Compound: digoxin
SMILES: O=C1OCC(=C1)[C@@H]2[C@@]3([C@@](O)([C@H]4[C@@H]([C@@]5([C@@H](C[C@@H](O[C@@H]6O[C@@H]([C@@H](O[C@@H]7O[C@@H]([C@@H](O[C@@H]8O[C@@H]([C@@H](O)[C@H](C8)O)C)[C@H](C7)O)C)[C@H](C6)O)C)CC5)CC4)C)C[C@H]3O)CC2)C
InChIKey: LTMHDMANZUZIPE-PUGKRICDSA-N
Synonyms: digoxin, 20830-75-5, Lanoxin, Dilanacin, Rougoxin, Digacin, Digosin, Dynamos, Vanoxin, 12beta-Hydroxydigitoxin, Digoxine, Fargoxin, Lanoxicaps, Mapluxin, Natigoxin, Davoxin, Cardiogoxin, Cordioxil, Digoxina, Digoxinum, Eudigox, Lanacrist, Lanocardin, Toloxin, Stillacor-, Neo-Lanicor, Digoxin Pediatric, SK-Digoxin, Homolle's digitalin, Lanacordin, Acygoxin, Cardioxin, Digoksyna, Digonix, Digossina, Saroxin, Dixina, Lanoxin PG, Cardoxin, CHEBI:4551, Chloroformic digitalin, DTXSID5022934, LANOXIN PEDIATRIC, Digoxigenin-tridigitoxosid, NSC-95100, Lenoxin, DTXCID502934, 73K4184T59, Digitalis glycoside, 3-[(3S,5R,8R,9S,10S,12R,13S,14S,17R)-3-[(2R,4S,5S,6R)-5-[(2S,4S,5S,6R)-5-[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-12,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one, 3beta,12beta,14-Trihydroxy-5beta,14beta-card-20(22)-enolid-3-tridigitoxosid, (3beta,5beta,12beta)-3-((O-2,6-Dideoxy-beta-D-ribo-hexapyranosyl-(1-4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy)-12,14-dihydroxycard-20(22)-enolide, 4-[(1S,2S,5S,7R,10R,11S,14R,15S,16R)-5-{[(2R,4S,5S,6R)-5-{[(2S,4S,5S,6R)-5-{[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-11,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2,5-dihydrofuran-2-one, Card-20(22)-enolide, 3-((O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy)-12,14-dihydroxy-, (3beta,5beta,12beta)-, Card-20(22)-enolide, 3-((O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1.fwdarw.4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1.fwdarw.4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy)-12,14-dihydroxy-, (3beta,5beta,12beta)-, Digamex, Digox, NSC95100, Lanoxin-PG, 3-((3S,5R,8R,9S,10S,12R,13S,14S,17R)-3-((2R,4S,5S,6R)-5-((2S,4S,5S,6R)-5-((2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl)oxy-4-hydroxy-6-methyloxan-2-yl)oxy-4-hydroxy-6-methyloxan-2-yl)oxy-12,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta(a)phenanthren-17-yl)-2H-furan-5-one, 4-((1S,2S,5S,7R,10R,11S,14R,15S,16R)-5-(((2R,4S,5S,6R)-5-(((2S,4S,5S,6R)-5-(((2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl)oxy)-4-hydroxy-6-methyloxan-2-yl)oxy)-4-hydroxy-6-methyloxan-2-yl)oxy)-11,16-dihydroxy-2,15-dimethyltetracyclo(8.7.0.0^(2,7).0^(11,15))heptadecan-14-yl)-2,5-dihydrofuran-2-one, Nativelle, Digoxine, Boehringer, Digoxina, Lanoxin-125, Nativelle, Hemigoxine, RefChem:5754, C01AA05, 244-068-1, 3beta-(2,6-Dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyloxy)-12beta,14-dihydroxy-5beta,14beta-card-20(22)-enolide, 4-((1S,2S,5S,7R,10R,11S,14R,15S,16R)-5-(((2R,4S,5S,6R)-5-(((2S,4S,5S,6R)-5-(((2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl)oxy)-4-hydroxy-6-methyloxan-2-yl)oxy)-4-hydroxy-6-methyloxan-2-yl)oxy)-11,16-dihydroxy-2,15-dimethyltetracyclo(8.7.0.02,7.011,15)heptadecan-14-yl)-2,5-dihydrofuran-2-one, MLS000069819, MFCD00003674, SMR000059217, Digoxin Nativelle, (3beta,5beta,12beta)-3-{[2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl]oxy}-12,14-dihydroxycard-20(22)-enolide, NCGC00090797-03, Digoxin, analytical standard, Coragoxine, Lenoxicaps, Neodioxanin, Cardigox, Digomal, Lanikor, Lanorale, Purgoxin, Grexin, Digon, Dokim, Lanoxicaps (TN), [3H]digoxin, 3-[(3S,5R,8R,9S,10S,12R,13S,14S,17R)-3-[(2R,4S,5S,6R)-5-[(2S,4S,5S,6R)-5-[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-4-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-4-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-12,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one, SMR000653537, Lanoxin (TN), [3H]-digoxin, Digitek, Dimecip, Lifusin, Digos, Digoxin-Sandoz, Digoxina-Sandoz, Digoxin-Zori, NSC 95100, Digoxin RS, Digoxin CRS, Digoxine Navtivelle, Novodigal [inj.], Prestwick_170, Digoksyna [Polish], Digossina [DCIT], Hemigoxine Nativelle, CAS-20830-75-5, 12b-Hydroxydigitoxin, 12A-Hydroxydigitoxin, 3b0w, DIGOXIN [VANDF], Digoxinum [INN-Latin], DIGOXIN [HSDB], DIGOXIN [IARC], DIGOXIN [INN], DIGOXIN [JAN], DIGOXIN [MI], Digoxina [INN-Spanish], DIGOXIN [MART.], Opera_ID_1134, Prestwick0_000437, Prestwick1_000437, Prestwick2_000437, Prestwick3_000437, Digoxin (JP18/USP), DIGOXIN [USP-RS], DIGOXIN [WHO-DD], DIGOXIN [WHO-IP], 12 beta -Hydroxydigitoxin, Epitope ID:122964, CHEMBL1751, BIDD:PXR0148, SCHEMBL20506, BSPBio_000454, Digoxin, 1mg/ml in Methanol, MLS001055371, MLS001076495, orb104782, DIGOXIN [ORANGE BOOK], digoxin for peak identification, SPBio_002393, DIGOXIN [EP MONOGRAPH], BPBio1_000500, GTPL4725, GTPL4726, HSDB 214, DIGOXIN [USP MONOGRAPH], Digoxin [USP:INN:BAN:JAN], Digoxin 1.0 mg/ml in Methanol, BDBM46355, cid_2724385, DIGOXINUM [WHO-IP LATIN], REGID_for_CID_2724385, HMS1569G16, HMS2096G16, HMS2232G20, HMS3713G16, Human Serum - Digoxin, low level, UNII-73K4184T59, Digoxigenin-tridigitoxosid [German], Digoxin for peak identification CRS, Human Serum - Digoxin, high level, HY-B1049, MSK10026, EINECS 244-068-1, Tox21_111025, Tox21_201678, Tox21_303050, EBC-08615, HB1138, s4290, AKOS015895113, AKOS024283494, CCG-220437, CS-4571, DB00390, OD01513, BRN 0077011, NCGC00090797-01, NCGC00090797-02, NCGC00090797-04, NCGC00090797-05, NCGC00090797-06, NCGC00090797-07, NCGC00090797-09, NCGC00090797-12, NCGC00090797-15, NCGC00257022-01, NCGC00259227-01, 4-[(1R,3aS,3bR,5aR,7S,9aS,9bS,11R,11aS)-7-{[(2R,4S,5S,6R)-5-{[(2S,4S,5S,6R)-5-{[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-3a,11-dihydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]-2,5-dihydrofuran-2-one, AS-13281, ST069334, D1828, NS00008620, C06956, D00298, EN300-6492954, 5-18-04-00381 (Beilstein Handbook Reference), Q422222, SR-01000721866, Digoxin, certified reference material, TraceCERT(R), J-013666, SR-01000721866-3, SR-01000721866-4, BRD-K23478508-001-03-7, Digoxin, European Pharmacopoeia (EP) Reference Standard, Z2108699066, 0B9662A7-264E-4ACD-94B2-9E1138C0CA5A, Digoxin, United States Pharmacopeia (USP) Reference Standard, Digoxin, Pharmaceutical Secondary Standard; Certified Reference Material, Digoxin for peak identification, European Pharmacopoeia (EP) Reference Standard, -6-methyltetrahydro-2H-pyran-2-yl)oxy)-12,14-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)furan-2(5H)-one, 20(22),5b-Cardenolid-3b,12b,14b-triol 3b-2,6-dideoxy-4-o-[2 ,6-dideoxy-4-o-(2 ,6-dideoxy-b-d-ribohexopyranosyl)-b-d-ribohex  opyranoside], 3-[(3S,5R,10S,12R,13S,14S,17R)-3-[(2R,4S,5S,6R)-5-[(2S,4S,5S,6R)-5-[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-12,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one, 3.BETA.-((O-2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL-(1->4)-O-2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL-(1->4)-2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL)OXY)-12.BETA.,14-DIHYDROXY-5.BETA.-CARD-20(22)-ENOLIDE, 3beta-((O-2,6-Dideoxy-beta-D-ribo-hexopyranosyl-(1-4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy)-12beta,14-dihydroxy-5beta-card-20(22)-enolide, 3beta-{[2,6-Dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl]oxy}-12beta,14-dihydroxy-5beta-card-20(22)-enolide, 4-((1S,2S,5S,11S,15S,7R,10R,14R,16R)-5-{5-[5-((2S,4S,5S,6R)-4,5-dihydroxy-6-me thyl(2H-3,4,5,6-tetrahydropyran-2-yloxy))(4S,5S,2R,6R)-4-hydroxy-6-methyl(2H-3 ,4,5,6-tetrahydropyran-2-yloxy)](4S,5S,2R,, 4-((1S,2S,5S,11S,15S,7R,10R,14R,16R)-5-{5-[5-((2S,4S,5S,6R)-4,5-dihydroxy-6-me thyl(2H-3,4,5,6-tetrahydropyran-2-yloxy))(4S,5S,2R,6R)-4-hydroxy-6-methyl(2H-3 ,4,5,6-tetrahydropyran-2-yloxy)](4S,5S,2R,6R)-4-hydroxy-6-methyl(2H-3,4,5,6-te trahydropyran-2-yl, 4-((3S,5R,8R,9S,10S,12R,13S,14S,17R)-3-(((2R,4S,5S,6R)-5-(((2S,4S,5S,6R)-5-(((2S,4S,5S,6R)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-hydroxy, 6R)-4-hydroxy-6-methyl(2H-3,4,5,6-te trahydropyran-2-yloxy)}-11,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0<2,7>.0 <11,15>]heptadec-14-yl)-5-hydrofuran-2-one, CARD-20(22)-ENOLIDE, 3-((O-2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL-(1->4)-O-2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL-(1->4)-2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL)OXY)-12,14-DIHYDROXY-,(3.BETA.,5.BETA.,12.BETA.)-, Card-20(22)-enolide, 3-((O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy)-12,14-dihydroxy-, (3beta,5beta,12beta)-, Card-20(22)-enolide, 3-[[O-2,6-dideoxy-.beta.-D-ribo-hexopyranosyl-(1-->4)-O-2,6-dideoxy-.beta.-D-ribo-hexopyranosyl-(1-->4)-2,6-dideoxy-.beta.-D-ribo-hexopyranosyl]oxy]-12,14-dihydroxy-, (3.beta.,5.beta.,12.beta.)-
Theoretical properties:
molecular_formula: C41H64O14
molecular_weight: 780.9 g/mol
exact_mass: 780.42960671 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 6
hydrogen_bond_acceptor_count: 14
rotatable_bond_count: 7
heavy_atom_count: 55
topological_polar_surface_area: 203 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Colorless to white crystals, or white crystalline powder
color: Colorless to white crystals, or white crystalline powder
odor: Odorless
melting_point: 446 to 509 °F Decomposes. (EPA, 1998)
density: 1.36 g/cu cm at 20 °C
Descriptions:
{"pubchem": "Digoxin is a cardenolide glycoside that is digitoxin beta-hydroxylated at C-12. A cardiac glycoside extracted from the foxglove plant, Digitalis lanata, it is used to control ventricular rate in atrial fibrillation and in the management of congestive heart failure with atrial fibrillation, but the margin between toxic and therapeutic doses is small. It has a role as an anti-arrhythmia drug, a cardiotonic drug, an epitope and an EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor. It is a cardenolide glycoside and a steroid saponin. It is a conjugate acid of a digoxin(1-).", "chebi": "A  cardenolide glycoside that is digitoxin \u03b2-hydroxylated at C-12. A cardiac glycoside extracted from the foxglove plant, <em>Digitalis lanata</em>, it is used to control ventricular rate in atrial fibrillation and in the management of congestive heart failure with atrial fibrillation, but the margin between toxic and therapeutic doses is small.", "chembl": "DIGOXIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Digoxin, sold under the brand name Lanoxin among others, is a medication used to treat various heart conditions. Most frequently it is used for atrial fibrillation, atrial flutter, and heart failure. Digoxin is one of the oldest medications used in the field of cardiology. It works by increasing myocardial contractility, increasing stroke volume and blood pressure, reducing heart rate, and somewhat extending the time frame of the contraction. Digoxin is taken by mouth or by injection into a vein. Digoxin has a half life of approximately 36 hours given at average doses in patients with normal renal function. It is excreted mostly unchanged in the urine.\nCommon side effects include breast enlargement with other side effects generally due to an excessive dose. These side effects may include loss of appetite, nausea, trouble seeing, confusion, and an irregular heartbeat. Greater care is required in older people and those with poor kidney function. It is unclear whether use during pregnancy is safe.\nDigoxin is in the cardiac glycoside family of medications. It was first isolated in 1930 from Grecian foxglove (Digitalis lanata). It is on the World Health Organization's List of Essential Medicines. In 2021, it was the 241st most commonly prescribed medication in the United States, with more than 1 million prescriptions."}