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 |
|---|---|---|
| [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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| [Study progress in Sinomenium acutum (Thunb.) Rehd. et Wils]. | 2002 Mar |
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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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| Sinomenine blocks tissue remodeling in a rat model of chronic cardiac allograft rejection. | 2003 Apr 15 |
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| Electropharmacological actions of the constituents of Sinomeni Caulis et Rhizome and Mokuboi-to in guinea pig heart. | 2005 |
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| The anti-angiogenic effect of sinomenine. | 2005 |
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| Effect of sinomenine on cytokine expression of macrophages and synoviocytes in adjuvant arthritis rats. | 2005 Apr 8 |
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| Sinomenine inhibits B7-H1 and B7-DC expression on human renal tubular epithelial cells. | 2005 Aug |
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| Behavioral effects of sinomenine in murine models of anxiety. | 2005 Dec 5 |
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| [Immunopharmacological action of sinomenine, an alkaloid isolated from Sinomenium acutum, and its mechanism of action in treating rheumatoid arthritis]. | 2005 Feb |
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| [Research on extracting process for Fengshitongbi capsules]. | 2005 Jun |
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| Determination of sinomenine in human plasma by HPLC/ESI/ion trap mass spectrum. | 2005 Jun |
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| [Changes in cAMP and cGMP levels in neonatal rat histaminergic neurons of tuberomammillary nucleus following 48-hour morphine exposure and effects of sinomenine intervention]. | 2005 Sep |
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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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| [Determination in vitro of rat plasma protein binding rate of sinomenine by using microdialysis method]. | 2006 Sep |
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| Effect of sinomenine on human cytochrome P450 activity. | 2007 Apr |
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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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| Voltammetric determination of sinomenine in biological fluid using a glassy carbon electrode modified by a composite film of polycysteic acid and carbon nanotubes. | 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 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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| A spectroscopic and molecular modeling study of sinomenine binding to transferrin. | 2007 Mar 15 |
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| Determination of sinomenine in Sinomenium acutum by capillary electrophoresis with electrochemiluminescence detection. | 2007 Mar 21 |
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| Effect of sinomenine on collagen-induced arthritis in mice. | 2007 Nov |
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| Sinomenine suppresses TNF-alpha-induced VCAM-1 expression in human umbilical vein endothelial cells. | 2007 Nov 1 |
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| [Studies on preparation of sinomenine hydrochloride-loaded bovine serum albumin microspheres]. | 2007 Oct |
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| Vasodilatation induced by sinomenine lowers blood pressure in spontaneously hypertensive rats. | 2007 Oct |
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| Sinomenine, a natural dextrorotatory morphinan analog, is anti-inflammatory and neuroprotective through inhibition of microglial NADPH oxidase. | 2007 Sep 19 |
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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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| [Effects of sinomenine on synovial fluid and serum content of interleukin-1beta in rabbits with osteoarthritis]. | 2008 Dec |
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| [Role of alkaloid sinomenine in chronic rejection in the rat heart transplantation model]. | 2008 Feb |
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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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| 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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| 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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| pH-dependent, stereoselective dimerization of sinomenine. | 2008 Sep 4 |
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| [Effect of sinomenine on the expression of chemokines and chemokine receptors in dendritic cells from patients with rheumatoid arthritis]. | 2009 Apr |
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| Stilbene glycosides are natural product inhibitors of FGF-2-induced angiogenesis. | 2009 Apr 23 |
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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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| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C1742
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NCI_THESAURUS |
C2139
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| Code System | Code | Type | Description | ||
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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
