Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C19H23NO4.ClH |
| Molecular Weight | 365.851 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.[H][C@@]12CC3=C(C(O)=C(OC)C=C3)[C@]4(CCN1C)CC(=O)C(OC)=C[C@]24[H]
InChI
InChIKey=YMEVIMJAUHZFMW-VUIDNZEBSA-N
InChI=1S/C19H23NO4.ClH/c1-20-7-6-19-10-14(21)16(24-3)9-12(19)13(20)8-11-4-5-15(23-2)18(22)17(11)19;/h4-5,9,12-13,22H,6-8,10H2,1-3H3;1H/t12-,13+,19-;/m1./s1
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/27585465
https://www.ncbi.nlm.nih.gov/pubmed/27901470
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/27585465
https://www.ncbi.nlm.nih.gov/pubmed/27901470
Sinomenine is a pure alkaloid extracted from the Chinese medical plant Sinomenium acutum. Caulis Sinomenii is the dried plant stems of Sinomenium acutum and Sinomenium acutum var. cinereum and has been used in Chinese medicine for treating rheumatic diseases for over a thousand years. Sinomenine possesses the anti-arthritic effect, that may be related to the suppression of both Th1 (T-helper 1) and Th2 immune responses, also this potential drug can be used to treat allergic rhinitis, and the mechanism may rely on the improvements of the Th1/Th2 imbalance. In addition, Sinomenine displays antinociceptive activity, possibly through activation of the μ-opioid receptor. Also was discovered, sinomenine significantly improves cardiac function in diabetic rats, which may be attributed to the deactivation of NF-κB and the blockade of inflammatory cytokine-mediated immune reactions.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Advances in the study on transdermal permeation of active elements of natural drugs in vitro]. | 2002 Jan |
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| [Effect of sinamine on withdrawal symptom and neurotransmitter of morphine-dependent rats]. | 2002 May |
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| [The effect of sinomenine on cyclooxygenase activity and the expression of COX-1 and COX-2 mRNA in human peripheral monocytes]. | 2003 Apr |
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| Effect of sinomenine on morphine dependence in isolated guinea pig ileum. | 2003 Apr |
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| Regulation of hepatobiliary excretion of sinomenine by P-glycoprotein in Sprague-Dawley rats. | 2003 Apr 11 |
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| Inhibition of MAO A and B by some plant-derived alkaloids, phenols and anthraquinones. | 2004 Apr |
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| [Synthesis and anti-inflammatory analgesic activities of sinomenine derivatives]. | 2004 Mar |
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| N-inversion-associated conformational dynamics is unusually rapid in morphine alkaloids. | 2004 Nov |
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| [Inhibitory effect of sinomenine on expression of cyclooxygenase-2 in lipopolysaccharide-induced PC-12 cells]. | 2004 Sep |
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| Behavioral effects of sinomenine in murine models of anxiety. | 2005 Dec 5 |
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| Determination of sinomenine in human plasma by HPLC/ESI/ion trap mass spectrum. | 2005 Jun |
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| Influence of co-administrated sinomenine on pharmacokinetic fate of paeoniflorin in unrestrained conscious rats. | 2005 May 13 |
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| [Effect of sinomenine on adjuvant arthritis and its mechanisms]. | 2005 Sep |
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| In vitro pharmacological actions of sinomenine on the smooth muscle and the endothelial cell activity in rat aorta. | 2006 Aug 15 |
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| Mechanisms responsible for poor oral bioavailability of paeoniflorin: Role of intestinal disposition and interactions with sinomenine. | 2006 Dec |
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| [Study on determination of entrapment efficiency of sinomenine liposomes]. | 2006 May |
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| Preparative isolation and purification of sinomenine from Sinomenium acutum by centrifugal partition chromatography. | 2007 Aug |
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| Assessment of in vitro and in vivo recovery of sinomenine using microdialysis. | 2007 Aug |
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| Sinomenine promotes differentiation but impedes maturation and co-stimulatory molecule expression of human monocyte-derived dendritic cells. | 2007 Aug |
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| Sinomenine inhibits activation of rat retinal microglia induced by advanced glycation end products. | 2007 Dec 5 |
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| Combinative method using HPLC quantitative and qualitative analyses for quality consistency assessment of a herbal medicinal preparation. | 2007 Jan 4 |
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| [Effects of sinomenine on NO/nNOS system in cerebellum and spinal cord of morphine-dependent and withdrawal mice]. | 2007 Jun 25 |
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| [Inhibitory effect of sinomenine on H2O2-induced apoptosis in neonatal rat cardiomyocytes]. | 2008 Apr |
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| Recent advances in the compound-oriented and pattern-oriented approaches to the quality control of herbal medicines. | 2008 Aug 4 |
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| [Dynamic determination of sinomenine in skin by microdialysis]. | 2008 Jul |
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| Chemical markers for the quality control of herbal medicines: an overview. | 2008 Jun 28 |
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| Inhibition of the antigen-induced activation of RBL-2H3 cells by sinomenine. | 2008 Mar |
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| Development and evaluation of the Sinomenine transdermal patch. | 2008 Oct |
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| Sinomenine versus NSAIDs for the treatment of rheumatoid arthritis: a systematic review and meta-analysis. | 2008 Oct |
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| Activation of opioid mu-receptor by sinomenine in cell and mice. | 2008 Oct 10 |
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| Sinomenine influences capacity for invasion and migration in activated human monocytic THP-1 cells by inhibiting the expression of MMP-2, MMP-9, and CD147. | 2009 Apr |
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| [Research advances of mechanism of sinomenine in treating rheumatoid arthritis]. | 2009 Aug |
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| Immunoregulatory effects of sinomenine on the T-bet/GATA-3 ratio and Th1/Th2 cytokine balance in the treatment of mesangial proliferative nephritis. | 2009 Jul |
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| [Preparation of gastric retenting and chronopharmacologic drug delivery tablets of sinomenine hydrochloride]. | 2009 Mar |
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| Anti-angiogenic effects of pterogynidine alkaloid isolated from Alchornea glandulosa. | 2009 May 22 |
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| Effect of sinomenine on the in vitro intestinal epithelial transport of selected compounds. | 2010 Feb |
Patents
Sample Use Guides
in rats: Acute sinomenine treatment: 10–40 mg/kg, i.p.
in mice: collagen-induced arthritis (CIA) in mice: Varying doses of sinomenine were orally administered daily commencing on day 0 daily over a period of 55 days
Route of Administration:
Other
Sinomenine was found to significantly inhibit TNF-α induced cell surface expression of vascular cell adhesion molecule (VCAM)-1 and release of inflammatory cytokine and chemokine IL-6, CCL2 and CXCL8 from both normal and rheumatoid arthritis fibroblast-like synoviocytes (RA-FLS) (all p<0.05). Moreover, the suppression of sinomenine on TNF-α induced VCAM-1 expression and IL-6 release of RA-FLS was significantly higher than that of normal (FLS).
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5459307
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76021
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SUB125913
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6080-33-7
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100000151627
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2J34HRJ45S
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ACTIVE MOIETY
SUBSTANCE RECORD
