Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C9H11NO4 |
Molecular Weight | 197.1879 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
N[C@@H](CC1=CC(O)=C(O)C=C1)C(O)=O
InChI
InChIKey=WTDRDQBEARUVNC-LURJTMIESA-N
InChI=1S/C9H11NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6,11-12H,3,10H2,(H,13,14)/t6-/m0/s1
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/21080185Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/23948989
http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021485s20lbl.pdf
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21080185
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/23948989
http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021485s20lbl.pdf
Levodopa (L-DOPA) was first isolated from seedlings of Vicia faba by Marcus Guggenheim in 1913. Levodopa, a dopamine precursor, is an effective and well-tolerated dopamine replacement agent used to treat Parkinson's disease. Oral levodopa has been widely used for over 40 years, often in combination with a dopa-decarboxylase inhibitor carbidopa, which reduces many treatment complications, extending its half-life and increasing levodopa availability to the brain. Entacapone, a catechol-O-methyltransferase inhibitor, can also be used to improve the bioavailability of levodopa, especially when used in conjunction with a carbidopa.
CNS Activity
Originator
Sources: https://newdrugapprovals.org/tag/levodopa/
Curator's Comment: # Hoffmann-La Roche
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2056 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18851961 |
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Target ID: CHEMBL2096905 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Stalevo Approved UseStalevo® (carbidopa, levodopa and entacapone) is indicated to treat patients with idiopathic Parkinson’s disease. Launch Date2003 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.946 μg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/22549097 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: CARBIDOPA, DL- |
LEVODOPA plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
84.8 μg × min/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/22549097 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: CARBIDOPA, DL- |
LEVODOPA plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
78.7 min EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/22549097 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: CARBIDOPA, DL- |
LEVODOPA plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
80% |
LEVODOPA plasma | Homo sapiens |
Doses
Dose | Population | Adverse events |
---|---|---|
3 g 1 times / day multiple, oral Dose: 3 g, 1 times / day Route: oral Route: multiple Dose: 3 g, 1 times / day Sources: |
unhealthy, 54 years |
Disc. AE: Alopecia... AEs leading to discontinuation/dose reduction: Alopecia (1 patient) Sources: |
420 mg 1 times / day multiple, respiratory Recommended Dose: 420 mg, 1 times / day Route: respiratory Route: multiple Dose: 420 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
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84 mg 2 times / day multiple, respiratory Recommended Dose: 84 mg, 2 times / day Route: respiratory Route: multiple Dose: 84 mg, 2 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Disc. AE: Cough... AEs leading to discontinuation/dose reduction: Cough (2%) Sources: |
0.51 mg/kg 3 times / day steady, oral Dose: 0.51 mg/kg, 3 times / day Route: oral Route: steady Dose: 0.51 mg/kg, 3 times / day Sources: |
unhealthy, child|adult Health Status: unhealthy Age Group: child|adult Sources: |
Other AEs: Headache, Nausea... Other AEs: Headache (below serious, 2 patients) Sources: Nausea (below serious, 2 patients) |
0.76 mg/kg 3 times / day steady, oral Dose: 0.76 mg/kg, 3 times / day Route: oral Route: steady Dose: 0.76 mg/kg, 3 times / day Sources: |
unhealthy, child|adult Health Status: unhealthy Age Group: child|adult Sources: |
Other AEs: Headache, Dry mouth... Other AEs: Headache (below serious, 1 patient) Sources: Dry mouth (below serious, 2 patients) Nausea (below serious, 1 patient) Fatigue (below serious, 2 patients) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Alopecia | 1 patient Disc. AE |
3 g 1 times / day multiple, oral Dose: 3 g, 1 times / day Route: oral Route: multiple Dose: 3 g, 1 times / day Sources: |
unhealthy, 54 years |
Cough | 2% Disc. AE |
84 mg 2 times / day multiple, respiratory Recommended Dose: 84 mg, 2 times / day Route: respiratory Route: multiple Dose: 84 mg, 2 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Headache | below serious, 2 patients | 0.51 mg/kg 3 times / day steady, oral Dose: 0.51 mg/kg, 3 times / day Route: oral Route: steady Dose: 0.51 mg/kg, 3 times / day Sources: |
unhealthy, child|adult Health Status: unhealthy Age Group: child|adult Sources: |
Nausea | below serious, 2 patients | 0.51 mg/kg 3 times / day steady, oral Dose: 0.51 mg/kg, 3 times / day Route: oral Route: steady Dose: 0.51 mg/kg, 3 times / day Sources: |
unhealthy, child|adult Health Status: unhealthy Age Group: child|adult Sources: |
Headache | below serious, 1 patient | 0.76 mg/kg 3 times / day steady, oral Dose: 0.76 mg/kg, 3 times / day Route: oral Route: steady Dose: 0.76 mg/kg, 3 times / day Sources: |
unhealthy, child|adult Health Status: unhealthy Age Group: child|adult Sources: |
Nausea | below serious, 1 patient | 0.76 mg/kg 3 times / day steady, oral Dose: 0.76 mg/kg, 3 times / day Route: oral Route: steady Dose: 0.76 mg/kg, 3 times / day Sources: |
unhealthy, child|adult Health Status: unhealthy Age Group: child|adult Sources: |
Dry mouth | below serious, 2 patients | 0.76 mg/kg 3 times / day steady, oral Dose: 0.76 mg/kg, 3 times / day Route: oral Route: steady Dose: 0.76 mg/kg, 3 times / day Sources: |
unhealthy, child|adult Health Status: unhealthy Age Group: child|adult Sources: |
Fatigue | below serious, 2 patients | 0.76 mg/kg 3 times / day steady, oral Dose: 0.76 mg/kg, 3 times / day Route: oral Route: steady Dose: 0.76 mg/kg, 3 times / day Sources: |
unhealthy, child|adult Health Status: unhealthy Age Group: child|adult Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
[Abnormal movements induced by L-dopa. New therapeutic possibilities]. | 1975 Jan 25 |
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Levodopa-induced myoclonus. | 1975 May |
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A unified dyskinesias rating scale for L-dopa-induced dyskinesias? | 1999 |
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Comparative effects of unilateral and bilateral subthalamic nucleus deep brain stimulation. | 1999 Aug 11 |
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Nigral endothelial dysfunction, homocysteine, and Parkinson's disease. | 1999 Jul 10 |
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Short-term effects of high-dose 17beta-estradiol in postmenopausal PD patients: a crossover study. | 1999 Jul 13 |
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Selective inhibition of cocaine-seeking behaviour by a partial dopamine D3 receptor agonist. | 1999 Jul 22 |
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Medication-induced hallucination and cerebral blood flow in Parkinson's disease. | 1999 May |
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Actions of adenosine A2A receptor antagonist KW-6002 on drug-induced catalepsy and hypokinesia caused by reserpine or MPTP. | 1999 Nov |
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Dopamine D2 receptor gene polymorphism and the risk of levodopa-induced dyskinesias in PD. | 1999 Oct 22 |
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Punding on L-dopa. | 1999 Sep |
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Functional mapping of the human globus pallidus: contrasting effect of stimulation in the internal and external pallidum in Parkinson's disease. | 2000 |
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Effects of oligonucleotide antisense to dopamine D(1A) receptor messenger RNA in a rodent model of levodopa-induced dyskinesia. | 2000 |
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Tolcapone increases maximum concentration of levodopa. | 2000 |
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Preventing levodopa-induced dyskinesias. | 2000 Apr |
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Investigating levodopa-induced dyskinesias in the parkinsonian primate. | 2000 Apr |
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Quetiapine for l-dopa-induced psychosis in PD. | 2000 Apr 11 |
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Sleep attacks and Parkinson's disease treatment. | 2000 Apr 15 |
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AMPA receptor blockade improves levodopa-induced dyskinesia in MPTP monkeys. | 2000 Apr 25 |
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[Dopaminergic agonists in the treatment of Parkinson's disease]. | 2000 Dec |
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Four novel mutations in the tyrosine hydroxylase gene in patients with infantile parkinsonism. | 2000 Jan |
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L-Dopa uptake and dopamine production in proximal tubular cells are regulated by beta(2)-adrenergic receptors. | 2000 Jul |
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Embryonic ventral mesencephalic grafts improve levodopa-induced dyskinesia in a rat model of Parkinson's disease. | 2000 Jul |
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Population pharmacokinetics of levodopa in patients with Parkinson's disease treated with tolcapone. | 2000 Jun |
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[Worsened orthostatic hypotension due to levodopa administration in a case of Parkinson's disease]. | 2000 Mar |
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The effect of amantadine on levodopa-induced dyskinesias in Parkinson's disease: a double-blind, placebo-controlled study. | 2000 Mar-Apr |
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Relationship among nigrostriatal denervation, parkinsonism, and dyskinesias in the MPTP primate model. | 2000 May |
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Levodopa-induced dyskinesias in Parkinson's disease: is sensitization reversible? | 2000 May |
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Workshop IV: drug treatment guidelines for the long-term management of Parkinson's disease. | 2000 Sep |
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Pathologic gambling in Parkinson's disease: a behavioral manifestation of pharmacologic treatment? | 2000 Sep |
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Apomorphine: an underutilized therapy for Parkinson's disease. | 2000 Sep |
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Pharmacokinetic-pharmacodynamic relationship of levodopa with and without tolcapone in patients with Parkinson's disease. | 2001 |
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A study of excessive daytime sleepiness and its clinical significance in three groups of Parkinson's disease patients taking pramipexole, cabergoline and levodopa mono and combination therapy. | 2001 |
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Efficacy and tolerability of entacapone as adjunctive therapy to levodopa in patients with Parkinson's disease and end-of-dose deterioration in daily medical practice: an open, multicenter study. | 2001 |
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High dose naltrexone for dyskinesias induced by levodopa. | 2001 Apr |
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Localization of a novel locus for autosomal recessive early-onset parkinsonism, PARK6, on human chromosome 1p35-p36. | 2001 Apr |
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Selective dopaminergic vulnerability: 3,4-dihydroxyphenylacetaldehyde targets mitochondria. | 2001 Apr 15 |
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SCH 58261, an A(2A) adenosine receptor antagonist, counteracts parkinsonian-like muscle rigidity in rats. | 2001 Aug |
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Dopamine D(2) receptors regulate tyrosine hydroxylase activity and phosphorylation at Ser40 in rat striatum. | 2001 Feb |
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Induction by dopamine D1 receptor agonist ABT-431 of dyskinesia similar to levodopa in patients with Parkinson disease. | 2001 Feb |
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Accelerometric assessment of levodopa-induced dyskinesias in Parkinson's disease. | 2001 Jan |
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SPECT imaging of the dopamine transporter in juvenile-onset dystonia. | 2001 Jan 23 |
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Biogenic aldehyde(s) derived from the action of monoamine oxidase may mediate the antidipsotropic effect of daidzin. | 2001 Jan 30 |
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Does stimulation of the GPi control dyskinesia by activating inhibitory axons? | 2001 Mar |
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Effects of N-(2-chloroethyl)-N-ethyl-2-bromobenzylamine (DSP4) on alpha2-adrenoceptors which regulate the synthesis and release of noradrenaline in the rat brain. | 2001 Mar |
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Event-related functional magnetic resonance imaging in Parkinson's disease before and after levodopa. | 2001 Mar |
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Comparative analysis of the gait disorder of normal pressure hydrocephalus and Parkinson's disease. | 2001 Mar |
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The effect of levodopa on vocal function in Parkinson's disease. | 2001 Mar-Apr |
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Levodopa-induced drowsiness in healthy volunteers: results of a choice reaction time test combined with a subjective evaluation of sedation. | 2001 Mar-Apr |
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Biperiden enhances L-DOPA methyl ester and dopamine D(l) receptor agonist SKF-82958 but antagonizes D(2)/D(3) receptor agonist rotigotine antihemiparkinsonian actions. | 2008 Dec 3 |
Patents
Sample Use Guides
Maximum dosage in a 24-hour period is eight tablets (Stalevo 50, containing 12.5 mg of carbidopa, 50 mg of levodopa and 200 mg of entacapone; Stalevo 75, containing 18.75 mg of carbidopa, 75 mg of levodopa and 200 mg of entacapone; Stalevo 100, containing 25 mg of carbidopa, 100 mg of levodopa and 200 mg of entacapone; Stalevo 125, containing 31.25 mg of carbidopa, 125 mg of levodopa and 200 mg of entacapone; Stalevo 150, containing 37.5 mg of carbidopa, 150 mg of levodopa and 200 mg of entacapone; Stalevo 200, containing 50 mg of carbidopa, 200 mg of levodopa and 200 mg of entacapone). The optimum daily dosage must be determined by careful titration in each patient.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24743653
Low dose (<30 uM) Levodopa protects PC12 cells against oxidative stress which might be related to the up-regulation of CD39 and pCREB expression.
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QN04BA03
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DSLD |
1198 (Number of products:24)
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WHO-ESSENTIAL MEDICINES LIST |
09 (LEV/CAR)
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EMA ASSESSMENT REPORTS |
CORBILTA (AUTHORIZED: PARKINSON DISEASE)
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EU-Orphan Drug |
EU/3/01/035
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EMA ASSESSMENT REPORTS |
STALEVO (AUTHORIZED: PARKINSON DISEASE)
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WHO-ATC |
N04BA01
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EMA ASSESSMENT REPORTS |
CORBILTA (AUTHORIZED: NEURODEGENERATIVE DISEASES)
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WHO-VATC |
QN04BA02
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WHO-ATC |
N04BA03
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WHO-VATC |
QN04BA01
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LOINC |
79577-3
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NDF-RT |
N0000193220
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LIVERTOX |
NBK548734
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FDA ORPHAN DRUG |
129499
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NDF-RT |
N0000175754
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WHO-ATC |
N04BA02
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NCI_THESAURUS |
C66884
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NDF-RT |
N0000175755
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EMA ASSESSMENT REPORTS |
LEVODOPA/CARBIDOPA/ENTACAPONE ORION (AUTHORIZED: PARKINSON DISEASE)
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EMA ASSESSMENT REPORTS |
CORBILTA (AUTHORIZED: NERVOUS SYSTEM DISEASES)
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6047
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L-DOPA
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Levodopa
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LEVODOPA
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PRIMARY | Description: A white or almost white, crystalline powder; odourless. Solubility: Soluble in 300 parts of water; practically insoluble in ethanol (~750 g/l) TS and ether R. Category: Antiparkinsonism drug. Storage: Levodopa should be kept in a tightly closed container.Definition: Levodopa contains not less than 98.5% and not more than 101.0% of C9H11NO4, calculated with reference to the dried substance. | ||
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D007980
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m6786
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2651
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200-445-2
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6375
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PRIMARY | RxNorm |
ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE ACTIVE (PRODRUG)
PARENT (METABOLITE)
PRODRUG (METABOLITE ACTIVE)
PRODRUG (METABOLITE ACTIVE)
PRODRUG (METABOLITE ACTIVE)
PRODRUG (METABOLITE ACTIVE)