Sinomenine

Names

[ CAS No. ]:
115-53-7

[ Name ]:
Sinomenine

[Synonym ]:
EINECS 204-094-6
MFCD00134303

Biological Activity

[Description]:

Sinomenine, an alkaloid extracted from Sinomenium acutum, is a blocker of the NF-κB activation[1]. Sinomenine also is an activator of μ-opioid receptor[2].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Signaling Pathways >> GPCR/G Protein >> Opioid Receptor

Signaling Pathways >> Autophagy >> Autophagy

Research Areas >> Inflammation/Immunology

Signaling Pathways >> Neuronal Signaling >> Opioid Receptor

Research Areas >> Neurological Disease

[Target]

NF-κB[1], μ-opioid receptor[2]

[In Vitro]

Cell viability gradually decreased with increasing Sinomenine concentration. The migration ability of MDA-MB-231 cells is significantly weakened by 0.25, 0.5, and 1 mM of Sinomenine treatment. The wound-healing assay reveals that 0.25 and 0.5 mM Sinomenine significantly suppress the healing of the wound. When the MDA-MB-231 cells are treated with 0.5 mM Sinomenine, the healing progress is about 50%, but in the group treated with 0.25 mM Sinomenine and the untreated control, the healing is about 80% and nearly 95%, respectively. The IB assay following inhibitor of NF-κB (IκB) antibody IP shows that the binding of NF-κB to IκB is inhibited by Sinomenine treatment in a dose-dependent manne[1].

[In Vivo]

Sinomenine (i.p.) produces antinociception in the hot plate and tail flick tests in male rats at 40 mg/kg, but not at lower doses (10 or 20 mg/kg). At 10 to 40 mg/kg Sinomenine does not produce any observable side effect such as sedation, allergy or motor impairments. At 80 mg/kg, Sinomenine is mildly sedative in rats. Antinociception is also seen mice at 60 min following 80 mg/kg i.p. Sinomenine, but not at lower doses (20 or 40 mg/kg), in the tail flick test. Sinomenine at 80 mg/kg i.p. does not produce any observable side effects in mice. I.p or p.o. Sinomenine at 40 or 80 mg/kg dose-dependently reduces mechanical hypersensitivity in nerve injured mice. I.p. Sinomenine at 40 mg/kg, but not lower doses or vehicle, significantly decreases mechanical and cold allodynia for up to 240 min without producing motor deficits or sedation[3]. At doses of 10 to 40 mg/kg, Sinomenine dose-dependently increases the paw withdrawal threshold. In non-chronic constriction injury (CCI) healthy rats, Sinomenine at the dose range of 10 to 40 mg/kg does not change the immobility behavior in the forced swimming test[4].

[Cell Assay]

The MDA-MB-231 human triple negative and 4T1 mouse breast cancer cell lines are used in this study. For the experiments, the cells are grown in 24-well plates at 3.5×104/well. Following incubation for 24 or 48 h in medium containing different concentrations of Sinomenine, proliferation of the cells are detected with Cell Counting Kit-8 solution according to the manufacturer's instructions[1].

[Animal admin]

Male Sprague-Dawley rats weighing of 250 to 300 g are used in this experiment. For the duration of action of acute Sinomenine study, different doses of Sinomenine (10 to 40 mg/kg) are administered 1 day after surgery and then paw withdrawal threshold is measured every 30 min for 4 hours. For the study involving daily Sinomenine treatment, mechanical hyperalgesia measure is performed 3 h after daily drug treatment. For antagonist studies, antagonists were given 10 min prior to 40 mg/kg Sinomenine administration[3].

[References]

[1]. Song L, et al. Sinomenine inhibits breast cancer cell invasion and migration by suppressing NF-κB activation mediated by IL-4/miR-324-5p/CUEDC2 axis. Biochem Biophys Res Commun. 2015 Aug 28;464(3):705-10.

[2]. Wang MH, et al. Activation of opioid mu-receptor by sinomenine in cell and mice.Neurosci Lett. 2008 Oct 10;443(3):209-12.

[3]. Gao T, et al. Analgesic effect of sinomenine in rodents after inflammation and nerve injury. Eur J Pharmacol. 2013 Dec 5;721(1-3):5-11.

[4]. Zhu Q, et al. Antinociceptive effects of sinomenine in a rat model of neuropathic pain. Sci Rep. 2014 Dec 1;4:7270.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
513.6±50.0 °C at 760 mmHg

[ Melting Point ]:
180ºC

[ Molecular Formula ]:
C₁₉H₂₃NO₄

[ Molecular Weight ]:
329.390

[ Flash Point ]:
264.4±30.1 °C

[ Exact Mass ]:
329.162720

[ PSA ]:
59.00000

[ LogP ]:
1.25

[ Vapour Pressure ]:
0.0±1.4 mmHg at 25°C

[ Index of Refraction ]:
1.625

[ Storage condition ]:
2~8°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: QD2170000

CHEMICAL NAME :: 9-alpha,13-alpha,14-alpha-Morphinan-6-one, 7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-

CAS REGISTRY NUMBER :: 115-53-7

BEILSTEIN REFERENCE NO. :: 0095280

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C19-H23-N-O4

MOLECULAR WEIGHT :: 329.43

WISWESSER LINE NOTATION :: T6 G666/FQ 2AF Q DV FX ON BUT&TTJ CO1 HQ IO1 O1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 580 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold

REFERENCE :: YHHPAL Yaoxue Xuebao. Acta Pharmaceutica Sinica. Pharmaceutical Journal. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1953- Suspended 1966-78. Volume(issue)/page/year: 10,673,1963

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 285 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: YHHPAL Yaoxue Xuebao. Acta Pharmaceutica Sinica. Pharmaceutical Journal. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1953- Suspended 1966-78. Volume(issue)/page/year: 8,177,1960

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H315-H319-H335

[ Precautionary Statements ]:
P301 + P312 + P330-P305 + P351 + P338

[ Hazard Codes ]:
T: Toxic;

[ Risk Phrases ]:
R45

[ Safety Phrases ]:
53-22-26-36/37/39-45

[ RIDADR ]:
UN 1544

[ WGK Germany ]:
3

[ RTECS ]:
QD2170000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

[Research advances of mechanism of sinomenine in treating rheumatoid arthritis].

Zhong Xi Yi Jie He Xue Bao 7(8) , 775-8, (2009)

[New study progress of sinomenine].

Zhongguo Zhong Yao Za Zhi 30(20) , 1573-6, (2005)

To further understand sinomenine, this paper has introduced the abstract technology, assaying, pharmaceutical chemistry, pharmacological action, pharmacotoxicology, pharmacokinetics and clinical appli...

Immunosuppressive and anti-inflammatory activities of sinomenine.

Int. Immunopharmacol. 11(3) , 373-6, (2011)

Sinomenine (SN), a pure compound extracted from the Sinomenium acutum plant, has been found to inhibit T- and B-lymphocyte activation, proliferation and function and to interfere with the differentiat...

Related Compounds

The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.