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Identification
NameMetyrosine
Accession NumberDB00765  (APRD01112)
TypeSmall Molecule
GroupsApproved
DescriptionAn inhibitor of the enzyme tyrosine 3-monooxygenase, and consequently of the synthesis of catecholamines. It is used to control the symptoms of excessive sympathetic stimulation in patients with pheochromocytoma. (Martindale, The Extra Pharmacopoeia, 30th ed)
Structure
Thumb
Synonyms
(-)-alpha-Methyl-L-tyrosine
(S)-alpha-Methyltyrosine
alpha-Methyl-L-P-tyrosine
alpha-Methyl-P-tyrosine
alpha-Methyl-para-tyrosine
alpha-Methyltyrosine
L-alpha-Methyltyrosine
Methyltyrosine
Metirosin
Metirosina
Métirosine
Metirosine
Metirosinum
Metyrosine
External Identifiers
  • 357 O
  • L 588
  • L 588357-0
  • MK 781
  • α-MPT
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Demsercapsule250 mg/1oralAton Pharma, Inc.1979-10-03Not applicableUs
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIDOQ0J0TPF7
CAS number672-87-7
WeightAverage: 195.2151
Monoisotopic: 195.089543287
Chemical FormulaC10H13NO3
InChI KeyInChIKey=NHTGHBARYWONDQ-JTQLQIEISA-N
InChI
InChI=1S/C10H13NO3/c1-10(11,9(13)14)6-7-2-4-8(12)5-3-7/h2-5,12H,6,11H2,1H3,(H,13,14)/t10-/m0/s1
IUPAC Name
(2S)-2-amino-3-(4-hydroxyphenyl)-2-methylpropanoic acid
SMILES
C[C@](N)(CC1=CC=C(O)C=C1)C(O)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpropanoic acids. These are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassPhenylpropanoic acids
Sub ClassNot Available
Direct ParentPhenylpropanoic acids
Alternative Parents
Substituents
  • 3-phenylpropanoic-acid
  • L-alpha-amino acid
  • D-alpha-amino acid
  • Amphetamine or derivatives
  • Alpha-amino acid or derivatives
  • Alpha-amino acid
  • Phenylpropane
  • Aralkylamine
  • Phenol
  • Amino fatty acid
  • Fatty acyl
  • Benzenoid
  • Monocyclic benzene moiety
  • 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 use in the treatment of patients with pheochromocytoma, for preoperative preparation of patients for surgery, management of patients when surgery is contraindicated, and chronic treatment of patients with malignant pheochromocytoma.
PharmacodynamicsIn patients with pheochromocytoma, who produce excessive amounts of norepinephrine and epinephrine, administration of one to four grams of metyrosine per day has reduced catecholamine biosynthesis from about 35 to 80 percent as measured by the total excretion of catecholamines and their metabolites (metanephrine and vanillylmandelic acid). The maximum biochemical effect usually occurs within two to three days, and the urinary concentration of catecholamines and their metabolites usually returns to pretreatment levels within three to four days after metyrosine is discontinued. Most patients with pheochromocytoma treated with metyrosine experience decreased frequency and severity of hypertensive attacks with their associated headache, nausea, sweating, and tachycardia. In patients who respond, blood pressure decreases progressively during the first two days of therapy with metyrosine; after withdrawal, blood pressure usually increases gradually to pretreatment values within two to three days.
Mechanism of actionMetyrosine inhibits tyrosine hydroxylase, which catalyzes the first transformation in catecholamine biosynthesis, i.e., the conversion of tyrosine to dihydroxyphenylalanine (DOPA). Because the first step is also the rate-limiting step, blockade of tyrosine hydroxylase activity results in decreased endogenous levels of catecholamines and their synthesis. This consequently, depletes the levels of the catecholamines dopamine, adrenaline and noradrenaline in the body,usually measured as decreased urinary excretion of catecholamines and their metabolites. One main end result of the catecholamine depletion is a decrease in blood presure.
Related Articles
AbsorptionWell absorbed from the gastrointestinal tract.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Little biotransformation, with catechol metabolites accounting for less than 1% of the administered dose.

Route of eliminationBecause the first step is also the rate-limiting step, blockade of tyrosine hydroxylase activity results in decreased endogenous levels of catecholamines, usually measured as decreased urinary excretion of catecholamines and their metabolites.
Half life3.4 to 3.7 hours
ClearanceNot Available
ToxicitySigns of metyrosine overdosage include those central nervous system effects observed in some patients even at low dosages. At doses exceeding 2000 mg/day, some degree of sedation or feeling of fatigue may persist. Doses of 2000-4000 mg/day can result in anxiety or agitated depression, neuromuscular effects (including fine tremor of the hands, gross tremor of the trunk, tightening of the jaw with trismus), diarrhea, and decreased salivation with dry mouth. The acute toxicity of metyrosine was 442 mg/kg and 752 mg/kg in the female mouse and rat respectively.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9918
Blood Brain Barrier-0.8678
Caco-2 permeable-0.7026
P-glycoprotein substrateSubstrate0.5286
P-glycoprotein inhibitor INon-inhibitor0.9891
P-glycoprotein inhibitor IINon-inhibitor0.9926
Renal organic cation transporterNon-inhibitor0.9278
CYP450 2C9 substrateNon-substrate0.8025
CYP450 2D6 substrateNon-substrate0.7432
CYP450 3A4 substrateNon-substrate0.6887
CYP450 1A2 substrateNon-inhibitor0.9459
CYP450 2C9 inhibitorNon-inhibitor0.951
CYP450 2D6 inhibitorNon-inhibitor0.9574
CYP450 2C19 inhibitorNon-inhibitor0.9116
CYP450 3A4 inhibitorNon-inhibitor0.892
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9735
Ames testNon AMES toxic0.9695
CarcinogenicityNon-carcinogens0.8681
BiodegradationNot ready biodegradable0.7891
Rat acute toxicity2.1516 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9852
hERG inhibition (predictor II)Non-inhibitor0.9728
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Aton pharma inc
Packagers
Dosage forms
FormRouteStrength
Capsuleoral250 mg/1
Prices
Unit descriptionCostUnit
Demser 250 mg capsule19.35USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point312.5 °CPhysProp
water solubilityVery slightly solubleNot Available
logP-1.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.48 mg/mLALOGPS
logP-1.9ALOGPS
logP-1.1ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)2.06ChemAxon
pKa (Strongest Basic)9.93ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity51.81 m3·mol-1ChemAxon
Polarizability19.9 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

DrugSyn.org

US2868818
General ReferencesNot Available
External Links
ATC CodesC02KB01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
7-Nitroindazole7-Nitroindazole may increase the sedative activities of Metyrosine.
AcepromazineAcepromazine may increase the sedative activities of Metyrosine.
AcepromazineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Acepromazine.
AceprometazineAceprometazine may increase the sedative activities of Metyrosine.
AceprometazineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Aceprometazine.
AcetophenazineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Acetophenazine.
adipiplonadipiplon may increase the sedative activities of Metyrosine.
AgomelatineAgomelatine may increase the sedative activities of Metyrosine.
AlfaxaloneAlfaxalone may increase the sedative activities of Metyrosine.
AlfentanilAlfentanil may increase the sedative activities of Metyrosine.
AlphacetylmethadolAlphacetylmethadol may increase the sedative activities of Metyrosine.
AlprazolamAlprazolam may increase the sedative activities of Metyrosine.
AmineptineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Amineptine.
AmisulprideAmisulpride may increase the sedative activities of Metyrosine.
AmisulprideThe risk or severity of adverse effects can be increased when Metyrosine is combined with Amisulpride.
AmitriptylineAmitriptyline may increase the sedative activities of Metyrosine.
AmitriptylineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Amitriptyline.
AmobarbitalAmobarbital may increase the sedative activities of Metyrosine.
AmoxapineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Amoxapine.
AmoxapineAmoxapine may increase the sedative activities of Metyrosine.
AmperozideAmperozide may increase the sedative activities of Metyrosine.
AmperozideThe risk or severity of adverse effects can be increased when Metyrosine is combined with Amperozide.
AripiprazoleAripiprazole may increase the sedative activities of Metyrosine.
AripiprazoleThe risk or severity of adverse effects can be increased when Metyrosine is combined with Aripiprazole.
ArticaineArticaine may increase the sedative activities of Metyrosine.
AsenapineAsenapine may increase the sedative activities of Metyrosine.
AsenapineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Asenapine.
AzaperoneAzaperone may increase the sedative activities of Metyrosine.
AzaperoneThe risk or severity of adverse effects can be increased when Metyrosine is combined with Azaperone.
AzelastineAzelastine may increase the sedative activities of Metyrosine.
BaclofenBaclofen may increase the sedative activities of Metyrosine.
BarbitalBarbital may increase the sedative activities of Metyrosine.
BenzocaineBenzocaine may increase the sedative activities of Metyrosine.
Benzyl alcoholBenzyl alcohol may increase the sedative activities of Metyrosine.
BifeprunoxThe risk or severity of adverse effects can be increased when Metyrosine is combined with Bifeprunox.
BrexpiprazoleBrexpiprazole may increase the sedative activities of Metyrosine.
BrexpiprazoleThe risk or severity of adverse effects can be increased when Metyrosine is combined with Brexpiprazole.
BrimonidineBrimonidine may increase the sedative activities of Metyrosine.
BromazepamBromazepam may increase the sedative activities of Metyrosine.
BrompheniramineBrompheniramine may increase the sedative activities of Metyrosine.
BrotizolamBrotizolam may increase the sedative activities of Metyrosine.
BupivacaineBupivacaine may increase the sedative activities of Metyrosine.
BuprenorphineBuprenorphine may increase the sedative activities of Metyrosine.
BuspironeBuspirone may increase the sedative activities of Metyrosine.
ButabarbitalButabarbital may increase the sedative activities of Metyrosine.
ButacaineButacaine may increase the sedative activities of Metyrosine.
ButalbitalButalbital may increase the sedative activities of Metyrosine.
ButambenButamben may increase the sedative activities of Metyrosine.
ButethalButethal may increase the sedative activities of Metyrosine.
ButorphanolButorphanol may increase the sedative activities of Metyrosine.
CarbamazepineCarbamazepine may increase the sedative activities of Metyrosine.
CarbinoxamineCarbinoxamine may increase the sedative activities of Metyrosine.
CarfentanilCarfentanil may increase the sedative activities of Metyrosine.
CariprazineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Cariprazine.
CarisoprodolCarisoprodol may increase the sedative activities of Metyrosine.
CetirizineCetirizine may increase the sedative activities of Metyrosine.
Chloral hydrateChloral hydrate may increase the sedative activities of Metyrosine.
ChlordiazepoxideChlordiazepoxide may increase the sedative activities of Metyrosine.
ChlormezanoneChlormezanone may increase the sedative activities of Metyrosine.
ChloroprocaineChloroprocaine may increase the sedative activities of Metyrosine.
ChlorphenamineChlorphenamine may increase the sedative activities of Metyrosine.
ChlorpromazineChlorpromazine may increase the sedative activities of Metyrosine.
ChlorpromazineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Chlorpromazine.
ChlorprothixeneChlorprothixene may increase the sedative activities of Metyrosine.
ChlorprothixeneThe risk or severity of adverse effects can be increased when Metyrosine is combined with Chlorprothixene.
ChlorzoxazoneChlorzoxazone may increase the sedative activities of Metyrosine.
CinchocaineCinchocaine may increase the sedative activities of Metyrosine.
CitalopramThe risk or severity of adverse effects can be increased when Metyrosine is combined with Citalopram.
ClemastineClemastine may increase the sedative activities of Metyrosine.
ClidiniumClidinium may increase the sedative activities of Metyrosine.
ClobazamClobazam may increase the sedative activities of Metyrosine.
clomethiazoleclomethiazole may increase the sedative activities of Metyrosine.
ClomipramineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Clomipramine.
ClomipramineClomipramine may increase the sedative activities of Metyrosine.
ClonazepamClonazepam may increase the sedative activities of Metyrosine.
ClonidineClonidine may increase the sedative activities of Metyrosine.
ClorazepateClorazepate may increase the sedative activities of Metyrosine.
ClozapineClozapine may increase the sedative activities of Metyrosine.
ClozapineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Clozapine.
CocaineCocaine may increase the sedative activities of Metyrosine.
CodeineCodeine may increase the sedative activities of Metyrosine.
CyamemazineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Cyamemazine.
CyclizineCyclizine may increase the sedative activities of Metyrosine.
CyclobenzaprineCyclobenzaprine may increase the sedative activities of Metyrosine.
CyclobenzaprineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Cyclobenzaprine.
CyproheptadineCyproheptadine may increase the sedative activities of Metyrosine.
DantroleneDantrolene may increase the sedative activities of Metyrosine.
DapiprazoleDapiprazole may increase the sedative activities of Metyrosine.
DapiprazoleThe risk or severity of adverse effects can be increased when Metyrosine is combined with Dapiprazole.
DapoxetineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Dapoxetine.
deramciclanederamciclane may increase the sedative activities of Metyrosine.
DesfluraneDesflurane may increase the sedative activities of Metyrosine.
DesipramineDesipramine may increase the sedative activities of Metyrosine.
DesipramineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Desipramine.
DesloratadineDesloratadine may increase the sedative activities of Metyrosine.
DetomidineDetomidine may increase the sedative activities of Metyrosine.
DexbrompheniramineDexbrompheniramine may increase the sedative activities of Metyrosine.
DexmedetomidineDexmedetomidine may increase the sedative activities of Metyrosine.
DextromoramideDextromoramide may increase the sedative activities of Metyrosine.
DextropropoxypheneDextropropoxyphene may increase the sedative activities of Metyrosine.
DezocineDezocine may increase the sedative activities of Metyrosine.
DiazepamDiazepam may increase the sedative activities of Metyrosine.
DifenoxinDifenoxin may increase the sedative activities of Metyrosine.
DihydrocodeineDihydrocodeine may increase the sedative activities of Metyrosine.
DihydroetorphineDihydroetorphine may increase the sedative activities of Metyrosine.
DihydromorphineDihydromorphine may increase the sedative activities of Metyrosine.
DimenhydrinateDimenhydrinate may increase the sedative activities of Metyrosine.
DiphenhydramineDiphenhydramine may increase the sedative activities of Metyrosine.
DiphenoxylateDiphenoxylate may increase the sedative activities of Metyrosine.
DoramectinDoramectin may increase the sedative activities of Metyrosine.
DosulepinThe risk or severity of adverse effects can be increased when Metyrosine is combined with Dosulepin.
DoxepinDoxepin may increase the sedative activities of Metyrosine.
DoxepinThe risk or severity of adverse effects can be increased when Metyrosine is combined with Doxepin.
DoxylamineDoxylamine may increase the sedative activities of Metyrosine.
DPDPEDPDPE may increase the sedative activities of Metyrosine.
DroperidolDroperidol may increase the sedative activities of Metyrosine.
DroperidolThe risk or severity of adverse effects can be increased when Metyrosine is combined with Droperidol.
DrotebanolDrotebanol may increase the sedative activities of Metyrosine.
DyclonineDyclonine may increase the sedative activities of Metyrosine.
EcgonineEcgonine may increase the sedative activities of Metyrosine.
ECGONINE METHYL ESTERECGONINE METHYL ESTER may increase the sedative activities of Metyrosine.
EfavirenzEfavirenz may increase the sedative activities of Metyrosine.
EnfluraneEnflurane may increase the sedative activities of Metyrosine.
EntacaponeEntacapone may increase the sedative activities of Metyrosine.
EscitalopramThe risk or severity of adverse effects can be increased when Metyrosine is combined with Escitalopram.
EsmirtazapineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Esmirtazapine.
EstazolamEstazolam may increase the sedative activities of Metyrosine.
EszopicloneEszopiclone may increase the sedative activities of Metyrosine.
EthanolEthanol may increase the sedative activities of Metyrosine.
EthchlorvynolEthchlorvynol may increase the sedative activities of Metyrosine.
EthosuximideEthosuximide may increase the sedative activities of Metyrosine.
EthotoinEthotoin may increase the sedative activities of Metyrosine.
Ethyl carbamateEthyl carbamate may increase the sedative activities of Metyrosine.
Ethyl loflazepateEthyl loflazepate may increase the sedative activities of Metyrosine.
EthylmorphineEthylmorphine may increase the sedative activities of Metyrosine.
EtidocaineEtidocaine may increase the sedative activities of Metyrosine.
EtifoxineEtifoxine may increase the sedative activities of Metyrosine.
EtizolamEtizolam may increase the sedative activities of Metyrosine.
EtomidateEtomidate may increase the sedative activities of Metyrosine.
EtoperidoneThe risk or severity of adverse effects can be increased when Metyrosine is combined with Etoperidone.
EtorphineEtorphine may increase the sedative activities of Metyrosine.
EzogabineEzogabine may increase the sedative activities of Metyrosine.
FelbamateFelbamate may increase the sedative activities of Metyrosine.
FencamfamineFencamfamine may increase the sedative activities of Metyrosine.
FencamfamineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Fencamfamine.
FenfluramineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Fenfluramine.
FentanylFentanyl may increase the sedative activities of Metyrosine.
FexofenadineFexofenadine may increase the sedative activities of Metyrosine.
FlibanserinFlibanserin may increase the sedative activities of Metyrosine.
FludiazepamFludiazepam may increase the sedative activities of Metyrosine.
FlunarizineFlunarizine may increase the sedative activities of Metyrosine.
FlunitrazepamFlunitrazepam may increase the sedative activities of Metyrosine.
FluoxetineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Fluoxetine.
FlupentixolFlupentixol may increase the sedative activities of Metyrosine.
FlupentixolThe risk or severity of adverse effects can be increased when Metyrosine is combined with Flupentixol.
FluphenazineFluphenazine may increase the sedative activities of Metyrosine.
FluphenazineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Fluphenazine.
FlurazepamFlurazepam may increase the sedative activities of Metyrosine.
FluspirileneFluspirilene may increase the sedative activities of Metyrosine.
FluspirileneThe risk or severity of adverse effects can be increased when Metyrosine is combined with Fluspirilene.
Fluticasone PropionateFluticasone Propionate may increase the sedative activities of Metyrosine.
FluvoxamineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Fluvoxamine.
FluvoxamineFluvoxamine may increase the sedative activities of Metyrosine.
FosphenytoinFosphenytoin may increase the sedative activities of Metyrosine.
FospropofolFospropofol may increase the sedative activities of Metyrosine.
GabapentinGabapentin may increase the sedative activities of Metyrosine.
gabapentin enacarbilgabapentin enacarbil may increase the sedative activities of Metyrosine.
Gamma Hydroxybutyric AcidGamma Hydroxybutyric Acid may increase the sedative activities of Metyrosine.
GlutethimideGlutethimide may increase the sedative activities of Metyrosine.
GuanfacineGuanfacine may increase the sedative activities of Metyrosine.
HalazepamHalazepam may increase the sedative activities of Metyrosine.
HaloperidolHaloperidol may increase the sedative activities of Metyrosine.
HaloperidolThe risk or severity of adverse effects can be increased when Metyrosine is combined with Haloperidol.
HalothaneHalothane may increase the sedative activities of Metyrosine.
HeroinHeroin may increase the sedative activities of Metyrosine.
HexobarbitalHexobarbital may increase the sedative activities of Metyrosine.
HydrocodoneHydrocodone may increase the sedative activities of Metyrosine.
HydromorphoneHydromorphone may increase the sedative activities of Metyrosine.
HydroxyzineHydroxyzine may increase the sedative activities of Metyrosine.
IloperidoneIloperidone may increase the sedative activities of Metyrosine.
IloperidoneThe risk or severity of adverse effects can be increased when Metyrosine is combined with Iloperidone.
ImipramineImipramine may increase the sedative activities of Metyrosine.
ImipramineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Imipramine.
IndalpineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Indalpine.
IsofluraneIsoflurane may increase the sedative activities of Metyrosine.
KetamineKetamine may increase the sedative activities of Metyrosine.
KetazolamKetazolam may increase the sedative activities of Metyrosine.
KetobemidoneKetobemidone may increase the sedative activities of Metyrosine.
LamotrigineLamotrigine may increase the sedative activities of Metyrosine.
LevetiracetamLevetiracetam may increase the sedative activities of Metyrosine.
LevobupivacaineLevobupivacaine may increase the sedative activities of Metyrosine.
LevocabastineLevocabastine may increase the sedative activities of Metyrosine.
LevocetirizineLevocetirizine may increase the sedative activities of Metyrosine.
LevodopaLevodopa may increase the sedative activities of Metyrosine.
Levomethadyl AcetateLevomethadyl Acetate may increase the sedative activities of Metyrosine.
LevomilnacipranThe risk or severity of adverse effects can be increased when Metyrosine is combined with Levomilnacipran.
LevorphanolLevorphanol may increase the sedative activities of Metyrosine.
LidocaineLidocaine may increase the sedative activities of Metyrosine.
LithiumLithium may increase the sedative activities of Metyrosine.
LithiumThe risk or severity of adverse effects can be increased when Metyrosine is combined with Lithium.
LofentanilLofentanil may increase the sedative activities of Metyrosine.
LoratadineLoratadine may increase the sedative activities of Metyrosine.
LorazepamLorazepam may increase the sedative activities of Metyrosine.
LoxapineLoxapine may increase the sedative activities of Metyrosine.
LoxapineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Loxapine.
Lu AA21004The risk or severity of adverse effects can be increased when Metyrosine is combined with Lu AA21004.
Lu AA21004Lu AA21004 may increase the sedative activities of Metyrosine.
LurasidoneLurasidone may increase the sedative activities of Metyrosine.
LurasidoneThe risk or severity of adverse effects can be increased when Metyrosine is combined with Lurasidone.
Magnesium SulfateMagnesium Sulfate may increase the sedative activities of Metyrosine.
MaprotilineMaprotiline may increase the sedative activities of Metyrosine.
MeclizineMeclizine may increase the sedative activities of Metyrosine.
MedetomidineMedetomidine may increase the sedative activities of Metyrosine.
MelatoninMelatonin may increase the sedative activities of Metyrosine.
MelperoneMelperone may increase the sedative activities of Metyrosine.
MelperoneThe risk or severity of adverse effects can be increased when Metyrosine is combined with Melperone.
MepivacaineMepivacaine may increase the sedative activities of Metyrosine.
MeprobamateMeprobamate may increase the sedative activities of Metyrosine.
MesoridazineMesoridazine may increase the sedative activities of Metyrosine.
MesoridazineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Mesoridazine.
MetaxaloneMetaxalone may increase the sedative activities of Metyrosine.
MethadoneMethadone may increase the sedative activities of Metyrosine.
Methadyl AcetateMethadyl Acetate may increase the sedative activities of Metyrosine.
MethapyrileneMethapyrilene may increase the sedative activities of Metyrosine.
MethaqualoneMethaqualone may increase the sedative activities of Metyrosine.
MethocarbamolMethocarbamol may increase the sedative activities of Metyrosine.
MethohexitalMethohexital may increase the sedative activities of Metyrosine.
MethotrimeprazineMethotrimeprazine may increase the sedative activities of Metyrosine.
MethotrimeprazineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Methotrimeprazine.
MethoxyfluraneMethoxyflurane may increase the sedative activities of Metyrosine.
MethsuximideMethsuximide may increase the sedative activities of Metyrosine.
MethylphenobarbitalMethylphenobarbital may increase the sedative activities of Metyrosine.
MetoclopramideThe risk or severity of adverse effects can be increased when Metyrosine is combined with Metoclopramide.
MidazolamMidazolam may increase the sedative activities of Metyrosine.
MilnacipranThe risk or severity of adverse effects can be increased when Metyrosine is combined with Milnacipran.
MirtazapineMirtazapine may increase the sedative activities of Metyrosine.
MirtazapineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Mirtazapine.
MolindoneMolindone may increase the sedative activities of Metyrosine.
MolindoneThe risk or severity of adverse effects can be increased when Metyrosine is combined with Molindone.
MorphineMorphine may increase the sedative activities of Metyrosine.
NabiloneNabilone may increase the sedative activities of Metyrosine.
NalbuphineNalbuphine may increase the sedative activities of Metyrosine.
NitrazepamNitrazepam may increase the sedative activities of Metyrosine.
Nitrous oxideNitrous oxide may increase the sedative activities of Metyrosine.
NormethadoneNormethadone may increase the sedative activities of Metyrosine.
NortriptylineNortriptyline may increase the sedative activities of Metyrosine.
NortriptylineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Nortriptyline.
OlanzapineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Olanzapine.
OlanzapineOlanzapine may increase the sedative activities of Metyrosine.
OlopatadineOlopatadine may increase the sedative activities of Metyrosine.
OndansetronOndansetron may increase the sedative activities of Metyrosine.
OndansetronThe risk or severity of adverse effects can be increased when Metyrosine is combined with Ondansetron.
OpiumOpium may increase the sedative activities of Metyrosine.
OrphenadrineOrphenadrine may increase the sedative activities of Metyrosine.
OsanetantOsanetant may increase the sedative activities of Metyrosine.
OsanetantThe risk or severity of adverse effects can be increased when Metyrosine is combined with Osanetant.
OxazepamOxazepam may increase the sedative activities of Metyrosine.
OxprenololOxprenolol may increase the sedative activities of Metyrosine.
OxybuprocaineOxybuprocaine may increase the sedative activities of Metyrosine.
OxycodoneOxycodone may increase the sedative activities of Metyrosine.
OxymorphoneOxymorphone may increase the sedative activities of Metyrosine.
PaliperidonePaliperidone may increase the sedative activities of Metyrosine.
PaliperidoneThe risk or severity of adverse effects can be increased when Metyrosine is combined with Paliperidone.
ParaldehydeParaldehyde may increase the sedative activities of Metyrosine.
ParoxetineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Paroxetine.
PentazocinePentazocine may increase the sedative activities of Metyrosine.
PentobarbitalPentobarbital may increase the sedative activities of Metyrosine.
PerampanelPerampanel may increase the sedative activities of Metyrosine.
PerospironePerospirone may increase the sedative activities of Metyrosine.
PerospironeThe risk or severity of adverse effects can be increased when Metyrosine is combined with Perospirone.
PerphenazinePerphenazine may increase the sedative activities of Metyrosine.
PerphenazineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Perphenazine.
PethidinePethidine may increase the sedative activities of Metyrosine.
PhenobarbitalPhenobarbital may increase the sedative activities of Metyrosine.
PhenoxyethanolPhenoxyethanol may increase the sedative activities of Metyrosine.
PhenytoinPhenytoin may increase the sedative activities of Metyrosine.
PimozidePimozide may increase the sedative activities of Metyrosine.
PimozideThe risk or severity of adverse effects can be increased when Metyrosine is combined with Pimozide.
PipamperonePipamperone may increase the sedative activities of Metyrosine.
PipamperoneThe risk or severity of adverse effects can be increased when Metyrosine is combined with Pipamperone.
PipotiazinePipotiazine may increase the sedative activities of Metyrosine.
PipotiazineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Pipotiazine.
PizotifenPizotifen may increase the sedative activities of Metyrosine.
PomalidomidePomalidomide may increase the sedative activities of Metyrosine.
PramocainePramocaine may increase the sedative activities of Metyrosine.
PrazepamPrazepam may increase the sedative activities of Metyrosine.
PregabalinPregabalin may increase the sedative activities of Metyrosine.
PrilocainePrilocaine may increase the sedative activities of Metyrosine.
PrimidonePrimidone may increase the sedative activities of Metyrosine.
ProcaineProcaine may increase the sedative activities of Metyrosine.
ProchlorperazineProchlorperazine may increase the sedative activities of Metyrosine.
ProchlorperazineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Prochlorperazine.
PromazinePromazine may increase the sedative activities of Metyrosine.
PromazineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Promazine.
PromethazinePromethazine may increase the sedative activities of Metyrosine.
PromethazineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Promethazine.
ProparacaineProparacaine may increase the sedative activities of Metyrosine.
PropericiazineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Propericiazine.
PropofolPropofol may increase the sedative activities of Metyrosine.
PropoxycainePropoxycaine may increase the sedative activities of Metyrosine.
ProtriptylineProtriptyline may increase the sedative activities of Metyrosine.
ProtriptylineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Protriptyline.
PSD502PSD502 may increase the sedative activities of Metyrosine.
QuazepamQuazepam may increase the sedative activities of Metyrosine.
QuetiapineQuetiapine may increase the sedative activities of Metyrosine.
QuetiapineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Quetiapine.
RamelteonRamelteon may increase the sedative activities of Metyrosine.
RemifentanilRemifentanil may increase the sedative activities of Metyrosine.
RemoxiprideRemoxipride may increase the sedative activities of Metyrosine.
RemoxiprideThe risk or severity of adverse effects can be increased when Metyrosine is combined with Remoxipride.
ReserpineReserpine may increase the sedative activities of Metyrosine.
ReserpineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Reserpine.
RisperidoneRisperidone may increase the sedative activities of Metyrosine.
RisperidoneThe risk or severity of adverse effects can be increased when Metyrosine is combined with Risperidone.
RomifidineRomifidine may increase the sedative activities of Metyrosine.
RopivacaineRopivacaine may increase the sedative activities of Metyrosine.
S-EthylisothioureaS-Ethylisothiourea may increase the sedative activities of Metyrosine.
ScopolamineScopolamine may increase the sedative activities of Metyrosine.
SecobarbitalSecobarbital may increase the sedative activities of Metyrosine.
SertindoleSertindole may increase the sedative activities of Metyrosine.
SertindoleThe risk or severity of adverse effects can be increased when Metyrosine is combined with Sertindole.
SertralineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Sertraline.
SevofluraneSevoflurane may increase the sedative activities of Metyrosine.
Sodium oxybateSodium oxybate may increase the sedative activities of Metyrosine.
StiripentolStiripentol may increase the sedative activities of Metyrosine.
SufentanilSufentanil may increase the sedative activities of Metyrosine.
SulpirideSulpiride may increase the sedative activities of Metyrosine.
SulpirideThe risk or severity of adverse effects can be increased when Metyrosine is combined with Sulpiride.
SuvorexantSuvorexant may increase the sedative activities of Metyrosine.
TapentadolTapentadol may increase the sedative activities of Metyrosine.
TasimelteonTasimelteon may increase the sedative activities of Metyrosine.
TemazepamTemazepam may increase the sedative activities of Metyrosine.
TetrabenazineTetrabenazine may increase the sedative activities of Metyrosine.
TetrabenazineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Tetrabenazine.
TetracaineTetracaine may increase the sedative activities of Metyrosine.
TetrodotoxinTetrodotoxin may increase the sedative activities of Metyrosine.
ThalidomideThalidomide may increase the sedative activities of Metyrosine.
ThiamylalThiamylal may increase the sedative activities of Metyrosine.
ThiopentalThiopental may increase the sedative activities of Metyrosine.
ThioproperazineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Thioproperazine.
ThioridazineThioridazine may increase the sedative activities of Metyrosine.
ThioridazineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Thioridazine.
ThiothixeneThiothixene may increase the sedative activities of Metyrosine.
ThiothixeneThe risk or severity of adverse effects can be increased when Metyrosine is combined with Thiothixene.
TiagabineTiagabine may increase the sedative activities of Metyrosine.
TianeptineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Tianeptine.
TiletamineTiletamine may increase the sedative activities of Metyrosine.
TizanidineTizanidine may increase the sedative activities of Metyrosine.
TolcaponeTolcapone may increase the sedative activities of Metyrosine.
TopiramateTopiramate may increase the sedative activities of Metyrosine.
TramadolTramadol may increase the sedative activities of Metyrosine.
Trans-2-PhenylcyclopropylamineTrans-2-Phenylcyclopropylamine may increase the sedative activities of Metyrosine.
TranylcypromineTranylcypromine may increase the sedative activities of Metyrosine.
TrazodoneThe risk or severity of adverse effects can be increased when Metyrosine is combined with Trazodone.
TrazodoneTrazodone may increase the sedative activities of Metyrosine.
TriazolamTriazolam may increase the sedative activities of Metyrosine.
TrifluoperazineTrifluoperazine may increase the sedative activities of Metyrosine.
TrifluoperazineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Trifluoperazine.
TriflupromazineTriflupromazine may increase the sedative activities of Metyrosine.
TriflupromazineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Triflupromazine.
TrimipramineTrimipramine may increase the sedative activities of Metyrosine.
TrimipramineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Trimipramine.
TriprolidineTriprolidine may increase the sedative activities of Metyrosine.
Valproic AcidValproic Acid may increase the sedative activities of Metyrosine.
VigabatrinVigabatrin may increase the sedative activities of Metyrosine.
VilazodoneThe risk or severity of adverse effects can be increased when Metyrosine is combined with Vilazodone.
VortioxetineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Vortioxetine.
VortioxetineVortioxetine may increase the sedative activities of Metyrosine.
XylazineXylazine may increase the sedative activities of Metyrosine.
ZaleplonZaleplon may increase the sedative activities of Metyrosine.
ZiconotideZiconotide may increase the sedative activities of Metyrosine.
ZimelidineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Zimelidine.
ZiprasidoneZiprasidone may increase the sedative activities of Metyrosine.
ZiprasidoneThe risk or severity of adverse effects can be increased when Metyrosine is combined with Ziprasidone.
ZolazepamZolazepam may increase the sedative activities of Metyrosine.
ZolpidemZolpidem may increase the sedative activities of Metyrosine.
ZonisamideZonisamide may increase the sedative activities of Metyrosine.
ZopicloneZopiclone may increase the sedative activities of Metyrosine.
ZotepineZotepine may increase the sedative activities of Metyrosine.
ZotepineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Zotepine.
ZuclopenthixolZuclopenthixol may increase the sedative activities of Metyrosine.
ZuclopenthixolThe risk or severity of adverse effects can be increased when Metyrosine is combined with Zuclopenthixol.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
binder
General Function:
Tyrosine 3-monooxygenase activity
Specific Function:
Plays an important role in the physiology of adrenergic neurons.
Gene Name:
TH
Uniprot ID:
P07101
Molecular Weight:
58599.545 Da
References
  1. Nasrallah HA, Donnelly EF, Bigelow LB, Rivera-Calimlim L, Rogol A, Potkin S, Rauscher FP, Wyatt RJ: Inhibition of dopamine synthesis in chronic schizophrenia. Clinical ineffectiveness of metyrosine. Arch Gen Psychiatry. 1977 Jun;34(6):649-55. [PubMed:17374 ]
  2. Yoshimoto Y, Nakaso K, Nakashima K: L-dopa and dopamine enhance the formation of aggregates under proteasome inhibition in PC12 cells. FEBS Lett. 2005 Feb 14;579(5):1197-202. Epub 2005 Jan 21. [PubMed:15710413 ]
  3. Shore PA, Dorris RL: On a prime role for newly synthesized dopamine in striatal function. Eur J Pharmacol. 1975 Feb;30(2):315-8. [PubMed:1168577 ]
  4. Moore KE, Demarest KT, Johnston CA: Influence of prolactin on dopaminergic neuronal systems in the hypothalamus. Fed Proc. 1980 Sep;39(11):2912-6. [PubMed:7409209 ]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23