SINOMENINE HYDROCHLORIDE

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

Structure Search

SMILES

Cl.COC1=C[C@@H]2[C@@H]3CC4=CC=C(OC)C(O)=C4[C@]2(CCN3C)CC1=O

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

HIDE SMILES / InChI

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

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 8504
Mu opioid receptor 231 Target ID: CHEMBL2858 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18692550	Activator 1447

Conditions

Condition	Modality	Highest Phase	Product
Rheumatoid arthritis 320 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 104 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23650707	Primary	Preclinical	Unknown Approved Use Unknown

C_max

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

T_1/2

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

F_unbound

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	19877829
Development of patch and spray formulations for enhancing topical delivery of sinomenine hydrochloride.	2010-04	19774661
Effect of sinomenine on the in vitro intestinal epithelial transport of selected compounds.	2010-02	19585475
[Research advances of mechanism of sinomenine in treating rheumatoid arthritis].	2009-08	19671418
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	19336263
Anti-angiogenic effects of pterogynidine alkaloid isolated from Alchornea glandulosa.	2009-05-22	19463163
Stilbene glycosides are natural product inhibitors of FGF-2-induced angiogenesis.	2009-04-23	19389252
[Effect of sinomenine on the expression of chemokines and chemokine receptors in dendritic cells from patients with rheumatoid arthritis].	2009-04	19403382
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	19305422
[Preparation of gastric retenting and chronopharmacologic drug delivery tablets of sinomenine hydrochloride].	2009-03	19526781
Screening of bioactive compounds from moutan cortex and their anti-inflammatory activities in rat synoviocytes.	2009-03	18955220
[Study on pharmacokinetics and absolute bioavailability of sinomenine in beagle dogs].	2009-02	19459314
[Study on optimization of formulation and preparation process of sinomenine liposomes].	2009-02	19445147
Separation and detection of isoquinoline alkaloids using MEEKC coupled with field-amplified sample injection induced by ACN.	2009-02	19156769
Fast screening and structural elucidation of G-quadruplex ligands from a mixture via G-quadruplex recognition and NMR methods.	2009-02	19014995
[Effects of sinomenine on synovial fluid and serum content of interleukin-1beta in rabbits with osteoarthritis].	2008-12	19063843
Sinomenine ameliorates arthritis via MMPs, TIMPs, and cytokines in rats.	2008-11-14	18782565
[Bioequivalence study of sinomenine patch by microdialysis].	2008-11	19149253
Activation of opioid mu-receptor by sinomenine in cell and mice.	2008-10-10	18692550
Development and evaluation of the Sinomenine transdermal patch.	2008-10	18930863
Sinomenine versus NSAIDs for the treatment of rheumatoid arthritis: a systematic review and meta-analysis.	2008-10	18683125
pH-dependent, stereoselective dimerization of sinomenine.	2008-09-04	18646768
Recent advances in the compound-oriented and pattern-oriented approaches to the quality control of herbal medicines.	2008-08-04	18680568
[Dynamic determination of sinomenine in skin by microdialysis].	2008-07	18973024
Chemical markers for the quality control of herbal medicines: an overview.	2008-06-28	18588699
[Inhibitory effect of sinomenine on H2O2-induced apoptosis in neonatal rat cardiomyocytes].	2008-04	18619358
Biocatalyzed cross-coupling of sinomenine and guaiacol by Antrodiella semisupina.	2008-03-20	18284247
Inhibition of the antigen-induced activation of RBL-2H3 cells by sinomenine.	2008-03	18279805
[Role of alkaloid sinomenine in chronic rejection in the rat heart transplantation model].	2008-02	19099959
Morphinane alkaloid dimers from Sinomenium acutum.	2008-01	18081254
Sinomenine inhibits activation of rat retinal microglia induced by advanced glycation end products.	2007-12-05	17920532
Sinomenine suppresses TNF-alpha-induced VCAM-1 expression in human umbilical vein endothelial cells.	2007-11-01	17869461
Effect of sinomenine on collagen-induced arthritis in mice.	2007-11	17966044
[Studies on preparation of sinomenine hydrochloride-loaded bovine serum albumin microspheres].	2007-10	18306744
[Preparation of sinomenine microemulsion and its transdermal absorption].	2007-10	18161292
Vasodilatation induced by sinomenine lowers blood pressure in spontaneously hypertensive rats.	2007-10	17714082
Sinomenine, a natural dextrorotatory morphinan analog, is anti-inflammatory and neuroprotective through inhibition of microglial NADPH oxidase.	2007-09-19	17880684
Vascular pharmacology of mokuboito (mu-fang-yi-tang) and its constituents on the smooth muscle and the endothelium in rat aorta.	2007-09	17965764
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	17979642
Sinomenine, an antirheumatic alkaloid, ameliorates clinical signs of disease in the Lewis rat model of acute experimental autoimmune encephalolmyelitis.	2007-08	17666800
Preparative isolation and purification of sinomenine from Sinomenium acutum by centrifugal partition chromatography.	2007-08	17654620
Assessment of in vitro and in vivo recovery of sinomenine using microdialysis.	2007-08	17610655
Sinomenine promotes differentiation but impedes maturation and co-stimulatory molecule expression of human monocyte-derived dendritic cells.	2007-08	17570327
Sinomenine inhibits primary CD4+ T-cell proliferation via apoptosis.	2007-08	17383204
Retraction: Pharmacokinetic interaction of paeoniflorin and sinomenine: pharmacokinetic parameters and tissue distribution characteristics in rats and protein binding ability in vitro.	2007-07	17652912
[Effects of sinomenine on NO/nNOS system in cerebellum and spinal cord of morphine-dependent and withdrawal mice].	2007-06-25	17579782
Sinomenine inhibits maturation of monocyte-derived dendritic cells through blocking activation of NF-kappa B.	2007-05	17386411
Sinomenine attenuates 2, 4, 6-trinitrobenzene sulfonic acid-induced colitis in mice.	2007-05	17386408
Determination of sinomenine in Sinomenium acutum by capillary electrophoresis with electrochemiluminescence detection.	2007-03-21	17386760
Three major urinary metabolites of sinomenine in rats.	2007-03-17	17365183

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 `Mon Mar 31 22:03:08 GMT 2025` Edited by `admin` on `Mon Mar 31 22:03:08 GMT 2025`
Record UNII	2J34HRJ45S
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SINOMENINE HYDROCHLORIDE

Common Name

English

CUCOLINE, HYDROCHLORIDE

Preferred Name

English

SINOMENIN HYDROCHLORIDE

Common Name

English

NSC-76021

Code

English

MORPHINAN-6-ONE, 7,8-DIDEHYDRO-4-HYDROXY-3,7-DIMETHOXY-17-METHYL-, HYDROCHLORIDE (1:1), (9.ALPHA.,13.ALPHA.,14.ALPHA.)-

Common Name

English

CUCOLINE HYDROCHLORIDE

Common Name

English

Sinomenine hydrochloride [WHO-DD]

Common Name

English

Code System Code Type Description

PUBCHEM

5459307