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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 of SINOMENINE

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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Preventing
Unknown
Primary
Unknown

PubMed

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
Record UNII
63LT81K70N
Record Status Validated (UNII)
Record Version