| 词条 | Digitoxin |
| 释义 |
| Watchedfields = changed | verifiedrevid = 297417192 | 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 | image = Digitoxin structure.svg | width = 250px | tradename = Digitaline | pregnancy_category = | legal_status = | routes_of_administration = | bioavailability = 95% (Oral) | metabolism = Liver | elimination_half-life = 5~7 days | excretion = | IUPHAR_ligand = 6782 | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 71-63-6 | ATC_prefix = C01 | ATC_suffix = AA04 | PubChem = 441207 | DrugBank_Ref = {{drugbankcite|changed|drugbank}} | DrugBank = DB01396 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 389987 | UNII_Ref = {{fdacite|changed|FDA}} | UNII = E90NZP2L9U | KEGG_Ref = {{keggcite|changed|kegg}} | KEGG = D00297 | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 28544 | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 254219 | C=41 | H=64 | O=13 | molecular_weight = 764.939 g/mol | smiles = O=C\\1OC/C(=C/1)[C@H]2CC[C@@]8(O)[C@]2(C)CC[C@H]7[C@H]8CC[C@H]6[C@]7(C)CC[C@H](O[C@@H]5O[C@H](C)[C@@H](O[C@@H]4O[C@@H]([C@@H](O[C@@H]3O[C@@H]([C@@H](O)[C@@H](O)C3)C)[C@@H](O)C4)C)[C@@H](O)C5)C6 | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 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)50-33(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)23-14-32(45)48-19-23/h14,20-22,24-31,33-38,42-44,46-47H,6-13,15-19H2,1-5H3/t20-,21-,22-,24-,25+,26-,27+,28-,29+,30+,31+,33+,34+,35+,36-,37-,38-,39+,40-,41+/m1/s1 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = WDJUZGPOPHTGOT-XUDUSOBPSA-N }}Digitoxin is a cardiac glycoside. It is a phytosteroid and is similar in 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 Western medical practice. While several controlled trials have shown digoxin to be effective in a proportion of patients treated for heart failure, the evidence base for digitoxin is not as strong, although it is presumed to be similarly effective.[1] ToxicityDigitoxin exhibits similar toxic effects to the more commonly used digoxin, namely: anorexia, nausea, vomiting, diarrhea, confusion, visual disturbances, and cardiac arrhythmias. Antidigoxin antibody fragments, the specific treatment for digoxin poisoning, are also effective in serious digitoxin toxicity.[2] HistoryThe first description of the use of foxglove dates back to 1775.[3] For quite some time, the active compound was not isolated. Oswald Schmiedeberg was able to obtain a pure sample in 1875. The modern therapeutic use of this molecule was made possible by the works of the pharmacist and the French chemist Claude-Adolphe Nativelle (1812-1889). The first structural analysis was done by Adolf Otto Reinhold Windaus in 1925, but the full structure with an exact determination of the sugar groups was not accomplished until 1962.[4][5] Use in fictionDigitoxin is used as a poison or murder weapon in:
In The Decemberists's song, "The Rake's Song" on The Hazards of Love album, the narrator murders his daughter by feeding her foxglove. Use in cancer chemotherapyDigitoxin and related cardenolides display potent anticancer activity against a range of human cancer cell lines in vitro but the clinical use of digitoxin to treat cancer has been restricted by its narrow therapeutic index.[6][7] Digitoxin glycorandomization led to the discovery of novel digitoxigenin neoglycosides which displayed improved anticancer potency and reduced inotropic activity (the perceived mechanism of general toxicity).[8] Steroidal glycosides based upon this latter discovery served as the basis for the development of a new class of antibody-drug conjugate known as extracellular drug conjugates (EDCs) as first in class agents to treat cancer by the biotechnology company Centrose. References1. ^{{cite journal |author1=Belz, G. G. |author2=Breithaupt-Grögler, K. |author3=Osowski, U. | title = Treatment of congestive heart failure—current status of use of digitoxin | journal = European Journal of Clinical Investigation | year = 2001 | volume = 31 | issue = Suppl 2 | pages = 10–17 | doi = 10.1046/j.1365-2362.2001.0310s2010.x | pmid = 11525233 | url = http://www3.interscience.wiley.com/resolve/openurl?genre=article&sid=nlm:pubmed&issn=0014-2972&date=2001&volume=31&issue=&spage=10 | archive-url = https://archive.today/20130105085338/http://www3.interscience.wiley.com/resolve/openurl?genre=article&sid=nlm:pubmed&issn=0014-2972&date=2001&volume=31&issue=&spage=10 | dead-url = yes | archive-date = 2013-01-05 }} {{refbegin}}2. ^{{cite journal |author1=Kurowski, V. |author2=Iven, H. |author3=Djonlagic, H. | title = Treatment of a patient with severe digitoxin intoxication by Fab fragments of anti-digitalis antibodies | journal = Intensive Care Medicine | volume = 18 | issue = 7 | pages = 439–442 | year = 1992 | pmid = 1469187 | doi = 10.1007/BF01694351 }} 3. ^{{cite book | url = https://books.google.com/books?id=tORsAAAAMAAJ | title = An Account of the Foxglove and Some of its Medical Uses: With Practical Remarks on Dropsy and other Diseases | author1 = Withering, William | year = 1785 }} 4. ^{{Cite journal | last1 = Diefenbach | first1 = W. C. | last2 = Meneely Jr | first2 = J. K. | title = Digitoxin; a critical review | journal = The Yale Journal of Biology and Medicine | volume = 21 | issue = 5 | pages = 421–431 | year = 1949 | pmid = 18127991 | pmc = 2598854}} 5. ^{{cite book | url = https://books.google.com/books?id=mYQxRY9umjcC&pg=PA107 | pages = 107 | title = Drug discovery: A history | isbn = 978-0-471-89980-8 | author1 = Sneader, Walter | year = 2005}} 6. ^{{cite journal|last1=Menger|first1=L|last2=Vacchelli|first2=E|last3=Kepp|first3=O|last4=Eggermont|first4=A|last5=Tartour|first5=E|last6=Zitvogel|first6=L|last7=Kroemer|first7=G|last8=Galluzzi|first8=L|title=Trial watch: Cardiac glycosides and cancer therapy|journal=Oncoimmunology|date=Feb 1, 2013|volume=2|issue=2|pages=e23082|pmid=23525565|doi=10.4161/onci.23082|pmc=3601180}} 7. ^{{cite journal|last1=Elbaz|first1=HA|last2=Stueckle|first2=TA|last3=Tse|first3=W|last4=Rojanasakul|first4=Y|last5=Dinu|first5=CZ|title=Digitoxin and its analogs as novel cancer therapeutics|journal=Experimental Hematology & Oncology|date=Apr 5, 2012|volume=1|issue=1|pages=4|pmid=23210930|doi=10.1186/2162-3619-1-4|pmc=3506989}} 8. ^{{cite journal|last1=Langenhan|first1=JM|last2=Peters|first2=NR|last3=Guzei|first3=IA|last4=Hoffmann|first4=FM|last5=Thorson|first5=JS|title=Enhancing the anticancer properties of cardiac glycosides by neoglycorandomization|journal=Proceedings of the National Academy of Sciences of the United States of America|date=Aug 30, 2005|volume=102|issue=35|pages=12305–10|pmid=16105948|doi=10.1073/pnas.0503270102|pmc=1194917}}
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