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Identification
NameLevodopa
Accession NumberDB01235  (APRD00309, EXPT01107)
TypeSmall Molecule
GroupsApproved
Description

The naturally occurring form of dihydroxyphenylalanine and the immediate precursor of dopamine. Unlike dopamine itself, it can be taken orally and crosses the blood-brain barrier. It is rapidly taken up by dopaminergic neurons and converted to dopamine. It is used for the treatment of parkinsonian disorders and is usually given with agents that inhibit its conversion to dopamine outside of the central nervous system. [PubChem]

Structure
Thumb
Synonyms
(-)-3-(3,4-Dihydroxyphenyl)-L-alanine
(-)-Dopa
(−)-3-(3,4-dihydroxyphenyl)-L-alanine
(−)-dopa
3-Hydroxy-L-tyrosine
3,4-Dihydroxy-L-phenylalanine
3,4-DIHYDROXYPHENYLALANINE
beta-(3,4-Dihydroxyphenyl)-L-alanine
beta-(3,4-Dihydroxyphenyl)alanine
Dihydroxy-L-phenylalanine
Dopar
L-3,4-dihydroxyphenylalanine
L-beta-(3,4-Dihydroxyphenyl)alanine
L-DOPA
Levodopa
Levodopum
β-(3,4-dihydroxyphenyl)alanine
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Carbidopa and Levodopatablet25 mg/1oralREMEDYREPACK INC.2013-02-27Not applicableUs
Carbidopa and Levodopatablet25 mg/1oralREMEDYREPACK INC.2013-03-25Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
BidopalGlaxoSmithKline
DoparNot Available
DoparlKyowa Hakko Kirin
DopasolDaiichi Sankyo
DopastonOhara Yakuhin
Brand mixtures
NameLabellerIngredients
Apo-levocarb - Tab 10mg/100mgApotex Inc
Apo-levocarb - Tab 25mg/250mgApotex Inc
Apo-levocarb CRApotex Inc
Apo-levocarb-tab 25mg/100mgApotex Inc
Carbidopa and LevodopaTeva Pharmaceuticals USA Inc
Carbidopa, Levodopa and EntacaponeMylan Pharmaceuticals Inc.
Carbidopa, Levodopa, and EntacaponeSandoz Inc
Dom-levo-carbidopaDominion Pharmacal
DuodopaAbbvie Corporation
DuopaAbb Vie Inc.
Nu-levocarb - Tab 10mg/100mgNu Pharm Inc
Nu-levocarb - Tab 25 Mg/100 mgNu Pharm Inc
Nu-levocarb - Tablets 25 Mg/250 mgNu Pharm Inc
ParcopaJazz Pharmaceuticals, Inc.
PMS-levocarb CRPharmascience Inc
Pro-lecarb-100/10 - TabPro Doc Limitee
Pro-lecarb-100/25 - TabPro Doc Limitee
Pro-levocarb - 100/25Pro Doc Limitee
Ratio-levodopa/carbidopaRatiopharm Inc Division Of Teva Canada Limited
RytaryImpax Specialty Pharma
SinemetMerck Sharp & Dohme Corp.
Sinemet 100/10Merck Canada Inc
Sinemet 100/25Merck Canada Inc
Sinemet 250/25Merck Canada Inc
Sinemet CRMerck Sharp & Dohme Corp.
Sinemet CR 100/25Merck Canada Inc
Sinemet CR 200/50Merck Canada Inc
StalevoNovartis Pharmaceuticals Corporation
Teva-levocarbidopaTeva Canada Limited
SaltsNot Available
Categories
UNII46627O600J
CAS number59-92-7
WeightAverage: 197.1879
Monoisotopic: 197.068807845
Chemical FormulaC9H11NO4
InChI KeyInChIKey=WTDRDQBEARUVNC-LURJTMIESA-N
InChI
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
IUPAC Name
(2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
SMILES
N[C@@H](CC1=CC(O)=C(O)C=C1)C(O)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as catecholamines and derivatives. These are compounds containing 4-(2-Aminoethyl)pyrocatechol [4-(2-aminoethyl)benzene-1,2-diol] or a derivative thereof formed by substitution.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenols and derivatives
Direct ParentCatecholamines and derivatives
Alternative Parents
Substituents
  • 3-phenylpropanoic-acid
  • Catecholamine
  • L-alpha-amino acid
  • Amphetamine or derivatives
  • Alpha-amino acid or derivatives
  • Alpha-amino acid
  • Aralkylamine
  • Amino fatty acid
  • Fatty acyl
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of idiopathic Parkinson's disease (Paralysis Agitans), postencephalitic parkinsonism, symptomatic parkinsonism which may follow injury to the nervous system by carbon monoxide intoxication, and manganese intoxication.
PharmacodynamicsLevodopa (L-dopa) is used to replace dopamine lost in Parkinson's disease because dopamine itself cannot cross the blood-brain barrier where its precursor can. However, L-DOPA is converted to dopamine in the periphery as well as in the CNS, so it is administered with a peripheral DDC (dopamine decarboxylase) inhibitor such as carbidopa, without which 90% is metabolised in the gut wall, and with a COMT inhibitor if possible; this prevents about a 5% loss. The form given therapeutically is therefore a prodrug which avoids decarboxylation in the stomach and periphery, can cross the blood-brain barrier, and once in the brain is converted to the neurotransmitter dopamine by the enzyme aromatic-L-amino-acid decarboxylase.
Mechanism of actionStriatal dopamine levels in symptomatic Parkinson's disease are decreased by 60 to 80%, striatal dopaminergic neurotransmission may be enhanced by exogenous supplementation of dopamine through administration of dopamine's precursor, levodopa. A small percentage of each levodopa dose crosses the blood-brain barrier and is decarboxylated to dopamine. This newly formed dopamine then is available to stimulate dopaminergic receptors, thus compensating for the depleted supply of endogenous dopamine.
Related Articles
AbsorptionLevodopa is rapidly absorbed from the proximal small intestine by the large neutral amino acid (LNAA) transport carrier system.
Volume of distributionNot Available
Protein bindingHigh
Metabolism

95% of an administered oral dose of levodopa is pre-systemically decarboxylated to dopamine by the L-aromatic amino acid decarboxylase (AAAD) enzyme in the stomach, lumen of the intestine, kidney, and liver. Levodopa also may be methoxylated by the hepatic catechol-O-methyltransferase (COMT) enzyme system to 3-O-methyldopa (3-OMD), which cannot be converted to central dopamine.

SubstrateEnzymesProduct
Levodopa
Not Available
DOPA sulfateDetails
Route of eliminationNot Available
Half life50 to 90 minutes
ClearanceNot Available
ToxicityOral, mouse: LD50 = 2363 mg/kg; Oral, rabbit: LD50 = 609 mg/kg; Oral, rat: LD50 = 1780 mg/kg.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Aromatic L-Aminoacid Decarboxylase DeficiencyDiseaseSMP00170
Catecholamine BiosynthesisMetabolicSMP00012
Tyrosinemia Type IDiseaseSMP00218
Disulfiram Action PathwayDrug actionSMP00429
Tyrosine hydroxylase deficiencyDiseaseSMP00497
Tyrosine MetabolismMetabolicSMP00006
Tyrosinemia, transient, of the newbornDiseaseSMP00494
AlkaptonuriaDiseaseSMP00169
HawkinsinuriaDiseaseSMP00190
Dopamine beta-hydroxylase deficiencyDiseaseSMP00498
Monoamine oxidase-a deficiency (MAO-A)DiseaseSMP00533
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8715
Blood Brain Barrier-0.9264
Caco-2 permeable-0.8957
P-glycoprotein substrateNon-substrate0.5734
P-glycoprotein inhibitor INon-inhibitor0.989
P-glycoprotein inhibitor IINon-inhibitor0.988
Renal organic cation transporterNon-inhibitor0.9211
CYP450 2C9 substrateNon-substrate0.8236
CYP450 2D6 substrateNon-substrate0.8514
CYP450 3A4 substrateNon-substrate0.7117
CYP450 1A2 substrateNon-inhibitor0.9467
CYP450 2C9 inhibitorNon-inhibitor0.9765
CYP450 2D6 inhibitorNon-inhibitor0.9576
CYP450 2C19 inhibitorNon-inhibitor0.9504
CYP450 3A4 inhibitorNon-inhibitor0.914
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9713
Ames testAMES toxic0.9106
CarcinogenicityNon-carcinogens0.941
BiodegradationReady biodegradable0.7332
Rat acute toxicity2.0131 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9872
hERG inhibition (predictor II)Non-inhibitor0.9524
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Tabletoral25 mg/1
Tablet, orally disintegratingoral
Gelintraintestinal (upper)
Suspensionenteral
Capsuleoral
Capsule, extended releaseoral
Tabletoral
Tablet, extended releaseoral
Tablet (extended-release)oral
Tablet, film coatedoral
Prices
Unit descriptionCostUnit
L-dopa powder15.19USD g
Levodopa powder7.31USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6500867 No2000-06-292020-06-29Us
US6797732 No2000-06-292020-06-29Us
US7094427 No2002-05-292022-05-29Us
US8377474 No2008-12-262028-12-26Us
US8454998 No2008-12-262028-12-26Us
US8557283 No2008-12-262028-12-26Us
US9089607 No2008-12-262028-12-26Us
US9089608 No2008-12-262028-12-26Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point284-285U.S. Patent 3,253,023.
water solubility5000 mg/L (at 20 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-2.39SANGSTER (1993)
logS-1.6ADME Research, USCD
pKa2.32 (at 25 °C)KORTUM,G ET AL (1961)
Predicted Properties
PropertyValueSource
Water Solubility3.3 mg/mLALOGPS
logP-2.3ALOGPS
logP-1.8ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)1.65ChemAxon
pKa (Strongest Basic)9.06ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area103.78 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity49.08 m3·mol-1ChemAxon
Polarizability18.91 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (7.19 KB)
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-014i-0790000000-b2f7f063a2c8197c7eddView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-014i-0690000000-622497b3104c6082a45dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-00xr-9350000000-b0cc4636931d2de64d81View in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-014i-0590000000-4474e81e4226bb4e1d4cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0uea-0900000000-8eb71aa0cc8622f097a2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a59-2900000000-bf63b9b719959b82b543View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-056r-9300000000-a78b0b31dd33fe8479a7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0f6t-0911000000-15affa616923dfb9c45aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-22d8267801d0eb0b73c2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-2c310034a1a871502b4cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0900000000-5e6020c952f741531fcbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0007-0970100000-49594dae82ce73e734e6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-2183a68f58b951f3f1c7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-03di-0900000000-0030db588fbd92c5b761View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0006-0090000000-544615463a975baae9e4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-0729111000-0a20b01f58fff8ad7ef0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0900000000-c8095a31ed4b3dbbc646View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0190000000-41515cba3a6929721859View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-0900000000-8074c509ef5bae1129fcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0006-0502193020-497bfad7ba247159ca00View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0900000000-0b0d4b6dcb7f1fa24e1aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0029800000-05f40324c8c1fec7963aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0006-0000090000-c0cd80185ce47b30e5feView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0002-0900000000-df116b84981cf4a1371aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-0f6t-0900000000-1c1c39a8880442ea18dfView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
Synthesis Reference

Vincenzo Cannata, Giancarlo Tamerlani, Mauro Morotti, “Process for the synthesis of the levodopa.” U.S. Patent US4962223, issued December, 1986.

US4962223
General References
  1. Pinho MJ, Serrao MP, Gomes P, Hopfer U, Jose PA, Soares-da-Silva P: Over-expression of renal LAT1 and LAT2 and enhanced L-DOPA uptake in SHR immortalized renal proximal tubular cells. Kidney Int. 2004 Jul;66(1):216-26. [PubMed:15200428 ]
  2. Kageyama T, Nakamura M, Matsuo A, Yamasaki Y, Takakura Y, Hashida M, Kanai Y, Naito M, Tsuruo T, Minato N, Shimohama S: The 4F2hc/LAT1 complex transports L-DOPA across the blood-brain barrier. Brain Res. 2000 Oct 6;879(1-2):115-21. [PubMed:11011012 ]
External Links
ATC CodesN04BA01N04BA02N04BA03
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (37.5 KB)
Interactions
Drug Interactions
Drug
AcebutololAcebutolol may increase the orthostatic hypotensive activities of Levodopa.
AcetazolamideAcetazolamide may increase the orthostatic hypotensive activities of Levodopa.
AldesleukinAldesleukin may increase the orthostatic hypotensive activities of Levodopa.
AliskirenAliskiren may increase the orthostatic hypotensive activities of Levodopa.
AmilorideAmiloride may increase the orthostatic hypotensive activities of Levodopa.
AmlodipineAmlodipine may increase the orthostatic hypotensive activities of Levodopa.
Amyl NitriteAmyl Nitrite may increase the orthostatic hypotensive activities of Levodopa.
ApraclonidineApraclonidine may increase the orthostatic hypotensive activities of Levodopa.
AtenololAtenolol may increase the orthostatic hypotensive activities of Levodopa.
AzelastineLevodopa may increase the central nervous system depressant (CNS depressant) activities of Azelastine.
Azilsartan medoxomilAzilsartan medoxomil may increase the orthostatic hypotensive activities of Levodopa.
BaclofenThe risk or severity of adverse effects can be increased when Baclofen is combined with Levodopa.
BenazeprilBenazepril may increase the orthostatic hypotensive activities of Levodopa.
BetaxololBetaxolol may increase the orthostatic hypotensive activities of Levodopa.
BisoprololBisoprolol may increase the orthostatic hypotensive activities of Levodopa.
BretyliumBretylium may increase the orthostatic hypotensive activities of Levodopa.
BrimonidineBrimonidine may increase the orthostatic hypotensive activities of Levodopa.
BumetanideBumetanide may increase the orthostatic hypotensive activities of Levodopa.
CandesartanCandesartan may increase the orthostatic hypotensive activities of Levodopa.
CaptoprilCaptopril may increase the orthostatic hypotensive activities of Levodopa.
CarteololCarteolol may increase the orthostatic hypotensive activities of Levodopa.
CarvedilolCarvedilol may increase the orthostatic hypotensive activities of Levodopa.
ChlorothiazideChlorothiazide may increase the orthostatic hypotensive activities of Levodopa.
ChlorthalidoneChlorthalidone may increase the orthostatic hypotensive activities of Levodopa.
CilazaprilCilazapril may increase the orthostatic hypotensive activities of Levodopa.
ClevidipineClevidipine may increase the orthostatic hypotensive activities of Levodopa.
ClonidineClonidine may increase the orthostatic hypotensive activities of Levodopa.
DapagliflozinDapagliflozin may increase the orthostatic hypotensive activities of Levodopa.
DexmedetomidineDexmedetomidine may increase the orthostatic hypotensive activities of Levodopa.
DiclofenamideDiclofenamide may increase the orthostatic hypotensive activities of Levodopa.
DiethylstilbestrolThe metabolism of Diethylstilbestrol can be decreased when combined with Levodopa.
DiltiazemDiltiazem may increase the orthostatic hypotensive activities of Levodopa.
DinutuximabDinutuximab may increase the orthostatic hypotensive activities of Levodopa.
DipyridamoleDipyridamole may increase the orthostatic hypotensive activities of Levodopa.
DoxazosinDoxazosin may increase the orthostatic hypotensive activities of Levodopa.
EmpagliflozinEmpagliflozin may increase the orthostatic hypotensive activities of Levodopa.
EnalaprilEnalapril may increase the orthostatic hypotensive activities of Levodopa.
EnalaprilatEnalaprilat may increase the orthostatic hypotensive activities of Levodopa.
EplerenoneEplerenone may increase the orthostatic hypotensive activities of Levodopa.
EprosartanEprosartan may increase the orthostatic hypotensive activities of Levodopa.
EsmololEsmolol may increase the orthostatic hypotensive activities of Levodopa.
Etacrynic acidEthacrynic acid may increase the orthostatic hypotensive activities of Levodopa.
EthanolLevodopa may increase the central nervous system depressant (CNS depressant) activities of Ethanol.
FelodipineFelodipine may increase the orthostatic hypotensive activities of Levodopa.
Ferric CitrateThe serum concentration of Levodopa can be decreased when it is combined with Ferric Citrate.
FosinoprilFosinopril may increase the orthostatic hypotensive activities of Levodopa.
FosphenytoinThe therapeutic efficacy of Levodopa can be decreased when used in combination with Fosphenytoin.
FurosemideFurosemide may increase the orthostatic hypotensive activities of Levodopa.
GlycopyrroniumThe serum concentration of Levodopa can be decreased when it is combined with Glycopyrrolate.
GuanfacineGuanfacine may increase the orthostatic hypotensive activities of Levodopa.
HydralazineHydralazine may increase the orthostatic hypotensive activities of Levodopa.
HydrochlorothiazideHydrochlorothiazide may increase the orthostatic hypotensive activities of Levodopa.
IndapamideIndapamide may increase the orthostatic hypotensive activities of Levodopa.
IrbesartanIrbesartan may increase the orthostatic hypotensive activities of Levodopa.
Iron DextranThe serum concentration of Levodopa can be decreased when it is combined with Iron Dextran.
IsocarboxazidThe risk or severity of adverse effects can be increased when Levodopa is combined with Isocarboxazid.
IsoniazidThe therapeutic efficacy of Levodopa can be decreased when used in combination with Isoniazid.
IsosorbideIsosorbide may increase the orthostatic hypotensive activities of Levodopa.
Isosorbide DinitrateIsosorbide Dinitrate may increase the orthostatic hypotensive activities of Levodopa.
Isosorbide MononitrateIsosorbide Mononitrate may increase the orthostatic hypotensive activities of Levodopa.
IsoxsuprineIsoxsuprine may increase the orthostatic hypotensive activities of Levodopa.
IsradipineIsradipine may increase the orthostatic hypotensive activities of Levodopa.
LabetalolLabetalol may increase the orthostatic hypotensive activities of Levodopa.
LevobunololLevobunolol may increase the orthostatic hypotensive activities of Levodopa.
LinezolidThe risk or severity of adverse effects can be increased when Levodopa is combined with Linezolid.
LisinoprilLisinopril may increase the orthostatic hypotensive activities of Levodopa.
LorazepamThe risk or severity of adverse effects can be increased when Lorazepam is combined with Levodopa.
LosartanLosartan may increase the orthostatic hypotensive activities of Levodopa.
LoxapineThe therapeutic efficacy of Loxapine can be decreased when used in combination with Levodopa.
MannitolMannitol may increase the orthostatic hypotensive activities of Levodopa.
MecamylamineMecamylamine may increase the orthostatic hypotensive activities of Levodopa.
MethazolamideMethazolamide may increase the orthostatic hypotensive activities of Levodopa.
MethyclothiazideMethyclothiazide may increase the orthostatic hypotensive activities of Levodopa.
MethyldopaMethyldopa may increase the orthostatic hypotensive activities of Levodopa.
MetipranololMetipranolol may increase the orthostatic hypotensive activities of Levodopa.
MetolazoneMetolazone may increase the orthostatic hypotensive activities of Levodopa.
MetoprololMetoprolol may increase the orthostatic hypotensive activities of Levodopa.
MinoxidilMinoxidil may increase the orthostatic hypotensive activities of Levodopa.
MoclobemideThe risk or severity of adverse effects can be increased when Levodopa is combined with Moclobemide.
MoexiprilMoexipril may increase the orthostatic hypotensive activities of Levodopa.
NadololNadolol may increase the orthostatic hypotensive activities of Levodopa.
NebivololNebivolol may increase the orthostatic hypotensive activities of Levodopa.
NesiritideNesiritide may increase the orthostatic hypotensive activities of Levodopa.
NicardipineNicardipine may increase the orthostatic hypotensive activities of Levodopa.
NifedipineNifedipine may increase the orthostatic hypotensive activities of Levodopa.
NimodipineNimodipine may increase the orthostatic hypotensive activities of Levodopa.
NisoldipineNisoldipine may increase the orthostatic hypotensive activities of Levodopa.
NitroglycerinNitroglycerin may increase the orthostatic hypotensive activities of Levodopa.
NitroprussideNitroprusside may increase the orthostatic hypotensive activities of Levodopa.
OlmesartanOlmesartan may increase the orthostatic hypotensive activities of Levodopa.
PapaverinePapaverine may increase the hypotensive activities of Levodopa.
ParoxetineThe risk or severity of adverse effects can be increased when Levodopa is combined with Paroxetine.
PenbutololPenbutolol may increase the orthostatic hypotensive activities of Levodopa.
PerindoprilPerindopril may increase the orthostatic hypotensive activities of Levodopa.
PhenelzineThe risk or severity of adverse effects can be increased when Levodopa is combined with Phenelzine.
PhenytoinThe therapeutic efficacy of Levodopa can be decreased when used in combination with Phenytoin.
PindololPindolol may increase the orthostatic hypotensive activities of Levodopa.
PrazosinPrazosin may increase the orthostatic hypotensive activities of Levodopa.
ProcarbazineThe risk or severity of adverse effects can be increased when Levodopa is combined with Procarbazine.
PropranololPropranolol may increase the orthostatic hypotensive activities of Levodopa.
PyridoxineThe therapeutic efficacy of Levodopa can be decreased when used in combination with Pyridoxine.
QuinaprilQuinapril may increase the orthostatic hypotensive activities of Levodopa.
RamiprilRamipril may increase the orthostatic hypotensive activities of Levodopa.
RasagilineThe risk or severity of adverse effects can be increased when Levodopa is combined with Rasagiline.
ReserpineReserpine may increase the orthostatic hypotensive activities of Levodopa.
RiociguatRiociguat may increase the orthostatic hypotensive activities of Levodopa.
SapropterinThe risk or severity of adverse effects can be increased when Tetrahydrobiopterin is combined with Levodopa.
SelegilineThe risk or severity of adverse effects can be increased when Levodopa is combined with Selegiline.
SotalolSotalol may increase the orthostatic hypotensive activities of Levodopa.
SpironolactoneSpironolactone may increase the orthostatic hypotensive activities of Levodopa.
Tedizolid PhosphateThe risk or severity of adverse effects can be increased when Levodopa is combined with Tedizolid Phosphate.
TelmisartanTelmisartan may increase the orthostatic hypotensive activities of Levodopa.
TerazosinTerazosin may increase the orthostatic hypotensive activities of Levodopa.
TimololTimolol may increase the orthostatic hypotensive activities of Levodopa.
TizanidineTizanidine may increase the orthostatic hypotensive activities of Levodopa.
TorasemideTorasemide may increase the orthostatic hypotensive activities of Levodopa.
TrandolaprilTrandolapril may increase the orthostatic hypotensive activities of Levodopa.
TranylcypromineThe risk or severity of adverse effects can be increased when Levodopa is combined with Tranylcypromine.
TriamtereneTriamterene may increase the orthostatic hypotensive activities of Levodopa.
ValsartanValsartan may increase the orthostatic hypotensive activities of Levodopa.
VerapamilVerapamil may increase the orthostatic hypotensive activities of Levodopa.
ZiprasidoneThe therapeutic efficacy of Levodopa can be decreased when used in combination with Ziprasidone.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
G-protein coupled amine receptor activity
Specific Function:
Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.
Gene Name:
DRD1
Uniprot ID:
P21728
Molecular Weight:
49292.765 Da
References
  1. Onofrj M, Bonanni L, Thomas A: An expert opinion on safinamide in Parkinson's disease. Expert Opin Investig Drugs. 2008 Jul;17(7):1115-25. doi: 10.1517/13543784.17.7.1115 . [PubMed:18549347 ]
  2. Deleu D, Northway MG, Hanssens Y: Clinical pharmacokinetic and pharmacodynamic properties of drugs used in the treatment of Parkinson's disease. Clin Pharmacokinet. 2002;41(4):261-309. [PubMed:11978145 ]
  3. Koller WC, Rueda MG: Mechanism of action of dopaminergic agents in Parkinson's disease. Neurology. 1998 Jun;50(6 Suppl 6):S11-4; discussion S44-8. [PubMed:9633680 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
G-protein coupled amine receptor activity
Specific Function:
Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.
Gene Name:
DRD5
Uniprot ID:
P21918
Molecular Weight:
52950.5 Da
References
  1. Onofrj M, Bonanni L, Thomas A: An expert opinion on safinamide in Parkinson's disease. Expert Opin Investig Drugs. 2008 Jul;17(7):1115-25. doi: 10.1517/13543784.17.7.1115 . [PubMed:18549347 ]
  2. Deleu D, Northway MG, Hanssens Y: Clinical pharmacokinetic and pharmacodynamic properties of drugs used in the treatment of Parkinson's disease. Clin Pharmacokinet. 2002;41(4):261-309. [PubMed:11978145 ]
  3. Koller WC, Rueda MG: Mechanism of action of dopaminergic agents in Parkinson's disease. Neurology. 1998 Jun;50(6 Suppl 6):S11-4; discussion S44-8. [PubMed:9633680 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Potassium channel regulator activity
Specific Function:
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name:
DRD2
Uniprot ID:
P14416
Molecular Weight:
50618.91 Da
References
  1. Dupre KB, Eskow KL, Negron G, Bishop C: The differential effects of 5-HT(1A) receptor stimulation on dopamine receptor-mediated abnormal involuntary movements and rotations in the primed hemiparkinsonian rat. Brain Res. 2007 Jul 16;1158:135-43. Epub 2007 May 8. [PubMed:17553470 ]
  2. Mori A, Ohashi S, Nakai M, Moriizumi T, Mitsumoto Y: Neural mechanisms underlying motor dysfunction as detected by the tail suspension test in MPTP-treated C57BL/6 mice. Neurosci Res. 2005 Mar;51(3):265-74. Epub 2005 Jan 8. [PubMed:15710490 ]
  3. Zappia M, Annesi G, Nicoletti G, Arabia G, Annesi F, Messina D, Pugliese P, Spadafora P, Tarantino P, Carrideo S, Civitelli D, De Marco EV, Ciro-Candiano IC, Gambardella A, Quattrone A: Sex differences in clinical and genetic determinants of levodopa peak-dose dyskinesias in Parkinson disease: an exploratory study. Arch Neurol. 2005 Apr;62(4):601-5. [PubMed:15824260 ]
  4. Kovoor A, Seyffarth P, Ebert J, Barghshoon S, Chen CK, Schwarz S, Axelrod JD, Cheyette BN, Simon MI, Lester HA, Schwarz J: D2 dopamine receptors colocalize regulator of G-protein signaling 9-2 (RGS9-2) via the RGS9 DEP domain, and RGS9 knock-out mice develop dyskinesias associated with dopamine pathways. J Neurosci. 2005 Feb 23;25(8):2157-65. [PubMed:15728856 ]
  5. Onofrj M, Bonanni L, Thomas A: An expert opinion on safinamide in Parkinson's disease. Expert Opin Investig Drugs. 2008 Jul;17(7):1115-25. doi: 10.1517/13543784.17.7.1115 . [PubMed:18549347 ]
  6. Deleu D, Northway MG, Hanssens Y: Clinical pharmacokinetic and pharmacodynamic properties of drugs used in the treatment of Parkinson's disease. Clin Pharmacokinet. 2002;41(4):261-309. [PubMed:11978145 ]
  7. Koller WC, Rueda MG: Mechanism of action of dopaminergic agents in Parkinson's disease. Neurology. 1998 Jun;50(6 Suppl 6):S11-4; discussion S44-8. [PubMed:9633680 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
G-protein coupled amine receptor activity
Specific Function:
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase. Promotes cell proliferation.
Gene Name:
DRD3
Uniprot ID:
P35462
Molecular Weight:
44224.335 Da
References
  1. Onofrj M, Bonanni L, Thomas A: An expert opinion on safinamide in Parkinson's disease. Expert Opin Investig Drugs. 2008 Jul;17(7):1115-25. doi: 10.1517/13543784.17.7.1115 . [PubMed:18549347 ]
  2. Deleu D, Northway MG, Hanssens Y: Clinical pharmacokinetic and pharmacodynamic properties of drugs used in the treatment of Parkinson's disease. Clin Pharmacokinet. 2002;41(4):261-309. [PubMed:11978145 ]
  3. Koller WC, Rueda MG: Mechanism of action of dopaminergic agents in Parkinson's disease. Neurology. 1998 Jun;50(6 Suppl 6):S11-4; discussion S44-8. [PubMed:9633680 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Sh3 domain binding
Specific Function:
Dopamine receptor responsible for neuronal signaling in the mesolimbic system of the brain, an area of the brain that regulates emotion and complex behavior. Its activity is mediated by G proteins which inhibit adenylyl cyclase. Modulates the circadian rhythm of contrast sensitivity by regulating the rhythmic expression of NPAS2 in the retinal ganglion cells (By similarity).
Gene Name:
DRD4
Uniprot ID:
P21917
Molecular Weight:
48359.86 Da
References
  1. Onofrj M, Bonanni L, Thomas A: An expert opinion on safinamide in Parkinson's disease. Expert Opin Investig Drugs. 2008 Jul;17(7):1115-25. doi: 10.1517/13543784.17.7.1115 . [PubMed:18549347 ]
  2. Deleu D, Northway MG, Hanssens Y: Clinical pharmacokinetic and pharmacodynamic properties of drugs used in the treatment of Parkinson's disease. Clin Pharmacokinet. 2002;41(4):261-309. [PubMed:11978145 ]
  3. Koller WC, Rueda MG: Mechanism of action of dopaminergic agents in Parkinson's disease. Neurology. 1998 Jun;50(6 Suppl 6):S11-4; discussion S44-8. [PubMed:9633680 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Pyridoxal phosphate binding
Specific Function:
Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name:
DDC
Uniprot ID:
P20711
Molecular Weight:
53925.815 Da
References
  1. BIRKMAYER W, HORNYKIEWICZ O: [The L-3,4-dioxyphenylalanine (DOPA)-effect in Parkinson-akinesia]. Wien Klin Wochenschr. 1961 Nov 10;73:787-8. [PubMed:13869404 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
Gene Name:
SLC15A1
Uniprot ID:
P46059
Molecular Weight:
78805.265 Da
References
  1. Han HK, Rhie JK, Oh DM, Saito G, Hsu CP, Stewart BH, Amidon GL: CHO/hPEPT1 cells overexpressing the human peptide transporter (hPEPT1) as an alternative in vitro model for peptidomimetic drugs. J Pharm Sci. 1999 Mar;88(3):347-50. [PubMed:10052994 ]
  2. Tamai I, Nakanishi T, Nakahara H, Sai Y, Ganapathy V, Leibach FH, Tsuji A: Improvement of L-dopa absorption by dipeptidyl derivation, utilizing peptide transporter PepT1. J Pharm Sci. 1998 Dec;87(12):1542-6. [PubMed:10189264 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Transporter activity
Specific Function:
Sodium-independent transporter that mediates the update of aromatic acid. Can function as a net efflux pathway for aromatic amino acids in the basosolateral epithelial cells (By similarity).
Gene Name:
SLC16A10
Uniprot ID:
Q8TF71
Molecular Weight:
55492.07 Da
References
  1. Kim DK, Kanai Y, Chairoungdua A, Matsuo H, Cha SH, Endou H: Expression cloning of a Na+-independent aromatic amino acid transporter with structural similarity to H+/monocarboxylate transporters. J Biol Chem. 2001 May 18;276(20):17221-8. Epub 2001 Feb 20. [PubMed:11278508 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Peptide antigen binding
Specific Function:
Sodium-independent, high-affinity transport of large neutral amino acids such as phenylalanine, tyrosine, leucine, arginine and tryptophan, when associated with SLC3A2/4F2hc. Involved in cellular amino acid uptake. Acts as an amino acid exchanger. Involved in the transport of L-DOPA across the blood-brain barrier, and that of thyroid hormones triiodothyronine (T3) and thyroxine (T4) across the ...
Gene Name:
SLC7A5
Uniprot ID:
Q01650
Molecular Weight:
55009.62 Da
References
  1. Pinho MJ, Serrao MP, Gomes P, Hopfer U, Jose PA, Soares-da-Silva P: Over-expression of renal LAT1 and LAT2 and enhanced L-DOPA uptake in SHR immortalized renal proximal tubular cells. Kidney Int. 2004 Jul;66(1):216-26. [PubMed:15200428 ]
  2. Kageyama T, Nakamura M, Matsuo A, Yamasaki Y, Takakura Y, Hashida M, Kanai Y, Naito M, Tsuruo T, Minato N, Shimohama S: The 4F2hc/LAT1 complex transports L-DOPA across the blood-brain barrier. Brain Res. 2000 Oct 6;879(1-2):115-21. [PubMed:11011012 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Toxin transporter activity
Specific Function:
Sodium-independent, high-affinity transport of small and large neutral amino acids such as alanine, serine, threonine, cysteine, phenylalanine, tyrosine, leucine, arginine and tryptophan, when associated with SLC3A2/4F2hc. Acts as an amino acid exchanger. Has higher affinity for L-phenylalanine than LAT1 but lower affinity for glutamine and serine. L-alanine is transported at physiological conc...
Gene Name:
SLC7A8
Uniprot ID:
Q9UHI5
Molecular Weight:
58381.12 Da
References
  1. Pinho MJ, Serrao MP, Gomes P, Hopfer U, Jose PA, Soares-da-Silva P: Over-expression of renal LAT1 and LAT2 and enhanced L-DOPA uptake in SHR immortalized renal proximal tubular cells. Kidney Int. 2004 Jul;66(1):216-26. [PubMed:15200428 ]
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Drug created on June 13, 2005 07:24 / Updated on July 24, 2016 01:53