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Related CAS#:
16837-52-8 54809-74-4
53230-10-7 108945-28-4

16837-52-8

16837-52-8 structure
16837-52-8 structure
  • Name: oxymatrine
  • Chemical Name: oxymatrine
  • CAS Number: 16837-52-8
  • Molecular Formula: C15H24N2O2
  • Molecular Weight: 264.363
  • Catalog: API Synthetic anti-infective drugs Natural source anti-infectives
  • Create Date: 2018-02-04 08:00:00
  • Modify Date: 2024-01-01 20:56:05
  • Oxymatrine, an alkaloid from the roots of Sophora species, with anti-inflammatory, antifibrosis, and antitumor effects, inhibits the iNOS expression and TGF-β/Smad pathway.
Name oxymatrine
Synonyms (7aS,13aR,13bR,13cS)-dodecahydro-1H,5H,10H-dipyrido[2,1-f:3’,2’,1’-ij][1,6]naphthyridin-10-one 4-oxide
(4R,7aS,13aR,13bR,13cS)-dodecahydro-1H,5H,10H-dipyrido[2,1-f:3’,2’,1’-ij][1,6]naphthyridin-10-one 4-oxide
Ammothamnine
Matrine N-oxide
(7aS,13aR,13bR,13cS)Dodecahydro-1H,5H,10H-dipyrido[2,1-f:3',2',1'-ij][1,6]naphthyridin-10-one 4-oxide
1H,5H,10H-Dipyrido[2,1-f:3',2',1'-ij][1,6]naphthyridin-10-one, dodecahydro-, 4-oxide, (7aS,13aR,13bR,13cS)-
Oxymatrine
Description Oxymatrine, an alkaloid from the roots of Sophora species, with anti-inflammatory, antifibrosis, and antitumor effects, inhibits the iNOS expression and TGF-β/Smad pathway.
Related Catalog
In Vitro Oxymatrine, an alkaloid component extracted from the roots of Sophora species, has been shown to have antiinflammatory, antifibrosis, and antitumor effects and the ability to protect against myocardial damage, etc. The potential signaling pathways involved in the clinical application of oxymatrine might include the TGF-β/Smad, tolllike receptor 4/nuclear factor kappa-light-chain-enhancer of activated B cells, toll-like receptor9/TRAF6, Janus kinase/signal transduction and activator of transcription, phosphatidylinositol-3 kinase/Akt, delta-opioid receptorarrestinl-Bcl-2, CD40, epidermal growth factor receptor, nuclear factor erythroid-2-related factor 2/hemeoxygenase-1 signaling pathways, and dimethylarginine dimethylaminohydrolase/asymmetric dimethylarginine metabolism pathway[1]. Oxymatrine significantly inhibits the proliferation of DU145 and PC-3 cell lines in a time- and dose-dependent manner. By contrast, following treatment with oxymatrine, PNT1B healthy human prostate cell proliferation is not inhibited[2].
In Vivo The volume and weight of tumors in mice significantly decreased in a dose-dependent manner. Oxymatrine may reduce prostate cancer cell growth by promoting cell apoptosis in vivo[2]. Oxymatrine is effective in reducing the production and deposition of collagen in the liver tissue of experimental rats. Oxymatrine could promote the expression of Smad 7 and inhibit the expression of Smad 3 and CBP in CCl4-induced hepatic fibrosis in SD rats, could modulate the fibrogenic signal transduction of TGFβ-Smad pathway[3].
Cell Assay DU145, PC-3 and PNT1B cell lines (3×104 cells/well) are seeded into 96-well plates and incubated overnight at 37°C in 5% CO2. Subsequently, the cells are incubated with different concentrations of oxymatrine (0, 2, 4, 6 and 8 mg/mL). MTT (10 mL; 5 mg/mL) is added and the mixture is incubated in darkness at 37°C for 2 h. Absorbance is measured at a wavelength of 490 nm using a microplate reader[2].
Animal Admin Rats: One hundred healthy male SD rats (weight 140-160 g) are used in the study. All 100 rats are randomLy divided into three groups: Control (n=20), Treatment (n=40) and Model group (n=40). For the model group, 300 g/L CCl4 soluted in liquid paraffin is injected subcutaneously at a dosage of 3 mL/kg twice per week[6]. The treated rats receive Oxymatrine celiac injections at 10 mg/kg twice a week besides the injection of CCl4[3]. Mice: BALB/c homozygous (nu/nu) nude mice are used in the study. 24 tumor-bearing mice are randomLy divided into three groups: The control group is treated with PBS, and two groups are treated with different concentrations of oxymatrine (50 mg/kg and 100 mg/kg body weight). Oxymatrine is administered to the mice, using daily intraperitoneal injections[2].
References

[1]. Lu ML, et al. Potential Signaling Pathways Involved in the Clinical Application of Oxymatrine. Phytother Res. 2016 Jul;30(7):1104-12.

[2]. Wu C, et al. Oxymatrine inhibits the proliferation of prostate cancer cells in vitro and in vivo. Mol Med Rep. 2015 Jun;11(6):4129-34.

[3]. Wu XL, et al. Effect of Oxymatrine on the TGFbeta-Smad signaling pathway in rats with CCl4-induced hepatic fibrosis. World J Gastroenterol. 2008 Apr 7;14(13):2100-5.
Molecular Formula C15H24N2O2
Molecular Weight 264.363
Exact Mass 264.183777
PSA 49.74000
LogP -0.35
Appearance white to off-white
Vapour Pressure 0mmHg at 25°C
Index of Refraction 1.637
Water Solubility methanol: soluble10mg/mL, clear, colorless

CHEMICAL IDENTIFICATION

RTECS NUMBER :
OQ1770000
CHEMICAL NAME :
Matrine, 1-oxide
CAS REGISTRY NUMBER :
16837-52-8
LAST UPDATED :
199412
DATA ITEMS CITED :
3
MOLECULAR FORMULA :
C15-H24-N2-O2

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
521 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YHTPAD Yaoxue Tongbao. Bulletin of Pharmacology. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.13-23, 1978-88. For publisher information, see ZYZAEU. Volume(issue)/page/year: 18(7),23,1983
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
150 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
CPBTAL Chemical and Pharmaceutical Bulletin. (Japan Pub. Trading Co., USA, 1255 Howard St., San Francisco, CA 94103) V.6- 1958- Volume(issue)/page/year: 18,2555,1970
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
257 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ZYZAEU Zhongguo Yaoxue Zazhi. Chinese Pharmacuetical Journal. (China International Book Trading Corp., POB 2820, Beijing, Peop. China) V.24- 1989- Volume(issue)/page/year: 27,201,1992
Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302
Hazard Codes Xn
Risk Phrases 22-20/22
Safety Phrases 24/25
RIDADR NONH for all modes of transport
RTECS OQ1770000
519-02-8 structure

519-02-8

~%

16837-52-8 structure

16837-52-8
Literature: WO2009/109496 A1, ; Page/Page column 10 ;
Precursor  1

DownStream  1


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