This article needs more reliable medical references for verification or relies too heavily on primary sources. Please review the contents of the article and add the appropriate references if you can. Unsourced or poorly sourced material may be challenged and removed. Find sources: "Tetrandrine" – news · newspapers · books · scholar · JSTOR (March 2015)
Tetrandrine
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 Edit this at Wikidata
KEGG
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).
☒N verify (what is checkY☒N ?)

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.

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]

Synonyms

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

References

  1. ^ a b Bhagya, N; Chandrashekar, KR (1 May 2016). "Tetrandrine – A molecule of wide bioactivity". Phytochemistry. 125: 5–13. Bibcode:2016PChem.125....5B. doi:10.1016/j.phytochem.2016.02.005. ISSN 0031-9422. PMID 26899361. Retrieved 24 February 2022.
  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.
  3. ^ Kwan, C. Y.; Achike, F. I. (2002). "Tetrandrine and related bis-benzylisoquinoline alkaloids from medicinal herbs: Cardiovascular effects and mechanisms of action". Acta Pharmacologica Sinica. 23 (12): 1057–68. PMID 12466042.
  4. ^ Feng, Dechun; Mei, Yunhua; Wang, Ying; Zhang, Bianhong; Wang, Chen; Xu, Lingyun (2008). "Tetrandrine protects mice from concanavalin A-induced hepatitis through inhibiting NF-κB activation". Immunology Letters. 121 (2): 127–133. doi:10.1016/j.imlet.2008.10.001. PMID 18992279.
  5. ^ Liu, Chaoyang; Gong, Ke; Mao, Xin; Li, Wenhua (2011). "Tetrandrine induces apoptosis by activating reactive oxygen species and repressing Akt activity in human hepatocellular carcinoma". International Journal of Cancer. 129 (6): 1519–1531. doi:10.1002/ijc.25817. PMID 21128229. S2CID 3163935.
  6. ^ Cheng, Zhixiang; Wang, Keming; Wei, Jia; Lu, Xiang; Liu, Baorui (2010). "Proteomic analysis of anti-tumor effects by tetrandrine treatment in HepG2 cells". Phytomedicine. 17 (13): 1000–1005. doi:10.1016/j.phymed.2010.03.018. PMID 20554191.
  7. ^ Deng, W. Y.; Luo, S. X.; Zhou, M. Q.; Li, N.; Chen, X. B.; Han, L. L. (2008). "The study of anti-tumor effect of Tetrandrine combined with Nedaplatin on human liver cancer cell line 7402". Zhong Yao Cai = Zhongyaocai = Journal of Chinese Medicinal Materials. 31 (10): 1522–5. PMID 19230406.
  8. ^ Kitano, Ai; Yamanaka, Osamu; Ikeda, Kazuo; Ishida-Nishikawa, Iku; Okada, Yuka; Shirai, Kumi; Saika, Shizuya (2008). "Tetrandrine Suppresses Activation of Human Subconjunctival Fibroblasts In Vitro". Current Eye Research. 33 (7): 559–565. doi:10.1080/02713680802220817. PMID 18600488. S2CID 37248080.
  9. ^ Kwan, C. Y.; Achike, F. I. (2002). "Tetrandrine and related bis-benzylisoquinoline alkaloids from medicinal herbs: Cardiovascular effects and mechanisms of action". Acta Pharmacologica Sinica. 23 (12): 1057–68. PMID 12466042.
  10. ^ Sakurai, Yasuteru; Kolokoltsov, Andrey A.; Chen, Cheng-Chang; Tidwell, Michael W.; Bauta, William E.; Klugbauer, Norbert; Grimm, Christian; Wahl-Schott, Christian; Biel, Martin; Davey, Robert A. (2015). "Two-pore channels control Ebola virus host cell entry and are drug targets for disease treatment". Science. 347 (6225): 995–998. Bibcode:2015Sci...347..995S. doi:10.1126/science.1258758. PMC 4550587. PMID 25722412.
  11. ^ US patent 10434097, Jianxin Bao & Xiaojie Chen, "Methods and compositions for treating hearing disorders", published 8 October 2019, assigned to Gateway Biotechnology Inc 
  12. ^ "Targeting multiple signaling pathways for tinnitus prevention and treatment (R44DC018759)". HHS Tracking Accountability in Government Grants System (TAGGS). US Department of Health & Human Services. Archived from the original on 24 February 2022. Retrieved 24 February 2022.
  13. ^ a b Dyhrfjeld-Johnsen, Jonas; Cederroth, Christopher R. (1 August 2020). "Current Clinical Trials for Tinnitus". Otolaryngologic Clinics of North America. 53 (4): 651–666. doi:10.1016/j.otc.2020.03.012. ISSN 0030-6665. PMID 32334870. S2CID 216557264. Retrieved 24 February 2022.
  14. ^ Bhakuni, Dewan S.; Jain, Sudha; Singh, Awadhesh N. (1980). "Biosynthesis of the bisbenzylisoquinoline alkaloid, tetrandrine". Phytochemistry. 19 (11): 2347–2350. Bibcode:1980PChem..19.2347B. doi:10.1016/S0031-9422(00)91024-0.
  15. ^ Tetrandrine(Fanchinine) | CAS 518-34-3 | calcium channel Inhibitor | Fanchinine, Hanfangchin A, NSC 77037, S,S-(+)-Tetrandrine, Sinomenine A, TTD, Tetrandrin, d...
Categories