Huperzine A (BioDeep_00000275578)
Secondary id: BioDeep_00000007668, BioDeep_00000229827, BioDeep_00000398764, BioDeep_00000411029, BioDeep_00001028496
natural product PANOMIX_OTCML-2023
代谢物信息卡片
化学式: C15H18N2O (242.1419)
中文名称: 石杉碱甲, (±)-石杉碱甲
谱图信息:
最多检出来源 Viridiplantae(plant) 79.87%
分子结构信息
SMILES: C/C=C1\C2C=C(C)CC1(N)c1ccc(O)nc1C2
InChI: InChI=1S/C15H18N2O/c1-3-11-10-6-9(2)8-15(11,16)12-4-5-14(18)17-13(12)7-10/h3-6,10H,7-8,16H2,1-2H3,(H,17,18)
描述信息
D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D002800 - Cholinesterase Inhibitors
D002491 - Central Nervous System Agents > D018696 - Neuroprotective Agents
Origin: Plant; SubCategory_DNP: Sesquiterpenoids
D020011 - Protective Agents
D004791 - Enzyme Inhibitors
(-)-Huperzine A (Huperzine A) is an alkaloid isolated from Huperzia serrata, with neuroprotective activity. (-)-Huperzine A is a potent, highly specific, reversible and blood-brain barrier penetrant inhibitor of acetylcholinesterase (AChE), with an IC50 of 82 nM. (-)-Huperzine A also is non-competitive antagonist of N-methyl-D-aspartate glutamate (NMDA) receptor. (-)-Huperzine A is developed for the research of neurodegenerative diseases, including Alzheimer’s disease[1][2][3][4][5].
(-)-Huperzine A (Huperzine A) is an alkaloid isolated from Huperzia serrata, with neuroprotective activity. (-)-Huperzine A is a potent, highly specific, reversible and blood-brain barrier penetrant inhibitor of acetylcholinesterase (AChE), with an IC50 of 82 nM. (-)-Huperzine A also is non-competitive antagonist of N-methyl-D-aspartate glutamate (NMDA) receptor. (-)-Huperzine A is developed for the research of neurodegenerative diseases, including Alzheimer’s disease[1][2][3][4][5].
(-)-Huperzine A (Huperzine A) is an alkaloid isolated from Huperzia serrata, with neuroprotective activity. (-)-Huperzine A is a potent, highly specific, reversible and blood-brain barrier penetrant inhibitor of acetylcholinesterase (AChE), with an IC50 of 82 nM. (-)-Huperzine A also is non-competitive antagonist of N-methyl-D-aspartate glutamate (NMDA) receptor. (-)-Huperzine A is developed for the research of neurodegenerative diseases, including Alzheimer’s disease[1][2][3][4][5].
(-)-Huperzine A (Huperzine A) is an alkaloid isolated from Huperzia serrata, with neuroprotective activity. (-)-Huperzine A is a potent, highly specific, reversible and blood-brain barrier penetrant inhibitor of acetylcholinesterase (AChE), with an IC50 of 82 nM. (-)-Huperzine A also is non-competitive antagonist of N-methyl-D-aspartate glutamate (NMDA) receptor. (-)-Huperzine A is developed for the research of neurodegenerative diseases, including Alzheimer’s disease[1][2][3][4][5].
(-)-Huperzine A (Huperzine A) is an alkaloid isolated from Huperzia serrata, with neuroprotective activity. (-)-Huperzine A is a potent, highly specific, reversible and blood-brain barrier penetrant inhibitor of acetylcholinesterase (AChE), with an IC50 of 82 nM. (-)-Huperzine A also is non-competitive antagonist of N-methyl-D-aspartate glutamate (NMDA) receptor. (-)-Huperzine A is developed for the research of neurodegenerative diseases, including Alzheimer’s disease[1][2][3][4][5].
(-)-Huperzine A (Huperzine A) is an alkaloid isolated from Huperzia serrata, with neuroprotective activity. (-)-Huperzine A is a potent, highly specific, reversible and blood-brain barrier penetrant inhibitor of acetylcholinesterase (AChE), with an IC50 of 82 nM. (-)-Huperzine A also is non-competitive antagonist of N-methyl-D-aspartate glutamate (NMDA) receptor. (-)-Huperzine A is developed for the research of neurodegenerative diseases, including Alzheimer’s disease[1][2][3][4][5].
(±)-Huperzine A, an active Lycopodium alkaloid extracted from traditional Chinese herb, is a potent, selective and reversible acetylcholinesterase (AChE) inhibitor and has been widely used in China for the treatment of Alzheimer's disease (AD). IC50 value: Target: AChE (±)-Huperzine A exhibited protective effects against d-gal-induced hepatotoxicity and inflamm-aging by inhibiting AChE activity and via the activation of the cholinergic anti-inflammatory pathway. The (±)-Huperzine A mechanism might be involved in the inhibition of DAMPs-mediated NF-κB nuclear localization and activation. (±)-Huperzine A is a potential therapeutic agent for Alzheimer's disease.
(±)-Huperzine A, an active Lycopodium alkaloid extracted from traditional Chinese herb, is a potent, selective and reversible acetylcholinesterase (AChE) inhibitor and has been widely used in China for the treatment of Alzheimer's disease (AD). IC50 value: Target: AChE (±)-Huperzine A exhibited protective effects against d-gal-induced hepatotoxicity and inflamm-aging by inhibiting AChE activity and via the activation of the cholinergic anti-inflammatory pathway. The (±)-Huperzine A mechanism might be involved in the inhibition of DAMPs-mediated NF-κB nuclear localization and activation. (±)-Huperzine A is a potential therapeutic agent for Alzheimer's disease.
同义名列表
数据库引用编号
48 个数据库交叉引用编号
- ChEBI: CHEBI:91724
- PubChem: 71308731
- PubChem: 5912039
- PubChem: 1253
- Metlin: METLIN44100
- ChEMBL: CHEMBL394259
- CAS: 102518-79-6
- CAS: 120786-18-7
- CAS: 103735-86-0
- MoNA: NGA03132
- MoNA: NGA03131
- MoNA: NGA03130
- MoNA: NGA03129
- MoNA: RIKENPlaSMA001133
- MoNA: RIKENPlaSMA001129
- MoNA: RIKENPlaSMA001125
- MoNA: RIKENPlaSMA001121
- MoNA: RIKENPlaSMA001117
- MoNA: RIKENPlaSMA001113
- MoNA: RIKENPlaSMA001109
- MoNA: RIKENPlaSMA001105
- MoNA: RIKENPlaSMA001101
- MoNA: RIKENPlaSMA001097
- MoNA: RIKENPlaSMA001093
- MoNA: RIKENPlaSMA001089
- MoNA: CCMSLIB00004746755
- MoNA: VF-NPL-LTQ007658
- MoNA: VF-NPL-LTQ007657
- MoNA: VF-NPL-LTQ007656
- MoNA: VF-NPL-LTQ007655
- MoNA: VF-NPL-QEHF027228
- MoNA: VF-NPL-QEHF027227
- MoNA: VF-NPL-QEHF027226
- MoNA: VF-NPL-QEHF027225
- MoNA: VF-NPL-QEHF027224
- MoNA: VF-NPL-QEHF027223
- MoNA: VF-NPL-QEHF027222
- MoNA: VF-NPL-QEHF027221
- MoNA: VF-NPL-QEHF027220
- MoNA: VF-NPL-QEHF027219
- MoNA: VF-NPL-QEHF027218
- MoNA: VF-NPL-QEHF027217
- MoNA: VF-NPL-QEHF027216
- MoNA: VF-NPL-QEHF027215
- MoNA: VF-NPL-QEHF027214
- PMhub: MS000008193
- medchemexpress: HY-17387
- medchemexpress: HY-17388
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
5 个相关的物种来源信息
- 70001 - Huperzia selago [Syn. Lycopodium selago ]: -
- 355589 - Huperzia serrata:
- 41007 - Phlegmariurus phlegmaria: 10.1248/CPB.56.1473
- 1158256 - Phlegmariurus varius: 10.1248/CPB.56.1473
- 33090 - Plants: -
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:
- PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。
亚细胞结构定位 | 关联基因列表 |
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文献列表
- Shuyao Ruan, Jiaqi Li, Hang Ruan, Qing Xia, Xiaolin Hou, Zhi Wang, Teng Guo, Chunyun Zhu, Nianping Feng, Yongtai Zhang. Microneedle-mediated nose-to-brain drug delivery for improved Alzheimer's disease treatment.
Journal of controlled release : official journal of the Controlled Release Society.
2024 Jan; 366(?):712-731. doi:
10.1016/j.jconrel.2024.01.013
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Nature.
2023 Nov; ?(?):. doi:
10.1038/s41586-023-06716-y
. [PMID: 37938780] - Xinran Guo, Yuhan Wu, Qingqing Wang, Jianbing Zhang, Xueping Sheng, Lanrong Zheng, Yule Wang. Huperzine A injection ameliorates motor and cognitive abnormalities via regulating multiple pathways in a murine model of Parkinson's disease.
European journal of pharmacology.
2023 Aug; ?(?):175970. doi:
10.1016/j.ejphar.2023.175970
. [PMID: 37549727] - Soura Challal, Adrianna Skiba, Mélanie Langlois, Camila V Esguerra, Jean-Luc Wolfender, Alexander D Crawford, Krystyna Skalicka-Woźniak. Natural product-derived therapies for treating drug-resistant epilepsies: From ethnopharmacology to evidence-based medicine.
Journal of ethnopharmacology.
2023 Jun; ?(?):116740. doi:
10.1016/j.jep.2023.116740
. [PMID: 37315641] - Ce Zhang, Mingan Li, Wei Xie, Min Li, Chunna You, Tian Wang, Fenghua Fu. Administration of Huperzine A microspheres ameliorates myocardial ischemic injury via α7nAChR-dependent JAK2/STAT3 signaling pathway.
European journal of pharmacology.
2023 Feb; 940(?):175478. doi:
10.1016/j.ejphar.2022.175478
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International journal of nanomedicine.
2023; 18(?):843-859. doi:
10.2147/ijn.s393346
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BMC microbiology.
2022 11; 22(1):281. doi:
10.1186/s12866-022-02702-y
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Biotechnology advances.
2022 11; 60(?):108026. doi:
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BMC microbiology.
2022 08; 22(1):191. doi:
10.1186/s12866-022-02605-y
. [PMID: 35931950] - Cecilia Villegas, Rebeca Perez, Lyvia Lintzmaier Petiz, Talita Glaser, Henning Ulrich, Cristian Paz. Ginkgolides and Huperzine A for complementary treatment of Alzheimer's disease.
IUBMB life.
2022 08; 74(8):763-779. doi:
10.1002/iub.2613
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Neurochemical research.
2022 May; 47(5):1166-1182. doi:
10.1007/s11064-022-03530-2
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Molecules (Basel, Switzerland).
2022 Jan; 27(3):. doi:
10.3390/molecules27030797
. [PMID: 35164061] - Amira G Zaki, El-Sayed R El-Sayed. New and potent production platform of the acetylcholinesterase inhibitor huperzine A by gamma-irradiated Alternaria brassicae under solid-state fermentation.
Applied microbiology and biotechnology.
2021 Dec; 105(23):8869-8880. doi:
10.1007/s00253-021-11678-0
. [PMID: 34748037] - Ryan S Nett, Yaereen Dho, Yun-Yee Low, Elizabeth S Sattely. A metabolic regulon reveals early and late acting enzymes in neuroactive Lycopodium alkaloid biosynthesis.
Proceedings of the National Academy of Sciences of the United States of America.
2021 06; 118(24):. doi:
10.1073/pnas.2102949118
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Cell reports.
2021 04; 35(4):109040. doi:
10.1016/j.celrep.2021.109040
. [PMID: 33910017] - Amira G Zaki, Einas H El-Shatoury, Ashraf S Ahmed, Ola E A Al-Hagar. Response surface methodology-mediated improvement of the irradiated endophytic fungal strain, Alternaria brassicae AGF041 for Huperzine A-hyperproduction.
Letters in applied microbiology.
2021 Apr; 72(4):427-437. doi:
10.1111/lam.13435
. [PMID: 33278032] - Lingli Cui, Hamza Armghan Noushahi, Yipeng Zhang, Jinxin Liu, Andreea Cosoveanu, Ying Liu, Ling Yan, Jing Zhang, Shaohua Shu. Endophytic Fungal Community of Huperzia serrata: Diversity and Relevance to the Production of Huperzine A by the Plant Host.
Molecules (Basel, Switzerland).
2021 Feb; 26(4):. doi:
10.3390/molecules26040892
. [PMID: 33567664] - Raul Riquelme, Freddy Ruz, Artur Mayerhofer, Hernán E Lara. Huperzine-A administration recovers rat ovary function after sympathetic stress.
Journal of neuroendocrinology.
2021 01; 33(1):e12914. doi:
10.1111/jne.12914
. [PMID: 33252842] - Xiang-Peng Kong, Hai-Qin Ren, Etta Y L Liu, Ka-Wing Leung, Shu-Chen Guo, Ran Duan, Tina T X Dong, Karl W K Tsim. The Cholinesterase Inhibitory Properties of Stephaniae Tetrandrae Radix.
Molecules (Basel, Switzerland).
2020 Dec; 25(24):. doi:
10.3390/molecules25245914
. [PMID: 33327436] - Han Wen-Xia, Han Zhong-Wen, Jia Min, Zhang Han, Li Wei-Ze, Yang Li-Bin, Liang Fei, Han Lu, Zhao Ning, Li Xiao-Feng. Five novel and highly efficient endophytic fungi isolated from Huperzia serrata expressing huperzine A for the treatment of Alzheimer's disease.
Applied microbiology and biotechnology.
2020 Nov; 104(21):9159-9177. doi:
10.1007/s00253-020-10894-4
. [PMID: 32970179] - Xiao Sang, Minhe Yang, Jingqian Su. Research on endophytic fungi for producing huperzine A on a large-scale.
Critical reviews in microbiology.
2020 Nov; 46(6):654-664. doi:
10.1080/1040841x.2020.1819771
. [PMID: 32970952] - Amira G Zaki, El-Sayed R El-Sayed, M Abd Elkodous, Gharieb S El-Sayyad. Microbial acetylcholinesterase inhibitors for Alzheimer's therapy: recent trends on extraction, detection, irradiation-assisted production improvement and nano-structured drug delivery.
Applied microbiology and biotechnology.
2020 Jun; 104(11):4717-4735. doi:
10.1007/s00253-020-10560-9
. [PMID: 32285176] - Olga Lidia Cruz-Miranda, Jorge Folch-Mallol, Fernando Martínez-Morales, Reinier Gesto-Borroto, María Luisa Villarreal, Alexandre Cardoso Taketa. Identification of a Huperzine A-producing endophytic fungus from Phlegmariurus taxifolius.
Molecular biology reports.
2020 Jan; 47(1):489-495. doi:
10.1007/s11033-019-05155-1
. [PMID: 31659691] - Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Molecular pharmacology.
2019 11; 96(5):629-640. doi:
10.1124/mol.119.115964
. [PMID: 31515284] - You-Min Ying, Yi-Lian Xu, Hang-Fei Yu, Cai-Xue Zhang, Wei Mao, Cui-Ping Tong, Zhi-Dong Zhang, Qi-Yong Tang, Yun Zhang, Wei-Guang Shan, Zha-Jun Zhan. Biotransformation of Huperzine A by Irpex lacteus-A fungal endophyte of Huperzia serrata.
Fitoterapia.
2019 Oct; 138(?):104341. doi:
10.1016/j.fitote.2019.104341
. [PMID: 31470066] - Gang Deng, Chao Wu, Xiaojuan Rong, Shuping Li, Zhengcai Ju, Youxu Wang, Chao Ma, Wenzheng Ding, Huida Guan, Xuemei Cheng, Wei Liu, Changhong Wang. Ameliorative effect of deoxyvasicine on scopolamine-induced cognitive dysfunction by restoration of cholinergic function in mice.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2019 Oct; 63(?):153007. doi:
10.1016/j.phymed.2019.153007
. [PMID: 31301537] - Yifan Chen, Gang Cheng, Rongfeng Hu, Shengqi Chen, Wenjie Lu, Song Gao, Hongmei Xia, Bin Wang, Chaojie Sun, Xiangjiang Nie, Qiang Shen, Wenyou Fang. A Nasal Temperature and pH Dual-Responsive In Situ Gel Delivery System Based on Microemulsion of Huperzine A: Formulation, Evaluation, and In Vivo Pharmacokinetic Study.
AAPS PharmSciTech.
2019 Sep; 20(7):301. doi:
10.1208/s12249-019-1513-x
. [PMID: 31485857] - Amira G Zaki, Einas H El-Shatoury, Ashraf S Ahmed, Ola E A Al-Hagar. Production and enhancement of the acetylcholinesterase inhibitor, huperzine A, from an endophytic Alternaria brassicae AGF041.
Applied microbiology and biotechnology.
2019 Jul; 103(14):5867-5878. doi:
10.1007/s00253-019-09897-7
. [PMID: 31119352] - Minky Son, Chanin Park, Shailima Rampogu, Amir Zeb, Keun Woo Lee. Discovery of Novel Acetylcholinesterase Inhibitors as Potential Candidates for the Treatment of Alzheimer's Disease.
International journal of molecular sciences.
2019 Feb; 20(4):. doi:
10.3390/ijms20041000
. [PMID: 30823604] - Po Huang, Bo Li, Yu-Hong Guo, Shuo Feng, Jing Hu, Qing-Quan Liu. [Efficacy and safety of huperzine A in treating patients with mild cognitive impairment: a systematic review and Meta-analysis].
Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica.
2019 Feb; 44(3):582-588. doi:
10.19540/j.cnki.cjcmm.20180925.008
. [PMID: 30989926] - Maonian Xu, Starri Heidmarsson, Margret Thorsteinsdottir, Pawel Wasowicz, Hang Sun, Tao Deng, Sesselja Omarsdottir, Elin Soffia Olafsdottir. Infraspecific Variation of Huperzine A and B in Icelandic Huperzia selago Complex.
Planta medica.
2019 Jan; 85(2):160-168. doi:
10.1055/a-0752-0295
. [PMID: 30290396] - Huan-Feng Zhu, Peng-Wei Yan, Li-Jun Wang, Ya-Tian Liu, Jing Wen, Qian Zhang, Yan-Xin Fan, Yan-Hong Luo. Protective properties of Huperzine A through activation Nrf2/ARE-mediated transcriptional response in X-rays radiation-induced NIH3T3 cells.
Journal of cellular biochemistry.
2018 11; 119(10):8359-8367. doi:
10.1002/jcb.26919
. [PMID: 29932247] - San-Lan Wu, Jun Gan, Jing Rao, Si-Jie He, Wen-Wen Zhu, Ying Zhao, Yong-Ning Lv, Jian-Geng Huang, Ya-Ni Liu. Pharmacokinetics and tolerability of oral dosage forms of huperzine a in healthy Chinese male volunteers: a randomized, single dose, three-period, six-sequence crossover study.
Journal of Huazhong University of Science and Technology. Medical sciences = Hua zhong ke ji da xue xue bao. Yi xue Ying De wen ban = Huazhong keji daxue xuebao. Yixue Yingdewen ban.
2017 Oct; 37(5):795-802. doi:
10.1007/s11596-017-1807-8
. [PMID: 29058298] - Jiajun Li, Mei Yue, Dandan Zhou, Meiyu Wang, Hongjian Zhang. Abcb1a but not Abcg2 played a predominant role in limiting the brain distribution of Huperzine A in mice.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2017 Sep; 107(Pt A):68-73. doi:
10.1016/j.fct.2017.06.005
. [PMID: 28587984] - Yuan Du, Haiyue Liang, Leiming Zhang, Fenghua Fu. Administration of Huperzine A exerts antidepressant-like activity in a rat model of post-stroke depression.
Pharmacology, biochemistry, and behavior.
2017 07; 158(?):32-38. doi:
10.1016/j.pbb.2017.06.002
. [PMID: 28583576] - Xiangmei Zhang, Zhangqian Wang, Saad Jan, Qian Yang, Mo Wang. Expression and functional analysis of the lysine decarboxylase and copper amine oxidase genes from the endophytic fungus Colletotrichum gloeosporioides ES026.
Scientific reports.
2017 06; 7(1):2766. doi:
10.1038/s41598-017-02834-6
. [PMID: 28584293] - Baofu Xu, Lei Lei, Xiaocen Zhu, Yiqing Zhou, Youli Xiao. Identification and characterization of L-lysine decarboxylase from Huperzia serrata and its role in the metabolic pathway of lycopodium alkaloid.
Phytochemistry.
2017 Apr; 136(?):23-30. doi:
10.1016/j.phytochem.2016.12.022
. [PMID: 28089246] - Mengquan Yang, Wenjing You, Shiwen Wu, Zhen Fan, Baofu Xu, Mulan Zhu, Xuan Li, Youli Xiao. Global transcriptome analysis of Huperzia serrata and identification of critical genes involved in the biosynthesis of huperzine A.
BMC genomics.
2017 03; 18(1):245. doi:
10.1186/s12864-017-3615-8
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Pakistan journal of pharmaceutical sciences.
2017 Jan; 30(1 Suppl):235-239. doi:
"
. [PMID: 28625948] - Lushuang Xie, Cen Jiang, Zhang Wang, Xiaohong Yi, Yuanyuan Gong, Yunhui Chen, Yan Fu. Effect of Huperzine A on Aβ-induced p65 of astrocyte in vitro.
Bioscience, biotechnology, and biochemistry.
2016 Dec; 80(12):2334-2337. doi:
10.1080/09168451.2016.1222265
. [PMID: 27554967] - Ping-Ping Lin, Xue-Ning Li, Fei Yuan, Wei-Li Chen, Meng-Jie Yang, Hong-Rong Xu. Evaluation of the in vitro and in vivo metabolic pathway and cytochrome P450 inhibition/induction profile of Huperzine A.
Biochemical and biophysical research communications.
2016 11; 480(2):248-253. doi:
10.1016/j.bbrc.2016.10.039
. [PMID: 27751854] - Lei Sheng, Yi Qu, Jing Yan, Gang-Yi Liu, Wei-Liang Wang, Yi-Jun Wang, Hong-Yi Wang, Meng-Qi Zhang, Chuan Lu, Yun Liu, Jing-Yin Jia, Chao-Ying Hu, Xue-Ning Li, Chen Yu, Hong-Rong Xu. Population pharmacokinetic modeling and simulation of huperzine A in elderly Chinese subjects.
Acta pharmacologica Sinica.
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