Tetrandrine

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Tetrandrine
Tetrandrine Structural Formula V4.svg
Names
IUPAC name
9,20,21,25-tetramethoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.23,6.18,12.114,18.027,31.022,33]hexatriaconta-3,5,8(34),9,11,18,20,22(33),24(32),25,27(31),35-dodecaene
Identifiers
3D model (JSmol)
ChEMBL
ECHA InfoCard 100.208.615 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • CN1CCC2=CC(=C3C=C2C1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)CC6C7=C(O3)C(=C(C=C7CCN6C)OC)OC)OC)OC
Properties
C38H42N2O6
Molar mass 622.74988
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Tetrandrine, a bis-benzylisoquinoline alkaloid, is a calcium channel blocker. [1] It is isolated from the plant Stephania tetrandra , [2] and other Chinese and Japanese herbs.

Contents

Pharmacology

It has anti-inflammatory, immunologic and antiallergenic effects. It inhibits the degranulation of mast cells. It has a quinidine-like anti-arrhythmic effect. It has vasodilatory properties and can therefore reduce blood pressure. [3] Tetrandrine may have potential use for the treatment of liver disease [4] and liver cancer. [5] [6] [7] Tetrandrine has potential therapeutic value to prevent excess scarring/fibrosis in conjunctiva following trabeculectomy or in patients with severe conjunctival inflammation. [8] Tetrandrine has anti-inflammatory and anti-fibrogenic actions, which make tetrandrine and related compounds potentially useful in the treatment of lung silicosis, liver cirrhosis, and rheumatoid arthritis. [9] Tetrandrine has also been shown to inhibit entry of Ebola virus into host cells in vitro and showed therapeutic efficacy against Ebola in preliminary studies on mice. [10] [1] Tetrandrine has also been studied and patented as a possible treatment for tinnitus. [11] [12] [13]

Biosynthesis

Tetrandrine is biosynthesized from a free radical coupled dimerization of S-N-methylcoclaurine: [14]

Tetrandrine proposed biosynthesis.png

Synonyms

Synonyms include fanchinine, hanfangchin A, NSC 77037, (S,S)-(+)-tetrandrine, sinomenine A, TTD, tetrandrin, d-tetrandrine, and GW-201. [15] [13]

Related Research Articles

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References

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  2. Zhang, Lijin; Geng, Yanling; Duan, Wenjuan; Wang, Daijie; Fu, Maorun; Wang, Xiao (2009). "Ionic liquid-based ultrasound-assisted extraction of fangchinoline and tetrandrine from Stephaniae tetrandrae". Journal of Separation Science. 32 (20): 3550–3554. doi:10.1002/jssc.200900413. PMID   19764054.
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  15. Tetrandrine(Fanchinine) | CAS 518-34-3 | calcium channel Inhibitor | Fanchinine, Hanfangchin A, NSC 77037, S,S-(+)-Tetrandrine, Sinomenine A, TTD, Tetrandrin, d...