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MedKoo Cat#: 574198 | Name: Cinobufotalin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Cinobufotalin is a steroid glycoside that reduces SRC-3 protein levels in MCF-7 breast cancer cells, Na+/K+ pump activity, viability, and cell attachment of C7-MDCK cells, and expression of the epithelial-mesenchymal (EMT) markers E-cadherin, vimentin, ZEB1, and Slug in. Cinobufotalin is cytotoxic to A549, H460, and HTB-58 lung cancer cells. In vivo, Cinobufotalin reduces tumor volume and increases survival in an A549 mouse xenograft model.

Chemical Structure

Cinobufotalin
Cinobufotalin
CAS#1108-68-5

Theoretical Analysis

MedKoo Cat#: 574198

Name: Cinobufotalin

CAS#: 1108-68-5

Chemical Formula: C26H34O7

Exact Mass: 458.2305

Molecular Weight: 458.55

Elemental Analysis: C, 68.10; H, 7.47; O, 24.42

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
10mg USD 600.00 2 Weeks
25mg USD 950.00 2 Weeks
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Related CAS #
No Data
Synonym
Cinobufotalin; NSC 90326; NSC90326; NSC-90326;
IUPAC/Chemical Name
(1R,2R,2aR,3aS,3bR,5aS,7S,9aR,9bS,11aR)-5a,7-dihydroxy-9a,11a-dimethyl-1-(2-oxo-2H-pyran-5-yl)hexadecahydronaphtho[1',2':6,7]indeno[1,7a-b]oxiren-2-yl acetate
InChi Key
KBKUJJFDSHBPPA-ZNCGZLKOSA-N
InChi Code
InChI=1S/C26H34O7/c1-14(27)32-21-20(15-4-5-19(29)31-13-15)24(3)10-7-17-18(26(24)22(21)33-26)8-11-25(30)12-16(28)6-9-23(17,25)2/h4-5,13,16-18,20-22,28,30H,6-12H2,1-3H3/t16-,17-,18+,20-,21+,22+,23+,24+,25-,26+/m0/s1
SMILES Code
O[C@H]1CC[C@@]2(C)[C@@](CC[C@]3([H])[C@]2([H])CC[C@@]4(C)[C@]3(O5)[C@H]5[C@H](OC(C)=O)[C@@H]4C6=COC(C=C6)=O)(O)C1
Appearance
A crystalline solid
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 458.55 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Wang J, Chang H, Su M, Zhao H, Qiao Y, Wang Y, Shang L, Shan C, Zhang S. The Potential Mechanisms of Cinobufotalin Treating Colon Adenocarcinoma by Network Pharmacology. Front Pharmacol. 2022 Jun 23;13:934729. doi: 10.3389/fphar.2022.934729. PMID: 35814224; PMCID: PMC9262105. 2: Chen R, Guan Z, Zhong X, Zhang W, Zhang Y. Network Pharmacology Prediction: The Possible Mechanisms of Cinobufotalin against Osteosarcoma. Comput Math Methods Med. 2022 Jan 13;2022:3197402. doi: 10.1155/2022/3197402. PMID: 35069780; PMCID: PMC8776428. 3: Li C, Guo H, Wang C, Zhan W, Tan Q, Xie C, Sharma A, Sharma HS, Chen L, Zhang Z. Network pharmacological mechanism of Cinobufotalin against glioma. Prog Brain Res. 2021;265:119-137. doi: 10.1016/bs.pbr.2021.06.001. Epub 2021 Aug 13. PMID: 34560920. 4: Liu JH, Yang HL, Deng ST, Hu Z, Chen WF, Yan WW, Hou RT, Li YH, Xian RT, Xie YY, Su Y, Wu LY, Xu P, Zhu ZB, Liu X, Deng YL, Wang YB, Liu Z, Fang WY. The small molecule chemical compound cinobufotalin attenuates resistance to DDP by inducing ENKUR expression to suppress MYH9-mediated c-Myc deubiquitination in lung adenocarcinoma. Acta Pharmacol Sin. 2022 Oct;43(10):2687-2695. doi: 10.1038/s41401-022-00890-x. Epub 2022 Mar 16. PMID: 35296779; PMCID: PMC9525298. 5: Hou R, Li Y, Luo X, Zhang W, Yang H, Zhang Y, Liu J, Liu S, Han S, Liu C, Huang Y, Liu Z, Li A, Fang W. ENKUR expression induced by chemically synthesized cinobufotalin suppresses malignant activities of hepatocellular carcinoma by modulating β-catenin/c-Jun/MYH9/USP7/c-Myc axis. Int J Biol Sci. 2022 Mar 21;18(6):2553-2567. doi: 10.7150/ijbs.67476. PMID: 35414777; PMCID: PMC8990461. 6: Li M, Wang X, Qiu Y, Zhang Y, Pan X, Tang N, Chen T, Ruan B, Shao S, He L, Li H, Ma J. Safety reassessment of cinobufotalin injection: new findings into cardiotoxicity. Toxicol Res (Camb). 2020 Jun 12;9(4):390-398. doi: 10.1093/toxres/tfaa035. PMID: 32905219; PMCID: PMC7467235. 7: Li W, Pei S, Zhang X, Qi D, Zhang W, Dou Y, Yang R, Yao X, Zhang Z, Xie S, Fang D, Sun H. Cinobufotalin inhibits the epithelial-mesenchymal transition of hepatocellular carcinoma cells through down-regulate β-catenin in vitro and in vivo. Eur J Pharmacol. 2022 May 5;922:174886. doi: 10.1016/j.ejphar.2022.174886. Epub 2022 Mar 12. PMID: 35292248. 8: Han Y, Ma R, Cao G, Liu H, He L, Tang L, Li H, Luo Q. Combined Treatment of Cinobufotalin and Gefitinib Exhibits Potent Efficacy against Lung Cancer. Evid Based Complement Alternat Med. 2021 Mar 20;2021:6612365. doi: 10.1155/2021/6612365. PMID: 34122599; PMCID: PMC8189783. 9: Huang J, Deng C, Guo T, Chen X, Chen P, Du S, Lu M. Cinobufotalin Induces Ferroptosis to Suppress Lung Cancer Cell Growth by lncRNA LINC00597/hsa- miR-367-3p/TFRC Pathway via Resibufogenin. Anticancer Agents Med Chem. 2023;23(6):717-725. doi: 10.2174/1871520622666221010092922. PMID: 36221890. 10: Sun H, Wang W, Bai M, Liu D. Cinobufotalin as an effective adjuvant therapy for advanced gastric cancer: a meta-analysis of randomized controlled trials. Onco Targets Ther. 2019 Apr 26;12:3139-3160. doi: 10.2147/OTT.S196684. PMID: 31118669; PMCID: PMC6507077. 11: Li LL, Su YX, Mao Y, Jiang PY, Chu XL, Xue P, Jia BH, Zhu SJ. The Effectiveness and Safety of Cinobufotalin Injection as an Adjunctive Treatment for Lung Cancer: A Meta-Analysis of Randomized Controlled Trials. Evid Based Complement Alternat Med. 2021 Feb 5;2021:8852261. doi: 10.1155/2021/8852261. PMID: 33628320; PMCID: PMC7881937. 12: Zhang X, Liu T, Zhang Y, Liu F, Li H, Fang D, Wang C, Sun H, Xie S. Elucidation of the Differences in Cinobufotalin's Pharmacokinetics Between Normal and Diethylnitrosamine-Injured Rats: The Role of P-Glycoprotein. Front Pharmacol. 2019 May 17;10:521. doi: 10.3389/fphar.2019.00521. PMID: 31156437; PMCID: PMC6533572. 13: Kai S, Lu JH, Hui PP, Zhao H. Pre-clinical evaluation of cinobufotalin as a potential anti-lung cancer agent. Biochem Biophys Res Commun. 2014 Sep 26;452(3):768-74. doi: 10.1016/j.bbrc.2014.08.147. Epub 2014 Sep 6. PMID: 25201730. 14: Mao Y, Peng X, Xue P, Lu D, Li L, Zhu S. Network Pharmacology Study on the Pharmacological Mechanism of Cinobufotalin Injection against Lung Cancer. Evid Based Complement Alternat Med. 2020 Feb 17;2020:1246742. doi: 10.1155/2020/1246742. PMID: 32148531; PMCID: PMC7048923. 15: Cheng L, Chen YZ, Peng Y, Yi N, Gu XS, Jin Y, Bai XM. Ceramide production mediates cinobufotalin-induced growth inhibition and apoptosis in cultured hepatocellular carcinoma cells. Tumour Biol. 2015 Aug;36(8):5763-71. doi: 10.1007/s13277-015-3245-1. Epub 2015 Feb 28. PMID: 25724183. 16: Liu Y, Jiang Q, Liu X, Lin X, Tang Z, Liu C, Zhou J, Zhao M, Li X, Cheng Z, Li L, Xie Y, Liu Z, Fang W. Cinobufotalin powerfully reversed EBV-miR- BART22-induced cisplatin resistance via stimulating MAP2K4 to antagonize non- muscle myosin heavy chain IIA/glycogen synthase 3β/β-catenin signaling pathway. EBioMedicine. 2019 Oct;48:386-404. doi: 10.1016/j.ebiom.2019.08.040. Epub 2019 Oct 5. PMID: 31594754; PMCID: PMC6838365. 17: Liu XX, Li CC, Yang J, Zhang WG, Jianati RA, Zhang XL, Xu ZQ, Dai XB, Tian F, Chen BQ, Zhu XJ. [Inhibitory Effect of Cinobufotalin on Macrophage Inflammatory Factor Storm and Its Mechanism]. Zhongguo Shi Yan Xue Ye Xue Za Zhi. 2023 Jun;31(3):880-888. Chinese. doi: 10.19746/j.cnki.issn.1009-2137.2023.03.039. PMID: 37356955. 18: Meng H, Shen M, Li J, Zhang R, Li X, Zhao L, Huang G, Liu J. Novel SREBP1 inhibitor cinobufotalin suppresses proliferation of hepatocellular carcinoma by targeting lipogenesis. Eur J Pharmacol. 2021 Sep 5;906:174280. doi: 10.1016/j.ejphar.2021.174280. Epub 2021 Jun 24. PMID: 34174265. 19: Xia Z, Li M, Hu M, Lin Y, Atteh LL, Fu W, Gao L, Bai M, Huang C, Yue P, Liu Y, Meng W. Phosphoproteomics reveals that cinobufotalin promotes intrahepatic cholangiocarcinoma cell apoptosis by activating the ATM/CHK2/p53 signaling pathway. Front Oncol. 2022 Sep 16;12:982961. doi: 10.3389/fonc.2022.982961. PMID: 36185307; PMCID: PMC9523695. 20: Shen X, Tao Y, Yang Y, Wang R, Fang J, Lian M. Combination of TPF regimen and cinobufotalin inhibits proliferation and induces apoptosis in human hypopharyngeal and laryngeal squamous cell carcinoma cells. Onco Targets Ther. 2018 Dec 31;12:341-348. doi: 10.2147/OTT.S185428. PMID: 30643431; PMCID: PMC6317469.