519-02-8

519-02-8 structure

Name: Matrine
Chemical Name: matrine
CAS Number: 519-02-8
Molecular Formula: C₁₅H₂₄N₂O
Molecular Weight: 248.364
Catalog: API Synthetic anti-infective drugs Natural source anti-infectives
Create Date: 2018-02-07 08:00:00
Modify Date: 2024-01-02 19:12:17
Matrine(Sophocarpidine; α-Matrine) is an alkaloid found in plants from the Sophora genus. It has a variety of pharmacological effects, including anti-cancer effects, and action as a kappa opioid receptor and u-receptor agonist.IC50 Value: 540 μg/ml (inhibit gastric cancer cell line MNK45, MTT) [1]Target: u-receptor/kappa opioid in vitro: MTT assay showed that the matrine was able to inhibit gastric cancer cell line MNK45 in a dose-dependent manner. The concentration required for 50% inhibition (IC50) was found to be 540 μg/ml. This anti-tumor function was achieved through modulation of the NF-κB, XIAP, CIAP, and p-ERK proteins expression in cell line MNK45. Matrine induces apoptosis of human NSCLC cells with anti-apoptotic factors inhibited and dependent on caspase activity. In addition, we found that matrine increases the phosphorylation of p38 but not its total protein, and inhibition of the p38 pathway with SB202190 partially prevents matrine-induced apoptosis. Furthermore, matrine generates reactive oxygen species (ROS) in a dose- and time-dependent manner, which is reversed by pretreatment with N-acetyl-L-cysteine (NAC) [2].in vivo: Oral administration of matrine (200, 100 and 50 mg/kg) significantly attenuated isoproterenol-induced cardiac necrosis and left ventricular dysfunction [3]. high dose of matrine significantly reduced the mortality rate of mice with LPS administration. Treatment with matrine improved LPS-induced lung histopathologic changes, alleviated pulmonary edema and lung vascular leak, inhibited MPO and MDA activity,and reduced the production of inflammatory mediators including TNF-α, IL-6 and HMGB1 [4].Toxicity: N/AClinical trial: N/A

Name	matrine
Synonyms	Maca extract Matrine (7aS,13aR,13bR,13cS)-dodecahydro-1H,5H,10H-dipyrido[2,1-f:3’,2’,1’-ij][1,6]naphthyridin-10-one Matrines Matridin-15-on EINECS 610-750-6 MATRINIUM MATRENE Sophocarpidine MASSMARK 1621 matridin-15-one MFCD00210527

Description	Matrine(Sophocarpidine; α-Matrine) is an alkaloid found in plants from the Sophora genus. It has a variety of pharmacological effects, including anti-cancer effects, and action as a kappa opioid receptor and u-receptor agonist.IC50 Value: 540 μg/ml (inhibit gastric cancer cell line MNK45, MTT) [1]Target: u-receptor/kappa opioid in vitro: MTT assay showed that the matrine was able to inhibit gastric cancer cell line MNK45 in a dose-dependent manner. The concentration required for 50% inhibition (IC50) was found to be 540 μg/ml. This anti-tumor function was achieved through modulation of the NF-κB, XIAP, CIAP, and p-ERK proteins expression in cell line MNK45. Matrine induces apoptosis of human NSCLC cells with anti-apoptotic factors inhibited and dependent on caspase activity. In addition, we found that matrine increases the phosphorylation of p38 but not its total protein, and inhibition of the p38 pathway with SB202190 partially prevents matrine-induced apoptosis. Furthermore, matrine generates reactive oxygen species (ROS) in a dose- and time-dependent manner, which is reversed by pretreatment with N-acetyl-L-cysteine (NAC) [2].in vivo: Oral administration of matrine (200, 100 and 50 mg/kg) significantly attenuated isoproterenol-induced cardiac necrosis and left ventricular dysfunction [3]. high dose of matrine significantly reduced the mortality rate of mice with LPS administration. Treatment with matrine improved LPS-induced lung histopathologic changes, alleviated pulmonary edema and lung vascular leak, inhibited MPO and MDA activity,and reduced the production of inflammatory mediators including TNF-α, IL-6 and HMGB1 [4].Toxicity: N/AClinical trial: N/A
Related Catalog	Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Autophagy >> Mitophagy Signaling Pathways >> GPCR/G Protein >> Opioid Receptor Signaling Pathways >> Neuronal Signaling >> Opioid Receptor Natural Products >> Alkaloid Research Areas >> Cancer
References	[1]. Luo C, et al. Inhibition of matrine against gastric cancer cell line MNK45 growth and its anti-tumor mechanism. Mol Biol Rep. 2012 May;39(5):5459-64. [2]. Tan C, et al. Matrine induction of reactive oxygen species activates p38 leading to caspase-dependent cell apoptosis in non-small cell lung cancer cells. Oncol Rep. 2013 Nov;30(5):2529-35. [3]. Li X, et al. Regulation of endothelial nitric oxide synthase and asymmetric dimethylarginine by matrine attenuates isoproterenol-induced acute myocardial injury in rats. J Pharm Pharmacol. 2012 Aug;64(8):1107-18. [4]. Zhang B, et al. Antiinflammatory effects of matrine in LPS-induced acute lung injury in mice. Eur J Pharm Sci. 2011 Dec 18;44(5):573-9.

Density	1.2±0.1 g/cm3
Boiling Point	396.7±31.0 °C at 760 mmHg
Melting Point	77°C
Molecular Formula	C₁₅H₂₄N₂O
Molecular Weight	248.364
Flash Point	172.7±17.2 °C
Exact Mass	248.188858
PSA	23.55000
LogP	1.44
Vapour Pressure	0.0±0.9 mmHg at 25°C
Index of Refraction	1.581

CHEMICAL IDENTIFICATION

RTECS NUMBER :: OQ1754000

CHEMICAL NAME :: Matrine

CAS REGISTRY NUMBER :: 519-02-8

BEILSTEIN REFERENCE NO. :: 0085851

LAST UPDATED :: 199709

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C15-H24-N2-O

MOLECULAR WEIGHT :: 248.41

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 125 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 :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 150 mg/kg

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

REFERENCE :: CTYAD8 Zhongcaoyao. Chinese Traditional and Herbal Medicine. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.11- 1980- Volume(issue)/page/year: 18,214,1987

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 64850 ug/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

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

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 74150 ug/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

Hazard Codes	Xn: Harmful;
Risk Phrases	R20/21/22
Safety Phrases	22-26-36/37/39-45
HS Code	1302199001

26904-64-3

16837-52-8

519-02-8

Literature: UNILEVER PLC; UNILEVER N.V.; HINDUSTAN UNILEVER LIMITED Patent: WO2009/109496 A1, 2009 ; Location in patent: Page/Page column 9-10 ;