CAS 633-65-8|Berberine hydrochloride

Introduction：Basic information about CAS 633-65-8|Berberine hydrochloride, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Berberine hydrochloride BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
MUTATION DATA
5. Safety Information
6. Customs
7. Articles54
8. Synonyms

Common Name	Berberine hydrochloride
CAS Number	633-65-8	Molecular Weight	372.822
Density	1.654g/cm3	Boiling Point	/
Molecular Formula	C₂₀H₁₈ClNO₄	Melting Point	200ºC
MSDS	ChineseUSA	Flash Point	/

Names

Name	berberine chloride
Synonym	More Synonyms

Berberine hydrochloride BiologicalActivity

Description	Berberine has shown to be effective in inhibiting cell proliferation and promoting apoptosis in various cancerous cells; MAPK and Wnt/β-catenin pathways affected by Berberine.IC50 value:Target: Anticancer agentThe plant-based alkaloid berberine has potential therapeutic applications for breast cancer, although a better understanding of the genes and cellular pathways regulated by this compound is needed to define the mechanism of its action in cancer treatment. In this review, the molecular targets of berberine in various cancers, particularly breast cancer, are discussed. Berberine was shown to be effective in inhibiting cell proliferation and promoting apoptosis in various cancerous cells. Some signaling pathways affected by berberine, including the MAP (mitogen-activated protein) kinase and Wnt/β-catenin pathways, are critical for reducing cellular migration and sensitivity to various growth factors [1]. Treatment with BBR(Berberine) in rats on the atherogenic diet reduced plasma total cholesterol and nonHDL cholesterol levels by 29%-33% and 31%-41%, respectively, with no significant differences being observed among the three doses [2]. Berberine induced both apoptotic and autophagic death of HepG2 cells, which was associated with a significant activation of AMPK and an increased expression of the inactive form of acetyl-CoA carboxylase (ACC) [3]. Berberine did not show major effects on viability of HEK-293 embryonic kidney and HCT116 colon carcinoma cells and was not toxic in concentrations up to 20 μM. Berberine inhibited β-catenin transcriptional activity and attenuated anchorage-independent growth. As a result of berberine treatment, cellular levels of active β-catenin were reduced concomitant with an increase in the expression of E-cadherin [4].
Related Catalog	Signaling Pathways >>Stem Cell/Wnt >>β-cateninSignaling Pathways >>Stem Cell/Wnt >>WntNatural Products >>AlkaloidResearch Areas >>Cancer
References	[1]. Jabbarzadeh Kaboli P, et al. Targets and mechanisms of berberine, a natural drug with potential to treat cancer with special focus on breast cancer. Eur J Pharmacol. 2014 Jun 26. pii: S0014-2999(14)00467-1. [2]. Wang Y, et al. Berberine decreases cholesterol levels in rats through multiple mechanisms, including inhibition of cholesterol absorption. Metabolism. 2014 Jun 4. pii: S0026-0495(14)00162-0. [3]. Yu R, et al. Berberine-induced apoptotic and autophagic death of HepG2 cells requires AMPK activation. Cancer Cell Int. 2014 Jun 11;14:49. [4]. Albring KF, et al. Berberine acts as a natural inhibitor of Wnt/β-catenin signaling--identification of more active 13-arylalkyl derivatives. Biofactors. 2013 Nov-Dec;39(6):652-62.

Description

Berberine has shown to be effective in inhibiting cell proliferation and promoting apoptosis in various cancerous cells; MAPK and Wnt/β-catenin pathways affected by Berberine.IC50 value:Target: Anticancer agentThe plant-based alkaloid berberine has potential therapeutic applications for breast cancer, although a better understanding of the genes and cellular pathways regulated by this compound is needed to define the mechanism of its action in cancer treatment. In this review, the molecular targets of berberine in various cancers, particularly breast cancer, are discussed. Berberine was shown to be effective in inhibiting cell proliferation and promoting apoptosis in various cancerous cells. Some signaling pathways affected by berberine, including the MAP (mitogen-activated protein) kinase and Wnt/β-catenin pathways, are critical for reducing cellular migration and sensitivity to various growth factors [1]. Treatment with BBR(Berberine) in rats on the atherogenic diet reduced plasma total cholesterol and nonHDL cholesterol levels by 29%-33% and 31%-41%, respectively, with no significant differences being observed among the three doses [2]. Berberine induced both apoptotic and autophagic death of HepG2 cells, which was associated with a significant activation of AMPK and an increased expression of the inactive form of acetyl-CoA carboxylase (ACC) [3]. Berberine did not show major effects on viability of HEK-293 embryonic kidney and HCT116 colon carcinoma cells and was not toxic in concentrations up to 20 μM. Berberine inhibited β-catenin transcriptional activity and attenuated anchorage-independent growth. As a result of berberine treatment, cellular levels of active β-catenin were reduced concomitant with an increase in the expression of E-cadherin [4].

Related Catalog

Signaling Pathways >>Stem Cell/Wnt >>β-cateninSignaling Pathways >>Stem Cell/Wnt >>WntNatural Products >>AlkaloidResearch Areas >>Cancer

References

[1]. Jabbarzadeh Kaboli P, et al. Targets and mechanisms of berberine, a natural drug with potential to treat cancer with special focus on breast cancer. Eur J Pharmacol. 2014 Jun 26. pii: S0014-2999(14)00467-1.

[2]. Wang Y, et al. Berberine decreases cholesterol levels in rats through multiple mechanisms, including inhibition of cholesterol absorption. Metabolism. 2014 Jun 4. pii: S0026-0495(14)00162-0.

[3]. Yu R, et al. Berberine-induced apoptotic and autophagic death of HepG2 cells requires AMPK activation. Cancer Cell Int. 2014 Jun 11;14:49.

[4]. Albring KF, et al. Berberine acts as a natural inhibitor of Wnt/β-catenin signaling--identification of more active 13-arylalkyl derivatives. Biofactors. 2013 Nov-Dec;39(6):652-62.

Chemical & Physical Properties

Density	1.654g/cm3
Melting Point	200ºC
Molecular Formula	C₂₀H₁₈ClNO₄
Molecular Weight	372.822
Exact Mass	372.099701
PSA	40.80000
LogP	0.10030
InChIKey	VKJGBAJNNALVAV-UHFFFAOYSA-M
SMILES	COc1ccc2cc3[n+](cc2c1OC)CCc1cc2c(cc1-3)OCO2.[Cl-]
Water Solubility	SOLUBLE IN COLD WATER

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DR9866400

CHEMICAL NAME :: Berbinium, 7,8,13,13a-tetradehydro-9,10-dimethoxy-2,3-(methylene dioxy)-, chloride

CAS REGISTRY NUMBER :: 633-65-8

LAST UPDATED :: 199701

DATA ITEMS CITED :: 9

MOLECULAR FORMULA :: C20-H18-N-O4.Cl

MOLECULAR WEIGHT :: 371.84

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >15 gm/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Nutritional and Gross Metabolic - body temperature decrease

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 60 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >29586 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Nutritional and Gross Metabolic - body temperature decrease

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 37 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - excitement Lungs, Thorax, or Respiration - dyspnea

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 30 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: DNA damage

TEST SYSTEM :: Mammal - species unspecified Lymphocyte

DOSE/DURATION :: 22 umol/L

REFERENCE :: IJBBBQ Indian Journal of Biochemistry and Biophysics. (Publications & Information Directorate, CSIR, Hillside Rd., New Delhi 110 012, India) V.8- 1971- Volume(issue)/page/year: 18,245,1981

Safety Information

Personal Protective Equipment	Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes	Xn: Harmful;
Risk Phrases	R20/21/22
Safety Phrases	S24/25
RIDADR	UN 1544
WGK Germany	2
RTECS	DR9866400
Packaging Group	III
Hazard Class	6.1(b)
HS Code	3003409000

Customs

HS Code	3003409000

Articles54

Berberine blocks the relapse of Clostridium difficile infection in C57BL/6 mice after standard vancomycin treatment.

Antimicrob. Agents Chemother. 59 , 3726-35, (2015)

Vancomycin is a preferred antibiotic for treating Clostridium difficile infection (CDI) and has been associated with a rate of recurrence of CDI of as high as 20% in treated patients. Recent studies h...

Functional cloning and characterization of the multidrug efflux pumps NorM from Neisseria gonorrhoeae and YdhE from Escherichia coli.

Antimicrob. Agents Chemother. 52 , 3052-60, (2008)

Active efflux of antimicrobial agents is one of the most important adapted strategies that bacteria use to defend against antimicrobial factors that are present in their environment. The NorM protein ...

Synergistic topical application of salt-processed Phellodendron amurense and Sanguisorba officinalis Linne alleviates atopic dermatitis symptoms by reducing levels of immunoglobulin E and pro-inflammatory cytokines in NC/Nga mice.

Mol. Med. Report. 12 , 7657-64, (2015)

Atopic dermatitis is a chronic inflammatory skin disease, and salt-processed Phellodendron amurense (CPE) and Sanguisorba officinalis Linne (SOE) are widely used as anti-inflammatory agents in Asia. T...

Synonyms

1,3-Benzodioxolo[5,6-a]benzo[g]quinolizinium, 5,6-dihydro-9,10-dimethoxy-, hydrochloride (1:1)

EINECS 211-195-9

berberine hydrochloride

BERBERINE HCL

5,6-dihydro-9,10-dimethoxy-1,3-benzodioxolo[5,6-a]benzo[g]quinolizinium chloride (1:1)

MFCD00011939

9,10-dimethoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ium chloride

Berberine (chloride)

Recommended......