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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...


More Articles

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