SINOMENINE

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

Structure Search

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

HIDE SMILES / InChI

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18692550
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

Targets

Primary Target	Pharmacology	Condition	Potency
T-helper 1 type immune response 3 Target ID: GO:0042088 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17966044	Inhibitor 8297
Mu opioid receptor 221 Target ID: CHEMBL2858 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18692550	Activator 1430

Conditions

Condition	Modality	Highest Phase	Product
Rheumatoid arthritis 316 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15635172	Primary	Preclinical	Unknown Approved Use Unknown
Diabetic cardiomyopathy 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27901470	Preventing	Preclinical	Unknown Approved Use Unknown
Allergic rhinitis 100 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23650707	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
The alkaloid sinomenine in rat transplant models: and yet it does move.	2001	11370167
[Advances in the study on transdermal permeation of active elements of natural drugs in vitro].	2002 Jan	14730719
[Study on the permeability of 125I-sinomenine via the transdermal delivery way in rats].	2002 Jun	12583333
[Study progress in Sinomenium acutum (Thunb.) Rehd. et Wils].	2002 Mar	12583167
[Effect of sinamine on withdrawal symptom and neurotransmitter of morphine-dependent rats].	2002 May	12583191
[The effect of sinomenine on cyclooxygenase activity and the expression of COX-1 and COX-2 mRNA in human peripheral monocytes].	2003 Apr	15139149
Effect of sinomenine on morphine dependence in isolated guinea pig ileum.	2003 Apr	12697465
Regulation of hepatobiliary excretion of sinomenine by P-glycoprotein in Sprague-Dawley rats.	2003 Apr 11	12639706
Sinomenine blocks tissue remodeling in a rat model of chronic cardiac allograft rejection.	2003 Apr 15	12698077
Inhibition of MAO A and B by some plant-derived alkaloids, phenols and anthraquinones.	2004 Apr	15120460
[Synthesis and anti-inflammatory analgesic activities of sinomenine derivatives].	2004 Mar	15171651
N-inversion-associated conformational dynamics is unusually rapid in morphine alkaloids.	2004 Nov	15568773
[Inhibitory effect of sinomenine on expression of cyclooxygenase-2 in lipopolysaccharide-induced PC-12 cells].	2004 Sep	15575215
Electropharmacological actions of the constituents of Sinomeni Caulis et Rhizome and Mokuboi-to in guinea pig heart.	2005	16355453
Requirement for ERK activation in sinomenine-induced apoptosis of macrophages.	2005 Apr 15	15790513
Effect of sinomenine on cytokine expression of macrophages and synoviocytes in adjuvant arthritis rats.	2005 Apr 8	15763362
Sinomenine inhibits B7-H1 and B7-DC expression on human renal tubular epithelial cells.	2005 Aug	15953571
Impact of release characteristics of sinomenine hydrochloride dosage forms on its pharmacokinetics in beagle dogs.	2005 Aug 7	16052686
[Study of the relative recovery of sinomenine microdialysis system and it's influential factor].	2005 Dec	16568662
Pharmacokinetic interaction of paeoniflorin and sinomenine: pharmacokinetic parameters and tissue distribution characteristics in rats and protein binding ability in vitro.	2005 Dec	16327213
Behavioral effects of sinomenine in murine models of anxiety.	2005 Dec 5	16111714
[Immunopharmacological action of sinomenine, an alkaloid isolated from Sinomenium acutum, and its mechanism of action in treating rheumatoid arthritis].	2005 Feb	15875667
Quantification of sinomenine in caulis sinomenii collected from different growing regions and wholesale herbal markets by a modified HPLC method.	2005 Jan	15635172
[Effect of penetration enhancers on the transdermal penetration of sinomenine liposome patch].	2005 Jul	16252723
Morphinane alkaloids with cell protective effects from Sinomenium acutum.	2005 Jul	16038566
[Research on extracting process for Fengshitongbi capsules].	2005 Jun	16209273
Determination of sinomenine in human plasma by HPLC/ESI/ion trap mass spectrum.	2005 Jun	15936320
Influence of co-administrated sinomenine on pharmacokinetic fate of paeoniflorin in unrestrained conscious rats.	2005 May 13	15848021
Supercritical fluid extraction of sinomenine from Sinomenium acutum (Thumb) Rehd et Wils.	2005 May 20	15974135
The pharmacokinetics and tissue distribution of sinomenine in rats and its protein binding ability in vitro.	2005 Nov 4	16019035
[New study progress of sinomenine].	2005 Oct	16422533
[Effect of sinomenine on adjuvant arthritis and its mechanisms].	2005 Sep	16323549
In vitro pharmacological actions of sinomenine on the smooth muscle and the endothelial cell activity in rat aorta.	2006 Aug 15	16643957
Suppression of Th1 and Th2 immune responses in mice by Sinomenine, an alkaloid extracted from the chinese medicinal plant Sinomenium acutum.	2006 Dec	17091433
Mechanisms responsible for poor oral bioavailability of paeoniflorin: Role of intestinal disposition and interactions with sinomenine.	2006 Dec	17063398
Effect of sinomenine on gene expression of the IL-1 beta-activated human synovial sarcoma.	2006 Jul 10	16566946
Assessment of in vitro and in vivo recovery of sinomenine using microdialysis.	2007 Aug	17610655
Sinomenine inhibits maturation of monocyte-derived dendritic cells through blocking activation of NF-kappa B.	2007 May	17386411
Sinomenine suppresses TNF-alpha-induced VCAM-1 expression in human umbilical vein endothelial cells.	2007 Nov 1	17869461
[Preparation of sinomenine microemulsion and its transdermal absorption].	2007 Oct	18161292
Vasodilatation induced by sinomenine lowers blood pressure in spontaneously hypertensive rats.	2007 Oct	17714082
Sinomenine, a natural dextrorotatory morphinan analog, is anti-inflammatory and neuroprotective through inhibition of microglial NADPH oxidase.	2007 Sep 19	17880684
Inhibition of the antigen-induced activation of RBL-2H3 cells by sinomenine.	2008 Mar	18279805
Development and evaluation of the Sinomenine transdermal patch.	2008 Oct	18930863
[Study on pharmacokinetics and absolute bioavailability of sinomenine in beagle dogs].	2009 Feb	19459314
[Study on optimization of formulation and preparation process of sinomenine liposomes].	2009 Feb	19445147
Fast screening and structural elucidation of G-quadruplex ligands from a mixture via G-quadruplex recognition and NMR methods.	2009 Feb	19014995
[Preparation of gastric retenting and chronopharmacologic drug delivery tablets of sinomenine hydrochloride].	2009 Mar	19526781

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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 `Sat Dec 16 07:53:06 GMT 2023` Edited by `admin` on `Sat Dec 16 07:53:06 GMT 2023`
Record UNII	63LT81K70N
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SINOMENINE

Common Name

English

KUKOLINE

Brand Name

English

Sinomenine [WHO-DD]

Common Name

English

MORPHINAN-6-ONE, 7,8-DIDEHYDRO-4-HYDROXY-3,7-DIMETHOXY-17-METHYL-, (9.ALPHA.,13.ALPHA.,14.ALPHA.)-

Common Name

English

SINOMENINE [MI]

Common Name

English

CUCOLINE

Brand Name

English

SINOMENIN

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1742