Identification

Name
Norepinephrine
Accession Number
DB00368  (APRD01299)
Type
Small Molecule
Groups
Approved
Description

Precursor 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
Product Ingredients
IngredientUNIICASInChI Key
Norepinephrine bitartrateIFY5PE3ZRW108341-18-0LNBCGLZYLJMGKP-LUDZCAPTSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
LevophedInjection, solution, concentrate1 mg/mLIntravenousCardinal Health1982-01-012017-11-14Us
LevophedInjection, solution, concentrate1 mg/mLIntravenousHospira, Inc.1950-07-13Not applicableUs
LevophedInjection, solution, concentrate1 mg/mLIntravenousHospira, Inc.1950-07-13Not applicableUs
LevophedSolution1 mgIntravenousPfizer2001-10-01Not applicableCanada
LevophedInjection, solution, concentrate1 mg/mLIntravenousGeneral Injectables & Vaccines2010-03-01Not applicableUs
Levophed Liq IV 1.0mg/mlLiquid1 mgIntravenousSanofi1951-12-312001-08-10Canada
Norepinephrine Bitartrate Inj 1mg/ml USPLiquid1 mgIntravenousSandoz Canada Incorporated1991-12-31Not applicableCanada
Norepinephrine Bitartrate Injection, USPSolution1 mgIntravenousSterimax IncNot applicableNot applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Norepinephrine bitartrateInjection1 mg/mLIntravenousCardinal Health2003-03-03Not applicableUs
Norepinephrine BitartrateInjection, solution, concentrate1 mg/mLIntravenousTeva Parenteral Medicines, Inc.2003-04-01Not applicableUs
Norepinephrine bitartrateInjection1 mg/mLIntravenousCardinal Health2012-04-01Not applicableUs
Norepinephrine bitartrateInjection1 mg/mLIntravenousClaris Lifesciences, Inc.2012-04-01Not applicableUs
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Norepinephrine BitartrateInjection, solution16 ug/mLIntravenousCantrell Drug Company2015-02-20Not applicableUs
Norepinephrine BitartrateInjection, solution32 ug/mLIntravenousCantrell Drug Company2015-03-06Not applicableUs
Norepinephrine BitartrateInjection, solution64 ug/mLIntravenousCantrell Drug Company2015-03-12Not applicableUs
Norepinephrine BitartrateInjection, solution32 ug/mLIntravenousCantrell Drug Company2015-02-18Not applicableUs
Norepinephrine BitartrateInjection, solution16 ug/mLIntravenousCantrell Drug Company2015-03-06Not applicableUs
Categories
UNII
X4W3ENH1CV
CAS number
51-41-2
Weight
Average: 169.1778
Monoisotopic: 169.073893223
Chemical Formula
C8H11NO3
InChI Key
SFLSHLFXELFNJZ-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

Indication

Mainly 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
Pharmacodynamics

Noradrenaline 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 action

Norepinephrine 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.

TargetActionsOrganism
AAlpha-1A adrenergic receptor
agonist
Human
AAlpha-1B adrenergic receptor
agonist
Human
AAlpha-1D adrenergic receptor
agonist
Human
AAlpha-2A adrenergic receptor
agonist
Human
AAlpha-2B adrenergic receptor
agonist
Human
AAlpha-2C adrenergic receptor
agonist
Human
ABeta-1 adrenergic receptor
agonist
Human
ABeta-2 adrenergic receptor
agonist
Human
ABeta-3 adrenergic receptor
agonist
Human
NPhenylalanine-4-hydroxylase
inhibitor
Human
USynaptic vesicular amine transporter
binder
Human
UChromaffin granule amine transporter
binder
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

In 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
PathwayCategory
Catecholamine BiosynthesisMetabolic
Prilocaine Action PathwayDrug action
Heroin Action PathwayDrug action
Methadone Action PathwayDrug action
Alfentanil Action PathwayDrug action
Carfentanil Action PathwayDrug action
Tramadol Action Action PathwayDrug action
Levallorphan Action PathwayDrug action
Aromatic L-Aminoacid Decarboxylase DeficiencyDisease
Levobupivacaine Action PathwayDrug action
Oxymorphone Action PathwayDrug action
Fentanyl Action PathwayDrug action
Fluoxetine Action PathwayDrug action
Nicotine Action PathwayDrug action
Levorphanol Action PathwayDrug action
Anileridine Action PathwayDrug action
Methadyl Acetate Action PathwayDrug action
Buprenorphine Action PathwayDrug action
Pentazocine Action PathwayDrug action
Nalbuphine Action PathwayDrug action
Tyrosine MetabolismMetabolic
Dibucaine Action PathwayDrug action
Procaine Action PathwayDrug action
Codeine Action PathwayDrug action
Hydromorphone Action PathwayDrug action
Remifentanil Action PathwayDrug action
Imipramine Action PathwayDrug action
Tyrosinemia, transient, of the newbornDisease
Propoxyphene Action PathwayDrug action
Diphenoxylate Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not 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
AlprenololNorepinephrine may increase the atrioventricular blocking (AV block) activities of Alprenolol.Approved, Withdrawn
AmineptineAmineptine may decrease the antihypertensive activities of Norepinephrine.Illicit, Withdrawn
AmitriptylineAmitriptyline may decrease the antihypertensive activities of Norepinephrine.Approved
AmoxapineAmoxapine may decrease the antihypertensive activities of Norepinephrine.Approved
AmphetamineAmphetamine may increase the hypertensive activities of Norepinephrine.Approved, Illicit
ArotinololNorepinephrine may increase the atrioventricular blocking (AV block) activities of Arotinolol.Approved, Investigational
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, Investigational
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
BopindololNorepinephrine may increase the atrioventricular blocking (AV block) activities of Bopindolol.Approved
BrofaromineBrofaromine may increase the hypertensive activities of Norepinephrine.Experimental
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
BunazosinBunazosin may decrease the vasoconstricting activities of Norepinephrine.Investigational
BupranololNorepinephrine may increase the atrioventricular blocking (AV block) activities of Bupranolol.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
CarteololNorepinephrine may increase the atrioventricular blocking (AV block) activities of Carteolol.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, Investigational, Vet Approved
ClomipramineClomipramine may decrease the antihypertensive activities of Norepinephrine.Approved, Vet Approved
CloranololNorepinephrine may increase the atrioventricular blocking (AV block) activities of Cloranolol.Experimental
CyclobenzaprineCyclobenzaprine may decrease the antihypertensive activities of Norepinephrine.Approved
CyclopenthiazideNorepinephrine may increase the hypokalemic activities of Cyclopenthiazide.Experimental
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
DibenzepinDibenzepin may decrease the antihypertensive activities of Norepinephrine.Experimental
Diethyl etherDiethyl ether may increase the arrhythmogenic activities of Norepinephrine.Experimental
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, Investigational, Vet Approved
EpanololNorepinephrine may increase the atrioventricular blocking (AV block) activities of Epanolol.Experimental
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, Investigational
FenozoloneThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Fenozolone.Experimental
FurazolidoneFurazolidone may increase the hypertensive activities of Norepinephrine.Approved, Investigational, Vet Approved
FurosemideNorepinephrine may increase the hypokalemic activities of Furosemide.Approved, Vet Approved
HalothaneHalothane may increase the arrhythmogenic activities of Norepinephrine.Approved, Vet Approved
HarmalineHarmaline may increase the hypertensive activities of Norepinephrine.Experimental
HyaluronidaseHyaluronidase may increase the vasoconstricting activities of Norepinephrine.Approved, Investigational
HydracarbazineHydracarbazine may increase the hypertensive activities of Norepinephrine.Experimental
HydrochlorothiazideNorepinephrine may increase the hypokalemic activities of Hydrochlorothiazide.Approved, Vet Approved
HydroflumethiazideNorepinephrine may increase the hypokalemic activities of Hydroflumethiazide.Approved, Investigational
HydroxyamphetamineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Hydroxyamphetamine.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, Investigational
Ioflupane I-123Norepinephrine may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved
IprindoleIprindole may decrease the antihypertensive activities of Norepinephrine.Experimental
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
LandiololNorepinephrine may increase the atrioventricular blocking (AV block) activities of Landiolol.Investigational
LevomilnacipranLevomilnacipran may increase the tachycardic activities of Norepinephrine.Approved
LinezolidLinezolid may increase the hypertensive activities of Norepinephrine.Approved, Investigational
LofepramineLofepramine may decrease the antihypertensive activities of Norepinephrine.Experimental
MebanazineMebanazine may increase the hypertensive activities of Norepinephrine.Withdrawn
MefenorexThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Mefenorex.Experimental
MephentermineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Mephentermine.Approved
MepindololNorepinephrine may increase the atrioventricular blocking (AV block) activities of Mepindolol.Experimental
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, Investigational
MethoxyfluraneMethoxyflurane may increase the arrhythmogenic activities of Norepinephrine.Approved, Investigational, Vet Approved
MethyclothiazideNorepinephrine may increase the hypokalemic activities of Methyclothiazide.Approved
Methylene blueMethylene blue may increase the hypertensive activities of Norepinephrine.Approved, Investigational
MethylergometrineMethylergometrine may increase the hypertensive activities of Norepinephrine.Approved
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, Investigational
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
NadololNorepinephrine may increase the atrioventricular blocking (AV block) activities of Nadolol.Approved
NebivololNorepinephrine may increase the atrioventricular blocking (AV block) activities of Nebivolol.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
OxprenololNorepinephrine may increase the atrioventricular blocking (AV block) activities of Oxprenolol.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
PenbutololNorepinephrine may increase the atrioventricular blocking (AV block) activities of Penbutolol.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 Phenylpropanolamine is combined with Norepinephrine.Approved, Vet Approved, Withdrawn
PindololNorepinephrine may increase the atrioventricular blocking (AV block) activities of Pindolol.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
Platelet Activating FactorNorepinephrine may increase the atrioventricular blocking (AV block) activities of Platelet Activating Factor.Experimental
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
PrenalterolThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Prenalterol.Experimental
ProcarbazineProcarbazine may increase the hypertensive activities of Norepinephrine.Approved
ProcaterolThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Procaterol.Approved, Investigational
PropranololNorepinephrine may increase the atrioventricular blocking (AV block) activities of Propranolol.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, Investigational
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
SotalolNorepinephrine may increase the atrioventricular blocking (AV block) activities of Sotalol.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
TalinololNorepinephrine may increase the atrioventricular blocking (AV block) activities of Talinolol.Investigational
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
TertatololNorepinephrine may increase the atrioventricular blocking (AV block) activities of Tertatolol.Experimental
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, Investigational
TimololNorepinephrine may increase the atrioventricular blocking (AV block) activities of Timolol.Approved
ToloxatoneToloxatone may increase the hypertensive activities of Norepinephrine.Approved
TorasemideNorepinephrine may increase the hypokalemic activities of Torasemide.Approved
TramazolineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Tramazoline.Investigational
Trans-2-PhenylcyclopropylamineTrans-2-Phenylcyclopropylamine may increase the hypertensive activities of Norepinephrine.Experimental
TranylcypromineTranylcypromine may increase the hypertensive activities of Norepinephrine.Approved
TretoquinolThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Tretoquinol.Experimental
TrichlormethiazideNorepinephrine may increase the hypokalemic activities of Trichlormethiazide.Approved, Vet Approved
TrichloroethyleneTrichloroethylene may increase the arrhythmogenic activities of Norepinephrine.Experimental
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
UrapidilUrapidil may decrease the vasoconstricting activities of Norepinephrine.Investigational
VenlafaxineVenlafaxine may increase the tachycardic activities of Norepinephrine.Approved
XenonXenon may increase the arrhythmogenic activities of Norepinephrine.Experimental
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB00216
KEGG Drug
D00076
KEGG Compound
C00547
PubChem Compound
439260
PubChem Substance
46506201
ChemSpider
388394
BindingDB
50029051
ChEBI
18357
ChEMBL
CHEMBL1437
Therapeutic Targets Database
DNC001034
PharmGKB
PA450649
HET
LNR
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Norepinephrine
ATC Codes
C01CA03 — Norepinephrine
AHFS Codes
  • 12:12.12 — Alpha-and Beta-adrenergic Agonists
PDB Entries
2qeo / 3dye / 3hcd / 4pah / 4y4j

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Not Yet RecruitingTreatmentCardiac Output,Low / Hemodynamics Instability / Obstetrical Complication of Anesthesia1
0RecruitingTreatmentHepatorenal Syndrome1
1Active Not RecruitingOtherHypertensive / Insulin Resistance1
1TerminatedSupportive CareHair Thinning / Radiodermatitis1
1TerminatedSupportive CareRadiodermatitis1
1, 2CompletedTreatmentOrthostatic Hypertension1
1, 2WithdrawnPreventionRadiodermatitis1
2CompletedPreventionAdverse Anesthesia Outcome1
2CompletedTreatmentAcute Ischemic Stroke (AIS)1
2CompletedTreatmentAcute Lung Injury (ALI)1
2CompletedTreatmentShock, Septic3
2RecruitingTreatmentSevere Traumatic Brain Injury With High Cerebral Pressure1
2, 3CompletedTreatmentInfection NOS / Severe Sepsis / Shock, Septic1
2, 3RecruitingPreventionPost-operative Cognitive Dysfunction1
2, 3RecruitingPreventionTransplant, Kidney1
3Active Not RecruitingTreatmentShock, Septic1
3CompletedTreatmentArterial Hypotension / Fluid Therapy1
3CompletedTreatmentSafety and Efficacy of Terlipressin and Noradrenaline and Predictive Factors of Response in Type 2 HRS1
3CompletedTreatmentShock, Septic1
3CompletedTreatmentVasoplegic Syndrome1
3Not Yet RecruitingTreatmentShock, Septic1
3RecruitingTreatmentSevere Septic Syndrome (Severe Sepsis and Septic Shock) Diagnosed and Treated by Mobile Intensive Care Unit1
3TerminatedTreatmentSepsis-associated Hypotension / Shock, Septic1
3Unknown StatusTreatmentShock1
4Active Not RecruitingTreatmentShock, Septic1
4CompletedBasic ScienceEndotoxaemia1
4CompletedDiagnosticArterial Hypotension / Free Flap / Head and Neck Carcinoma / Oral Cancers1
4CompletedPreventionAdverse Effects / Anesthesia, Spinal and Epidural / Arterial Hypotension / Complications, Cesarean Section1
4CompletedPreventionAnesthesia; Adverse Effect, Spinal and Epidural / Arterial Hypotension / Complications; Cesarean Section1
4CompletedPreventionEffects of; Anesthesia, in Labor and Delivery1
4CompletedTreatmentHead and Neck Carcinoma1
4CompletedTreatmentShock, Cardiogenic1
4CompletedTreatmentShock, Septic1
4Not Yet RecruitingPreventionCesarean Section Complications / Spinal Anaesthesia1
4RecruitingPreventionCesarean Section Complications2
4RecruitingPreventionCesarean Section Complications / Spinal Anaesthesia1
4RecruitingPreventionSpinal Anesthetics Causing Adverse Effects in Therapeutic Use1
4RecruitingTreatmentArterial Hypotension1
4RecruitingTreatmentShock1
4TerminatedTreatmentCritical Illness1
4Unknown StatusTreatmentArrythmias / Sepsis / Shock / Shock, Septic / Tachycardia1
4Unknown StatusTreatmentMicrocirculation / Severe Sepsis1
4Unknown StatusTreatmentShock / Ventilations, Mechanical1
Not AvailableActive Not RecruitingOtherDiabetes Mellitus (DM)1
Not AvailableActive Not RecruitingOtherHypertensive1
Not AvailableCompletedBasic ScienceHeart Diseases / Vasodilation1
Not AvailableCompletedScreeningAbdominal Abscess / Appendicitis / Digestive System Fistula / Pancreatitis / Severe Sepsis1
Not AvailableCompletedTreatmentAcute Kidney Injury (AKI) / Hepatic Failure1
Not AvailableCompletedTreatmentArterial Hypotension2
Not AvailableCompletedTreatmentArterial Hypotension / Complications; Cesarean Section / Obstetrical Complication of Anesthesia1
Not AvailableCompletedTreatmentArterial Hypotension / Shock1
Not AvailableCompletedTreatmentBloodpressure1
Not AvailableCompletedTreatmentC.Surgical Procedure; Digestive System / Perioperative/Postoperative Complications1
Not AvailableCompletedTreatmentCirrhosis With Septic Shock2
Not AvailableCompletedTreatmentOptimal Tissue Perfusion1
Not AvailableNot Yet RecruitingPreventionSpinal Anaesthesia1
Not AvailableRecruitingNot AvailableLeiomyomas1
Not AvailableRecruitingBasic ScienceAnaesthesia therapy / Blood Pressures1
Not AvailableRecruitingOtherAcute Kidney Injury (AKI) / Sepsis1
Not AvailableRecruitingPreventionArterial Hypotension1
Not AvailableRecruitingPreventionGastrointestinal Bleedings / Gastrointestinal Diseases1
Not AvailableRecruitingTreatmentAcute Kidney Injury (AKI)1
Not AvailableRecruitingTreatmentPostoperative Vasoplegic Syndrome1
Not AvailableRecruitingTreatmentShock, Septic1
Not AvailableTerminatedSupportive CareShock, Septic1
Not AvailableUnknown StatusNot AvailableEchocardiography, Transesophageal / Endarterectomy, Carotid / Vasopressor Agents1
Not AvailableUnknown StatusBasic ScienceAnaesthesia therapy / Blood Pressures / Hematocrit Change1
Not AvailableUnknown StatusTreatmentShock, Septic1
Not AvailableUnknown StatusTreatmentShock, Septic / Terlipressin1

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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)217 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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (5 TMS)GC-MSsplash10-00di-1900000000-c9b4a0a230d610dd0e61
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-000l-4900000000-b0893c23c186c5f8a344
GC-MS Spectrum - GC-MSGC-MSsplash10-00di-1900000000-c9b4a0a230d610dd0e61
MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)LC-MS/MSsplash10-0udi-0900000000-5610e21bd478a4ca7bde
MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)LC-MS/MSsplash10-0a6r-5900000000-5d7cd24a6af23a36af3a
MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)LC-MS/MSsplash10-004i-9000000000-3c8de1511861fa1d028c
MS/MS Spectrum - EI-B (HITACHI M-80) , PositiveLC-MS/MSsplash10-000l-4900000000-b0893c23c186c5f8a344
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-0udi-0900000000-11725b1d61843966aa7c
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-0udi-1900000000-6931e73a397f3917ad96
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-0a4i-3900000000-bddd6ee748aa9ebecb15
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-056r-9500000000-6abd3337785c1b580668
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-004i-9100000000-ede02e0e3e74bdddc9f4
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udi-0900000000-11725b1d61843966aa7c
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udi-1900000000-6931e73a397f3917ad96
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4i-3900000000-918c4cbdffc5e02eafd5
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-056r-9500000000-6abd3337785c1b580668
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-004i-9100000000-ede02e0e3e74bdddc9f4
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as catechols. These are compounds containing a 1,2-benzenediol moiety.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenols
Sub Class
Benzenediols
Direct Parent
Catechols
Alternative Parents
Aralkylamines / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / Secondary alcohols / 1,2-aminoalcohols / Organopnictogen compounds / Monoalkylamines / Hydrocarbon derivatives / Aromatic alcohols
Substituents
Catechol / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Aralkylamine / Monocyclic benzene moiety / 1,2-aminoalcohol / Secondary alcohol / Organic nitrogen compound / Aromatic alcohol / Hydrocarbon derivative
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
noradrenaline (CHEBI:18357) / Biogenic amines, Adrenalines (C00547)

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) prot...
Gene Name
ADRA1A
Uniprot ID
P35348
Uniprot Name
Alpha-1A adrenergic receptor
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) prot...
Gene Name
ADRA1B
Uniprot ID
P35368
Uniprot Name
Alpha-1B adrenergic receptor
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
Uniprot Name
Alpha-1D adrenergic receptor
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 oxymetazo...
Gene Name
ADRA2A
Uniprot ID
P08913
Uniprot Name
Alpha-2A adrenergic receptor
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...
Gene Name
ADRA2B
Uniprot ID
P18089
Uniprot Name
Alpha-2B adrenergic receptor
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
Uniprot Name
Alpha-2C adrenergic receptor
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 e...
Gene Name
ADRB1
Uniprot ID
P08588
Uniprot Name
Beta-1 adrenergic receptor
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 ...
Gene Name
ADRB2
Uniprot ID
P07550
Uniprot Name
Beta-2 adrenergic receptor
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
Uniprot Name
Beta-3 adrenergic receptor
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
Uniprot Name
Phenylalanine-4-hydroxylase
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...
Gene Name
SLC18A2
Uniprot ID
Q05940
Uniprot Name
Synaptic vesicular amine transporter
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
Uniprot Name
Chromaffin granule amine transporter
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 un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
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
Uniprot Name
Sodium-dependent noradrenaline transporter
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
Substrate
Inhibitor
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, creat...
Gene Name
SLC22A2
Uniprot ID
O15244
Uniprot Name
Solute carrier family 22 member 2
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
Substrate
Inhibitor
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
Uniprot Name
Solute carrier family 22 member 3
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 cat...
Gene Name
SLC22A5
Uniprot ID
O76082
Uniprot Name
Solute carrier family 22 member 5
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-methylnico...
Gene Name
SLC22A1
Uniprot ID
O15245
Uniprot Name
Solute carrier family 22 member 1
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 s...
Gene Name
POU5F1
Uniprot ID
Q01860
Uniprot Name
POU domain, class 5, transcription factor 1
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]

Drug created on June 13, 2005 07:24 / Updated on November 19, 2017 20:33