Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C19H23NO4 |
| Molecular Weight | 329.3902 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC3=C(C(O)=C(OC)C=C3)[C@]4(CCN1C)CC(=O)C(OC)=C[C@]24[H]
InChI
InChIKey=INYYVPJSBIVGPH-QHRIQVFBSA-N
InChI=1S/C19H23NO4/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/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 |
|---|---|---|
| The alkaloid sinomenine in rat transplant models: and yet it does move. | 2001 |
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| [Advances in the study on transdermal permeation of active elements of natural drugs in vitro]. | 2002 Jan |
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| [Study on the permeability of 125I-sinomenine via the transdermal delivery way in rats]. | 2002 Jun |
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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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| Sinomenine blocks tissue remodeling in a rat model of chronic cardiac allograft rejection. | 2003 Apr 15 |
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| Inhibition of MAO A and B by some plant-derived alkaloids, phenols and anthraquinones. | 2004 Apr |
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| Behavioral effects of sinomenine in murine models of anxiety. | 2005 Dec 5 |
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| Morphinane alkaloids with cell protective effects from Sinomenium acutum. | 2005 Jul |
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| Determination of sinomenine in human plasma by HPLC/ESI/ion trap mass spectrum. | 2005 Jun |
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| The pharmacokinetics and tissue distribution of sinomenine in rats and its protein binding ability in vitro. | 2005 Nov 4 |
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| [Effect of sinomenine on adjuvant arthritis and its mechanisms]. | 2005 Sep |
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| [Effects of the alkaloid sinomenine on COX-2 activity and acute rejection in heart allografts: an experiment with rats]. | 2006 Apr 4 |
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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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| Suppression of Th1 and Th2 immune responses in mice by Sinomenine, an alkaloid extracted from the chinese medicinal plant Sinomenium acutum. | 2006 Dec |
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| The effects of sinomenine on intestinal absorption of paeoniflorin by the everted rat gut sac model. | 2006 Feb 20 |
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| In vivo analysis and spatial profiling of phytochemicals in herbal tissue by matrix-assisted laser desorption/ionization mass spectrometry. | 2007 Apr 1 |
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| Sinomenine attenuates 2, 4, 6-trinitrobenzene sulfonic acid-induced colitis in mice. | 2007 May |
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| [Role of alkaloid sinomenine in chronic rejection in the rat heart transplantation model]. | 2008 Feb |
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| Inhibition of the antigen-induced activation of RBL-2H3 cells by sinomenine. | 2008 Mar |
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| Biocatalyzed cross-coupling of sinomenine and guaiacol by Antrodiella semisupina. | 2008 Mar 20 |
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| Sinomenine ameliorates arthritis via MMPs, TIMPs, and cytokines in rats. | 2008 Nov 14 |
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| Development and evaluation of the Sinomenine transdermal patch. | 2008 Oct |
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| Activation of opioid mu-receptor by sinomenine in cell and mice. | 2008 Oct 10 |
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| pH-dependent, stereoselective dimerization of sinomenine. | 2008 Sep 4 |
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| [Research advances of mechanism of sinomenine in treating rheumatoid arthritis]. | 2009 Aug |
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| Screening of bioactive compounds from moutan cortex and their anti-inflammatory activities in rat synoviocytes. | 2009 Mar |
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| Preparation and characterization of novel sinomenine microcapsules for oral controlled drug delivery. | 2010 Apr |
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| Development of patch and spray formulations for enhancing topical delivery of sinomenine hydrochloride. | 2010 Apr |
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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NCI_THESAURUS |
C1742
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NCI_THESAURUS |
C2139
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115-53-7
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100000130215
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SUB41719
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Sinomenine
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C64766
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DTXSID00871595
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m9954
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63LT81K70N
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204-094-6
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5459308
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SALT/SOLVATE (PARENT)
SUBSTANCE RECORD
