Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C43H66O14 |
Molecular Weight | 806.9757 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 20 / 20 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]1(C[C@H](O)[C@H](O[C@@]2([H])C[C@H](O)[C@H](O[C@@]3([H])C[C@H](OC(C)=O)[C@H](O)[C@@H](C)O3)[C@@H](C)O2)[C@@H](C)O1)O[C@H]4CC[C@@]5(C)[C@]([H])(CC[C@]6([H])[C@]5([H])CC[C@]7(C)[C@H](CC[C@]67O)C8=CC(=O)OC8)C4
InChI
InChIKey=HPMZBILYSWLILX-UMDUKNJSSA-N
InChI=1S/C43H66O14/c1-21-38(48)33(54-24(4)44)19-37(51-21)57-40-23(3)53-36(18-32(40)46)56-39-22(2)52-35(17-31(39)45)55-27-9-12-41(5)26(16-27)7-8-30-29(41)10-13-42(6)28(11-14-43(30,42)49)25-15-34(47)50-20-25/h15,21-23,26-33,35-40,45-46,48-49H,7-14,16-20H2,1-6H3/t21-,22-,23-,26-,27+,28-,29+,30-,31+,32+,33+,35+,36+,37+,38-,39-,40-,41+,42-,43+/m1/s1
DescriptionCurator's Comment: description was created based on several sources, including
http://www.medscape.com/viewarticle/842364
Curator's Comment: description was created based on several sources, including
http://www.medscape.com/viewarticle/842364
Digoxin is a cardiac glycoside derived from the purple foxglove flower. In 1785, the English chemist, botanist, and physician Sir William Withering published his findings that Digitalis purpurea could be used to treat cardiac dropsy (congestive heart failure; CHF). Digoxin has been in use for many years, but was not approved by the FDA for treatment of heart failure (HF) until the late 1990s. Another FDA indication for digoxin is atrial fibrillation (AF). Digoxin also has numerous off-label uses, such as in fetal tachycardia, supra-ventricular tachycardia, cor pulmonale, and pulmonary hypertension. Digitoxin inhibits the Na-K-ATPase membrane pump, resulting in an increase in intracellular sodium and calcium concentrations. Increased intracellular concentrations of calcium may promote activation of contractile proteins (e.g., actin, myosin). Digoxin also has Para sympathomimetic properties. By increasing vagal tone in the sinoatrial and atrioventricular (AV) nodes, it slows the heart rate and AV nodal conduction.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2095186 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19751721 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | CRYSTODIGIN Approved UseIn adults, digoxin is indicated for the treatment of mild to moderate heart failure and for the control of resting ventricular rate in patients with chronic atrial fibrillation. (1). In pediatric patients with heart failure, digoxin increases myocardial contractility |
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Diagnostic | CRYSTODIGIN Approved UseIn adults, digoxin is indicated for the treatment of mild to moderate heart failure and for the control of resting ventricular rate in patients with chronic atrial fibrillation. (1). In pediatric patients with heart failure, digoxin increases myocardial contractility |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.76 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18823299/ |
0.25 mg 1 times / day steady-state, oral dose: 0.25 mg route of administration: Oral experiment type: STEADY-STATE co-administered: ETORICOXIB |
DIGITOXIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
1.32 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18823299/ |
0.25 mg 1 times / day steady-state, oral dose: 0.25 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
DIGITOXIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
13.3 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18823299/ |
0.25 mg 1 times / day steady-state, oral dose: 0.25 mg route of administration: Oral experiment type: STEADY-STATE co-administered: ETORICOXIB |
DIGITOXIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
12.5 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18823299/ |
0.25 mg 1 times / day steady-state, oral dose: 0.25 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
DIGITOXIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
9.5 day EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/914188/ |
0.5 mg single, intravenous dose: 0.5 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
DIGITOXIN unknown | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
7.4 day EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/914188/ |
0.5 mg single, oral dose: 0.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
DIGITOXIN unknown | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
9.7 day EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/914188/ |
0.5 mg single, oral dose: 0.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
DIGITOXIN unknown | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
0.1 mg 1 times / day multiple, oral Studied dose Dose: 0.1 mg, 1 times / day Route: oral Route: multiple Dose: 0.1 mg, 1 times / day Sources: |
healthy, 23 to 29 years n = 10 Health Status: healthy Age Group: 23 to 29 years Sex: M Population Size: 10 Sources: |
Other AEs: Color blindness acquired... |
0.2 mg 2 times / day multiple, oral (mean) Studied dose Dose: 0.2 mg, 2 times / day Route: oral Route: multiple Dose: 0.2 mg, 2 times / day Co-administed with:: digoxin(0.05 mg; 2 tablets per day) Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: heart failure Age Group: adult Sex: M+F Population Size: 179 Sources: |
Other AEs: Fatigue, Visual disorders NEC... Other AEs: Fatigue (53.1%) Sources: Visual disorders NEC (53.1%) Muscular weakness (45.8%) Nausea (45.2%) Anorexia (44.7%) Psychic disorder NOS (36.3%) Abdominal pain (36.3%) Dizziness (33%) Bad dreams (30.2%) Headache (25.1%) Diarrhoea (22.9%) Vomiting (22.3%) Pain retrosternal (5%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Color blindness acquired | 0.1 mg 1 times / day multiple, oral Studied dose Dose: 0.1 mg, 1 times / day Route: oral Route: multiple Dose: 0.1 mg, 1 times / day Sources: |
healthy, 23 to 29 years n = 10 Health Status: healthy Age Group: 23 to 29 years Sex: M Population Size: 10 Sources: |
|
Vomiting | 22.3% | 0.2 mg 2 times / day multiple, oral (mean) Studied dose Dose: 0.2 mg, 2 times / day Route: oral Route: multiple Dose: 0.2 mg, 2 times / day Co-administed with:: digoxin(0.05 mg; 2 tablets per day) Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: heart failure Age Group: adult Sex: M+F Population Size: 179 Sources: |
Diarrhoea | 22.9% | 0.2 mg 2 times / day multiple, oral (mean) Studied dose Dose: 0.2 mg, 2 times / day Route: oral Route: multiple Dose: 0.2 mg, 2 times / day Co-administed with:: digoxin(0.05 mg; 2 tablets per day) Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: heart failure Age Group: adult Sex: M+F Population Size: 179 Sources: |
Headache | 25.1% | 0.2 mg 2 times / day multiple, oral (mean) Studied dose Dose: 0.2 mg, 2 times / day Route: oral Route: multiple Dose: 0.2 mg, 2 times / day Co-administed with:: digoxin(0.05 mg; 2 tablets per day) Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: heart failure Age Group: adult Sex: M+F Population Size: 179 Sources: |
Bad dreams | 30.2% | 0.2 mg 2 times / day multiple, oral (mean) Studied dose Dose: 0.2 mg, 2 times / day Route: oral Route: multiple Dose: 0.2 mg, 2 times / day Co-administed with:: digoxin(0.05 mg; 2 tablets per day) Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: heart failure Age Group: adult Sex: M+F Population Size: 179 Sources: |
Dizziness | 33% | 0.2 mg 2 times / day multiple, oral (mean) Studied dose Dose: 0.2 mg, 2 times / day Route: oral Route: multiple Dose: 0.2 mg, 2 times / day Co-administed with:: digoxin(0.05 mg; 2 tablets per day) Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: heart failure Age Group: adult Sex: M+F Population Size: 179 Sources: |
Abdominal pain | 36.3% | 0.2 mg 2 times / day multiple, oral (mean) Studied dose Dose: 0.2 mg, 2 times / day Route: oral Route: multiple Dose: 0.2 mg, 2 times / day Co-administed with:: digoxin(0.05 mg; 2 tablets per day) Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: heart failure Age Group: adult Sex: M+F Population Size: 179 Sources: |
Psychic disorder NOS | 36.3% | 0.2 mg 2 times / day multiple, oral (mean) Studied dose Dose: 0.2 mg, 2 times / day Route: oral Route: multiple Dose: 0.2 mg, 2 times / day Co-administed with:: digoxin(0.05 mg; 2 tablets per day) Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: heart failure Age Group: adult Sex: M+F Population Size: 179 Sources: |
Anorexia | 44.7% | 0.2 mg 2 times / day multiple, oral (mean) Studied dose Dose: 0.2 mg, 2 times / day Route: oral Route: multiple Dose: 0.2 mg, 2 times / day Co-administed with:: digoxin(0.05 mg; 2 tablets per day) Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: heart failure Age Group: adult Sex: M+F Population Size: 179 Sources: |
Nausea | 45.2% | 0.2 mg 2 times / day multiple, oral (mean) Studied dose Dose: 0.2 mg, 2 times / day Route: oral Route: multiple Dose: 0.2 mg, 2 times / day Co-administed with:: digoxin(0.05 mg; 2 tablets per day) Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: heart failure Age Group: adult Sex: M+F Population Size: 179 Sources: |
Muscular weakness | 45.8% | 0.2 mg 2 times / day multiple, oral (mean) Studied dose Dose: 0.2 mg, 2 times / day Route: oral Route: multiple Dose: 0.2 mg, 2 times / day Co-administed with:: digoxin(0.05 mg; 2 tablets per day) Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: heart failure Age Group: adult Sex: M+F Population Size: 179 Sources: |
Pain retrosternal | 5% | 0.2 mg 2 times / day multiple, oral (mean) Studied dose Dose: 0.2 mg, 2 times / day Route: oral Route: multiple Dose: 0.2 mg, 2 times / day Co-administed with:: digoxin(0.05 mg; 2 tablets per day) Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: heart failure Age Group: adult Sex: M+F Population Size: 179 Sources: |
Fatigue | 53.1% | 0.2 mg 2 times / day multiple, oral (mean) Studied dose Dose: 0.2 mg, 2 times / day Route: oral Route: multiple Dose: 0.2 mg, 2 times / day Co-administed with:: digoxin(0.05 mg; 2 tablets per day) Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: heart failure Age Group: adult Sex: M+F Population Size: 179 Sources: |
Visual disorders NEC | 53.1% | 0.2 mg 2 times / day multiple, oral (mean) Studied dose Dose: 0.2 mg, 2 times / day Route: oral Route: multiple Dose: 0.2 mg, 2 times / day Co-administed with:: digoxin(0.05 mg; 2 tablets per day) Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: heart failure Age Group: adult Sex: M+F Population Size: 179 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes [IC50 14.2 uM] | ||||
yes [IC50 36 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
[Cardiac arrhythmia in old age caused by digitalis intoxication]. | 1967 Apr 27 |
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Influence of drugs, implanted into the hypothalamus, on the water consumption of rats. | 1968 Jan |
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Atrial dissociation due to digitalis toxicity. | 1968 Jun |
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[On the treatment of the digitalis-induced atrial tachycardia with AV conduction disorder. Experiences with sodium-magnesium aspartate]. | 1968 Mar 29 |
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Digitoxin induced cardiac necrosis and its inhibition. | 1969 |
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[Acute digitalic poisoning]. | 1970 Feb |
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[Spironolactone protection against experimental cardiopathy due to digitoxin, disodium phosphate and oil]. | 1970 Feb |
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Possible mechanism of the prevention of digitoxin toxicity by spironolactone in the mouse. | 1971 Jan |
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The clinical value of serum digitalis glycoside concentrations in the evaluation of drug toxicity. | 1971 Jul 6 |
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Protection by spironolactone and oxandrolone against chronic digitoxin or indomethacin intoxication. | 1971 Mar |
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His bundle electrocardiography during bidirectional tachycardia. | 1973 Jul |
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Effect of microsomal enzyme inducers on the biliary excretion of cardiac glycosides. | 1974 Nov |
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Transient global amnesia associated with cardiac arrhythmia and digitalis intoxication. | 1975 Sep-Oct |
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Hypotensive and antiarrhythmic effects of a new alkaloid, the 13-hydroxylupanine-2-pyrrolcarbonic acid ester, from the Madagascan plant Cadia ellisiana. | 1976 |
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Reversal of advanced digitoxin toxicity and modification of pharmacokinetics by specific antibodies and Fab fragments. | 1977 Dec |
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Digitalis delirium: a reminder. | 1980 Mar |
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Effects of atropine on the cardiac arrest induced by propranolol and digitoxin in dogs. | 1982 |
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[Digitoxin poisoning: reversing ventricular fibrillation with Fab fragments of anti-digoxin antibody]. | 1982 Dec 25 |
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Reversal of digitalis-induced mesenteric vasospasm by sodium nitroprusside. | 1982 Feb |
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Effect of age, clonidine or propranolol on behavioral toxicity induced with digitoxin in mice. | 1982 Sep |
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Study of the factors influencing cardiac growth. II. Digitoxin treatment and isoproterenol-induced cardiac hypertrophy in the rat. | 1985 |
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Effect of long-term administration of digoxin on exercise performance in chronic airflow obstruction. | 1985 Apr |
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Effect of digitoxin on cardiac arrhythmias in hemodialysis patients. | 1987 Nov 16 |
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Treatment of a patient with severe digitoxin intoxication by Fab fragments of anti-digitalis antibodies. | 1992 |
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[Digitoxin-induced thrombocytopenia]. | 1993 |
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Synthesis of 20-hydroxy-, 20-amino-, and 20-nitro-14-hydroxy-21-nor-5 beta,14 beta-pregnane C-3 glycosides and related derivatives: structure-activity relationships of pregnanes that bind to the digitalis receptor. | 1993 Jan 8 |
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Hepatorenal syndrome in cirrhotic patients: terlipressine is a safe and efficient treatment; propranolol and digitalic treatments: precipitating and preventing factors? | 2000 Oct |
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Chronic hypertension induced by ouabain but not digoxin in the rat: antihypertensive effect of digoxin and digitoxin. | 2000 Sep |
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Digitoxin medication and cancer; case control and internal dose-response studies. | 2001 |
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Treatment of congestive heart failure--current status of use of digitoxin. | 2001 |
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Adverse drug reaction monitoring--digitoxin overdosage in the elderly. | 2001 Aug |
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Cytotoxicity of digitoxin and related cardiac glycosides in human tumor cells. | 2001 Jun |
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Bidirectional tachycardia: two cases and a review. | 2002 Aug |
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Posterior encephalopathy with vasospasm: MRI and angiography. | 2003 Dec |
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Digitoxin mimics gene therapy with CFTR and suppresses hypersecretion of IL-8 from cystic fibrosis lung epithelial cells. | 2004 May 18 |
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Bidirectional ventricular tachycardia due to digitalis intoxication. | 2005 Feb |
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Iatrogenic sick sinus syndrome. | 2007 May |
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Heart failure drug digitoxin induces calcium uptake into cells by forming transmembrane calcium channels. | 2008 Feb 19 |
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Digitoxin elicits anti-inflammatory and vasoprotective properties in endothelial cells: Therapeutic implications for the treatment of atherosclerosis? | 2009 Oct |
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Antiherpes activity of glucoevatromonoside, a cardenolide isolated from a Brazilian cultivar of Digitalis lanata. | 2011 Oct |
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Digitoxin and a synthetic monosaccharide analog inhibit cell viability in lung cancer cells. | 2012 Jan 1 |
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Ouabain, a cardiac glycoside, inhibits the Fanconi anemia/BRCA pathway activated by DNA interstrand cross-linking agents. | 2013 |
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Interaction of digitalis-like compounds with p-glycoprotein. | 2013 Feb |
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A novel cell-based high-throughput screen for inhibitors of HIV-1 gene expression and budding identifies the cardiac glycosides. | 2014 Apr |
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Utilization of human nuclear receptors as an early counter screen for off-target activity: a case study with a compendium of 615 known drugs. | 2015 Jun |
Patents
Sample Use Guides
Age Oral Loading Dose, mcg/kg
Premature: 20 - 30; Full-Term 25 - 35; 1 to 24 months 35 - 60; 2 to 5 years 30 - 45; 5 to 10 years 20 - 35; Over 10 years 10 - 15
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23858296
Curator's Comment: digitoxin inhibits interaction of NFAT1 with the proximal c-MYC promoter
Unknown
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QC01AA01
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WHO-ATC |
C01AA01
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NCI_THESAURUS |
C47793
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NCI_THESAURUS |
C66894
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0ZV4Q4L2FU
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ACETYLDIGITOXIN
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CHEMBL3545057
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53773
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0ZV4Q4L2FU
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SUB05230MIG
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67
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DB00511
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m1354
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1111-39-3
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DTXSID6022551
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214-178-4
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6794
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100000084600
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5284512
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792
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C65212
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132871
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PRIMARY | RxNorm |
ACTIVE MOIETY
SUBSTANCE RECORD