Difference between revisions of "Digitoxin"
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{{Drugbox| | {{Drugbox| | ||
| − | | IUPAC_name = (3β,5β)-3-[(O-2,6-dideoxy-<br>β-D-ribo-hexapyranosyl-(1->4)-<br>2,6-dideoxy-β-D-ribo-hexopyranosyl)oxy]-<br>14-hydroxycard-20(22)-enolide | + | | IUPAC_name = (3β,5β)-3-[(O-2,6-dideoxy-<br/>β-D-ribo-hexapyranosyl-(1->4)-<br/>2,6-dideoxy-β-D-ribo-hexopyranosyl)oxy]-<br/>14-hydroxycard-20(22)-enolide |
| image = Digitoxin.png | | image = Digitoxin.png | ||
| − | | | + | | InChI = {{InChIwrap|1/C41H64O13/c1-20-36(46) 29(42)16-34(49-20)53-38-22(3)5 1-35(18-31(38)44)54-37-21(2)50 -33(17-30(37)43)52-25-8-11-39( 4)24(15-25)6-7-28-27(39)9-12-4 0(5)26(10-13-41(28,40)47)23-14 -32(45)48-19-23/h14,20-22,24-3 1,33-38,42-44,46-47H,6-13,15-1 9H2,1-5H3/t20-,21-,22-,24-,25+ ,26-,27+,28-,29+,30+,31+,33+,3 4+,35+,36-,37-,38-,39+,40-,41+ /m1/s1}} |
| + | | StdInChI = {{InChIwrap|1S/C41H64O13/c1-20-36(46 )29(42)16-34(49-20)53-38-22(3) 51-35(18-31(38)44)54-37-21(2)5 0-33(17-30(37)43)52-25-8-11-39 (4)24(15-25)6-7-28-27(39)9-12- 40(5)26(10-13-41(28,40)47)23-1 4-32(45)48-19-2 3/h14,20-22,24 -31,33-38,42-44,46-47H,6-13,15 -19H2,1-5H3/t20-,21-,22-,24-,2 5+,26-,27+,28-,29+,30+,31+,33+ ,34+,35+,36-,37-,38-,39+,40-,4 1+/m1/s1}} | ||
| + | | InChIKey = WDJUZGPOPHTGOT-XUDUSOBPBI | ||
| + | | StdInChIKey = WDJUZGPOPHTGOT-XUDUSOBPSA-N | ||
| + | | CASNo = 71-63-6 | ||
| + | | CASNo_Ref = {{cascite}} | ||
| + | | EC-number = 200-760-5 | ||
| + | | ChemSpiderID = 389987 | ||
| ATC_prefix = C01 | | ATC_prefix = C01 | ||
| ATC_suffix = AA04 | | ATC_suffix = AA04 | ||
| Line 9: | Line 16: | ||
| DrugBank = | | DrugBank = | ||
| C=41 | H=64 | O=13 | | C=41 | H=64 | O=13 | ||
| − | | molecular_weight = 764. | + | | molecular_weight = 764.94 g/mol |
| bioavailability= 95% (Oral) | | bioavailability= 95% (Oral) | ||
| metabolism = Liver | | metabolism = Liver | ||
| − | | elimination_half-life= | + | | elimination_half-life= 5–7 days |
| excretion = | | excretion = | ||
| pregnancy_category = | | pregnancy_category = | ||
| Line 19: | Line 26: | ||
}} | }} | ||
| − | '''Digitoxin''' is a [[cardiac]] [[glycoside]]. It has similar structure and effects to [[digoxin]] (though the effects are longer-lasting). Unlike digoxin (which is eliminated from the body via the kidneys), it is eliminated via the liver, so could be used in patients with poor or erratic kidney function. However, it is now rarely used in current UK medical practice. While there have been several controlled trials which have shown digoxin to be effective in a proportion of patients treated for heart failure, there is not the same strong evidence base for digitoxin, although it is presumed to be similarly effective. <ref name=Belz> Treatment of congestive heart failure | + | '''Digitoxin''' is a [[cardiac]] [[glycoside]]. It has similar structure and effects to [[digoxin]] (though the effects are longer-lasting). Unlike digoxin (which is eliminated from the body via the kidneys), it is eliminated via the liver, so could be used in patients with poor or erratic kidney function. However, it is now rarely used in current UK medical practice. While there have been several controlled trials which have shown digoxin to be effective in a proportion of patients treated for heart failure, there is not the same strong evidence base for digitoxin, although it is presumed to be similarly effective. <ref name="Belz">{{citation | last1 = Belz | first1 = G. | last2 = Breithaupt-Grögler | first2 = K. | last3 = Osowski | first3 = U. | title = Treatment of congestive heart failure – current status of use of digitoxin | journal = Eur. J. Clin. Invest. | volume = 31 | issue = Suppl 2 | pages = 10–7 | year = 2001 | pmid = 11525233}}.</ref> |
== Toxicity== | == Toxicity== | ||
| − | Digitoxin exhibits similar toxic effects to the more-commonly used [[digoxin]], namely: anorexia, nausea, vomiting, diarrhea, confusion, visual disturbances, and cardiac [[arrhythmias]]. Anti-digoxin antibody fragments, the specific treatment for digoxin poisoning, are also effective in serious digitoxin toxicity.<ref name= | + | Digitoxin exhibits similar toxic effects to the more-commonly used [[digoxin]], namely: anorexia, nausea, vomiting, diarrhea, confusion, visual disturbances, and cardiac [[arrhythmias]]. Anti-digoxin antibody fragments, the specific treatment for digoxin poisoning, are also effective in serious digitoxin toxicity.<ref name="Kurowski">{{citation | title = Treatment of a patient with severe digitoxin intoxication by Fab fragments of anti-digitalis antibodies | last1 = Kurowski | first1 = V. | last2 = Iven | first2 = H. | last3 = Djonlagic | first3 = H. | journal = Intensive Care Med. | year = 1992 | volume = 18 | issue = 7 | pages = 439–42 | pmid = 1469187}}.</ref> |
==References== | ==References== | ||
{{reflist}} | {{reflist}} | ||
| − | + | ||
| − | * {{ | + | ==Further reading== |
| − | * {{ | + | * {{citation | last1 = Johansson | first1 = S. | last2 = Lindholm | first2 = P. | last3 = Gullbo | first3 = J. | last4 = Larsson | first4 = R. | last5 = Bohlin | first5 = L. | last6 = Claeson | first6 = P | title = Cytotoxicity of digitoxin and related cardiac glycosides in human tumor cells | journal = Anticancer Drugs | volume = 12 | issue = 5 | pages = 475–83 | year = 2001 | pmid = 11395576 | doi = 10.1097/00001813-200106000-00009}}. |
| − | * {{ | + | * {{citation | last1 = Hippius | first1 = M. | last2 = Humaid | first2 = B. | last3 = Sicker | first3 = T. | last4 = Hoffmann | first4 = A. | last5 = Göttler | first5 = M. | last6 = Hasford | first6 = J. | title = Adverse drug reaction monitoring – digitoxin overdosage in the elderly | journal = Int. J. Clin. Pharmacol. Ther. | volume = 39 | issue = 8 | pages = 336–43 | year = 2001 | pmid = 11515708}}. |
| − | + | * {{citation | last1 = Haux | first1 = J. | last2 = Klepp | first2 = O. | last3 = Spigset | first3 = O. | last4 = Tretli | first4 = S. | title = Digitoxin medication and cancer; case control and internal dose-response studies | journal = BMC Cancer | volume = 1 | issue = | pages = 11 | year = 2001 | pmid = 11532201 | doi = 10.1186/1471-2407-1-11}}. | |
| − | * {{ | + | * {{citation | last1 = Srivastava | first1 = M. | last2 = Eidelman | first2 = O. | last3 = Zhang | first3 = J. | last4 = Paweletz | first4 = C. | last5 = Caohuy | first5 = H. | last6 = Yang | first6 = Q. | last7 = Jacobson | first7 = K. | last8 = Heldman | first8 = E. | last9 = Huang | first9 = W. | last10 = Jozwik | first10 = C. | last11 = Pollard | first11 = B. | last12 = Pollard | first12 = H. | title = Digitoxin mimics gene therapy with CFTR and suppresses hypersecretion of IL-8 from cystic fibrosis lung epithelial cells | journal = Proc. Natl. Acad. Sci. USA | volume = 101 | issue = 20 | pages = 7693–98 | year = 2004 | pmid = 15136726 | doi = 10.1073/pnas.0402030101}}. |
| − | |||
==External links== | ==External links== | ||
* [http://www.medscape.com/viewarticle/410488 "Comparing the Toxicity of Digoxin and Digitoxin in a Geriatric Population: Should an Old Drug Be Rediscovered?"] | * [http://www.medscape.com/viewarticle/410488 "Comparing the Toxicity of Digoxin and Digitoxin in a Geriatric Population: Should an Old Drug Be Rediscovered?"] | ||
| − | + | [[Category:Cardiac glycosides]] | |
| − | + | [[Category:Cardanolide steroids]] | |
| − | |||
| − | [[Category: | ||
| − | [[Category: | ||
{{Imported from Wikipedia|name=Digitoxin|id=297417192}} | {{Imported from Wikipedia|name=Digitoxin|id=297417192}} | ||
Latest revision as of 15:54, 8 March 2010
| |
Digitoxin
| |
| Systematic (IUPAC) name | |
| (3β,5β)-3-[(O-2,6-dideoxy- β-D-ribo-hexapyranosyl-(1->4)- 2,6-dideoxy-β-D-ribo-hexopyranosyl)oxy]- 14-hydroxycard-20(22)-enolide | |
| Identifiers | |
| CAS number | ? |
| ATC code | C01 |
| PubChem | |
| ChemSpider | |
| Chemical data | |
| Formula | C41H64O13 |
| Mol. mass | 764.94 g/mol |
| Pharmacokinetic data | |
| Bioavailability | 95% (Oral) |
| Metabolism | Liver |
| Half life | 5–7 days |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
? |
| Legal status | |
| Routes | ? |
Digitoxin is a cardiac glycoside. It has similar structure and effects to digoxin (though the effects are longer-lasting). Unlike digoxin (which is eliminated from the body via the kidneys), it is eliminated via the liver, so could be used in patients with poor or erratic kidney function. However, it is now rarely used in current UK medical practice. While there have been several controlled trials which have shown digoxin to be effective in a proportion of patients treated for heart failure, there is not the same strong evidence base for digitoxin, although it is presumed to be similarly effective. [1]
Toxicity
Digitoxin exhibits similar toxic effects to the more-commonly used digoxin, namely: anorexia, nausea, vomiting, diarrhea, confusion, visual disturbances, and cardiac arrhythmias. Anti-digoxin antibody fragments, the specific treatment for digoxin poisoning, are also effective in serious digitoxin toxicity.[2]
References
- ↑ Belz, G.; Breithaupt-Grögler, K.; Osowski, U. Treatment of congestive heart failure – current status of use of digitoxin. Eur. J. Clin. Invest. 2001, 31 (Suppl 2), 10–7. PMID 11525233.
- ↑ Kurowski, V.; Iven, H.; Djonlagic, H. Treatment of a patient with severe digitoxin intoxication by Fab fragments of anti-digitalis antibodies. Intensive Care Med. 1992, 18 (7), 439–42. PMID 1469187.
Further reading
- Johansson, S.; Lindholm, P.; Gullbo, J.; Larsson, R.; Bohlin, L.; Claeson, P Cytotoxicity of digitoxin and related cardiac glycosides in human tumor cells. Anticancer Drugs 2001, 12 (5), 475–83. PMID 11395576. DOI: 10.1097/00001813-200106000-00009.
- Hippius, M.; Humaid, B.; Sicker, T.; Hoffmann, A.; Göttler, M.; Hasford, J. Adverse drug reaction monitoring – digitoxin overdosage in the elderly. Int. J. Clin. Pharmacol. Ther. 2001, 39 (8), 336–43. PMID 11515708.
- Haux, J.; Klepp, O.; Spigset, O.; Tretli, S. Digitoxin medication and cancer; case control and internal dose-response studies. BMC Cancer 2001, 1, 11. PMID 11532201. DOI: 10.1186/1471-2407-1-11.
- Srivastava, M.; Eidelman, O.; Zhang, J.; Paweletz, C.; Caohuy, H.; Yang, Q.; Jacobson, K.; Heldman, E., et al. Digitoxin mimics gene therapy with CFTR and suppresses hypersecretion of IL-8 from cystic fibrosis lung epithelial cells. Proc. Natl. Acad. Sci. USA 2004, 101 (20), 7693–98. PMID 15136726. DOI: 10.1073/pnas.0402030101.
External links
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This page was originally imported from Wikipedia, specifically this version of the article "Digitoxin". Please see the history page on Wikipedia for the original authors. This WikiChem article may have been modified since it was imported. It is licensed under the Creative Commons Attribution–Share Alike 3.0 Unported license. |
