U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of LEVODOPA

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

HIDE SMILES / InChI

Description
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.

Originator

Curator's Comment: # Hoffmann-La Roche

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Stalevo

Approved Use

Stalevo® (carbidopa, levodopa and entacapone) is indicated to treat patients with idiopathic Parkinson’s disease.

Launch Date

2003
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.946 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
84.8 μg × min/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
78.7 min
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

Funbound

ValueDoseCo-administeredAnalytePopulation
80%
LEVODOPA plasma
Homo sapiens
Doses

Doses

DosePopulationAdverse 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
n = 1
Health Status: unhealthy
Condition: idiopathic Parkinson's disease
Age Group: 54 years
Sex: F
Population Size: 1
Sources:
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
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
n = 114
Health Status: unhealthy
Condition: Parkinson’s disease
Age Group: adult
Population Size: 114
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
n = 15
Health Status: unhealthy
Condition: Vision Impairment
Age Group: child|adult
Population Size: 15
Sources:
Other AEs: Headache, Nausea...
Other AEs:
Headache (below serious, 2 patients)
Nausea (below serious, 2 patients)
Sources:
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
n = 15
Health Status: unhealthy
Condition: Vision Impairment
Age Group: child|adult
Population Size: 15
Sources:
Other AEs: Headache, Dry mouth...
Other AEs:
Headache (below serious, 1 patient)
Dry mouth (below serious, 2 patients)
Nausea (below serious, 1 patient)
Fatigue (below serious, 2 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
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
n = 1
Health Status: unhealthy
Condition: idiopathic Parkinson's disease
Age Group: 54 years
Sex: F
Population Size: 1
Sources:
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
n = 114
Health Status: unhealthy
Condition: Parkinson’s disease
Age Group: adult
Population Size: 114
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
n = 15
Health Status: unhealthy
Condition: Vision Impairment
Age Group: child|adult
Population Size: 15
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
n = 15
Health Status: unhealthy
Condition: Vision Impairment
Age Group: child|adult
Population Size: 15
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
n = 15
Health Status: unhealthy
Condition: Vision Impairment
Age Group: child|adult
Population Size: 15
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
n = 15
Health Status: unhealthy
Condition: Vision Impairment
Age Group: child|adult
Population Size: 15
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
n = 15
Health Status: unhealthy
Condition: Vision Impairment
Age Group: child|adult
Population Size: 15
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
n = 15
Health Status: unhealthy
Condition: Vision Impairment
Age Group: child|adult
Population Size: 15
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Metoclopramide and pimozide in Parkinson's disease and levodopa-induced dyskinesias.
1975 Apr
The effects of combining carbidopa with levodopa for Parkinson's disease.
1975 Dec
Levodopa-induced postural hypotension. Treatment with fludrocortisone.
1975 Jan
[Abnormal movements induced by L-dopa. New therapeutic possibilities].
1975 Jan 25
Persistent parkinsonism following neuroleptanalgesia.
1975 May
Functional mapping of the human globus pallidus: contrasting effect of stimulation in the internal and external pallidum in Parkinson's disease.
2000
[Amantadine for the treatment of levodopa dyskinesias in Parkinson's disease].
2000
Tolcapone increases maximum concentration of levodopa.
2000
Preventing levodopa-induced dyskinesias.
2000 Apr
Investigating levodopa-induced dyskinesias in the parkinsonian primate.
2000 Apr
Bilateral subthalamic stimulation for Parkinson's disease by using three-dimensional stereotactic magnetic resonance imaging and electrophysiological guidance.
2000 Apr
Quetiapine for l-dopa-induced psychosis in PD.
2000 Apr 11
Evidence of functional somatotopy in GPi from results of pallidotomy.
2000 Dec
Four novel mutations in the tyrosine hydroxylase gene in patients with infantile parkinsonism.
2000 Jan
Idazoxan is ineffective for levodopa-induced dyskinesias in Parkinson's disease.
2000 Mar
The effect of amantadine on levodopa-induced dyskinesias in Parkinson's disease: a double-blind, placebo-controlled study.
2000 Mar-Apr
Relationship among nigrostriatal denervation, parkinsonism, and dyskinesias in the MPTP primate model.
2000 May
Centrally initiated postural adjustments in parkinsonian patients on and off levodopa.
2000 Nov
Expression of metallothionein-III mRNA and its regulation by levodopa in the basal ganglia of hemi-parkinsonian rats.
2000 Oct 20
Workshop IV: drug treatment guidelines for the long-term management of Parkinson's disease.
2000 Sep
Apomorphine: an underutilized therapy for Parkinson's disease.
2000 Sep
Adverse drug reactions to selegiline: a review of the French pharmacovigilance database.
2000 Sep-Oct
Pharmacokinetic-pharmacodynamic relationship of levodopa with and without tolcapone in patients with Parkinson's disease.
2001
Melanogenesis by tyrosinase action on 3,4-dihydroxyphenylalanine (DOPA) in the presence of polyethylene glycol: a matrix-assisted laser desorption/ionization mass spectrometric investigation.
2001
Inhibition of potato polyphenol oxidase by anions and activity in various carboxylate buffers (pH 4.8) at constant ionic strength.
2001
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
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
High dose naltrexone for dyskinesias induced by levodopa.
2001 Apr
Localization of a novel locus for autosomal recessive early-onset parkinsonism, PARK6, on human chromosome 1p35-p36.
2001 Apr
Selective dopaminergic vulnerability: 3,4-dihydroxyphenylacetaldehyde targets mitochondria.
2001 Apr 15
Dimeric L-dopa derivatives as potential prodrugs.
2001 Apr 23
SCH 58261, an A(2A) adenosine receptor antagonist, counteracts parkinsonian-like muscle rigidity in rats.
2001 Aug
Dopamine D(2) receptors regulate tyrosine hydroxylase activity and phosphorylation at Ser40 in rat striatum.
2001 Feb
Accelerometric assessment of levodopa-induced dyskinesias in Parkinson's disease.
2001 Jan
SPECT imaging of the dopamine transporter in juvenile-onset dystonia.
2001 Jan 23
Enhanced abilities of highly swollen chitosan beads for color removal and tyrosinase immobilization.
2001 Jan 29
Biogenic aldehyde(s) derived from the action of monoamine oxidase may mediate the antidipsotropic effect of daidzin.
2001 Jan 30
Role of peroxynitrite in macrophage microbicidal mechanisms in vivo revealed by protein nitration and hydroxylation.
2001 Jun 1
Resveratrol and a novel tyrosinase in Carignan grape juice.
2001 Mar
Does stimulation of the GPi control dyskinesia by activating inhibitory axons?
2001 Mar
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
Event-related functional magnetic resonance imaging in Parkinson's disease before and after levodopa.
2001 Mar
The effect of levodopa on vocal function in Parkinson's disease.
2001 Mar-Apr
Levodopa-induced drowsiness in healthy volunteers: results of a choice reaction time test combined with a subjective evaluation of sedation.
2001 Mar-Apr
Parkinsonism after glycine-derivate exposure.
2001 May
Speech dysfluency exacerbated by levodopa in Parkinson's disease.
2001 May
Intravenous amantadine improves levadopa-induced dyskinesias: an acute double-blind placebo-controlled study.
2001 May
Chromium(VI) reduction by catechol(amine)s results in DNA cleavage in vitro: relevance to chromium genotoxicity.
2001 May
Coadministration of (-)-OSU6162 with l-DOPA normalizes preproenkephalin mRNA expression in the sensorimotor striatum of primates with unilateral 6-OHDA lesions.
2001 May
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
Low dose (<30 uM) Levodopa protects PC12 cells against oxidative stress which might be related to the up-regulation of CD39 and pCREB expression.
Name Type Language
LEVODOPA
EMA EPAR   EP   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
INN   USAN  
Official Name English
LEVODOPA [JAN]
Common Name English
RYTARY COMPONENT LEVODOPA
Brand Name English
CARBILEV COMPONENT LEVODOPA
Common Name English
levodopa [INN]
Common Name English
LEVODOPA COMPONENT OF SINEMET
Common Name English
V-1512
Code English
LEVODOPA [WHO-IP]
Common Name English
LEVODOPA [ORANGE BOOK]
Common Name English
CORBILTA COMPONENT LEVODOPA
Brand Name English
LEVODOPA [EMA EPAR]
Common Name English
L-DOPA
Systematic Name English
LEVODOPA [USP-RS]
Common Name English
LEVODOPA COMPONENT OF DUOPA
Brand Name English
BENDOPA
Brand Name English
LEVODOPA COMPONENT OF STALEVO
Brand Name English
LEVODOPA [USAN]
Common Name English
LEVODOPA COMPONENT OF DOPASNAP
Common Name English
LEVODOPA [USP MONOGRAPH]
Common Name English
LEVODOPA/CARBIDOPA/ENTACAPONE ORION COMPONENT LEVODOPA
Brand Name English
LEVODOPA COMPONENT OF CORBILTA
Brand Name English
LEVODOPA [EP IMPURITY]
Common Name English
STALEVO COMPONENT LEVODOPA
Brand Name English
LEVODOPA COMPONENT OF PARCOPA
Common Name English
LARODOPA
Brand Name English
LEVODOPA COMPONENT OF LEVODOPA/CARBIDOPA/ENTACAPONE ORION
Brand Name English
IPX203 COMPONENT LEVODOPA
Common Name English
DOPAR
Brand Name English
DUOPA COMPONENT LEVODOPA
Brand Name English
PARCOPA COMPONENT LEVODOPA
Common Name English
LEVODOPA [HSDB]
Common Name English
LEVODOPA [EP MONOGRAPH]
Common Name English
IPX-203 COMPONENT LEVODOPA
Common Name English
LEVODOPA [MI]
Common Name English
LEVODOPA COMPONENT OF CARBILEV
Common Name English
DIHYDROXYPHENYLALANINE
Systematic Name English
NSC-118381
Code English
(-)-3-(3,4-DIHYDROXYPHENYL)-L-ALANINE
Systematic Name English
Levodopa [WHO-DD]
Common Name English
LEVODOPA COMPONENT OF DHIVY
Brand Name English
DHIVY COMPONENT LEVODOPA
Brand Name English
LEVODOPUM [WHO-IP LATIN]
Common Name English
LEVODOPA COMPONENT OF RYTARY
Brand Name English
L-TYROSINE, 3-HYDROXY-
Systematic Name English
DOPASNAP COMPONENT LEVODOPA
Common Name English
DOPA, L-
Systematic Name English
CVT-301
Common Name English
LEVODOPA [MART.]
Common Name English
INBRIJA
Brand Name English
LEVODOPA [VANDF]
Common Name English
Classification Tree Code System Code
WHO-VATC QN04BA03
Created by admin on Sat Dec 16 17:02:48 GMT 2023 , Edited by admin on Sat Dec 16 17:02:48 GMT 2023
DSLD 1198 (Number of products:24)
Created by admin on Sat Dec 16 17:02:48 GMT 2023 , Edited by admin on Sat Dec 16 17:02:48 GMT 2023
WHO-ESSENTIAL MEDICINES LIST 09 (LEV/CAR)
Created by admin on Sat Dec 16 17:02:48 GMT 2023 , Edited by admin on Sat Dec 16 17:02:48 GMT 2023
EMA ASSESSMENT REPORTS CORBILTA (AUTHORIZED: PARKINSON DISEASE)
Created by admin on Sat Dec 16 17:02:48 GMT 2023 , Edited by admin on Sat Dec 16 17:02:48 GMT 2023
EU-Orphan Drug EU/3/01/035
Created by admin on Sat Dec 16 17:02:48 GMT 2023 , Edited by admin on Sat Dec 16 17:02:48 GMT 2023
EMA ASSESSMENT REPORTS STALEVO (AUTHORIZED: PARKINSON DISEASE)
Created by admin on Sat Dec 16 17:02:48 GMT 2023 , Edited by admin on Sat Dec 16 17:02:48 GMT 2023
WHO-ATC N04BA01
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EMA ASSESSMENT REPORTS CORBILTA (AUTHORIZED: NEURODEGENERATIVE DISEASES)
Created by admin on Sat Dec 16 17:02:48 GMT 2023 , Edited by admin on Sat Dec 16 17:02:48 GMT 2023
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
Created by admin on Sat Dec 16 17:02:48 GMT 2023 , Edited by admin on Sat Dec 16 17:02:48 GMT 2023
WHO-ATC N04BA02
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NCI_THESAURUS C66884
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NDF-RT N0000175755
Created by admin on Sat Dec 16 17:02:48 GMT 2023 , Edited by admin on Sat Dec 16 17:02:48 GMT 2023
EMA ASSESSMENT REPORTS LEVODOPA/CARBIDOPA/ENTACAPONE ORION (AUTHORIZED: PARKINSON DISEASE)
Created by admin on Sat Dec 16 17:02:48 GMT 2023 , Edited by admin on Sat Dec 16 17:02:48 GMT 2023
EMA ASSESSMENT REPORTS CORBILTA (AUTHORIZED: NERVOUS SYSTEM DISEASES)
Created by admin on Sat Dec 16 17:02:48 GMT 2023 , Edited by admin on Sat Dec 16 17:02:48 GMT 2023
Code System Code Type Description
PUBCHEM
6047
Created by admin on Sat Dec 16 17:02:48 GMT 2023 , Edited by admin on Sat Dec 16 17:02:48 GMT 2023
PRIMARY
WIKIPEDIA
L-DOPA
Created by admin on Sat Dec 16 17:02:48 GMT 2023 , Edited by admin on Sat Dec 16 17:02:48 GMT 2023
PRIMARY
LACTMED
Levodopa
Created by admin on Sat Dec 16 17:02:48 GMT 2023 , Edited by admin on Sat Dec 16 17:02:48 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
LEVODOPA
Created by admin on Sat Dec 16 17:02:48 GMT 2023 , Edited by admin on Sat Dec 16 17:02:48 GMT 2023
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.
MESH
D007980
Created by admin on Sat Dec 16 17:02:48 GMT 2023 , Edited by admin on Sat Dec 16 17:02:48 GMT 2023
PRIMARY
DRUG CENTRAL
1567
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PRIMARY
NSC
118381
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PRIMARY
NCI_THESAURUS
C611
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PRIMARY
EVMPD
SUB08468MIG
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PRIMARY
EPA CompTox
DTXSID9023209
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PRIMARY
FDA UNII
46627O600J
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PRIMARY
ChEMBL
CHEMBL1009
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PRIMARY
DAILYMED
46627O600J
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PRIMARY
CHEBI
57504
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PRIMARY
HSDB
3348
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PRIMARY
SMS_ID
100000085446
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PRIMARY
CHEBI
15765
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PRIMARY
IUPHAR
3639
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PRIMARY
MERCK INDEX
m6786
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PRIMARY Merck Index
INN
2651
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PRIMARY
ECHA (EC/EINECS)
200-445-2
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PRIMARY
CAS
59-92-7
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PRIMARY
RS_ITEM_NUM
1361009
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PRIMARY
DRUG BANK
DB01235
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PRIMARY
RXCUI
6375
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PRIMARY RxNorm