DGX

DIGOXIN

Created:	1999-07-08
Last modified:	2011-06-27

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4 entries where DGX is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	119
Chiral Atom Count	21
Bond Count	126
Aromatic Bond Count	0

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Chemical Component Summary
Name	DIGOXIN
Systematic Name (OpenEye OEToolkits)	3-[(3S,5R,8R,9S,10S,12R,13S,14S,17R)-10,13-dimethyl-3-[(2R,4S,5S,6R)-6-methyl-5-[(2S,4S,5S,6R)-6-methyl-5-[(2S,4S,5S,6R)-6-methyl-4,5-bis(oxidanyl)oxan-2-yl]oxy-4-oxidanyl-oxan-2-yl]oxy-4-oxidanyl-oxan-2-yl]oxy-12,14-bis(oxidanyl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
Formula	C₄₁ H₆₄ O₁₄
Molecular Weight	780.938
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	O=C1OCC(=C1)C2CCC8(O)C2(C)C(O)CC7C8CCC6CC(OC5OC(C(OC4OC(C(OC3OC(C)C(O)C(O)C3)C(O)C4)C)C(O)C5)C)CCC67C
SMILES	CACTVS	3.370	C[CH]1O[CH](C[CH](O)[CH]1O)O[CH]2[CH](O)C[CH](O[CH]2C)O[CH]3[CH](O)C[CH](O[CH]3C)O[CH]4CC[C]5(C)[CH](CC[CH]6[CH]5C[CH](O)[C]7(C)[CH](CC[C]67O)C8=CC(=O)OC8)C4
SMILES	OpenEye OEToolkits	1.7.2	CC1C(C(CC(O1)OC2C(OC(CC2O)OC3C(OC(CC3O)OC4CCC5(C(C4)CCC6C5CC(C7(C6(CCC7C8=CC(=O)OC8)O)C)O)C)C)C)O)O
Canonical SMILES	CACTVS	3.370	C[C@H]1O[C@H](C[C@H](O)[C@@H]1O)O[C@H]2[C@@H](O)C[C@@H](O[C@@H]2C)O[C@H]3[C@@H](O)C[C@@H](O[C@@H]3C)O[C@H]4CC[C@@]5(C)[C@H](CC[C@@H]6[C@@H]5C[C@@H](O)[C@]7(C)[C@H](CC[C@]67O)C8=CC(=O)OC8)C4
Canonical SMILES	OpenEye OEToolkits	1.7.2	C[C@@H]1[C@H]([C@H](C[C@@H](O1)O[C@@H]2[C@H](O[C@H](C[C@@H]2O)O[C@@H]3[C@H](O[C@H](C[C@@H]3O)O[C@H]4CC[C@]5([C@@H](C4)CC[C@@H]6[C@@H]5C[C@H]([C@]7([C@@]6(CC[C@@H]7C8=CC(=O)OC8)O)C)O)C)C)C)O)O
InChI	InChI	1.03	InChI=1S/C41H64O14/c1-19-36(47)28(42)15-34(50-19)54-38-21(3)52-35(17-30(38)44)55-37-20(2)51-33(16-29(37)43)53-24-8-10-39(4)23(13-24)6-7-26-27(39)14-31(45)40(5)25(9-11-41(26,40)48)22-12-32(46)49-18-22/h12,19-21,23-31,33-38,42-45,47-48H,6-11,13-18H2,1-5H3/t19-,20-,21-,23-,24+,25-,26-,27+,28+,29+,30+,31-,33+,34+,35+,36-,37-,38-,39+,40+,41+/m1/s1
InChIKey	InChI	1.03	LTMHDMANZUZIPE-PUGKRICDSA-N

Drug Info: DrugBank

DrugBank ID	DB00390
Name	Digoxin
Groups	approved
Description	Digoxin is one of the oldest cardiovascular medications used today.[A178225] It is a common agent used to manage atrial fibrillation and the symptoms of heart failure.[A178234] Digoxin is classified as a cardiac glycoside and was initially approved by the FDA in 1954.[L9143] This drug originates from the foxglove plant, also known as the _Digitalis_ plant[T610], studied by William Withering, an English physician and botanist in the 1780s.[A178237,A178240] Prior to this, a Welsh family, historically referred to as the _Physicians of Myddvai_, formulated drugs from this plant. They were one of the first to prescribe cardiac glycosides, according to ancient literature dating as early as the 1250s.[A178240]
Synonyms	Digossina 12β-hydroxydigitoxin Digoxine Digoxin Digoxina Digoxinum
Brand Names	Lanoxin Elx 0.05mg/ml Pediatric Lanoxin Inj 0.05mg/ml Pediatric Digox Lanoxin Tab 0.25mg Lanoxin Pediatric Digoxin Injection C.S.D. Truemed Group LLC Apo-digoxin Digoxin Injection C.S.D. PMS-digoxin Novo-digoxin Tab 0.25mg Digoxin Digitek Lanoxin Tab 0.0625mg Lanoxin Inj 0.25mg/ml Lanoxicaps Jamp Digoxin Lanoxin Tab 0.125mg
Indication	Digoxin is indicated in the following conditions: 1) For the treatment of mild to moderate heart failure in adult patients.[L9143] 2) To increase myocardial contraction in children diagnosed with heart failure.[L9143] 3) To maintain control ventricular rate in adult patients diagnosed with chronic atrial fibrillation.[L9143] In adults with heart failure, when it is clinically possible, digoxin should be administered in conjunction with a diuretic and an angiotensin-converting enzyme (ACE) inhibitor for optimum effects.[L9143]
Categories	Agents causing hyperkalemia Antiarrhythmic agents Bradycardia-Causing Agents BSEP/ABCB11 Substrates BSEP/ABCB11 Substrates with a Narrow Therapeutic Index Carbohydrates Cardanolides Cardenolides Cardiac Glycosides Cardiac Therapy Cardiotonic Agents Cardiovascular Agents Compounds used in a research, industrial, or household setting Digitalis Glycosides Digoxin and derivatives Digoxin, immunology Drugs that are Mainly Renally Excreted Drugs that are Mainly Renally Excreted with a Narrow Therapeutic Index Fused-Ring Compounds Glycosides Narrow Therapeutic Index Drugs OATP1B1/SLCO1B1 Inhibitors OATP1B1/SLCO1B1 Substrates P-glycoprotein inducers P-glycoprotein inhibitors P-glycoprotein substrates P-glycoprotein substrates with a Narrow Therapeutic Index Potential QTc-Prolonging Agents Protective Agents QTc Prolonging Agents
ATC-Code	C01AA05
CAS number	20830-75-5

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Sodium/potassium-transporting ATPase subunit alpha-1	MGKGVGRDKYEPAAVSEQGDKKGKKGKKDRDMDELKKEVSMDDHKLSLDE...	unknown	inhibitor
Cholesterol side-chain cleavage enzyme, mitochondrial	MLAKGLPPRSVLVKGCQTFLSAPREGLGRLRVPTGEGAGISTRSPRPFNE...	unknown	inhibitor
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	substrate,inhibitor,inducer
Solute carrier organic anion transporter family member 4C1	MKSAKGIENLAFVPSSPDILRRLSASPSQIEVSALSSDPQRENSQPQELQ...	unknown	substrate
Bile salt export pump	MSDSVILRSIKKFGEENDGFESDKSYNNDKKSRLQDEKKGDGVRVGFFQL...	unknown	substrate
Solute carrier organic anion transporter family member 1A2	MGETEKRIETHRIRCLSKLKMFLLAITCAFVSKTLSGSYMNSMLTQIERQ...	unknown	substrate
Organic solute transporter subunit alpha	MEPGRTQIKLDPRYTADLLEVLKTNYGIPSACFSQPPTAAQLLRALGPVE...	unknown	substrate
Organic solute transporter subunit beta	MEHSEGAPGDPAGTVVPQELLEEMLWFFRVEDASPWNHSILALAAVVVII...	unknown	substrate
Solute carrier organic anion transporter family member 1B1	MDQNQHLNKTAEAQPSENKKTRYCNGLKMFLAALSLSFIAKTLGAIIMKS...	unknown	substrate,inhibitor
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682