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Tetrandrine

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This articleneeds morereliable medical references forverification or relies too heavily onprimary sources. Please review the contents of the article andadd the appropriate references if you can. Unsourced or poorly sourced material may be challenged andremoved.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)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard100.208.615Edit this at Wikidata
EC Number
  • 683-095-7
KEGG
UNII
  • InChI=1S/C38H42N2O6/c1-39-15-13-25-20-32(42-4)34-22-28(25)29(39)17-23-7-10-27(11-8-23)45-33-19-24(9-12-31(33)41-3)18-30-36-26(14-16-40(30)2)21-35(43-5)37(44-6)38(36)46-34/h7-12,19-22,29-30H,13-18H2,1-6H3/t29-,30-/m0/s1
    Key: WVTKBKWTSCPRNU-KYJUHHDHSA-N
  • 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 mass622.74988
Hazards
GHS labelling:[1]
GHS06: Toxic
Danger
H300
P264,P270,P301+P316,P301+P317,P321,P330,P405,P501
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Tetrandrine, abis-benzylisoquinoline alkaloid, is acalcium channel blocker.[1] It is isolated from the plantStephania tetrandra,[2] and other Chinese and Japanese herbs.

Pharmacology

[edit]

It has anti-inflammatory, immunologic and antiallergenic effects. It inhibits the degranulation ofmast cells. It has aquinidine-like anti-arrhythmic effect. It hasvasodilatory 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 followingtrabeculectomy or in patients with severeconjunctival inflammation.[8] Tetrandrine has anti-inflammatory and anti-fibrogenic actions, which make tetrandrine and related compounds potentially useful in the treatment oflung silicosis, liver cirrhosis, and rheumatoid arthritis.[9] Tetrandrine has also been shown to inhibit entry ofEbola virus into host cellsin 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 fortinnitus.[11][12][13]

Biosynthesis

[edit]

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

Synonyms

[edit]

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

References

[edit]
  1. ^abBhagya, 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. Retrieved24 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 fromStephaniae 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 FibroblastsIn 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 fromthe original on 24 February 2022. Retrieved24 February 2022.
  13. ^abDyhrfjeld-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. Retrieved24 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...
Calcium
VDCCsTooltip Voltage-dependent calcium channels
Blockers
Activators
Potassium
VGKCsTooltip Voltage-gated potassium channels
Blockers
Activators
IRKsTooltip Inwardly rectifying potassium channel
Blockers
Activators
KCaTooltip Calcium-activated potassium channel
Blockers
Activators
K2PsTooltip Tandem pore domain potassium channel
Blockers
Activators
Sodium
VGSCsTooltip Voltage-gated sodium channels
Blockers
Activators
ENaCTooltip Epithelial sodium channel
Blockers
Activators
ASICsTooltip Acid-sensing ion channel
Blockers
Chloride
CaCCsTooltip Calcium-activated chloride channel
Blockers
Activators
CFTRTooltip Cystic fibrosis transmembrane conductance regulator
Blockers
Activators
Unsorted
Blockers
Others
TRPsTooltip Transient receptor potential channels
LGICsTooltip Ligand gated ion channels
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