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Identification
NameNorepinephrine
Accession NumberDB00368  (APRD01299)
TypeSmall Molecule
GroupsApproved
DescriptionPrecursor of epinephrine that is secreted by the adrenal medulla and is a widespread central and autonomic neurotransmitter. Norepinephrine is the principal transmitter of most postganglionic sympathetic fibers and of the diffuse projection system in the brain arising from the locus ceruleus. It is also found in plants and is used pharmacologically as a sympathomimetic. [PubChem]
Structure
Thumb
Synonyms
(-)-Arterenol
(-)-Noradrenaline
(-)-Norepinephrine
(R)-(-)-Norepinephrine
(R)-4-(2-amino-1-Hydroxyethyl)-1,2-benzenediol
(R)-Norepinephrine
4-[(1R)-2-Amino-1-hydroxyethyl]-1,2-benzenediol
Arterenol
L-noradrenaline
L-Norepinephrine
Nor-adrenaline
Noradrenaline
Norepinefrina
Norepinephrine
Norepinephrinum
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
LevophedInjection, solution, concentrate1 mg/mLIntravenousHospira, Inc.1950-07-13Not applicableUs
LevophedInjection, solution, concentrate1 mg/mLIntravenousHospira, Inc.1950-07-13Not applicableUs
LevophedInjection, solution, concentrate1 mg/mLIntravenousGeneral Injectables & Vaccines, Inc2010-03-01Not applicableUs
LevophedInjection, solution, concentrate1 mg/mLIntravenousCardinal Health1982-01-01Not applicableUs
Levophed 1.0 mg/mlSolution1 mgIntravenousHospira Healthcare Corporation2001-10-01Not applicableCanada
Levophed Liq IV 1.0mg/mlLiquid1 mgIntravenousSanofi Canada, Inc.1951-12-312001-08-10Canada
Norepinephrine Bitartrate Inj 1mg/ml USPLiquid1 mgIntravenousSandoz Canada Incorporated1991-12-31Not applicableCanada
Norepinephrine Bitartrate Injection, USPSolution1 mgIntravenousSterimax IncNot applicableNot applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Norepinephrine BitartrateInjection1 mg/mLIntravenousCardinal Health2003-03-03Not applicableUs
Norepinephrine BitartrateInjection1 mg/mLIntravenousCardinal Health2012-04-01Not applicableUs
Norepinephrine BitartrateInjection, solution, concentrate1 mg/mLIntravenousTeva Parenteral Medicines, Inc.2003-04-01Not applicableUs
Norepinephrine BitartrateInjection1 mg/mLIntravenousClaris Lifesciences Inc.2012-04-01Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Norepinephrine BitartrateInjection, solution16 ug/mLIntravenousCantrell Drug Company2015-02-20Not applicableUs
Norepinephrine BitartrateInjection, solution32 ug/mLIntravenousCantrell Drug Company2015-02-18Not applicableUs
Norepinephrine BitartrateInjection, solution64 ug/mLIntravenousCantrell Drug Company2015-03-12Not applicableUs
Norepinephrine BitartrateInjection, solution16 ug/mLIntravenousCantrell Drug Company2015-03-06Not applicableUs
Norepinephrine BitartrateInjection, solution32 ug/mLIntravenousCantrell Drug Company2015-03-06Not applicableUs
International BrandsNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Norepinephrine bitartrate
108341-18-0
Thumb
  • InChI Key: LNBCGLZYLJMGKP-LUDZCAPTSA-N
  • Monoisotopic Mass: 337.100895816
  • Average Mass: 337.281
DBSALT001247
Categories
UNIIX4W3ENH1CV
CAS number51-41-2
WeightAverage: 169.1778
Monoisotopic: 169.073893223
Chemical FormulaC8H11NO3
InChI KeySFLSHLFXELFNJZ-QMMMGPOBSA-N
InChI
InChI=1S/C8H11NO3/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8,10-12H,4,9H2/t8-/m0/s1
IUPAC Name
4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diol
SMILES
NC[[email protected]](O)C1=CC(O)=C(O)C=C1
Pharmacology
IndicationMainly used to treat patients in vasodilatory shock states such as septic shock and neurogenic shock and has shown a survival benefit over dopamine. Also used as a vasopressor medication for patients with critical hypotension.
Structured Indications
PharmacodynamicsNoradrenaline acts on both alpha-1 and alpha-2 adrenergic receptors to cause vasoconstriction. Its effect in-vitro is often limited to the increasing of blood pressure through antagonising alpha-1 and alpha-2 receptors and causing a resultant increase in systemic vascular resistance.
Mechanism of actionNorepinephrine functions as a peripheral vasoconstrictor by acting on alpha-adrenergic receptors. It is also an inotropic stimulator of the heart and dilator of coronary arteries as a result of it's activity at the beta-adrenergic receptors.
TargetKindPharmacological actionActionsOrganismUniProt ID
Alpha-1A adrenergic receptorProteinyes
agonist
HumanP35348 details
Alpha-1B adrenergic receptorProteinyes
agonist
HumanP35368 details
Alpha-1D adrenergic receptorProteinyes
agonist
HumanP25100 details
Alpha-2A adrenergic receptorProteinyes
agonist
HumanP08913 details
Alpha-2B adrenergic receptorProteinyes
agonist
HumanP18089 details
Alpha-2C adrenergic receptorProteinyes
agonist
HumanP18825 details
Beta-1 adrenergic receptorProteinyes
agonist
HumanP08588 details
Beta-2 adrenergic receptorProteinyes
agonist
HumanP07550 details
Beta-3 adrenergic receptorProteinyes
agonist
HumanP13945 details
Phenylalanine-4-hydroxylaseProteinno
inhibitor
HumanP00439 details
Synaptic vesicular amine transporterProteinunknown
binder
HumanQ05940 details
Chromaffin granule amine transporterProteinunknown
binder
HumanP54219 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
SubstrateEnzymesProduct
Norepinephrine
Not Available
Norepinephrine sulfateDetails
Norepinephrine
Not Available
3-Methoxy-4-Hydroxyphenylglycol sulfateDetails
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityIn high dose and especially when it is combined with other vasopressors, it can lead to limb ischemia and limb death.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Catecholamine BiosynthesisMetabolicSMP00012
Prilocaine Action PathwayDrug actionSMP00401
Heroin Action PathwayDrug actionSMP00407
Methadone Action PathwayDrug actionSMP00408
Alfentanil Action PathwayDrug actionSMP00413
Carfentanil Action PathwayDrug actionSMP00414
Tramadol Action Action PathwayDrug actionSMP00671
Levallorphan Action PathwayDrug actionSMP00683
Aromatic L-Aminoacid Decarboxylase DeficiencyDiseaseSMP00170
Levobupivacaine Action PathwayDrug actionSMP00397
Oxymorphone Action PathwayDrug actionSMP00412
Fentanyl Action PathwayDrug actionSMP00415
Fluoxetine Action PathwayDrug actionSMP00426
Nicotine Action PathwayDrug actionSMP00431
Levorphanol Action PathwayDrug actionSMP00673
Anileridine Action PathwayDrug actionSMP00674
Methadyl Acetate Action PathwayDrug actionSMP00678
Buprenorphine Action PathwayDrug actionSMP00684
Pentazocine Action PathwayDrug actionSMP00686
Nalbuphine Action PathwayDrug actionSMP00691
Tyrosinemia Type IDiseaseSMP00218
Benzocaine Action PathwayDrug actionSMP00392
Mepivacaine Action PathwayDrug actionSMP00399
Morphine Action PathwayDrug actionSMP00406
Oxycodone Action PathwayDrug actionSMP00409
Hydrocodone Action PathwayDrug actionSMP00411
Desipramine Action PathwayDrug actionSMP00423
Citalopram Action PathwayDrug actionSMP00424
Disulfiram Action PathwayDrug actionSMP00429
Tyrosine hydroxylase deficiencyDiseaseSMP00497
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE may increase the hypertensive activities of Norepinephrine.Experimental
AcebutololNorepinephrine may increase the atrioventricular blocking (AV block) activities of Acebutolol.Approved
AlfuzosinAlfuzosin may decrease the vasoconstricting activities of Norepinephrine.Approved, Investigational
AlprenololAlprenolol may decrease the bronchodilatory activities of Norepinephrine.Approved, Withdrawn
AmineptineAmineptine may decrease the antihypertensive activities of Norepinephrine.Illicit, Withdrawn
AmitriptylineAmitriptyline may decrease the antihypertensive activities of Norepinephrine.Approved
AmphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Norepinephrine.Approved, Illicit
Aop200704Norepinephrine may increase the atrioventricular blocking (AV block) activities of Aop200704.Investigational
ArotinololNorepinephrine may increase the atrioventricular blocking (AV block) activities of Arotinolol.Approved
AtenololNorepinephrine may increase the atrioventricular blocking (AV block) activities of Atenolol.Approved
AtomoxetineAtomoxetine may increase the hypertensive activities of Norepinephrine.Approved
AtosibanThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Atosiban.Approved
BefunololNorepinephrine may increase the atrioventricular blocking (AV block) activities of Befunolol.Experimental
BendroflumethiazideNorepinephrine may increase the hypokalemic activities of Bendroflumethiazide.Approved
BenmoxinBenmoxin may increase the hypertensive activities of Norepinephrine.Withdrawn
BenzphetamineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Benzphetamine.Approved, Illicit
Benzylpenicilloyl PolylysineNorepinephrine may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.Approved
BetahistineThe therapeutic efficacy of Norepinephrine can be decreased when used in combination with Betahistine.Approved
BetaxololNorepinephrine may increase the atrioventricular blocking (AV block) activities of Betaxolol.Approved
BevantololNorepinephrine may increase the atrioventricular blocking (AV block) activities of Bevantolol.Approved
BisoprololNorepinephrine may increase the atrioventricular blocking (AV block) activities of Bisoprolol.Approved
BopindololBopindolol may decrease the bronchodilatory activities of Norepinephrine.Approved
BromocriptineBromocriptine may increase the hypertensive activities of Norepinephrine.Approved, Investigational
BucindololNorepinephrine may increase the atrioventricular blocking (AV block) activities of Bucindolol.Investigational
BufuralolNorepinephrine may increase the atrioventricular blocking (AV block) activities of Bufuralol.Experimental, Investigational
BumetanideNorepinephrine may increase the hypokalemic activities of Bumetanide.Approved
BupranololBupranolol may decrease the bronchodilatory activities of Norepinephrine.Approved
BupropionThe serum concentration of Norepinephrine can be increased when it is combined with Bupropion.Approved
CabergolineCabergoline may increase the hypertensive activities of Norepinephrine.Approved
CaroxazoneCaroxazone may increase the hypertensive activities of Norepinephrine.Withdrawn
CarteololCarteolol may decrease the bronchodilatory activities of Norepinephrine.Approved
CarvedilolNorepinephrine may increase the atrioventricular blocking (AV block) activities of Carvedilol.Approved, Investigational
CeliprololNorepinephrine may increase the atrioventricular blocking (AV block) activities of Celiprolol.Approved, Investigational
ChlorothiazideNorepinephrine may increase the hypokalemic activities of Chlorothiazide.Approved, Vet Approved
ChlorphentermineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Chlorphentermine.Illicit, Withdrawn
ChlorthalidoneNorepinephrine may increase the hypokalemic activities of Chlorthalidone.Approved
ClenbuterolThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Clenbuterol.Approved, Vet Approved
ClomipramineClomipramine may decrease the antihypertensive activities of Norepinephrine.Approved, Vet Approved
CyclobenzaprineCyclobenzaprine may decrease the antihypertensive activities of Norepinephrine.Approved
DesfluraneDesflurane may increase the arrhythmogenic activities of Norepinephrine.Approved
DesipramineDesipramine may decrease the antihypertensive activities of Norepinephrine.Approved
DesvenlafaxineDesvenlafaxine may increase the tachycardic activities of Norepinephrine.Approved
DihydroergotamineDihydroergotamine may increase the hypertensive activities of Norepinephrine.Approved
DobutamineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Dobutamine.Approved
DopamineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Dopamine.Approved
DosulepinDosulepin may decrease the antihypertensive activities of Norepinephrine.Approved
DoxazosinDoxazosin may decrease the vasoconstricting activities of Norepinephrine.Approved
DoxepinDoxepin may decrease the antihypertensive activities of Norepinephrine.Approved
DoxofyllineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Doxofylline.Approved
DronabinolDronabinol may increase the tachycardic activities of Norepinephrine.Approved, Illicit
DroxidopaNorepinephrine may increase the hypertensive activities of Droxidopa.Approved, Investigational
DuloxetineDuloxetine may increase the tachycardic activities of Norepinephrine.Approved
EnfluraneEnflurane may increase the arrhythmogenic activities of Norepinephrine.Approved, Vet Approved
EphedrineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Ephedrine.Approved
EpinephrineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Epinephrine.Approved, Vet Approved
Ergoloid mesylateErgoloid mesylate may increase the hypertensive activities of Norepinephrine.Approved
ErgonovineErgonovine may increase the hypertensive activities of Norepinephrine.Approved
ErgotamineErgotamine may increase the hypertensive activities of Norepinephrine.Approved
EsmirtazapineEsmirtazapine may decrease the antihypertensive activities of Norepinephrine.Investigational
EsmololNorepinephrine may increase the atrioventricular blocking (AV block) activities of Esmolol.Approved
Etacrynic acidNorepinephrine may increase the hypokalemic activities of Etacrynic acid.Approved
EtilefrineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Etilefrine.Withdrawn
FenoterolThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Fenoterol.Approved
FurazolidoneFurazolidone may increase the hypertensive activities of Norepinephrine.Approved, Vet Approved
FurosemideNorepinephrine may increase the hypokalemic activities of Furosemide.Approved, Vet Approved
HalothaneHalothane may increase the arrhythmogenic activities of Norepinephrine.Approved, Vet Approved
HyaluronidaseHyaluronidase may increase the vasoconstricting activities of Norepinephrine.Approved, Investigational
HydracarbazineHydracarbazine may increase the hypertensive activities of Norepinephrine.Approved
HydrochlorothiazideNorepinephrine may increase the hypokalemic activities of Hydrochlorothiazide.Approved, Vet Approved
HydroflumethiazideNorepinephrine may increase the hypokalemic activities of Hydroflumethiazide.Approved
Hydroxyamphetamine hydrobromideThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Hydroxyamphetamine hydrobromide.Approved
ImipramineImipramine may decrease the antihypertensive activities of Norepinephrine.Approved
IndapamideNorepinephrine may increase the hypokalemic activities of Indapamide.Approved
IndenololNorepinephrine may increase the atrioventricular blocking (AV block) activities of Indenolol.Withdrawn
IndoraminIndoramin may decrease the vasoconstricting activities of Norepinephrine.Withdrawn
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Norepinephrine.Approved
Ioflupane I-123Norepinephrine may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved
IproclozideIproclozide may increase the hypertensive activities of Norepinephrine.Withdrawn
IproniazidIproniazid may increase the hypertensive activities of Norepinephrine.Withdrawn
IsocarboxazidIsocarboxazid may increase the hypertensive activities of Norepinephrine.Approved
IsofluraneIsoflurane may increase the arrhythmogenic activities of Norepinephrine.Approved, Vet Approved
IsoprenalineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Isoprenaline.Approved
IsoxsuprineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Isoxsuprine.Approved, Withdrawn
LabetalolNorepinephrine may increase the atrioventricular blocking (AV block) activities of Labetalol.Approved
LevomilnacipranLevomilnacipran may increase the tachycardic activities of Norepinephrine.Approved
LinezolidLinezolid may increase the hypertensive activities of Norepinephrine.Approved, Investigational
MebanazineMebanazine may increase the hypertensive activities of Norepinephrine.Withdrawn
MephentermineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Mephentermine.Approved
MetaraminolThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Metaraminol.Approved, Investigational
MethamphetamineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Methamphetamine.Approved, Illicit
MethoxamineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Methoxamine.Approved
MethoxyfluraneMethoxyflurane may increase the arrhythmogenic activities of Norepinephrine.Approved, Vet Approved
MethyclothiazideNorepinephrine may increase the hypokalemic activities of Methyclothiazide.Approved
Methylene blueMethylene blue may increase the hypertensive activities of Norepinephrine.Investigational
MetolazoneNorepinephrine may increase the hypokalemic activities of Metolazone.Approved
MetoprololNorepinephrine may increase the atrioventricular blocking (AV block) activities of Metoprolol.Approved, Investigational
MianserinThe therapeutic efficacy of Norepinephrine can be decreased when used in combination with Mianserin.Approved
MidodrineThe risk or severity of adverse effects can be increased when Midodrine is combined with Norepinephrine.Approved
MilnacipranMilnacipran may increase the tachycardic activities of Norepinephrine.Approved
MinaprineMinaprine may increase the hypertensive activities of Norepinephrine.Approved
MirtazapineMirtazapine may decrease the antihypertensive activities of Norepinephrine.Approved
MoclobemideMoclobemide may increase the hypertensive activities of Norepinephrine.Approved
NabiloneNabilone may increase the tachycardic activities of Norepinephrine.Approved, Investigational
NadololNadolol may decrease the bronchodilatory activities of Norepinephrine.Approved
NebivololNebivolol may decrease the bronchodilatory activities of Norepinephrine.Approved, Investigational
NialamideNialamide may increase the hypertensive activities of Norepinephrine.Withdrawn
Nitrous oxideNitrous oxide may increase the arrhythmogenic activities of Norepinephrine.Approved, Vet Approved
NortriptylineNortriptyline may decrease the antihypertensive activities of Norepinephrine.Approved
NylidrinThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Nylidrin.Approved
OctamoxinOctamoxin may increase the hypertensive activities of Norepinephrine.Withdrawn
OpipramolOpipramol may decrease the antihypertensive activities of Norepinephrine.Investigational
OrciprenalineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Orciprenaline.Approved
OxprenololOxprenolol may decrease the bronchodilatory activities of Norepinephrine.Approved
OxymetazolineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Oxymetazoline.Approved
PargylinePargyline may increase the hypertensive activities of Norepinephrine.Approved
PenbutololPenbutolol may decrease the bronchodilatory activities of Norepinephrine.Approved, Investigational
PhenelzinePhenelzine may increase the hypertensive activities of Norepinephrine.Approved
PheniprazinePheniprazine may increase the hypertensive activities of Norepinephrine.Withdrawn
PhenmetrazineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Phenmetrazine.Approved, Illicit
PhenoxypropazinePhenoxypropazine may increase the hypertensive activities of Norepinephrine.Withdrawn
PhentermineThe risk or severity of adverse effects can be increased when Phentermine is combined with Norepinephrine.Approved, Illicit
PhenylephrineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Phenylephrine.Approved
PhenylpropanolamineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Phenylpropanolamine.Approved, Vet Approved, Withdrawn
PindololPindolol may decrease the bronchodilatory activities of Norepinephrine.Approved
PiretanideNorepinephrine may increase the hypokalemic activities of Piretanide.Experimental
PirlindolePirlindole may increase the hypertensive activities of Norepinephrine.Approved
PivhydrazinePivhydrazine may increase the hypertensive activities of Norepinephrine.Withdrawn
PolythiazideNorepinephrine may increase the hypokalemic activities of Polythiazide.Approved
PractololNorepinephrine may increase the atrioventricular blocking (AV block) activities of Practolol.Approved
PrazosinPrazosin may decrease the vasoconstricting activities of Norepinephrine.Approved
ProcaterolThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Procaterol.Approved
PropranololPropranolol may decrease the bronchodilatory activities of Norepinephrine.Approved, Investigational
ProtriptylineProtriptyline may decrease the antihypertensive activities of Norepinephrine.Approved
PseudoephedrineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Pseudoephedrine.Approved
QuinethazoneNorepinephrine may increase the hypokalemic activities of Quinethazone.Approved
RacepinephrineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Racepinephrine.Approved
RasagilineRasagiline may increase the hypertensive activities of Norepinephrine.Approved
RitodrineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Ritodrine.Approved
SafrazineSafrazine may increase the hypertensive activities of Norepinephrine.Withdrawn
SelegilineSelegiline may increase the hypertensive activities of Norepinephrine.Approved, Investigational, Vet Approved
SevofluraneSevoflurane may increase the arrhythmogenic activities of Norepinephrine.Approved, Vet Approved
SilodosinSilodosin may decrease the vasoconstricting activities of Norepinephrine.Approved
SotalolSotalol may decrease the bronchodilatory activities of Norepinephrine.Approved
SpironolactoneSpironolactone may decrease the vasoconstricting activities of Norepinephrine.Approved
SynephrineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Synephrine.Experimental
TamsulosinTamsulosin may decrease the vasoconstricting activities of Norepinephrine.Approved, Investigational
Tedizolid PhosphateTedizolid Phosphate may increase the hypertensive activities of Norepinephrine.Approved
TerazosinTerazosin may decrease the vasoconstricting activities of Norepinephrine.Approved
TerbutalineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Terbutaline.Approved
TetryzolineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Tetryzoline.Approved
TianeptineTianeptine may decrease the antihypertensive activities of Norepinephrine.Approved
TimololTimolol may decrease the bronchodilatory activities of Norepinephrine.Approved
ToloxatoneToloxatone may increase the hypertensive activities of Norepinephrine.Approved
TorasemideNorepinephrine may increase the hypokalemic activities of Torasemide.Approved
Trans-2-PhenylcyclopropylamineTrans-2-Phenylcyclopropylamine may increase the hypertensive activities of Norepinephrine.Experimental
TranylcypromineTranylcypromine may increase the hypertensive activities of Norepinephrine.Approved
TrichlormethiazideNorepinephrine may increase the hypokalemic activities of Trichlormethiazide.Approved, Vet Approved
TrimazosinTrimazosin may decrease the vasoconstricting activities of Norepinephrine.Experimental
TrimipramineTrimipramine may decrease the antihypertensive activities of Norepinephrine.Approved
TyramineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Tyramine.Investigational, Nutraceutical
VenlafaxineVenlafaxine may increase the tachycardic activities of Norepinephrine.Approved
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesC01CA03
AHFS Codes
  • 12:12.12
  • 68:12.00
PDB Entries
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9837
Blood Brain Barrier-0.9762
Caco-2 permeable-0.7985
P-glycoprotein substrateNon-substrate0.6046
P-glycoprotein inhibitor INon-inhibitor0.9441
P-glycoprotein inhibitor IINon-inhibitor0.9285
Renal organic cation transporterNon-inhibitor0.9004
CYP450 2C9 substrateNon-substrate0.8702
CYP450 2D6 substrateNon-substrate0.8667
CYP450 3A4 substrateNon-substrate0.7986
CYP450 1A2 substrateNon-inhibitor0.9135
CYP450 2C9 inhibitorNon-inhibitor0.9675
CYP450 2D6 inhibitorNon-inhibitor0.9798
CYP450 2C19 inhibitorNon-inhibitor0.9446
CYP450 3A4 inhibitorNon-inhibitor0.9209
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8839
Ames testNon AMES toxic0.5053
CarcinogenicityNon-carcinogens0.8942
BiodegradationReady biodegradable0.5401
Rat acute toxicity2.2298 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9028
hERG inhibition (predictor II)Non-inhibitor0.7864
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Hospira inc
Packagers
Dosage forms
FormRouteStrength
Injection, solution, concentrateIntravenous1 mg/mL
SolutionIntravenous1 mg
InjectionIntravenous1 mg/mL
Injection, solutionIntravenous16 ug/mL
Injection, solutionIntravenous32 ug/mL
Injection, solutionIntravenous64 ug/mL
LiquidIntravenous1 mg
Prices
Unit descriptionCostUnit
Norepinephrine 4 mg/4 ml amp2.68USD ml
Levophed 1 mg/ml ampul1.49USD ml
Norepinephrine 1 mg/ml vial0.96USD ml
Levophed 1 mg/ml vial0.48USD ml
Norepinephrine-d5w 4 mg/250 ml0.16USD ml
Norepinephrine-ns 4 mg/250 ml0.16USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point217 dec °CPhysProp
logP-1.24HANSCH,C ET AL. (1995)
pKa8.58PERRIN,DD (1965)
Predicted Properties
PropertyValueSource
Water Solubility12.5 mg/mLALOGPS
logP-1.4ALOGPS
logP-0.68ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)9.5ChemAxon
pKa (Strongest Basic)8.85ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area86.71 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.46 m3·mol-1ChemAxon
Polarizability16.96 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
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-00di-1900000000-c9b4a0a230d610dd0e61View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-0udi-0900000000-5610e21bd478a4ca7bdeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0a6r-5900000000-5d7cd24a6af23a36af3aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-004i-9000000000-3c8de1511861fa1d028cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-000l-4900000000-b0893c23c186c5f8a344View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0udi-0900000000-11725b1d61843966aa7cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0udi-1900000000-6931e73a397f3917ad96View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0a4i-3900000000-bddd6ee748aa9ebecb15View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-056r-9500000000-6abd3337785c1b580668View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-004i-9100000000-ede02e0e3e74bdddc9f4View in MoNA
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
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
  • Catecholamine
  • Aralkylamine
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Protein heterodimerization activity
Specific Function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine(PE)-stimulated ERK signaling in cardiac myocytes.
Gene Name:
ADRA1A
Uniprot ID:
P35348
Molecular Weight:
51486.005 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Lachnit WG, Tran AM, Clarke DE, Ford AP: Pharmacological characterization of an alpha 1A-adrenoceptor mediating contractile responses to noradrenaline in isolated caudal artery of rat. Br J Pharmacol. 1997 Mar;120(5):819-26. [PubMed:9138687 ]
  4. Burt RP, Chapple CR, Marshall I: The role of diacylglycerol and activation of protein kinase C in alpha 1A-adrenoceptor-mediated contraction to noradrenaline of rat isolated epididymal vas deferens. Br J Pharmacol. 1996 Jan;117(1):224-30. [PubMed:8825367 ]
  5. Bishop MJ: Recent advances in the discovery of alpha1-adrenoceptor agonists. Curr Top Med Chem. 2007;7(2):135-45. [PubMed:17266602 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Protein heterodimerization activity
Specific Function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine (PE)-stimulated ERK signaling in cardiac myocytes.
Gene Name:
ADRA1B
Uniprot ID:
P35368
Molecular Weight:
56835.375 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Izzo NJ Jr, Tulenko TN, Colucci WS: Phorbol esters and norepinephrine destabilize alpha 1B-adrenergic receptor mRNA in vascular smooth muscle cells. J Biol Chem. 1994 Jan 21;269(3):1705-10. [PubMed:8294418 ]
  4. Testa R, Guarneri L, Poggesi E, Simonazzi I, Taddei C, Leonardi A: Mediation of noradrenaline-induced contractions of rat aorta by the alpha 1B-adrenoceptor subtype. Br J Pharmacol. 1995 Feb;114(4):745-50. [PubMed:7773533 ]
  5. Izzo NJ Jr, Colucci WS: Regulation of alpha 1B-adrenergic receptor half-life: protein synthesis dependence and effect of norepinephrine. Am J Physiol. 1994 Mar;266(3 Pt 1):C771-5. [PubMed:8166240 ]
  6. Bishop MJ: Recent advances in the discovery of alpha1-adrenoceptor agonists. Curr Top Med Chem. 2007;7(2):135-45. [PubMed:17266602 ]
  7. Gilsbach R, Hein L: Presynaptic metabotropic receptors for acetylcholine and adrenaline/noradrenaline. Handb Exp Pharmacol. 2008;(184):261-88. [PubMed:18064417 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Alpha1-adrenergic receptor activity
Specific Function:
This alpha-adrenergic receptor mediates its effect through the influx of extracellular calcium.
Gene Name:
ADRA1D
Uniprot ID:
P25100
Molecular Weight:
60462.205 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Cleary L, Slattery J, Bexis S, Docherty JR: Sympathectomy reveals alpha 1A- and alpha 1D-adrenoceptor components to contractions to noradrenaline in rat vas deferens. Br J Pharmacol. 2004 Nov;143(6):745-52. Epub 2004 Sep 27. [PubMed:15451776 ]
  4. Kenny BA, Chalmers DH, Philpott PC, Naylor AM: Characterization of an alpha 1D-adrenoceptor mediating the contractile response of rat aorta to noradrenaline. Br J Pharmacol. 1995 Jul;115(6):981-6. [PubMed:7582530 ]
  5. Testa R, Destefani C, Guarneri L, Poggesi E, Simonazzi I, Taddei C, Leonardi A: The alpha 1d-adrenoceptor subtype is involved in the noradrenaline-induced contractions of rat aorta. Life Sci. 1995;57(13):PL159-63. [PubMed:7674815 ]
  6. Bishop MJ: Recent advances in the discovery of alpha1-adrenoceptor agonists. Curr Top Med Chem. 2007;7(2):135-45. [PubMed:17266602 ]
  7. Gilsbach R, Hein L: Presynaptic metabotropic receptors for acetylcholine and adrenaline/noradrenaline. Handb Exp Pharmacol. 2008;(184):261-88. [PubMed:18064417 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Thioesterase binding
Specific Function:
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianser...
Gene Name:
ADRA2A
Uniprot ID:
P08913
Molecular Weight:
48956.275 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Nyronen T, Pihlavisto M, Peltonen JM, Hoffren AM, Varis M, Salminen T, Wurster S, Marjamaki A, Kanerva L, Katainen E, Laaksonen L, Savola JM, Scheinin M, Johnson MS: Molecular mechanism for agonist-promoted alpha(2A)-adrenoceptor activation by norepinephrine and epinephrine. Mol Pharmacol. 2001 May;59(5):1343-54. [PubMed:11306720 ]
  4. MacLennan SJ, Reynen PH, Martin RS, Eglen RM, Martin GR: Characterization of human recombinant alpha(2A)-adrenoceptors expressed in Chinese hamster lung cells using extracellular acidification rate changes. Br J Pharmacol. 2000 Apr;129(7):1333-8. [PubMed:10742288 ]
  5. Hieble JP, Hehr A, Li YO, Ruffolo RR Jr: Molecular basis for the stereoselective interactions of catecholamines with alpha-adrenoceptors. Proc West Pharmacol Soc. 1998;41:225-8. [PubMed:9836297 ]
  6. Nash DT: Alpha-adrenergic blockers: mechanism of action, blood pressure control, and effects of lipoprotein metabolism. Clin Cardiol. 1990 Nov;13(11):764-72. [PubMed:1980236 ]
  7. Giovannoni MP, Ghelardini C, Vergelli C, Dal Piaz V: Alpha2-agonists as analgesic agents. Med Res Rev. 2009 Mar;29(2):339-68. doi: 10.1002/med.20134. [PubMed:18680204 ]
  8. Gilsbach R, Hein L: Presynaptic metabotropic receptors for acetylcholine and adrenaline/noradrenaline. Handb Exp Pharmacol. 2008;(184):261-88. [PubMed:18064417 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Epinephrine binding
Specific Function:
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phent...
Gene Name:
ADRA2B
Uniprot ID:
P18089
Molecular Weight:
49565.8 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Gobbi M, Frittoli E, Mennini T: The modulation of [3H]noradrenaline and [3H]serotonin release from rat brain synaptosomes is not mediated by the alpha 2B-adrenoceptor subtype. Naunyn Schmiedebergs Arch Pharmacol. 1990 Oct;342(4):382-6. [PubMed:1979424 ]
  4. Vizi ES, Katona I, Freund TF: Evidence for presynaptic cannabinoid CB(1) receptor-mediated inhibition of noradrenaline release in the guinea pig lung. Eur J Pharmacol. 2001 Nov 16;431(2):237-44. [PubMed:11728431 ]
  5. Rudling JE, Richardson J, Evans PD: A comparison of agonist-specific coupling of cloned human alpha(2)-adrenoceptor subtypes. Br J Pharmacol. 2000 Nov;131(5):933-41. [PubMed:11053214 ]
  6. Nash DT: Alpha-adrenergic blockers: mechanism of action, blood pressure control, and effects of lipoprotein metabolism. Clin Cardiol. 1990 Nov;13(11):764-72. [PubMed:1980236 ]
  7. Gilsbach R, Hein L: Presynaptic metabotropic receptors for acetylcholine and adrenaline/noradrenaline. Handb Exp Pharmacol. 2008;(184):261-88. [PubMed:18064417 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Protein homodimerization activity
Specific Function:
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins.
Gene Name:
ADRA2C
Uniprot ID:
P18825
Molecular Weight:
49521.585 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Shreve PE, Toews ML, Bylund DB: Alpha 2A- and alpha 2C-adrenoceptor subtypes are differentially down-regulated by norepinephrine. Eur J Pharmacol. 1991 Jul 12;207(3):275-6. [PubMed:1654268 ]
  4. Rump LC, Bohmann C, Schaible U, Schollhorn J, Limberger N: Alpha 2C-adrenoceptor-modulated release of noradrenaline in human right atrium. Br J Pharmacol. 1995 Nov;116(6):2617-24. [PubMed:8590979 ]
  5. Bruck H, Schwerdtfeger T, Toliat M, Leineweber K, Heusch G, Philipp T, Nurnberg P, Brodde OE: Presynaptic alpha-2C adrenoceptor-mediated control of noradrenaline release in humans: genotype- or age-dependent? Clin Pharmacol Ther. 2007 Nov;82(5):525-30. Epub 2007 Apr 4. [PubMed:17410123 ]
  6. Nash DT: Alpha-adrenergic blockers: mechanism of action, blood pressure control, and effects of lipoprotein metabolism. Clin Cardiol. 1990 Nov;13(11):764-72. [PubMed:1980236 ]
  7. Gilsbach R, Hein L: Presynaptic metabotropic receptors for acetylcholine and adrenaline/noradrenaline. Handb Exp Pharmacol. 2008;(184):261-88. [PubMed:18064417 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Receptor signaling protein activity
Specific Function:
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately equal affinity. Mediates Ras activation through G(s)-alpha- and cAMP-mediated signaling.
Gene Name:
ADRB1
Uniprot ID:
P08588
Molecular Weight:
51322.1 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Mersmann HJ: Overview of the effects of beta-adrenergic receptor agonists on animal growth including mechanisms of action. J Anim Sci. 1998 Jan;76(1):160-72. [PubMed:9464897 ]
  3. El-Armouche A, Eschenhagen T: Beta-adrenergic stimulation and myocardial function in the failing heart. Heart Fail Rev. 2009 Dec;14(4):225-41. doi: 10.1007/s10741-008-9132-8. [PubMed:19110970 ]
  4. Gilsbach R, Hein L: Presynaptic metabotropic receptors for acetylcholine and adrenaline/noradrenaline. Handb Exp Pharmacol. 2008;(184):261-88. [PubMed:18064417 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Protein homodimerization activity
Specific Function:
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine.
Gene Name:
ADRB2
Uniprot ID:
P07550
Molecular Weight:
46458.32 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Sanders VM: The role of norepinephrine and beta-2-adrenergic receptor stimulation in the modulation of Th1, Th2, and B lymphocyte function. Adv Exp Med Biol. 1998;437:269-78. [PubMed:9666280 ]
  4. Tarizzo VI, Coppes RP, Dahlof C, Zaagsma J: Pre- and postganglionic stimulation-induced noradrenaline overflow is markedly facilitated by a prejunctional beta 2-adrenoceptor-mediated control mechanism in the pithed rat. Naunyn Schmiedebergs Arch Pharmacol. 1994 Jun;349(6):570-7. [PubMed:7969507 ]
  5. Weinshenker D, Szot P, Miller NS, Palmiter RD: Alpha(1) and beta(2) adrenoreceptor agonists inhibit pentylenetetrazole-induced seizures in mice lacking norepinephrine. J Pharmacol Exp Ther. 2001 Sep;298(3):1042-8. [PubMed:11504801 ]
  6. Mersmann HJ: Overview of the effects of beta-adrenergic receptor agonists on animal growth including mechanisms of action. J Anim Sci. 1998 Jan;76(1):160-72. [PubMed:9464897 ]
  7. El-Armouche A, Eschenhagen T: Beta-adrenergic stimulation and myocardial function in the failing heart. Heart Fail Rev. 2009 Dec;14(4):225-41. doi: 10.1007/s10741-008-9132-8. [PubMed:19110970 ]
  8. Gilsbach R, Hein L: Presynaptic metabotropic receptors for acetylcholine and adrenaline/noradrenaline. Handb Exp Pharmacol. 2008;(184):261-88. [PubMed:18064417 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Protein homodimerization activity
Specific Function:
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. Beta-3 is involved in the regulation of lipolysis and thermogenesis.
Gene Name:
ADRB3
Uniprot ID:
P13945
Molecular Weight:
43518.615 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Carpene C, Galitzky J, Collon P, Esclapez F, Dauzats M, Lafontan M: Desensitization of beta-1 and beta-2, but not beta-3, adrenoceptor-mediated lipolytic responses of adipocytes after long-term norepinephrine infusion. J Pharmacol Exp Ther. 1993 Apr;265(1):237-47. [PubMed:8097243 ]
  4. Galitzky J, Carpene C, Lafontan M, Berlan M: [Specific stimulation of adipose tissue adrenergic beta 3 receptors by octopamine]. C R Acad Sci III. 1993;316(5):519-23. [PubMed:8106131 ]
  5. Tamaoki J, Chiyotani A, Sakai N, Konno K: Stimulation of ciliary motility mediated by atypical beta-adrenoceptor in canine bronchial epithelium. Life Sci. 1993;53(20):1509-15. [PubMed:8105356 ]
  6. Mersmann HJ: Overview of the effects of beta-adrenergic receptor agonists on animal growth including mechanisms of action. J Anim Sci. 1998 Jan;76(1):160-72. [PubMed:9464897 ]
Kind
Protein
Organism
Human
Pharmacological action
no
Actions
inhibitor
General Function:
Phenylalanine 4-monooxygenase activity
Specific Function:
Not Available
Gene Name:
PAH
Uniprot ID:
P00439
Molecular Weight:
51861.565 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Martinez A, Andersson KK, Haavik J, Flatmark T: EPR and 1H-NMR spectroscopic studies on the paramagnetic iron at the active site of phenylalanine hydroxylase and its interaction with substrates and inhibitors. Eur J Biochem. 1991 Jun 15;198(3):675-82. [PubMed:1646718 ]
  4. Martinez A, Haavik J, Flatmark T: Cooperative homotropic interaction of L-noradrenaline with the catalytic site of phenylalanine 4-monooxygenase. Eur J Biochem. 1990 Oct 5;193(1):211-9. [PubMed:2226440 ]
  5. Molinoff PB: The regulation of the noradrenergic neuron. J Psychiatr Res. 1974;11:339-45. [PubMed:4156788 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
binder
General Function:
Monoamine transmembrane transporter activity
Specific Function:
Involved in the ATP-dependent vesicular transport of biogenic amine neurotransmitters. Pumps cytosolic monoamines including dopamine, norepinephrine, serotonin, and histamine into synaptic vesicles. Requisite for vesicular amine storage prior to secretion via exocytosis.
Gene Name:
SLC18A2
Uniprot ID:
Q05940
Molecular Weight:
55712.075 Da
References
  1. Erickson JD, Schafer MK, Bonner TI, Eiden LE, Weihe E: Distinct pharmacological properties and distribution in neurons and endocrine cells of two isoforms of the human vesicular monoamine transporter. Proc Natl Acad Sci U S A. 1996 May 14;93(10):5166-71. [PubMed:8643547 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
binder
General Function:
Serotonin transmembrane transporter activity
Specific Function:
Involved in the transport of biogenic monoamines, such as serotonin, from the cytoplasm into the secretory vesicles of neuroendocrine and endocrine cells.
Gene Name:
SLC18A1
Uniprot ID:
P54219
Molecular Weight:
56256.71 Da
References
  1. Erickson JD, Schafer MK, Bonner TI, Eiden LE, Weihe E: Distinct pharmacological properties and distribution in neurons and endocrine cells of two isoforms of the human vesicular monoamine transporter. Proc Natl Acad Sci U S A. 1996 May 14;93(10):5166-71. [PubMed:8643547 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 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
substrate
General Function:
Norepinephrine:sodium symporter activity
Specific Function:
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:
SLC6A2
Uniprot ID:
P23975
Molecular Weight:
69331.42 Da
References
  1. Habecker BA, Willison BD, Shi X, Woodward WR: Chronic depolarization stimulates norepinephrine transporter expression via catecholamines. J Neurochem. 2006 May;97(4):1044-51. Epub 2006 Mar 29. [PubMed:16573647 ]
  2. Bonisch H, Bruss M: The norepinephrine transporter in physiology and disease. Handb Exp Pharmacol. 2006;(175):485-524. [PubMed:16722247 ]
  3. Mandela P, Ordway GA: KCl stimulation increases norepinephrine transporter function in PC12 cells. J Neurochem. 2006 Sep;98(5):1521-30. Epub 2006 Jul 31. [PubMed:16879714 ]
  4. Gutman DA, Owens MJ: Serotonin and norepinephrine transporter binding profile of SSRIs. Essent Psychopharmacol. 2006;7(1):35-41. [PubMed:16989291 ]
  5. Ksiazek P, Buraczynska K, Buraczynska M: Norepinephrine transporter gene (NET) polymorphism in patients with type 2 diabetes. Kidney Blood Press Res. 2006;29(6):338-43. Epub 2006 Nov 23. [PubMed:17124432 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Quaternary ammonium group transmembrane transporter activity
Specific Function:
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridiniu...
Gene Name:
SLC22A2
Uniprot ID:
O15244
Molecular Weight:
62579.99 Da
References
  1. Urakami Y, Akazawa M, Saito H, Okuda M, Inui K: cDNA cloning, functional characterization, and tissue distribution of an alternatively spliced variant of organic cation transporter hOCT2 predominantly expressed in the human kidney. J Am Soc Nephrol. 2002 Jul;13(7):1703-10. [PubMed:12089365 ]
  2. Wu X, Kekuda R, Huang W, Fei YJ, Leibach FH, Chen J, Conway SJ, Ganapathy V: Identity of the organic cation transporter OCT3 as the extraneuronal monoamine transporter (uptake2) and evidence for the expression of the transporter in the brain. J Biol Chem. 1998 Dec 4;273(49):32776-86. [PubMed:9830022 ]
  3. Busch AE, Karbach U, Miska D, Gorboulev V, Akhoundova A, Volk C, Arndt P, Ulzheimer JC, Sonders MS, Baumann C, Waldegger S, Lang F, Koepsell H: Human neurons express the polyspecific cation transporter hOCT2, which translocates monoamine neurotransmitters, amantadine, and memantine. Mol Pharmacol. 1998 Aug;54(2):342-52. [PubMed:9687576 ]
  4. Grundemann D, Koster S, Kiefer N, Breidert T, Engelhardt M, Spitzenberger F, Obermuller N, Schomig E: Transport of monoamine transmitters by the organic cation transporter type 2, OCT2. J Biol Chem. 1998 Nov 20;273(47):30915-20. [PubMed:9812985 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Toxin transporter activity
Specific Function:
Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain.
Gene Name:
SLC22A3
Uniprot ID:
O75751
Molecular Weight:
61279.485 Da
References
  1. Wu X, Kekuda R, Huang W, Fei YJ, Leibach FH, Chen J, Conway SJ, Ganapathy V: Identity of the organic cation transporter OCT3 as the extraneuronal monoamine transporter (uptake2) and evidence for the expression of the transporter in the brain. J Biol Chem. 1998 Dec 4;273(49):32776-86. [PubMed:9830022 ]
  2. Grundemann D, Schechinger B, Rappold GA, Schomig E: Molecular identification of the corticosterone-sensitive extraneuronal catecholamine transporter. Nat Neurosci. 1998 Sep;1(5):349-51. [PubMed:10196521 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Symporter activity
Specific Function:
Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3.
Gene Name:
SLC22A5
Uniprot ID:
O76082
Molecular Weight:
62751.08 Da
References
  1. Ohashi R, Tamai I, Nezu Ji J, Nikaido H, Hashimoto N, Oku A, Sai Y, Shimane M, Tsuji A: Molecular and physiological evidence for multifunctionality of carnitine/organic cation transporter OCTN2. Mol Pharmacol. 2001 Feb;59(2):358-66. [PubMed:11160873 ]
  2. Wu X, Huang W, Prasad PD, Seth P, Rajan DP, Leibach FH, Chen J, Conway SJ, Ganapathy V: Functional characteristics and tissue distribution pattern of organic cation transporter 2 (OCTN2), an organic cation/carnitine transporter. J Pharmacol Exp Ther. 1999 Sep;290(3):1482-92. [PubMed:10454528 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Secondary active organic cation transmembrane transporter activity
Specific Function:
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine...
Gene Name:
SLC22A1
Uniprot ID:
O15245
Molecular Weight:
61153.345 Da
References
  1. Busch AE, Quester S, Ulzheimer JC, Gorboulev V, Akhoundova A, Waldegger S, Lang F, Koepsell H: Monoamine neurotransmitter transport mediated by the polyspecific cation transporter rOCT1. FEBS Lett. 1996 Oct 21;395(2-3):153-6. [PubMed:8898084 ]
  2. Breidert T, Spitzenberger F, Grundemann D, Schomig E: Catecholamine transport by the organic cation transporter type 1 (OCT1). Br J Pharmacol. 1998 Sep;125(1):218-24. [PubMed:9776363 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Ubiquitin protein ligase binding
Specific Function:
Transcription factor that binds to the octamer motif (5'-ATTTGCAT-3'). Forms a trimeric complex with SOX2 on DNA and controls the expression of a number of genes involved in embryonic development such as YES1, FGF4, UTF1 and ZFP206. Critical for early embryogenesis and for embryonic stem cell pluripotency.
Gene Name:
POU5F1
Uniprot ID:
Q01860
Molecular Weight:
38570.415 Da
References
  1. Zhu HJ, Appel DI, Grundemann D, Markowitz JS: Interaction of organic cation transporter 3 (SLC22A3) and amphetamine. J Neurochem. 2010 Jul;114(1):142-9. doi: 10.1111/j.1471-4159.2010.06738.x. Epub 2010 Apr 6. [PubMed:20402963 ]
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Drug created on June 13, 2005 07:24 / Updated on December 08, 2016 11:46