Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0497)
Drug Name
Digitoxin
Synonyms
Digicor; Digilong; Digimerck; Digipural; Digisidin; Digitaline; Digitaline nativelle; Digitoksim; Digitoksin; Digitophyllin; Digitossina [DCIT]; Digitoxigenin tridigitoxoside; Digitoxinum; Digitoxoside; Digitoxosidum; Digitrin; Ditaven; Asthenthilo; Cardidigin; Cardigin; Carditalin; Carditoxin; Coramedan; Cristapurat; Crystalline digitalin; Crystodigin; Crystodigin (TN); De-Tone; Glucodigin; Lanatoxin; Mono-glycocard; Monodigitoxoside; Myodigin; Natigal; Purodigin; Purpurid; Tardigal; Unidigin; digitoxin; 71-63-6; Acedoxin; UNII-E90NZP2L9U
Indication Congestive heart failure [ICD11: BD10] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 764.9 Topological Polar Surface Area 183
Heavy Atom Count 54 Rotatable Bond Count 7
Hydrogen Bond Donor Count 5 Hydrogen Bond Acceptor Count 13
Cross-matching ID
PubChem CID
441207
PubChem SID
9170 ; 3139545 ; 7847363 ; 7979082 ; 10298760 ; 11533060 ; 12015761 ; 14889043 ; 16335905 ; 24434759 ; 24893976 ; 26754429 ; 29204037 ; 36885098 ; 46506035 ; 47349645 ; 48169692 ; 48318721 ; 48394206 ; 48415893 ; 48496158 ; 50109842 ; 50333813 ; 53787897 ; 57287891 ; 57403584 ; 85300744 ; 85842716 ; 87567202 ; 92298457 ; 103556970 ; 104624909 ; 124573763 ; 127284350 ; 127284351 ; 127303961 ; 127303962 ; 127303963 ; 127303964 ; 127303965 ; 127303966 ; 127303967 ; 127303968 ; 127303969 ; 127303970 ; 134337444 ; 134972304 ; 135377837 ; 135756584 ; 137004198
ChEBI ID
ChEBI:28544
CAS Number
71-63-6
TTD Drug ID
D0M3QP
Formula
C41H64O13
Canonical SMILES
CC1C(C(CC(O1)OC2C(OC(CC2O)OC3C(OC(CC3O)OC4CCC5(C(C4)CCC6C5CCC7(C6(CCC7C8=CC(=O)OC8)O)C)C)C)C)O)O
InChI
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
InChIKey
WDJUZGPOPHTGOT-XUDUSOBPSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Digitoxigenin DM000078
4369270
Unclear 1 [6]
Digitoxigenin-bisdigitoxoside DM000081
13084076
Oxidation - Oxidation 1 [2] , [3]
Digitoxigenin-monodigitoxoside DM000082
11961867
Oxidation - Oxidation 1 [2]
Digoxin DM003057
2724385
Unclear 1 [6]
Dihydrodigitoxin DM000080
19621
Unclear 1 [6]
Epidigitoxigenin DM000083
12305991
Unclear 1 [7]
Digitoxigenin sulfated cardioinactive compound DM000079 N. A. Conjugation - Conjugation 2 [6]
Unclear DM009999 N. A. Conjugation - Conjugation 2 [7]
Unclear DM009999 N. A. Unclear 2 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000842 Digitoxin Digitoxigenin Unclear Unclear [6]
MR000843 Digitoxin Dihydrodigitoxin Unclear Unclear [6]
MR000844 Digitoxin Digitoxigenin-bisdigitoxoside Oxidation - Oxidation CYP [2], [3]
MR000845 Digitoxin Digitoxigenin-monodigitoxoside Oxidation - Oxidation Unclear [2]
MR000846 Digitoxin Epidigitoxigenin Unclear Unclear [7]
MR000847 Digitoxin Digoxin Unclear Unclear [6]
MR000839 Digitoxigenin Digitoxigenin sulfated cardioinactive compound Conjugation - Conjugation Unclear [6]
MR000840 Digitoxigenin-monodigitoxoside . Unclear UGT [3]
MR000841 Epidigitoxigenin . Conjugation - Conjugation Unclear [7]
⏷ Show the Full List of 9 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Sulfotransferase 1A1 (SULT1A1) DME0008 Homo sapiens
ST1A1_HUMAN
2.8.2.1
[3]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[4]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1364 Bacteroides coprophilus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1366 Bacteroides eggerthii Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1376 Bacteroides ovatus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1379 Bacteroides stercoris Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1393 Blautia hansenii Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1404 Clostridium sporogenes Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1445 Parabacteroides distasonis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1446 Parabacteroides johnsonii Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1447 Parabacteroides merdae Not Available Not Available [5]
⏷ Show the Full List of 20  DME(s)
References
1 Digitoxin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Species differences in the toxicity and cytochrome P450 IIIA-dependent metabolism of digitoxin. Mol Pharmacol. 1991 Nov;40(5):859-67.
3 Hydroxysteroid sulfotransferase and a specific UDP-glucuronosyltransferase are involved in the metabolism of digitoxin in man. Naunyn Schmiedebergs Arch Pharmacol. 1992 Aug;346(2):226-33.
4 Use of a human liver microsome bank in drug glucuronidation studies. Toxicol In Vitro. 1991;5(5-6):559-62.
5 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
6 McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 1999. Bethesda, MD:American Society of Health-System Pharmacists, Inc. 1999 (Plus Supplements)., p. 1760
7 Ellenhorn, M.J. and D.G. Barceloux. Medical Toxicology - Diagnosis and Treatment of Human Poisoning. New York, NY:Elsevier Science Publishing Co., Inc. 1988., p. 201

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