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
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C19H23NO4 |
| Molecular Weight | 329.3902 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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 |
|---|---|---|
| Sinomenine blocks tissue remodeling in a rat model of chronic cardiac allograft rejection. | 2003 Apr 15 |
|
| [Inhibitory effect of sinomenine on expression of cyclooxygenase-2 in lipopolysaccharide-induced PC-12 cells]. | 2004 Sep |
|
| Sinomenine inhibits B7-H1 and B7-DC expression on human renal tubular epithelial cells. | 2005 Aug |
|
| [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 |
|
| In vitro pharmacological actions of sinomenine on the smooth muscle and the endothelial cell activity in rat aorta. | 2006 Aug 15 |
|
| Effect of sinomenine on gene expression of the IL-1 beta-activated human synovial sarcoma. | 2006 Jul 10 |
|
| Synthesis and anti-inflammatory activities investigation of sinomenine derivatives on ring C. | 2006 Sep |
|
| Effect of sinomenine on human cytochrome P450 activity. | 2007 Apr |
|
| Sinomenine, an antirheumatic alkaloid, ameliorates clinical signs of disease in the Lewis rat model of acute experimental autoimmune encephalolmyelitis. | 2007 Aug |
|
| Assessment of in vitro and in vivo recovery of sinomenine using microdialysis. | 2007 Aug |
|
| Retraction: Pharmacokinetic interaction of paeoniflorin and sinomenine: pharmacokinetic parameters and tissue distribution characteristics in rats and protein binding ability in vitro. | 2007 Jul |
|
| [Preparation of sinomenine microemulsion and its transdermal absorption]. | 2007 Oct |
|
| Vasodilatation induced by sinomenine lowers blood pressure in spontaneously hypertensive rats. | 2007 Oct |
|
| [Role of alkaloid sinomenine in chronic rejection in the rat heart transplantation model]. | 2008 Feb |
|
| Activation of opioid mu-receptor by sinomenine in cell and mice. | 2008 Oct 10 |
|
| 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 |
|
| [Research advances of mechanism of sinomenine in treating rheumatoid arthritis]. | 2009 Aug |
|
| Separation and detection of isoquinoline alkaloids using MEEKC coupled with field-amplified sample injection induced by ACN. | 2009 Feb |
|
| Screening of bioactive compounds from moutan cortex and their anti-inflammatory activities in rat synoviocytes. | 2009 Mar |
|
| 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).
| Substance Class |
Chemical
Created
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admin
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Edited
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Sat Dec 16 08:24:09 GMT 2023
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| Record UNII |
2J34HRJ45S
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| Record Status |
Validated (UNII)
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| Record Version |
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SOLVATE->ANHYDROUS | |||
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |