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633-65-8

633-65-8 structure
633-65-8 structure
  • Name: Berberine hydrochloride
  • Chemical Name: berberine chloride
  • CAS Number: 633-65-8
  • Molecular Formula: C20H18ClNO4
  • Molecular Weight: 372.822
  • Catalog: API Synthetic anti-infective drugs Natural source anti-infectives
  • Create Date: 2018-06-28 16:46:25
  • Modify Date: 2024-01-01 20:10:11
  • 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].
Name berberine chloride
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)
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
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.
Density 1.654g/cm3
Melting Point 200ºC
Molecular Formula C20H18ClNO4
Molecular Weight 372.822
Exact Mass 372.099701
PSA 40.80000
LogP 0.10030
Water Solubility SOLUBLE IN COLD WATER

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
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
483-15-8 structure

483-15-8

~7%

633-65-8 structure

633-65-8

62595-72-6 structure

62595-72-6

Literature: Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), , p. 911 - 918
HS Code 3003409000

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title: CAS No. 633-65-8 | Chemsrc address: https://m.chemsrc.com/en/baike/840741.html

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