 350 2 weeks
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Synonym: Bicyclol; SY 801; SY-801; SY801.

IUPAC/Chemical Name: 5'-(hydroxymethyl)-7,7'-dimethoxy-[4,4'-bi-1,3-benzodioxole]-5-carboxylic acid, methyl ester

InChi Key: KXMTXZACPVCDMH-UHFFFAOYSA-N

InChi Code: InChI=1S/C19H18O9/c1-22-11-4-9(6-20)13(17-15(11)25-7-27-17)14-10(19(21)24-3)5-12(23-2)16-18(14)28-8-26-16/h4-5,20H,6-8H2,1-3H3

SMILES Code: O=C(C1=CC(OC)=C(OCO2)C2=C1C3=C4OCOC4=C(OC)C=C3CO)OC

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 390.34 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Zhen YZ, Li NR, He HW, Zhao SS, Zhang GL, Hao XF, Shao RG. Protective effect of bicyclol against bile duct ligation-induced hepatic fibrosis in rats. World J Gastroenterol. 2015 Jun 21;21(23):7155-64. doi: 10.3748/wjg.v21.i23.7155. PubMed PMID: 26109801; PubMed Central PMCID: PMC4476876.

2: Chen X, Zhang J, Han C, Dai H, Kong X, Xu L, Xia Q, Zhang M, Zhang J. A sexual dimorphism influences bicyclol-induced hepatic heat shock factor 1 activation and hepatoprotection. Mol Pharmacol. 2015 Jul;88(1):38-47. doi: 10.1124/mol.114.097584. Epub 2015 Apr 21. PubMed PMID: 25901028.

3: Zhang J, Fu B, Zhang X, Zhang L, Bai X, Zhao X, Chen L, Cui L, Zhu C, Wang L, Zhao Y, Zhao T, Wang X. Bicyclol upregulates transcription factor Nrf2, HO-1 expression and protects rat brains against focal ischemia. Brain Res Bull. 2014 Jan;100:38-43. doi: 10.1016/j.brainresbull.2013.11.001. Epub 2013 Nov 16. PubMed PMID: 24252362.

4: Wang Y, Nie H, Zhao X, Qin Y, Gong X. 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 Sep 21;16(1):742. PubMed PMID: 27654866; PubMed Central PMCID: PMC5031284.

5: Yao XM, Li Y, Li HW, Cheng XY, Lin AB, Qu JG. Bicyclol attenuates tetracycline-induced fatty liver associated with inhibition of hepatic ER stress and apoptosis in mice. Can J Physiol Pharmacol. 2016 Jan;94(1):1-8. doi: 10.1139/cjpp-2015-0074. Epub 2015 Sep 22. PubMed PMID: 26640164.

6: Zhang YW, Guo YS, Bao XQ, Sun H, Zhang D. Bicyclol promotes toll-like 2 receptor recruiting inosine 5'-monophosphate dehydrogenase II to exert its anti-inflammatory effect. J Asian Nat Prod Res. 2016 May;18(5):475-85. doi: 10.1080/10286020.2015.1131678. Epub 2016 Jan 8. PubMed PMID: 26744808.

7: Zhang J, Fu B, Zhang X, Chen L, Zhang L, Zhao X, Bai X, Zhu C, Cui L, Wang L. Neuroprotective effect of bicyclol in rat ischemic stroke: down-regulates TLR4, TLR9, TRAF6, NF-κB, MMP-9 and up-regulates claudin-5 expression. Brain Res. 2013 Aug 28;1528:80-8. doi: 10.1016/j.brainres.2013.06.032. Epub 2013 Jul 10. PubMed PMID: 23850770.

8: Han Y, Shi JP, Ma AL, Xu Y, Ding XD, Fan JG. Randomized, vitamin E-controlled trial of bicyclol plus metformin in non-alcoholic fatty liver disease patients with impaired fasting glucose. Clin Drug Investig. 2014 Jan;34(1):1-7. doi: 10.1007/s40261-013-0136-3. PubMed PMID: 24081374.

9: Dai HJ, Li DW, Wang YX, Sun AJ, Lu YX, Ding X, Zhang M, Song YG, Huang XD. Induction of heat shock protein 27 by bicyclol attenuates d-galactosamine/lipopolysaccharide-induced liver injury. Eur J Pharmacol. 2016 Nov 15;791:482-490. doi: 10.1016/j.ejphar.2016.09.002. Epub 2016 Sep 3. PubMed PMID: 27597162.

10: Wang B, Liu Z, Li D, Yang S, Hu J, Chen H, Sheng L, Li Y. Application of physiologically based pharmacokinetic modeling in the prediction of pharmacokinetics of bicyclol controlled-release formulation in human. Eur J Pharm Sci. 2015 Sep 18;77:265-72. doi: 10.1016/j.ejps.2015.06.020. Epub 2015 Jun 24. PubMed PMID: 26116279.

11: Chu NH, Li L, Zhang X, Gu J, Du YD, Cai C, Xiao HP. Role of bicyclol in preventing drug-induced liver injury in tuberculosis patients with liver disease. Int J Tuberc Lung Dis. 2015 Apr;19(4):475-80. doi: 10.5588/ijtld.14.0579. PubMed PMID: 25860005.

12: Ryu JK, Yoo SD. Preparation and evaluation of bicyclol microemulsions for enhanced oral bioavailability. Drug Dev Ind Pharm. 2012 Nov;38(11):1313-8. Epub 2012 Jan 28. PubMed PMID: 22283588.

13: Cui J, Li Z, Qian LB, Gao Q, Wang J, Xue M, Lou XE, Bruce IC, Xia Q, Wang HP. Reducing the oxidative stress mediates the cardioprotection of bicyclol against ischemia-reperfusion injury in rats. J Zhejiang Univ Sci B. 2013 Jun;14(6):487-95. doi: 10.1631/jzus.B1200263. PubMed PMID: 23733425; PubMed Central PMCID: PMC3682164.

14: Liu YH, Jia MY, Liang GJ, Guan HS, Yan AP. [Bicyclol combined with ganciclovir for treatment of infantile cytomegalovirus hepatitis]. Nan Fang Yi Ke Da Xue Xue Bao. 2015 Oct;35(10):1505-7. Chinese. PubMed PMID: 26547351.

15: Li L, Dong WJ, Sheng L, Xia XJ, Li Y, Liu YL. [Preparation, formation mechanism and preliminary evaluation of oral absorption of a Bicyclol-phospholipid complex]. Yao Xue Xue Bao. 2014 Nov;49(11):1600-6. Chinese. PubMed PMID: 25757289.

16: Li X, Zhou J, Chen S, Guan M, Wang Y, Zhao L, Ying H, Zhou Y. Role of bicyclol in preventing chemotherapeutic agent-induced liver injury in patients over 60 years of age with cancer. J Int Med Res. 2014 Aug;42(4):906-14. doi: 10.1177/0300060514527058. Epub 2014 Jun 5. PubMed PMID: 24903556.

17: Sun H, Yu L, Wei H, Liu G. A novel antihepatitis drug, bicyclol, prevents liver carcinogenesis in diethylnitrosamine-initiated and phenobarbital-promoted mice tumor model. J Biomed Biotechnol. 2012;2012:584728. doi: 10.1155/2012/584728. Epub 2012 Feb 21. PubMed PMID: 22500097; PubMed Central PMCID: PMC3303747.

18: He W, Dou H, Zhang L, Wang L, Wang R, Chang J. Spectroscopic study on the interaction of Trypsin with Bicyclol and analogs. Spectrochim Acta A Mol Biomol Spectrosc. 2014 Jan 24;118:510-9. doi: 10.1016/j.saa.2013.09.027. Epub 2013 Sep 12. PubMed PMID: 24084479.

19: Zhang Y, Xie Y, Zhang Y, Liu Y, Zhuang Y. Hepatitis B patients exhibiting mild alanine aminotransferase elevation: A comparative analysis of treatment with and without Bicyclol tablets. Biomed Rep. 2016 Nov;5(5):595-600. Epub 2016 Sep 29. PubMed PMID: 27882223; PubMed Central PMCID: PMC5103681.

20: Luo Y, Zhang B, Xu DQ, Liu Y, Dong MQ, Zhao PT, Li ZC. Protective effect of bicyclol on lipopolysaccharide-induced acute lung injury in mice. Pulm Pharmacol Ther. 2011 Apr;24(2):240-6. doi: 10.1016/j.pupt.2010.12.005. Epub 2011 Jan 1. PubMed PMID: 21199676.