β-Acetyldigoxin (BioDeep_00000015258)

   

Chemicals and Drugs natural product PANOMIX_OTCML-2023


代谢物信息卡片


[(2R,3S,4S,6S)-6-[(2R,3S,4S,6S)-6-[(2R,3S,4S,6R)-6-[[(3S,5R,8R,9S,10S,12R,13S,14S,17R)-12,14-dihydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]-4-hydroxy-2-methyloxan-3-yl]oxy-4-hydroxy-2-methyloxan-3-yl]oxy-4-hydroxy-2-methyloxan-3-yl] acetate

化学式: C43H66O15 (822.4401486)
中文名称: 乙酰洋地黄毒苷
谱图信息: 最多检出来源 Escherichia coli(natural_products) 25%

Reviewed

Last reviewed on 2024-10-11.

Cite this Page

β-Acetyldigoxin. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/β-acetyldigoxin (retrieved 2024-11-22) (BioDeep RN: BioDeep_00000015258). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CC(=O)O[C@H]1[C@@H](O)C[C@H](O[C@H]2[C@@H](O)C[C@H](O[C@H]3[C@@H](O)C[C@H](O[C@H]4CC[C@]5(C)[C@H]6C[C@@H](O)[C@]7(C)[C@@H](C8=CC(=O)OC8)CC[C@]7(O)[C@@H]6CC[C@@H]5C4)O[C@@H]3C)O[C@@H]2C)O[C@@H]1C
InChI: InChI=1S/C43H66O15/c1-20-38(55-23(4)44)30(45)17-36(53-20)57-40-22(3)54-37(18-32(40)47)58-39-21(2)52-35(16-31(39)46)56-26-9-11-41(5)25(14-26)7-8-28-29(41)15-33(48)42(6)27(10-12-43(28,42)50)24-13-34(49)51-19-24/h13,20-22,25-33,35-40,45-48,50H,7-12,14-19H2,1-6H3/t20-,21-,22-,25-,26+,27-,28-,29+,30+,31+,32+,33-,35+,36+,37+,38-,39-,40-,41+,42+,43+/m1/s1

描述信息

Alpha- or beta-acetyl derivatives of DIGOXIN or lanatoside C from Digitalis lanata. They are better absorbed and longer acting than digoxin and are used in congestive heart failure.

β-Acetyldigoxin is a derivative of digoxin, a well-known cardiac glycoside used in the treatment of heart conditions such as heart failure and certain arrhythmias. Cardiac glycosides are compounds that consist of a sugar moiety (glycoside) and a steroid nucleus (aglycone), and they exert their effects on the heart by inhibiting the sodium-potassium ATPase pump, leading to increased intracellular calcium levels and enhanced cardiac contractility.
In the case of β-acetyldigoxin, the digoxin molecule is modified by the addition of an acetyl group at the C-16 hydroxyl position of the steroid nucleus. This acetylation can alter the physicochemical properties of the compound, potentially affecting its absorption, distribution, metabolism, and excretion (ADME) profile. As a result, β-acetyldigoxin may exhibit different pharmacokinetic properties compared to digoxin, such as altered bioavailability and tissue distribution.
The primary therapeutic use of β-acetyldigoxin, like digoxin, is in the management of chronic heart failure and atrial fibrillation. It is important to note that while β-acetyldigoxin and digoxin share similar mechanisms of action, they are not identical compounds, and their use should be guided by specific clinical indications and patient requirements. Due to the potential for variations in pharmacokinetics and pharmacodynamics, the dosing and monitoring of β-acetyldigoxin may differ from that of digoxin.


D020011 - Protective Agents > D002316 - Cardiotonic Agents > D004071 - Digitalis Glycosides
D020011 - Protective Agents > D002316 - Cardiotonic Agents > D002301 - Cardiac Glycosides
D020011 - Protective Agents > D002316 - Cardiotonic Agents > D000113 - Acetyldigoxins
D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents
D004791 - Enzyme Inhibitors

β-Acetyldigoxin. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=5355-48-6 (retrieved 2024-10-11) (CAS RN: 5355-48-6). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

同义名列表

2 个代谢物同义名

beta-Acetyldigoxin; β-ACETYLDIGOXIN



数据库引用编号

6 个数据库交叉引用编号

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)

20 个相关的物种来源信息

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。



文献列表

  • P Kh Dzhanashiya, O V Vladytskaya, N V Salibegashvili. Efficiency and mechanisms of the antioxidant effect of standard therapy and refracterin in the treatment of chronic heart failure in elderly patients with postinfarction cardiosclerosis. Bulletin of experimental biology and medicine. 2004 Oct; 138(4):412-4. doi: 10.1007/s10517-005-0056-1. [PMID: 15665959]
  • J Schrickel, H Bielik, A Yang, J O Schwab, N Shlevkov, R Schimpf, B Lüderitz, T Lewalter. Amiodarone-associated 'torsade de pointes'. Relevance of concomitant cardiovascular medication in a patient with atrial fibrillation and structural heart disease. Zeitschrift fur Kardiologie. 2003 Oct; 92(10):889-92. doi: 10.1007/s00392-003-0985-5. [PMID: 14579055]
  • Mary K Short, Rustem A Krykbaev, Philip D Jeffrey, Michael N Margolies. Complementary combining site contact residue mutations of the anti-digoxin Fab 26-10 permit high affinity wild-type binding. The Journal of biological chemistry. 2002 May; 277(19):16365-70. doi: 10.1074/jbc.m110444200. [PMID: 11854275]
  • C Pauli-Magnus, T Mürdter, A Godel, T Mettang, M Eichelbaum, U Klotz, M F Fromm. P-glycoprotein-mediated transport of digitoxin, alpha-methyldigoxin and beta-acetyldigoxin. Naunyn-Schmiedeberg's archives of pharmacology. 2001 Mar; 363(3):337-43. doi: 10.1007/s002100000354. [PMID: 11284449]
  • W N Moore, L T Taylor. Extraction and quantitation of digoxin and acetyldigoxin from the Digitalis lanata leaf via near-supercritical methanol-modified carbon dioxide. Journal of natural products. 1996 Jul; 59(7):690-3. doi: 10.1021/np960432g. [PMID: 8759168]
  • M Dreyer, H G Dammann, W Endell, M Rudolph, H Iven. [Absolute bioavailability of beta-acetyldigoxin from tablets and drops in healthy subjects]. Arzneimittel-Forschung. 1992 Mar; 42(3):303-6. doi: NULL. [PMID: 1497688]
  • Y Ikeda, Y Fujii, M Yamazaki. High-performance liquid chromatographic determination of alpha-acetyldigoxin in Digitalis lanata leaves. Analytical biochemistry. 1991 Aug; 196(2):451-5. doi: 10.1016/0003-2697(91)90493-d. [PMID: 1776696]
  • P Demol, W Wingender, J Kuhlmann. Effect of rioprostil, a methyl-prostaglandin E1, on plasma level and renal excretion of beta-acetyldigoxin. Scandinavian journal of gastroenterology. Supplement. 1989; 164(?):68-71; discussion 71. doi: NULL. [PMID: 2510284]
  • K O Haustein, C Schmidt. Differences in color discrimination between three cardioactive glycosides. International journal of clinical pharmacology, therapy, and toxicology. 1988 Oct; 26(10):517-20. doi: NULL. [PMID: 3235219]
  • K O Haustein, M Wesser. Pharmacokinetics of pengitoxin and its therapeutic efficacy in congestive heart failure. International journal of clinical pharmacology, therapy, and toxicology. 1988 Jan; 26(1):8-15. doi: . [PMID: 3403092]
  • W Koenig, N Rietbrock, B G Woodcock, W Lehmacher. [Determinants of plasma digoxin and digitoxin concentrations in elderly patients. A multivariate analysis]. Klinische Wochenschrift. 1987 Nov; 65(22):1073-80. doi: 10.1007/bf01736113. [PMID: 3695294]
  • K O Haustein, H Sensing, M Wesser. Elimination of 16-acetyl-gitoxin in patients suffering from impaired liver function. International journal of clinical pharmacology, therapy, and toxicology. 1987 Jul; 25(7):379-81. doi: . [PMID: 3623742]
  • K O Haustein, H Hentschel. Dose-dependent shortening of systolic time intervals after intake of pengitoxin. International journal of clinical pharmacology research. 1987; 7(1):19-25. doi: NULL. [PMID: 3583485]
  • K Bachmayer, R Wytek. [What value do body weight, age and drug anamnesis have as an index of elevated digoxin level?]. Wiener klinische Wochenschrift. 1986 Mar; 98(6):165-70. doi: NULL. [PMID: 3705594]
  • J Kuhlmann, S Marcin. [Pharmacokinetic and cardiac efficacy of beta-acetyldigoxin and digitoxin in combination therapy with diltiazem]. Klinische Wochenschrift. 1985 Jul; 63(14):636-42. doi: 10.1007/bf01732859. [PMID: 4032988]
  • H Rameis. Quinidine-digoxin interaction: are the pharmacokinetics of both drugs altered?. International journal of clinical pharmacology, therapy, and toxicology. 1985 Mar; 23(3):145-53. doi: NULL. [PMID: 3997300]
  • J Kuhlmann. Effects of nifedipine and diltiazem on plasma levels and renal excretion of beta-acetyldigoxin. Clinical pharmacology and therapeutics. 1985 Feb; 37(2):150-6. doi: 10.1038/clpt.1985.27. [PMID: 3967458]
  • J Kuhlmann. Use of cholestyramine in three patients with beta-acetyldigoxin, beta-methyldigoxin and digitoxin intoxication. International journal of clinical pharmacology, therapy, and toxicology. 1984 Oct; 22(10):543-8. doi: . [PMID: 6511130]
  • B Zöller, H J Engel, G Faust-Tinnefeldt, H J Gilfrich, M Zimmer. [Interaction of isoxicam and digoxin]. Zeitschrift fur Rheumatologie. 1984 Jul; 43(4):182-4. doi: NULL. [PMID: 6495892]
  • R Rossi, J U Leititis, K J Hagel, A Smolarz, M Brandis. Severe digoxin intoxication in a child treated by infusion of digoxin-specific Fab-antibody-fragments. European journal of pediatrics. 1984 Jun; 142(2):138-40. doi: 10.1007/bf00445597. [PMID: 6468431]
  • W Koenig, U Keil, J Stieber, A Döring, S J Pöppl, W Mraz. [Epidemiology of digitalis medication. Results of the Munich blood-pressure study]. Deutsche medizinische Wochenschrift (1946). 1984 Mar; 109(11):412-8. doi: 10.1055/s-2008-1069204. [PMID: 6697899]
  • H Rameis, B Woodcock, J Bonelli, H Waginger. Changes in metildigoxin pharmacokinetics in cirrhosis of the liver: a comparison with beta-acetyldigoxin. International journal of clinical pharmacology, therapy, and toxicology. 1984 Mar; 22(3):145-51. doi: NULL. [PMID: 6715083]
  • A Smolarz, E Roesch, H Lenz, P Neubert, U Abshagen. [Report of experiences in the treatment of 16 cases of severe glycoside poisoning with digitalis antibody fragments (Fab)]. Zeitschrift fur Kardiologie. 1984 Feb; 73(2):113-9. doi: NULL. [PMID: 6719984]
  • T Risler. [Renal and extracorporeal elimination of digoxin and its methylated and acetylated derivatives]. Fortschritte der Medizin. 1983 Dec; 101(47-48):2185-8. doi: NULL. [PMID: 6671635]
  • K O Haustein, R G Alken, H J Lach, U Becker, N Rietbrock. On the pharmacokinetics of pengitoxin and its cardioactive derivative 16-acetyl-gitoxin. European journal of clinical pharmacology. 1983; 25(3):369-73. doi: 10.1007/bf01037950. [PMID: 6628525]
  • R Botzler, U Ritter. [Effect of laxative measures on the serum concentration of digoxin in the human]. Leber, Magen, Darm. 1982 Nov; 12(6):255-7. doi: NULL. [PMID: 7183885]
  • K O Haustein, G Oltmanns, N Rietbrock, R G Alken. Differences in color vision impairment caused by digoxin, digitoxin, or pengitoxin. Journal of cardiovascular pharmacology. 1982 Jul; 4(4):536-41. doi: 10.1097/00005344-198207000-00003. [PMID: 6181326]
  • H Rameis, J Bonelli, H Waginger, K Hruby. [Pharmacokinetics of beta-methyldigoxin and beta-acetyldigoxin in patients with cirrhosis of the liver (author's transl)]. Wiener klinische Wochenschrift. 1981 Oct; 93(18):572-6. doi: NULL. [PMID: 7303703]
  • J Kuhlmann, W Zilly, J Wilke. Effects of cytostatic drugs on plasma level and renal excretion of beta-acetyldigoxin. Clinical pharmacology and therapeutics. 1981 Oct; 30(4):518-27. doi: 10.1038/clpt.1981.197. [PMID: 7285486]
  • H R Ochs, D J Greenblatt, J S Harmatz, G Bodem, H J Dengler. Clinical implications of serum digoxin concentrations. Klinische Wochenschrift. 1981 May; 59(10):501-7. doi: 10.1007/bf01696212. [PMID: 7241950]
  • R Hirschberg, K Schaefer, D von Herrath, G Kreutz, H Kewitz. Digoxin-quinidine interaction in patients with renal failure. Klinische Wochenschrift. 1981 May; 59(10):521-2. doi: 10.1007/bf01696215. [PMID: 7241953]
  • G Hüller, K O Haustein, D Murawski. On the plasma protein binding of 16-acetyl-gitoxin. International journal of clinical pharmacology, therapy, and toxicology. 1981 May; 19(5):200-2. doi: NULL. [PMID: 7251233]
  • J Bonelli, H Rameis, H Waginger. Digoxin concentration in cerebrospinal fluid-a study carried out after 9 days of treatment of beta-methyldigoxin or beta-acetyldigoxin. International journal of clinical pharmacology, therapy, and toxicology. 1981 Mar; 19(3):93-5. doi: NULL. [PMID: 7228456]
  • N Rietbrock, R G Alken. [Disorders of the ability to distinguish colors during digitalis therapy (author's transl)]. MMW, Munchener medizinische Wochenschrift. 1980 Nov; 122(46):1624-6. doi: NULL. [PMID: 6780853]
  • R Haasis. [Glycoside therapy in elderly patients (author's transl)]. Aktuelle Gerontologie. 1980 Oct; 10(10):435-8. doi: NULL. [PMID: 6110348]
  • E W Weiler, H J Lach. Direct radioimmunoassay for the determination of 16-acetyl-gitoxin in serum. Clinica chimica acta; international journal of clinical chemistry. 1980 Jul; 104(3):337-43. doi: 10.1016/0009-8981(80)90391-5. [PMID: 7389142]
  • N Rietbrock, R G Alken. Color vision deficiencies: a common sign of intoxication in chronically digoxin-treated patients. Journal of cardiovascular pharmacology. 1980 Jan; 2(1):93-9. doi: NULL. [PMID: 6154209]
  • H Kasper, W Zilly, H Fassl, F Fehle. The effect of dietary fiber on postprandial serum digoxin concentration in man. The American journal of clinical nutrition. 1979 Dec; 32(12):2436-8. doi: 10.1093/ajcn/32.12.2436. [PMID: 506966]
  • R Clasen, H Kemmeter, H J Gilfrich. [Biological availability of digoxin and beta-acetyldigoxin after single-dose administration (author's transl)]. Deutsche medizinische Wochenschrift (1946). 1979 Apr; 104(15):543-6. doi: 10.1055/s-0028-1103942. [PMID: 436626]
  • K O Haustein, C Pachaly, R Megges, P Franke. Investigation into the species-specific deacylation of penta-acetyl-gitoxin. European journal of clinical pharmacology. 1978 Dec; 14(6):425-30. doi: 10.1007/bf00716384. [PMID: 738349]
  • G BAUMGARTEN. [On oleandrigenin-tridigitoxoside (16-acetylgitoxin)]. Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft. 1962 Apr; 295/67(?):305-10. doi: 10.1002/ardp.19622950411. [PMID: 13865948]