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
COC1=C[C@@H]2[C@@H]3CC4=CC=C(OC)C(O)=C4[C@]2(CCN3C)CC1=O
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
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
123 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22342119/ |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
SINOMENINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
279 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22342119/ |
60 mg 2 times / day steady-state, oral dose: 60 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
SINOMENINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3064 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22342119/ |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
SINOMENINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
7436 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22342119/ |
60 mg 2 times / day steady-state, oral dose: 60 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
SINOMENINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
13.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22342119/ |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
SINOMENINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
15.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22342119/ |
60 mg 2 times / day steady-state, oral dose: 60 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
SINOMENINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
37.9% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16019035/ |
SINOMENINE serum | Homo sapiens |
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Advances in the study on transdermal permeation of active elements of natural drugs in vitro]. | 2002 Jan |
|
| [The effect of sinomenine on cyclooxygenase activity and the expression of COX-1 and COX-2 mRNA in human peripheral monocytes]. | 2003 Apr |
|
| Effect of sinomenine on morphine dependence in isolated guinea pig ileum. | 2003 Apr |
|
| Sinomenine blocks tissue remodeling in a rat model of chronic cardiac allograft rejection. | 2003 Apr 15 |
|
| Inhibition of MAO A and B by some plant-derived alkaloids, phenols and anthraquinones. | 2004 Apr |
|
| [Synthesis and anti-inflammatory analgesic activities of sinomenine derivatives]. | 2004 Mar |
|
| N-inversion-associated conformational dynamics is unusually rapid in morphine alkaloids. | 2004 Nov |
|
| [Inhibitory effect of sinomenine on expression of cyclooxygenase-2 in lipopolysaccharide-induced PC-12 cells]. | 2004 Sep |
|
| Requirement for ERK activation in sinomenine-induced apoptosis of macrophages. | 2005 Apr 15 |
|
| Effect of sinomenine on cytokine expression of macrophages and synoviocytes in adjuvant arthritis rats. | 2005 Apr 8 |
|
| Sinomenine inhibits B7-H1 and B7-DC expression on human renal tubular epithelial cells. | 2005 Aug |
|
| [Immunopharmacological action of sinomenine, an alkaloid isolated from Sinomenium acutum, and its mechanism of action in treating rheumatoid arthritis]. | 2005 Feb |
|
| Quantification of sinomenine in caulis sinomenii collected from different growing regions and wholesale herbal markets by a modified HPLC method. | 2005 Jan |
|
| Determination of sinomenine in human plasma by HPLC/ESI/ion trap mass spectrum. | 2005 Jun |
|
| Influence of co-administrated sinomenine on pharmacokinetic fate of paeoniflorin in unrestrained conscious rats. | 2005 May 13 |
|
| Supercritical fluid extraction of sinomenine from Sinomenium acutum (Thumb) Rehd et Wils. | 2005 May 20 |
|
| [Study on determination of entrapment efficiency of sinomenine liposomes]. | 2006 May |
|
| Effect of sinomenine on human cytochrome P450 activity. | 2007 Apr |
|
| In vivo analysis and spatial profiling of phytochemicals in herbal tissue by matrix-assisted laser desorption/ionization mass spectrometry. | 2007 Apr 1 |
|
| Sinomenine promotes differentiation but impedes maturation and co-stimulatory molecule expression of human monocyte-derived dendritic cells. | 2007 Aug |
|
| Sinomenine inhibits primary CD4+ T-cell proliferation via apoptosis. | 2007 Aug |
|
| Sinomenine inhibits activation of rat retinal microglia induced by advanced glycation end products. | 2007 Dec 5 |
|
| Three major urinary metabolites of sinomenine in rats. | 2007 Jan-Feb |
|
| [Effects of sinomenine on NO/nNOS system in cerebellum and spinal cord of morphine-dependent and withdrawal mice]. | 2007 Jun 25 |
|
| [The effects of sinomenine on the expresssion of ICAM-1 and IL-2 during the rejection of rat cardiac allograft]. | 2007 Mar |
|
| Determination of sinomenine in Sinomenium acutum by capillary electrophoresis with electrochemiluminescence detection. | 2007 Mar 21 |
|
| Sinomenine inhibits maturation of monocyte-derived dendritic cells through blocking activation of NF-kappa B. | 2007 May |
|
| Sinomenine attenuates 2, 4, 6-trinitrobenzene sulfonic acid-induced colitis in mice. | 2007 May |
|
| [Studies on preparation of sinomenine hydrochloride-loaded bovine serum albumin microspheres]. | 2007 Oct |
|
| [Inhibitory effect of sinomenine on H2O2-induced apoptosis in neonatal rat cardiomyocytes]. | 2008 Apr |
|
| [Role of alkaloid sinomenine in chronic rejection in the rat heart transplantation model]. | 2008 Feb |
|
| Chemical markers for the quality control of herbal medicines: an overview. | 2008 Jun 28 |
|
| Sinomenine ameliorates arthritis via MMPs, TIMPs, and cytokines in rats. | 2008 Nov 14 |
|
| pH-dependent, stereoselective dimerization of sinomenine. | 2008 Sep 4 |
|
| Anti-angiogenic effects of pterogynidine alkaloid isolated from Alchornea glandulosa. | 2009 May 22 |
|
| 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
