Basic Description

Synonyms	Metformin hydrochloride \| 1115-70-4 \| Metformin HCL \| 1,1-Dimethylbiguanide hydrochloride \| Glucophage \| Diabefagos \| Riomet \| Benofomin \| Fortamet \| Siamformet \| Walaphage \| Meguan \| Denkaform \| Diaberit \| Diabesin \| Diabetex \| Diabetmin \| Diaformin \| Diaphage \| Diformin \| Glibomet \| Glucofago \| G
Specifications & Purity	10mM in DMSO
Biochemical and Physiological Mechanisms	Metformin is an antidiabetic agent that reduces blood glucose levels and improves insulin sensitivity. Its metabolic effects, including the inhibition of hepatic gluconeogenesis, are mediated at least in part by activation of the LKB1-AMPK (AMP-activated
Storage Temp	Store at -80°C
Shipped In	Ice chest + Ice pads
Product Description	1,1-Dimethylbiguanide hydrochloride (metformin) is a strong base. It forms well defined salts and possessing excellent coordination capacity with transition metals, forming highly colored bidentate chelate complexes. Metformin (MET) exists in various forms: diprotonated (H2MET)2+ in strong acidic solution, monoprotonated (HMET)+ in weak acid, MET in neutral and deprotonated (MET)- in strong alkali solution. It is an oral antidiabetic drug. Pharmacokinetics of metformin has been studied. Determination of metformin in human plasma has been described by simple HPLC-UV method. Metformin is reported to increase plasma active Glukagon-like peptide-1 (GLP-1) in humans.

Associated Targets(Human)

GMNN Tbio Geminin (0 Activities)

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RUNX1 Tbio Runt-related transcription factor 1 (0 Activities)

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SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (0 Activities)

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SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (0 Activities)

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (0 Activities)

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PRKAA2 Tchem 5'-AMP-activated protein kinase catalytic subunit alpha-2 (0 Activities)

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TARDBP Tchem TAR DNA-binding protein 43 (0 Activities)

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HTT Tchem Huntingtin (0 Activities)

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MTOR Tclin Serine/threonine-protein kinase mTOR (0 Activities)

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PRKAA2 Tchem AMP-activated protein kinase, alpha-2 subunit (1328 Activities)

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MTOR Tclin Serine/threonine-protein kinase mTOR (13850 Activities)

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Homo sapiens (32628 Activities)

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Hs-578T (29457 Activities)

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HepG2 (196354 Activities)

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MDA-MB-231 (73002 Activities)

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HTT Tchem Huntingtin (19182 Activities)

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Liver (3974 Activities)

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

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GMNN Tbio Geminin (128009 Activities)

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SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

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SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

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RUNX1 Tbio Runt-related transcription factor 1/Core-binding factor subunit beta (7867 Activities)

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TARDBP Tchem TAR DNA-binding protein 43 (40113 Activities)

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Associated Targets(non-human)

ampC Beta-lactamase AmpC (62480 Activities)

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Streptococcus (3973 Activities)

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Pseudomonas aeruginosa (123386 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Staphylococcus aureus (210822 Activities)

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Acinetobacter baumannii (41033 Activities)

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Escherichia coli (133304 Activities)

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Cryptococcus neoformans (21258 Activities)

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Candida albicans (78123 Activities)

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Mus musculus (284745 Activities)

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Streptococcus sp. 'group A' (3417 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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Kidney (1278 Activities)

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ska Streptokinase A (5805 Activities)

Discover Target: ska

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SARS-CoV-2 (38078 Activities)

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Names and Identifiers

IUPAC Name	3-(diaminomethylidene)-1,1-dimethylguanidine;hydrochloride
INCHI	InChI=1S/C4H11N5.ClH/c1-9(2)4(7)8-3(5)6;/h1-2H3,(H5,5,6,7,8);1H
InChi Key	OETHQSJEHLVLGH-UHFFFAOYSA-N
Canonical SMILES	CN(C)C(=N)N=C(N)N.Cl
Isomeric SMILES	CN(C)C(=N)N=C(N)N.Cl
WGK Germany	3
RTECS	DU1800000
PubChem CID	14219
Molecular Weight	165.62
Beilstein	4(4)227
Reaxy-Rn	3626131

Certificates

Certificate of Analysis(COA)

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Chemical and Physical Properties

Sensitivity	Moisture sensitive.
Melt Point(°C)	219-226 °C

Safety and Hazards(GHS)

Pictogram(s)	GHS07
Signal	Warning
Hazard Statements	H315:Causes skin irritation H319:Causes serious eye irritation H335:May cause respiratory irritation H412:Harmful to aquatic life with long lasting effects H302:Harmful if swallowed
Precautionary Statements	P261:Avoid breathing dust/fume/gas/mist/vapors/spray. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do - continue rinsing. P273:Avoid release to the environment. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of water. P321:Specific treatment (see ... on this label). P405:Store locked up. P501:Dispose of contents/container to ... P264:Wash hands [and …] thoroughly after handling. P271:Use only outdoors or in a well-ventilated area. P270:Do not eat, drink or smoke when using this product. P304+P340:IF INHALED: Remove person to fresh air and keep comfortable for breathing. P403+P233:Store in a well-ventilated place. Keep container tightly closed. P362+P364:Take off contaminated clothing and wash it before reuse. P330:Rinse mouth. P264+P265:Wash hands [and …] thoroughly after handling. Do not touch eyes. P301+P317:IF SWALLOWED: Get medical help. P337+P317:If eye irritation persists: Get medical help. P332+P317:If skin irritation occurs: Get medical help. P319:Get medical help if you feel unwell.
WGK Germany	3
RTECS	DU1800000
Reaxy-Rn	3626131
Merck Index	5938

Citations of This Product

1. Guang-Li Fu, Qin-Yuan Meng, Yu Chen, Jin-Zhao Xin, Jia-Hui Liu, Wei Dang, Hong-Liang Lu. (2023) Metformin exposure altered intestinal microbiota composition and metabolites in amphibian larvae. ECOTOXICOLOGY AND ENVIRONMENTAL SAFETY, 267 (115617). [PMID:37866109]
2. Yong-Yu Yang, Jing-Jing Qi, Si-Yi Jiang, Ling Ye. (2023) Esculin ameliorates obesity-induced insulin resistance by improving adipose tissue remodeling and activating the IRS1/PI3K/AKT/GLUT4 pathway. JOURNAL OF ETHNOPHARMACOLOGY, (6): (117251). [PMID:37778516]
3. Xiaobang Liu, Junpeng Sun, Jiaqun Du, Jinyu An, Yingqiao Li, Yu Hu, Ying Xiong, Yanan Yu, He Tian, Xifan Mei, Chao Wu. (2023) Encapsulation of Selenium Nanoparticles and Metformin in Macrophage-Derived Cell Membranes for the Treatment of Spinal Cord Injury. ACS Biomaterials Science & Engineering, [PMID:37713674]
4. Yaodong Yi, Hengbin Zhang, Mingyang Chen, Binxin Chen, Yingchun Chen, Ping Li, Hui Zhou, Zhiyuan Ma, Huidi Jiang. (2023) Inhibition of multiple uptake transporters in cardiomyocytes/mitochondria alleviates doxorubicin-induced cardiotoxicity. CHEMICO-BIOLOGICAL INTERACTIONS, 382 (110627). [PMID:37453608]
5. Yu-Pei Xia. (2023) Crystal structure of N-(diaminomethylene)-1-(dimethylamino)-1-iminiomethanaminium dichloride, C4H13Cl2N5. ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 238 (4): (799-800). [PMID:]
6. Shengnan Duan, Meiting Zhang, Hao Zeng, Jinyi Song, Min Zhang, Song Gao, Hua Yang, Ming Ding, Ping Li. (2023) Integrated proteomics and phosphoproteomics profiling reveals the cardioprotective mechanism of bioactive compounds derived from Salvia miltiorrhiza Burge. PHYTOMEDICINE, 117 (154897). [PMID:37307738]
7. Jing Zuo, Yamin Shen, Haikun Wang, Shuji Gao, Shuo Yuan, Dong Song, Yuxin Wang, Yang Wang. (2023) Effects of metformin on Streptococcus suis LuxS/AI-2 quorum sensing system and biofilm formation. MICROBIAL PATHOGENESIS, 181 (106183). [PMID:37263449]
8. Guilin Chen, Yongbing Xu, Hui Zhang, Felix Wambua Muema, Mingquan Guo. (2023) Gymnema sylvestre extract ameliorated streptozotocin-induced hyperglycemia in T2DM rats via gut microbiota. Food Frontiers, [PMID:]
9. Lidong Yu, Yi Wang, Kai Li, Xueting Li, Mingyue He, Ce Chen, Fangshun Li, Bing Liang, Li Li, Ning Gu, Zhiguo Liu, Bingsheng Li, Guixue Wang, Jianglin Fan. (2023) Metformin-based carbon dots based on biguanide functional groups for simultaneous chelation of copper ions and inhibitable colorectal cancer therapy. CARBON, 212 (118095). [PMID:]
10. Yuting Hao, Hao Zhang, Xizhuang Yue, Zhen Zhao, Shuang Zhao. (2023) A novel electrochemical sensor based on Cu(Ⅱ) metal organic framework for the determination of metformin. MICROCHEMICAL JOURNAL, 191 (108849). [PMID:]
11. Huanan Huang, Yihui Chen, Meilin Ni, Jing Du, Chunyan Hou, Xiaoqiang Qiao, Guozhou Cao, Tingting Wang. (2023) Sodium hexametaphosphate-treated halloysite based solid-phase extraction of biguanides from dietary supplements. Analytical Methods, 15 (21): (2685-2692). [PMID:37226487]
12. Jing Zhou, Tongyu Wu, Chun Li, Zhuozhou Hu, Liang Han, Xiangxiang Li, Jingjing Liu, Wenyang Zhao, Jia Kang, Xinping Chen. (2023) Alfuzosin ameliorates diabetes by boosting PGK1 activity in diabetic mice. LIFE SCIENCES, 317 (121491). [PMID:36758669]
13. Gu Yurong, Zhang Yi, Jiang Chengchun, Dong Zijun, Bai Xue. (2023) Efficient metformin transformation in sulfite/UV process co-present with oxygen. Frontiers in Environmental Science, 10 [PMID:]
14. Yilong Li, Zhiyong Li, Ruipeng Li, Huiyong Wang, Yang Zhao, Yuanchao Pei, Jianji Wang. (2023) Highly efficient triiodide ion adsorption from water by ionic liquid hybrid metal–organic frameworks. JOURNAL OF MOLECULAR LIQUIDS, 370 (121009). [PMID:]
15. Yuan Tao, Luyao Jia, Honglin Qin, Ruiting Niu, Lizhen Qiao. (2022) A new magnetic ionic liquid based salting-out assisted dispersive liquid–liquid microextraction for the determination of parabens in environmental water samples. Analytical Methods, 14 (46): (4775-4783). [PMID:36374117]
16. Jie Yang, Xiuhua Pan, Jun Zhang, Siyu Ma, Jianeng Zhou, Zengguang Jia, Yawen Wei, Zengyi Liu, Ning Yang, Qi Shen. (2022) Reprogramming dysfunctional dendritic cells by a versatile metabolism nano-intervenor for enhancing cancer combinatorial immunotherapy. Nano Today, 46 (101618). [PMID:]
17. Ling Li, Xiaolong Zhu, Huaiyu Yang, Bangchao Liang, Lei Yuan, Yueqiang Hu, Feng Chen, Xiaoxiao Han. (2022) Phase-Field Model for Drug Release of Water-Swellable Filaments for Fused Filament Fabrication. MOLECULAR PHARMACEUTICS, 19 (8): (2854–2867). [PMID:35801946]
18. Jingmin Liu, Xiaochen Zhu, Liqin Sun, Yonglin Gao. (2022) Characterization and anti-diabetic evaluation of sulfated polysaccharide from Spirulina platensis. Journal of Functional Foods, 95 (105155). [PMID:]
19. Lizhen Qiao, Yuan Tao, Wang Yao, Jieyu Zhao, Yang Yan. (2022) A magnetic ionic liquid based vortex-assisted dispersive liquid-liquid microextraction coupled with back-extraction for the enrichment of fluoroquinolone antibiotics. JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 219 (114903). [PMID:35759827]
20. Xueliang Wang, Zhe Wang, Di Liu, Hao Jiang, Chao Cai, Guoyun Li, Guangli Yu. (2022) Canagliflozin Prevents Lipid Accumulation, Mitochondrial Dysfunction, and Gut Microbiota Dysbiosis in Mice With Diabetic Cardiovascular Disease. Frontiers in Pharmacology, 13 (839640). [PMID:35281938]
21. Hui Zhou, Yuanyuan Wu, Eunhye Kim, Haibo Pan, Puming He, Bo Li, Yi Charlie Chen, Youying Tu. (2021) Simultaneous Tests of Theaflavin-3,3′-digallate as an Anti-Diabetic Drug in Human Hepatoma G2 Cells and Zebrafish (Danio rerio). Nutrients, 13 (12): (4379). [PMID:34959930]
22. Xiangyu Meng, Jia Song, Yunfeng Lei, Xuezhong Zhang, Zhixin Chen, Zhuoxuan Lu, Liming Zhang, Zhifei Wang. (2021) A metformin-based nanoreactor alleviates hypoxia and reduces ATP for cancer synergistic therapy. Biomaterials Science, 9 (22): (7456-7470). [PMID:34609385]
23. Hui Zhang,Junfeng Hui,Jing Yang,Jianjun Deng,Daidi Fan. (2020-09-19) Eurocristatine, a plant alkaloid from Eurotium cristatum, alleviates insulin resistance in db/db diabetic mice via activation of PI3K/AKT signaling pathway.. European journal of pharmacology, 887 (173557-173557). [PMID:32946868]
24. Enfang Shan,Zhu Zhu,Shuangcheng He,Dongbao Chu,Dinghao Ge,Yunran Zhan,Wei Liu,Jian Yang,Jing Xiong. (2017-02-28) Involvement of pregnane X receptor in the suppression of carboxylesterases by metformin in vivo and in vitro, mediated by the activation of AMPK and JNK signaling pathway.. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 102 (14-23). [PMID:28238946]

References

1. Zhao, X. Y. Liu, Y. Zhang, X. Zhao, B. C. Burley, G. Yang, Z. C. Luo, Y. Li, A. Q. Zhang, R. X. Liu, Z. Y. Shi, Y. C. Wang, Q. P.. (2023) The combined effect of metformin and mirabegron on diet-induced obesity. MedComm, 2 (4): (e207). [PMID:]
2. Guang-Li Fu, Qin-Yuan Meng, Yu Chen, Jin-Zhao Xin, Jia-Hui Liu, Wei Dang, Hong-Liang Lu. (2023) Metformin exposure altered intestinal microbiota composition and metabolites in amphibian larvae. ECOTOXICOLOGY AND ENVIRONMENTAL SAFETY, 267 (115617). [PMID:37866109]
3. Yong-Yu Yang, Jing-Jing Qi, Si-Yi Jiang, Ling Ye. (2023) Esculin ameliorates obesity-induced insulin resistance by improving adipose tissue remodeling and activating the IRS1/PI3K/AKT/GLUT4 pathway. JOURNAL OF ETHNOPHARMACOLOGY, (6): (117251). [PMID:37778516]
4. Xiaobang Liu, Junpeng Sun, Jiaqun Du, Jinyu An, Yingqiao Li, Yu Hu, Ying Xiong, Yanan Yu, He Tian, Xifan Mei, Chao Wu. (2023) Encapsulation of Selenium Nanoparticles and Metformin in Macrophage-Derived Cell Membranes for the Treatment of Spinal Cord Injury. ACS Biomaterials Science & Engineering, [PMID:37713674]
5. Yaodong Yi, Hengbin Zhang, Mingyang Chen, Binxin Chen, Yingchun Chen, Ping Li, Hui Zhou, Zhiyuan Ma, Huidi Jiang. (2023) Inhibition of multiple uptake transporters in cardiomyocytes/mitochondria alleviates doxorubicin-induced cardiotoxicity. CHEMICO-BIOLOGICAL INTERACTIONS, 382 (110627). [PMID:37453608]
6. Yu-Pei Xia. (2023) Crystal structure of N-(diaminomethylene)-1-(dimethylamino)-1-iminiomethanaminium dichloride, C4H13Cl2N5. ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 238 (4): (799-800). [PMID:]
7. Shengnan Duan, Meiting Zhang, Hao Zeng, Jinyi Song, Min Zhang, Song Gao, Hua Yang, Ming Ding, Ping Li. (2023) Integrated proteomics and phosphoproteomics profiling reveals the cardioprotective mechanism of bioactive compounds derived from Salvia miltiorrhiza Burge. PHYTOMEDICINE, 117 (154897). [PMID:37307738]
8. Jing Zuo, Yamin Shen, Haikun Wang, Shuji Gao, Shuo Yuan, Dong Song, Yuxin Wang, Yang Wang. (2023) Effects of metformin on Streptococcus suis LuxS/AI-2 quorum sensing system and biofilm formation. MICROBIAL PATHOGENESIS, 181 (106183). [PMID:37263449]
9. Guilin Chen, Yongbing Xu, Hui Zhang, Felix Wambua Muema, Mingquan Guo. (2023) Gymnema sylvestre extract ameliorated streptozotocin-induced hyperglycemia in T2DM rats via gut microbiota. Food Frontiers, [PMID:]
10. Lidong Yu, Yi Wang, Kai Li, Xueting Li, Mingyue He, Ce Chen, Fangshun Li, Bing Liang, Li Li, Ning Gu, Zhiguo Liu, Bingsheng Li, Guixue Wang, Jianglin Fan. (2023) Metformin-based carbon dots based on biguanide functional groups for simultaneous chelation of copper ions and inhibitable colorectal cancer therapy. CARBON, 212 (118095). [PMID:]
11. Yuting Hao, Hao Zhang, Xizhuang Yue, Zhen Zhao, Shuang Zhao. (2023) A novel electrochemical sensor based on Cu(Ⅱ) metal organic framework for the determination of metformin. MICROCHEMICAL JOURNAL, 191 (108849). [PMID:]
12. Huanan Huang, Yihui Chen, Meilin Ni, Jing Du, Chunyan Hou, Xiaoqiang Qiao, Guozhou Cao, Tingting Wang. (2023) Sodium hexametaphosphate-treated halloysite based solid-phase extraction of biguanides from dietary supplements. Analytical Methods, 15 (21): (2685-2692). [PMID:37226487]
13. Jing Zhou, Tongyu Wu, Chun Li, Zhuozhou Hu, Liang Han, Xiangxiang Li, Jingjing Liu, Wenyang Zhao, Jia Kang, Xinping Chen. (2023) Alfuzosin ameliorates diabetes by boosting PGK1 activity in diabetic mice. LIFE SCIENCES, 317 (121491). [PMID:36758669]
14. Gu Yurong, Zhang Yi, Jiang Chengchun, Dong Zijun, Bai Xue. (2023) Efficient metformin transformation in sulfite/UV process co-present with oxygen. Frontiers in Environmental Science, 10 [PMID:]
15. Yilong Li, Zhiyong Li, Ruipeng Li, Huiyong Wang, Yang Zhao, Yuanchao Pei, Jianji Wang. (2023) Highly efficient triiodide ion adsorption from water by ionic liquid hybrid metal–organic frameworks. JOURNAL OF MOLECULAR LIQUIDS, 370 (121009). [PMID:]
16. Yuan Tao, Luyao Jia, Honglin Qin, Ruiting Niu, Lizhen Qiao. (2022) A new magnetic ionic liquid based salting-out assisted dispersive liquid–liquid microextraction for the determination of parabens in environmental water samples. Analytical Methods, 14 (46): (4775-4783). [PMID:36374117]
17. Jie Yang, Xiuhua Pan, Jun Zhang, Siyu Ma, Jianeng Zhou, Zengguang Jia, Yawen Wei, Zengyi Liu, Ning Yang, Qi Shen. (2022) Reprogramming dysfunctional dendritic cells by a versatile metabolism nano-intervenor for enhancing cancer combinatorial immunotherapy. Nano Today, 46 (101618). [PMID:]
18. Ling Li, Xiaolong Zhu, Huaiyu Yang, Bangchao Liang, Lei Yuan, Yueqiang Hu, Feng Chen, Xiaoxiao Han. (2022) Phase-Field Model for Drug Release of Water-Swellable Filaments for Fused Filament Fabrication. MOLECULAR PHARMACEUTICS, 19 (8): (2854–2867). [PMID:35801946]
19. Jingmin Liu, Xiaochen Zhu, Liqin Sun, Yonglin Gao. (2022) Characterization and anti-diabetic evaluation of sulfated polysaccharide from Spirulina platensis. Journal of Functional Foods, 95 (105155). [PMID:]
20. Lizhen Qiao, Yuan Tao, Wang Yao, Jieyu Zhao, Yang Yan. (2022) A magnetic ionic liquid based vortex-assisted dispersive liquid-liquid microextraction coupled with back-extraction for the enrichment of fluoroquinolone antibiotics. JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 219 (114903). [PMID:35759827]
21. Xueliang Wang, Zhe Wang, Di Liu, Hao Jiang, Chao Cai, Guoyun Li, Guangli Yu. (2022) Canagliflozin Prevents Lipid Accumulation, Mitochondrial Dysfunction, and Gut Microbiota Dysbiosis in Mice With Diabetic Cardiovascular Disease. Frontiers in Pharmacology, 13 (839640). [PMID:35281938]
22. Hui Zhou, Yuanyuan Wu, Eunhye Kim, Haibo Pan, Puming He, Bo Li, Yi Charlie Chen, Youying Tu. (2021) Simultaneous Tests of Theaflavin-3,3′-digallate as an Anti-Diabetic Drug in Human Hepatoma G2 Cells and Zebrafish (Danio rerio). Nutrients, 13 (12): (4379). [PMID:34959930]
23. Xiangyu Meng, Jia Song, Yunfeng Lei, Xuezhong Zhang, Zhixin Chen, Zhuoxuan Lu, Liming Zhang, Zhifei Wang. (2021) A metformin-based nanoreactor alleviates hypoxia and reduces ATP for cancer synergistic therapy. Biomaterials Science, 9 (22): (7456-7470). [PMID:34609385]
24. Hui Zhang,Junfeng Hui,Jing Yang,Jianjun Deng,Daidi Fan. (2020-09-19) Eurocristatine, a plant alkaloid from Eurotium cristatum, alleviates insulin resistance in db/db diabetic mice via activation of PI3K/AKT signaling pathway.. European journal of pharmacology, 887 (173557-173557). [PMID:32946868]
25. Enfang Shan,Zhu Zhu,Shuangcheng He,Dongbao Chu,Dinghao Ge,Yunran Zhan,Wei Liu,Jian Yang,Jing Xiong. (2017-02-28) Involvement of pregnane X receptor in the suppression of carboxylesterases by metformin in vivo and in vitro, mediated by the activation of AMPK and JNK signaling pathway.. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 102 (14-23). [PMID:28238946]

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Metformin hydrochloride - 10mM in DMSO, high purity , CAS No.1115-70-4

Basic Description

Associated Targets(Human)

Associated Targets(non-human)

Names and Identifiers

Certificates

Certificate of Analysis(COA)

Chemical and Physical Properties

Safety and Hazards(GHS)

Related Documents

Citations of This Product

References

Solution Calculators

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