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
| 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
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 |
|---|---|---|
| Preparation and characterization of novel sinomenine microcapsules for oral controlled drug delivery. | 2010-04 |
|
| Development of patch and spray formulations for enhancing topical delivery of sinomenine hydrochloride. | 2010-04 |
|
| Effect of sinomenine on the in vitro intestinal epithelial transport of selected compounds. | 2010-02 |
|
| [Research advances of mechanism of sinomenine in treating rheumatoid arthritis]. | 2009-08 |
|
| Immunoregulatory effects of sinomenine on the T-bet/GATA-3 ratio and Th1/Th2 cytokine balance in the treatment of mesangial proliferative nephritis. | 2009-07 |
|
| Anti-angiogenic effects of pterogynidine alkaloid isolated from Alchornea glandulosa. | 2009-05-22 |
|
| Stilbene glycosides are natural product inhibitors of FGF-2-induced angiogenesis. | 2009-04-23 |
|
| [Effect of sinomenine on the expression of chemokines and chemokine receptors in dendritic cells from patients with rheumatoid arthritis]. | 2009-04 |
|
| 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. | 2009-04 |
|
| [Preparation of gastric retenting and chronopharmacologic drug delivery tablets of sinomenine hydrochloride]. | 2009-03 |
|
| Screening of bioactive compounds from moutan cortex and their anti-inflammatory activities in rat synoviocytes. | 2009-03 |
|
| [Study on pharmacokinetics and absolute bioavailability of sinomenine in beagle dogs]. | 2009-02 |
|
| [Study on optimization of formulation and preparation process of sinomenine liposomes]. | 2009-02 |
|
| Separation and detection of isoquinoline alkaloids using MEEKC coupled with field-amplified sample injection induced by ACN. | 2009-02 |
|
| Fast screening and structural elucidation of G-quadruplex ligands from a mixture via G-quadruplex recognition and NMR methods. | 2009-02 |
|
| [Effects of sinomenine on synovial fluid and serum content of interleukin-1beta in rabbits with osteoarthritis]. | 2008-12 |
|
| Sinomenine ameliorates arthritis via MMPs, TIMPs, and cytokines in rats. | 2008-11-14 |
|
| [Bioequivalence study of sinomenine patch by microdialysis]. | 2008-11 |
|
| Activation of opioid mu-receptor by sinomenine in cell and mice. | 2008-10-10 |
|
| Development and evaluation of the Sinomenine transdermal patch. | 2008-10 |
|
| Sinomenine versus NSAIDs for the treatment of rheumatoid arthritis: a systematic review and meta-analysis. | 2008-10 |
|
| pH-dependent, stereoselective dimerization of sinomenine. | 2008-09-04 |
|
| Recent advances in the compound-oriented and pattern-oriented approaches to the quality control of herbal medicines. | 2008-08-04 |
|
| [Dynamic determination of sinomenine in skin by microdialysis]. | 2008-07 |
|
| Chemical markers for the quality control of herbal medicines: an overview. | 2008-06-28 |
|
| [Inhibitory effect of sinomenine on H2O2-induced apoptosis in neonatal rat cardiomyocytes]. | 2008-04 |
|
| Biocatalyzed cross-coupling of sinomenine and guaiacol by Antrodiella semisupina. | 2008-03-20 |
|
| Inhibition of the antigen-induced activation of RBL-2H3 cells by sinomenine. | 2008-03 |
|
| [Role of alkaloid sinomenine in chronic rejection in the rat heart transplantation model]. | 2008-02 |
|
| Morphinane alkaloid dimers from Sinomenium acutum. | 2008-01 |
|
| Sinomenine inhibits activation of rat retinal microglia induced by advanced glycation end products. | 2007-12-05 |
|
| Sinomenine suppresses TNF-alpha-induced VCAM-1 expression in human umbilical vein endothelial cells. | 2007-11-01 |
|
| Effect of sinomenine on collagen-induced arthritis in mice. | 2007-11 |
|
| [Studies on preparation of sinomenine hydrochloride-loaded bovine serum albumin microspheres]. | 2007-10 |
|
| [Preparation of sinomenine microemulsion and its transdermal absorption]. | 2007-10 |
|
| Vasodilatation induced by sinomenine lowers blood pressure in spontaneously hypertensive rats. | 2007-10 |
|
| Sinomenine, a natural dextrorotatory morphinan analog, is anti-inflammatory and neuroprotective through inhibition of microglial NADPH oxidase. | 2007-09-19 |
|
| Vascular pharmacology of mokuboito (mu-fang-yi-tang) and its constituents on the smooth muscle and the endothelium in rat aorta. | 2007-09 |
|
| Voltammetric determination of sinomenine in biological fluid using a glassy carbon electrode modified by a composite film of polycysteic acid and carbon nanotubes. | 2007-08 |
|
| Sinomenine, an antirheumatic alkaloid, ameliorates clinical signs of disease in the Lewis rat model of acute experimental autoimmune encephalolmyelitis. | 2007-08 |
|
| Preparative isolation and purification of sinomenine from Sinomenium acutum by centrifugal partition chromatography. | 2007-08 |
|
| Assessment of in vitro and in vivo recovery of sinomenine using microdialysis. | 2007-08 |
|
| Sinomenine promotes differentiation but impedes maturation and co-stimulatory molecule expression of human monocyte-derived dendritic cells. | 2007-08 |
|
| Sinomenine inhibits primary CD4+ T-cell proliferation via apoptosis. | 2007-08 |
|
| Retraction: Pharmacokinetic interaction of paeoniflorin and sinomenine: pharmacokinetic parameters and tissue distribution characteristics in rats and protein binding ability in vitro. | 2007-07 |
|
| [Effects of sinomenine on NO/nNOS system in cerebellum and spinal cord of morphine-dependent and withdrawal mice]. | 2007-06-25 |
|
| Sinomenine inhibits maturation of monocyte-derived dendritic cells through blocking activation of NF-kappa B. | 2007-05 |
|
| Sinomenine attenuates 2, 4, 6-trinitrobenzene sulfonic acid-induced colitis in mice. | 2007-05 |
|
| Determination of sinomenine in Sinomenium acutum by capillary electrophoresis with electrochemiluminescence detection. | 2007-03-21 |
|
| Three major urinary metabolites of sinomenine in rats. | 2007-03-17 |
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
by
admin
on
Edited
Mon Mar 31 21:44:45 GMT 2025
by
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on
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| Record UNII |
63LT81K70N
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| Record Status |
Validated (UNII)
|
| Record Version |
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-
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Common Name | English | ||
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Preferred Name | English | ||
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Common Name | English |
| 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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PRIMARY | Merck Index | ||
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63LT81K70N
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204-094-6
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5459308
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SALT/SOLVATE -> PARENT |
