Tetrandrine

Structural formula
General
Surname	Tetrandrine
Molecular formula	C 38 H 42 N 2 O 6
Brief description	light yellow solid
External identifiers / databases
EC number	683-095-7
ECHA InfoCard	100.208.615
PubChem	73078
ChemSpider	4479515
DrugBank	DB14066
Wikidata	Q7706612
properties
Molar mass	622.75 g mol −1
Physical state	firmly
Melting point	219-222 ° C
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Tetrandrine is an alkaloid that belongs to the group of bisbenzylisoquinoline alkaloids . It is a light yellow solid .

Occurrence

Tetrandrine occurs in the plants of the Cocculus and Stephania species, mainly in the plant Stephania tetrandra .

Pharmacological properties

Tetrandrine is believed to have anti-inflammatory and anesthetic properties. It also has a vasodilator effect and can lower blood pressure. Tetrandrine also inhibits the entry of the Ebola virus into the host cells in vitro and has shown therapeutic effectiveness against Ebola in preliminary studies on mice.

In animal experiments, tetrandrine protected mice from concanavalin-A -induced hepatitis ; other studies on liver cancer cells showed anti - tumor properties, so the authors see potential for the treatment of liver diseases and liver cancer. Tetrandrine has anti-inflammatory and anti- fibrogenic properties in vitro that could potentially be useful in the treatment of pulmonary silicosis , cirrhosis, and rheumatoid arthritis, and in preventing excessive scarring / fibrosis in the conjunctiva after eye surgery or in patients with severe conjunctivitis .

use

Tetrandrine is used in the Chinese root drug han-fang-ji ( Stephania tetrandra root , Fourstamen stephania root , fenfangji ( hanfangji ), 粉防己 (汉防己)) because of its analgesic and antipyretic effects. For use as a single substance, tetrandrine is extracted from the root drug or manufactured synthetically.

Individual evidence

↑ ^a ^b ^c ^d Tetrandrine data sheet at Sigma-Aldrich , accessed on June 2, 2020 ( PDF ).

↑ Entry on bisbenzylisoquinoline alkaloids. In: Römpp Online . Georg Thieme Verlag, accessed on June 2, 2020.

↑ CY Kwan, FI Achike: Tetrandrine and related bis-benzylisoquinoline alkaloids from medicinal herbs: Cardiovascular effects and mechanisms of action . In: Acta Pharmacologica Sinica . 23, No. 12, 2002, pp. 1057-68. PMID 12466042 .

↑ Yasuteru Sakurai, Andrey A. Kolokoltsov, Cheng-Chang Chen, Michael W. Tidwell, William E. Bauta, Norbert Klugbauer, Christian Grimm, Christian Wahl-Schott, Martin Biel, Robert A. Davey: Two-pore channels control Ebola virus host cell entry and are drug targets for disease treatment . In: Science . 347, No. 6225, 2015, pp. 995-998. bibcode : 2015Sci ... 347..995S . doi : 10.1126 / science.1258758 . PMID 25722412 . PMC 4550587 (free full text).

↑ Dechun Feng, Yunhua Mei, Ying Wang, Bianhong Zhang, Chen Wang, Lingyun Xu: Tetrandrine protects mice from concanavalin A-induced hepatitis through inhibiting NF-κB activation . In: Immunology Letters . 121, No. 2, 2008, pp. 127-133. doi : 10.1016 / j.imlet.2008.10.001 . PMID 18992279 .

↑ Chaoyang Liu, Ke Gong, Xin Mao, Wenhua Li: Tetrandrine induces apoptosis by activating reactive oxygen species and repressing Akt activity in human hepatocellular carcinoma . In: International Journal of Cancer . 129, No. 6, 2011, pp. 1519-1531. doi : 10.1002 / ijc.25817 . PMID 21128229 .

↑ Zhixiang Cheng, Keming Wang, Jia Wei, Xiang Lu, Baorui Liu: Proteomic analysis of anti-tumor effects by tetrandrine treatment in HepG2 cells . In: Phytomedicine . 17, No. 13, 2010, pp. 1000-1005. doi : 10.1016 / j.phymed.2010.03.018 . PMID 20554191 .

↑ WY Deng, SX Luo, MQ Zhou, N. Li, XB Chen, LL Han: The study of anti-tumor effect of Tetrandrine combined with Nedaplatin on human liver cancer cell line 7402 . In: Zhong Yao Cai = Zhongyaocai = Journal of Chinese Medicinal Materials . 31, No. 10, 2008, pp. 1522-5. PMID 19230406 .

↑ Ai Kitano, Osamu Yamanaka, Kazuo Ikeda, Iku Ishida-Nishikawa, Yuka Okada, Kumi Shirai, Shizuya Saika: Tetrandrine Suppresses Activation of Human Subconjunctival Fibroblasts In Vitro . In: Current Eye Research . 33, No. 7, 2008, pp. 559-565. doi : 10.1080 / 02713680802220817 . PMID 18600488 .

↑ CY Kwan, FI Achike: Tetrandrine and related bis-benzylisoquinoline alkaloids from medicinal herbs: Cardiovascular effects and mechanisms of action . In: Acta Pharmacologica Sinica . 23, No. 12, 2002, pp. 1057-68. PMID 12466042 .

↑ 5.22 Names of Herbal Drugs Used in Traditional Chinese Medicine . In: Deutscher Apotheker Verlag (Ed.): European Pharmacopoeia, 9th edition, 8th supplement (2019); Monograph 2478 .

↑ E. Breitmaier: Alkaloids . Springer Fachmedien, Wiesbaden 1997, ISBN 978-3-519-03542-8 , pp. 63 f .

↑ Pascal Heitel, Daniel Merk, Manfred Schubert-Zsilavecz: Stop the infection . In: Pharmaceutical newspaper . July 22, 2015.

[Sigma-1] Tetrandrine data sheet at Sigma-Aldrich , accessed on June 2, 2020 ( PDF ).

[Römpp-2] Entry on bisbenzylisoquinoline alkaloids. In: Römpp Online . Georg Thieme Verlag, accessed on June 2, 2020.

[3] CY Kwan, FI Achike: Tetrandrine and related bis-benzylisoquinoline alkaloids from medicinal herbs: Cardiovascular effects and mechanisms of action . In: Acta Pharmacologica Sinica . 23, No. 12, 2002, pp. 1057-68. PMID 12466042 .

[4] Yasuteru Sakurai, Andrey A. Kolokoltsov, Cheng-Chang Chen, Michael W. Tidwell, William E. Bauta, Norbert Klugbauer, Christian Grimm, Christian Wahl-Schott, Martin Biel, Robert A. Davey: Two-pore channels control Ebola virus host cell entry and are drug targets for disease treatment . In: Science . 347, No. 6225, 2015, pp. 995-998. bibcode : 2015Sci ... 347..995S . doi : 10.1126 / science.1258758 . PMID 25722412 . PMC 4550587 (free full text).

[5] Dechun Feng, Yunhua Mei, Ying Wang, Bianhong Zhang, Chen Wang, Lingyun Xu: Tetrandrine protects mice from concanavalin A-induced hepatitis through inhibiting NF-κB activation . In: Immunology Letters . 121, No. 2, 2008, pp. 127-133. doi : 10.1016 / j.imlet.2008.10.001 . PMID 18992279 .

[6] Chaoyang Liu, Ke Gong, Xin Mao, Wenhua Li: Tetrandrine induces apoptosis by activating reactive oxygen species and repressing Akt activity in human hepatocellular carcinoma . In: International Journal of Cancer . 129, No. 6, 2011, pp. 1519-1531. doi : 10.1002 / ijc.25817 . PMID 21128229 .

[7] Zhixiang Cheng, Keming Wang, Jia Wei, Xiang Lu, Baorui Liu: Proteomic analysis of anti-tumor effects by tetrandrine treatment in HepG2 cells . In: Phytomedicine . 17, No. 13, 2010, pp. 1000-1005. doi : 10.1016 / j.phymed.2010.03.018 . PMID 20554191 .

[8] WY Deng, SX Luo, MQ Zhou, N. Li, XB Chen, LL Han: The study of anti-tumor effect of Tetrandrine combined with Nedaplatin on human liver cancer cell line 7402 . In: Zhong Yao Cai = Zhongyaocai = Journal of Chinese Medicinal Materials . 31, No. 10, 2008, pp. 1522-5. PMID 19230406 .

[9] Ai Kitano, Osamu Yamanaka, Kazuo Ikeda, Iku Ishida-Nishikawa, Yuka Okada, Kumi Shirai, Shizuya Saika: Tetrandrine Suppresses Activation of Human Subconjunctival Fibroblasts In Vitro . In: Current Eye Research . 33, No. 7, 2008, pp. 559-565. doi : 10.1080 / 02713680802220817 . PMID 18600488 .

[10] CY Kwan, FI Achike: Tetrandrine and related bis-benzylisoquinoline alkaloids from medicinal herbs: Cardiovascular effects and mechanisms of action . In: Acta Pharmacologica Sinica . 23, No. 12, 2002, pp. 1057-68. PMID 12466042 .

[11] 5.22 Names of Herbal Drugs Used in Traditional Chinese Medicine . In: Deutscher Apotheker Verlag (Ed.): European Pharmacopoeia, 9th edition, 8th supplement (2019); Monograph 2478 .

[Alkaloide-12] E. Breitmaier: Alkaloids . Springer Fachmedien, Wiesbaden 1997, ISBN 978-3-519-03542-8 , pp. 63 f .

[13] Pascal Heitel, Daniel Merk, Manfred Schubert-Zsilavecz: Stop the infection . In: Pharmaceutical newspaper . July 22, 2015.