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MedKoo Cat#: 584139 | Name: Cyclovirobuxine D
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Description:

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

Cyclovirobuxine D is the main active component of the traditional Chinese medicine Buxus microphylla. It has shown anti-arrhythmic abilities as well as reduced cell viability and colony formation ability of MGC-803 and MKN28 cells in a time- and concentration-dependent manner. Flow cytometry showed that cell cycle of Cyclovirobuxine D treated cells was arrested at the S-phase. Cyclovirobuxine D also induced apoptosis in MGC-803 and MKN28 cells, especially early stage apoptosis. Furthermore, mitochondria membrane potential was reduced and apoptosis-related proteins, cleaved Caspase-3 and Bax/Bcl-2, were up-regulated in Cyclovirobuxine D treated MGC-803 and MKN28 cells.

Chemical Structure

Cyclovirobuxine D
Cyclovirobuxine D
CAS#860-79-7

Theoretical Analysis

MedKoo Cat#: 584139

Name: Cyclovirobuxine D

CAS#: 860-79-7

Chemical Formula: C26H46N2O

Exact Mass: 402.3610

Molecular Weight: 402.66

Elemental Analysis: C, 77.55; H, 11.52; N, 6.96; O, 3.97

Price and Availability

Size Price Availability Quantity
10mg USD 350.00 Back order
25mg USD 600.00 Back order
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Related CAS #
No Data
Synonym
Cyclovirobuxine D; Bebuxine; CVB-D; CVB D; CVBD; NSC 91722; NSC-91722; NSC91722
IUPAC/Chemical Name
9,19-Cyclo-5-alpha,9-beta-pregnan-16-alpha-ol, 4,4,14-trimethyl-3-beta,20-alpha-bis(methylamino)-
InChi Key
GMNAPBAUIVITMI-RZWOIDSXSA-N
InChi Code
InChI=1S/C26H46N2O/c1-16(27-6)21-17(29)14-24(5)19-9-8-18-22(2,3)20(28-7)10-11-25(18)15-26(19,25)13-12-23(21,24)4/h16-21,27-29H,8-15H2,1-7H3/t16-,17+,18-,19-,20-,21-,23+,24-,25+,26+/m0/s1
SMILES Code
C[C@H](NC)[C@H]1[C@H](O)C[C@@]2(C)[C@]3([H])CC[C@@]4([H])C(C)(C)[C@@H](NC)CC[C@]4(C5)[C@@]35CC[C@]12C
Appearance
Solid powder
Purity
>95% (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
>2 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 402.66 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: Ke Z, Hou X, Jia XB. Design and optimization of self-nanoemulsifying drug delivery systems for improved bioavailability of cyclovirobuxine D. Drug Des Devel Ther. 2016 Jun 28;10:2049-60. doi: 10.2147/DDDT.S106356. eCollection 2016. PubMed PMID: 27418807; PubMed Central PMCID: PMC4933569. 2: Wu J, Tan Z, Chen J, Dong C. Cyclovirobuxine D Inhibits Cell Proliferation and Induces Mitochondria-Mediated Apoptosis in Human Gastric Cancer Cells. Molecules. 2015 Nov 19;20(11):20659-68. doi: 10.3390/molecules201119729. PubMed PMID: 26610442. 3: Wei JB, Lai Q, Shumyak SP, Xu LF, Zhang CX, Ling JJ, Yu Y. An LC/MS quantitative and microdialysis method for cyclovirobuxine D pharmacokinetics in rat plasma and brain: The pharmacokinetic comparison of three different drug delivery routes. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Oct 1;1002:185-93. doi: 10.1016/j.jchromb.2015.08.022. Epub 2015 Aug 24. PubMed PMID: 26342162. 4: Guo Q, Guo J, Yang R, Peng H, Zhao J, Li L, Peng S. Cyclovirobuxine D Attenuates Doxorubicin-Induced Cardiomyopathy by Suppression of Oxidative Damage and Mitochondrial Biogenesis Impairment. Oxid Med Cell Longev. 2015;2015:151972. doi: 10.1155/2015/151972. Epub 2015 May 14. PubMed PMID: 26075032; PubMed Central PMCID: PMC4446494. 5: Xu YN, Wang Y, Bo S, Jiang Y, Liu XD, Shen XC. [Ameliorated effects of cyclovirobuxine D on oxidative stress and energy metabolism in experimental cardiac injured rats induced by sympathetic overactivity in vivo]. Zhong Yao Cai. 2014 Jul;37(7):1213-7. Chinese. PubMed PMID: 25566659. 6: Lu J, Sun D, Gao S, Gao Y, Ye J, Liu P. Cyclovirobuxine D induces autophagy-associated cell death via the Akt/mTOR pathway in MCF-7 human breast cancer cells. J Pharmacol Sci. 2014;125(1):74-82. Epub 2014 Apr 24. PubMed PMID: 24758922. 7: Yue Y, Liu R, Liu J, Dong Q, Fan J. Experimental and theoretical investigation on the interaction between cyclovirobuxine D and human serum albumin. Spectrochim Acta A Mol Biomol Spectrosc. 2014 Jul 15;128:552-8. doi: 10.1016/j.saa.2014.03.007. Epub 2014 Mar 20. PubMed PMID: 24691369. 8: Yu B, Ruan M, Zhou L, Xu L, Fang T. Influence of cyclovirobuxine D on intracellular [Ca(2+)] regulation and the expression of the calcium cycling proteins in rat myocytes. Fitoterapia. 2012 Dec;83(8):1653-65. doi: 10.1016/j.fitote.2012.09.019. Epub 2012 Sep 27. PubMed PMID: 23022536. 9: Yu B, Fang TH, Lü GH, Xu HQ, Lu JF. Beneficial effect of Cyclovirobuxine D on heart failure rats following myocardial infarction. Fitoterapia. 2011 Sep;82(6):868-77. doi: 10.1016/j.fitote.2011.04.016. Epub 2011 May 6. PubMed PMID: 21575690. 10: Zhao J, Wang Q, Xu J, Zhao J, Liu G, Peng S. Cyclovirobuxine D inhibits the currents of HERG potassium channels stably expressed in HEK293 cells. Eur J Pharmacol. 2011 Jun 25;660(2-3):259-67. doi: 10.1016/j.ejphar.2011.03.039. Epub 2011 Apr 12. PubMed PMID: 21497594. 11: Yu Y, Zhou L, Li X. [Studies of in vitro releasing properties on cyclovirobuxine D matrix-type patch]. Zhongguo Zhong Yao Za Zhi. 2009 Apr;34(7):825-8. Chinese. PubMed PMID: 19623972. 12: Chen Y, Fan XJ, Gong Q. [Determination of cyclovirobuxine-D in huangyangning tablets by RP-HPLC with gradient elution]. Zhongguo Zhong Yao Za Zhi. 2006 Jul;31(14):1155-7. Chinese. PubMed PMID: 17048582. 13: Ding L, Hu J, Jiang M, Xiong N. Sensitive HPLC-APCI-MS method for the determination of cyclovirobuxine D in human plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Oct 20;843(1):78-83. Epub 2006 Jul 5. PubMed PMID: 16822726. 14: Yu P, Zou L, Liu W, Wu C, Sun D, Xu J, Rao J, Yang Q. High performance liquid chromatography - tandem mass spectrometric determination of cyclovirobuxine D in human plasma. J Pharm Biomed Anal. 2006 Oct 11;42(4):488-93. Epub 2006 Jun 9. PubMed PMID: 16765010. 15: Deng L, Huang H, Xu MX. [Structural modification of cyclovirobuxine D and their inhibition activity on lipid peroxidation]. Yao Xue Xue Bao. 2006 Feb;41(2):121-4. Chinese. PubMed PMID: 16671540. 16: Deng L, Huang H, Xu MX, Zhou SQ, Ren F, Wang XW, Li DQ. [Prodrug structural modifications of cyclovirobuxine D and their biological activity]. Yao Xue Xue Bao. 2005 Sep;40(9):820-4. Chinese. PubMed PMID: 16342684. 17: Grossini E, Avanzi G, Gallicchio M, Molinari C, Vacca G, Bellomo G. Regulation of Ca2+ movements by cyclovirobuxine D in ECV304 endothelial cells. Pharmacol Res. 2005 Aug;52(2):154-61. PubMed PMID: 15967381. 18: Chen ZQ, Hu SJ, Shi WY, Du J, Shen Y, Xia Q. [Electrophysiologic study of the biphasic effects of cyclovirobuxine D on arrhythmias]. Zhongguo Zhong Xi Yi Jie He Za Zhi. 2004 Nov;24(11):1010-3. Chinese. PubMed PMID: 15609602. 19: Chen QW, Shan HL, Sun HL, Wang H, Yang BF. [Effects of cyclovirobuxine D on intracellular Ca2+ and L-type Ca2+ current in rat ventricular cardiomyocytes]. Yao Xue Xue Bao. 2004 Jul;39(7):500-3. Chinese. PubMed PMID: 15493836.

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