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Identification
NameNorepinephrine
Accession NumberDB00368  (APRD01299)
Typesmall molecule
Groupsapproved
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
SynonymLanguageCode
(-)-ArterenolNot AvailableNot Available
(-)-NoradrenalineNot AvailableNot Available
(-)-NorepinephrineNot AvailableNot Available
(R)-(-)-NorepinephrineNot AvailableNot Available
(R)-4-(2-amino-1-Hydroxyethyl)-1,2-benzenediolNot AvailableNot Available
(R)-NorepinephrineNot AvailableNot Available
4-[(1R)-2-Amino-1-hydroxyethyl]-1,2-benzenediolNot AvailableNot Available
ArterenolNot AvailableNot Available
L-noradrenalineNot AvailableNot Available
L-NorepinephrineNot AvailableNot Available
NoradrenalineNot AvailableNot Available
NorepinefrinaNot AvailableNot Available
NorepinephrineNot AvailableNot Available
NorepinephrinumNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
LevophedNot Available
Brand mixturesNot Available
Categories
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[C@H](O)C1=CC(O)=C(O)C=C1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassPhenols and Derivatives
Direct parentCatecholamines and Derivatives
Alternative parentsSecondary Alcohols; Polyols; 1,2-Aminoalcohols; Polyamines; Enols; Monoalkylamines
Substituents1,2-aminoalcohol; secondary alcohol; polyol; enol; polyamine; amine; primary amine; primary aliphatic amine; alcohol; organonitrogen compound
Classification descriptionThis compound belongs to the 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.
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.
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.
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
3-Methylthiofentanyl Action PathwayDrug actionSMP00679
Monoamine oxidase-a deficiency (MAO-A)DiseaseSMP00533
Methadyl Acetate Action PathwayDrug actionSMP00678
Levomethadyl Acetate Action Action PathwayDrug actionSMP00677
Proparacaine Action PathwayDrug actionSMP00403
Dibucaine Action PathwayDrug actionSMP00396
Procaine Action PathwayDrug actionSMP00402
Oxybuprocaine Action PathwayDrug actionSMP00400
Morphine Action PathwayDrug actionSMP00406
Codeine Action PathwayDrug actionSMP00405
Hydromorphone Action PathwayDrug actionSMP00410
Oxycodone Action PathwayDrug actionSMP00409
Imipramine Action PathwayDrug actionSMP00422
Desipramine Action PathwayDrug actionSMP00423
Fentanyl Action PathwayDrug actionSMP00415
Propoxyphene Action PathwayDrug actionSMP00672
Dezocine Action PathwayDrug actionSMP00676
Buprenorphine Action PathwayDrug actionSMP00684
Dimethylthiambutene Action PathwayDrug actionSMP00680
Alvimopan Action PathwayDrug actionSMP00685
Nalbuphine Action PathwayDrug actionSMP00691
Dihydromorphine Action PathwayDrug actionSMP00689
Nicotine Action PathwayDrug actionSMP00431
Levobupivacaine Action PathwayDrug actionSMP00397
Methadone Action PathwayDrug actionSMP00408
Citalopram Action PathwayDrug actionSMP00424
Escitalopram Action PathwayDrug actionSMP00425
Remifentanil Action PathwayDrug actionSMP00416
Levallorphan Action PathwayDrug actionSMP00683
Sufentanil Action PathwayDrug actionSMP00417
Carfentanil Action PathwayDrug actionSMP00414
Cocaine Action PathwayDrug actionSMP00395
Benzocaine Action PathwayDrug actionSMP00392
Prilocaine Action PathwayDrug actionSMP00401
Hydrocodone Action PathwayDrug actionSMP00411
Anileridine Action PathwayDrug actionSMP00674
Naltrexone Action PathwayDrug actionSMP00687
Chloroprocaine Action PathwayDrug actionSMP00394
Bupivacaine Action PathwayDrug actionSMP00393
Mepivacaine Action PathwayDrug actionSMP00399
Heroin Action PathwayDrug actionSMP00407
Oxymorphone Action PathwayDrug actionSMP00412
Alfentanil Action PathwayDrug actionSMP00413
Fluoxetine Action PathwayDrug actionSMP00426
Tramadol Action Action PathwayDrug actionSMP00671
Diphenoxylate Action PathwayDrug actionSMP00675
Ethylmorphine Action PathwayDrug actionSMP00681
Pentazocine Action PathwayDrug actionSMP00686
Disulfiram Action PathwayDrug actionSMP00429
Lidocaine (Local Anaesthetic) Action PathwayDrug actionSMP00398
Ropivacaine Action PathwayDrug actionSMP00404
Levorphanol Action PathwayDrug actionSMP00673
Ketobemidone Action PathwayDrug actionSMP00690
Naloxone Action PathwayDrug actionSMP00688
AlkaptonuriaDiseaseSMP00169
Aromatic L-Aminoacid Decarboxylase DeficiencyDiseaseSMP00170
Dopamine beta-hydroxylase deficiencyDiseaseSMP00498
Catecholamine BiosynthesisMetabolicSMP00012
Tyrosine hydroxylase deficiencyDiseaseSMP00497
HawkinsinuriaDiseaseSMP00190
Tyrosinemia Type IDiseaseSMP00218
Tyrosine MetabolismMetabolicSMP00006
Tyrosinemia, transient, of the newbornDiseaseSMP00494
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9837
Blood Brain Barrier - 0.9762
Caco-2 permeable - 0.7985
P-glycoprotein substrate Non-substrate 0.6046
P-glycoprotein inhibitor I Non-inhibitor 0.9441
P-glycoprotein inhibitor II Non-inhibitor 0.9285
Renal organic cation transporter Non-inhibitor 0.9004
CYP450 2C9 substrate Non-substrate 0.8702
CYP450 2D6 substrate Non-substrate 0.8667
CYP450 3A4 substrate Non-substrate 0.7986
CYP450 1A2 substrate Non-inhibitor 0.9135
CYP450 2C9 substrate Non-inhibitor 0.9675
CYP450 2D6 substrate Non-inhibitor 0.9798
CYP450 2C19 substrate Non-inhibitor 0.9446
CYP450 3A4 substrate Non-inhibitor 0.9209
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8839
Ames test Non AMES toxic 0.5053
Carcinogenicity Non-carcinogens 0.8942
Biodegradation Ready biodegradable 0.5401
Rat acute toxicity 2.2298 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9028
hERG inhibition (predictor II) Non-inhibitor 0.7864
Pharmacoeconomics
Manufacturers
  • Hospira inc
Packagers
Dosage forms
FormRouteStrength
Insert, extended releaseIntrauterine
LiquidIntravenous
SolutionIntravenous
TabletOral
Prices
Unit descriptionCostUnit
Norepinephrine 4 mg/4 ml amp2.68USDml
Levophed 1 mg/ml ampul1.49USDml
Norepinephrine 1 mg/ml vial0.96USDml
Levophed 1 mg/ml vial0.48USDml
Norepinephrine-d5w 4 mg/250 ml0.16USDml
Norepinephrine-ns 4 mg/250 ml0.16USDml
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 solubility1.25e+01 g/lALOGPS
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 area86.71ChemAxon
rotatable bond count2ChemAxon
refractivity44.46ChemAxon
polarizability16.96ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD00076
KEGG CompoundC00547
PubChem Compound439260
PubChem Substance46506201
ChemSpider388394
ChEBI18357
ChEMBLCHEMBL1437
Therapeutic Targets DatabaseDNC001034
PharmGKBPA450649
HETLNR
RxListhttp://www.rxlist.com/cgi/generic/norepinephrine.htm
Drugs.comhttp://www.drugs.com/mtm/norepinephrine.html
WikipediaNorepinephrine
ATC CodesC01CA03
AHFS Codes
  • 12:12.12
  • 68:12.00
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AmitriptylineThe tricyclic antidepressant, amitriptyline, increases the sympathomimetic effect of norepinephrine.
AmoxapineThe tricyclic antidepressant, amoxapine, increases the sympathomimetic effect of norepinephrine.
ClomipramineThe tricyclic antidepressant, clomipramine, increases the sympathomimetic effect of norepinephrine.
DesipramineThe tricyclic antidepressant, desipramine, increases the sympathomimetic effect of norepinephrine.
DesvenlafaxineDesvenlafaxine may increase the tachycardic and vasopressor effects of norepinephrine. Consider alternate therapy or monitor for increased sympathomimetic effects, such as increased blood pressure, chest pain and headache.
DoxepinThe tricyclic antidepressant, doxepin, increases the sympathomimetic effect of norepinephrine.
EntacaponeEntacapone increases the effect and toxicity of the sympathomimetic, norepinephrine.
GuanethidineNorepinephrine may decrease the effect of guanethidine.
ImipramineThe tricyclic antidepressant, imipramine, increases the sympathomimetic effect of norepinephrine.
IsocarboxazidIncreased arterial pressure
LinezolidPossible increase of arterial pressure
MethyldopaIncreased arterial pressure
MidodrineIncreased arterial pressure
MoclobemideMoclobemide increases the sympathomimetic effect of norepinephrine.
NortriptylineThe tricyclic antidepressant, nortriptyline, increases the sympathomimetic effect of norepinephrine.
PhenelzineIncreased arterial pressure
RasagilineIncreased arterial pressure
ReserpineIncreased arterial pressure
TrimipramineTrimipramine may increase the vasopressor effect of the direct-acting alpha-/beta-agonist, Norepinephrine. Avoid combination if possible. Monitor sympathetic response to therapy if used concomitantly.
VenlafaxineVenlafaxine may increase the tachycardic and vasopressor effects of Norepinephrine. Consider alternate therapy or monitor for increased sympathomimetic effects, such as increased blood pressure, chest pain and headache.
Food InteractionsNot Available

Targets

1. Alpha-1A adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Alpha-1A adrenergic receptor P35348 Details

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
  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
  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
  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
  5. Bishop MJ: Recent advances in the discovery of alpha1-adrenoceptor agonists. Curr Top Med Chem. 2007;7(2):135-45. Pubmed

2. Alpha-1B adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Alpha-1B adrenergic receptor P35368 Details

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
  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
  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
  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
  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
  6. Bishop MJ: Recent advances in the discovery of alpha1-adrenoceptor agonists. Curr Top Med Chem. 2007;7(2):135-45. Pubmed
  7. Gilsbach R, Hein L: Presynaptic metabotropic receptors for acetylcholine and adrenaline/noradrenaline. Handb Exp Pharmacol. 2008;(184):261-88. Pubmed

3. Alpha-1D adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Alpha-1D adrenergic receptor P25100 Details

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
  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
  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
  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
  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
  6. Bishop MJ: Recent advances in the discovery of alpha1-adrenoceptor agonists. Curr Top Med Chem. 2007;7(2):135-45. Pubmed
  7. Gilsbach R, Hein L: Presynaptic metabotropic receptors for acetylcholine and adrenaline/noradrenaline. Handb Exp Pharmacol. 2008;(184):261-88. Pubmed

4. Alpha-2A adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Alpha-2A adrenergic receptor P08913 Details

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
  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
  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
  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
  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
  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
  7. Giovannoni MP, Ghelardini C, Vergelli C, Dal Piaz V: Alpha2-agonists as analgesic agents. Med Res Rev. 2009 Mar;29(2):339-68. Pubmed
  8. Gilsbach R, Hein L: Presynaptic metabotropic receptors for acetylcholine and adrenaline/noradrenaline. Handb Exp Pharmacol. 2008;(184):261-88. Pubmed

5. Alpha-2B adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Alpha-2B adrenergic receptor P18089 Details

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
  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
  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
  4. Vizi ES, Katona I, Freund TF: Evidence for presynaptic cannabinoid CB receptor-mediated inhibition of noradrenaline release in the guinea pig lung. Eur J Pharmacol. 2001 Nov 16;431(2):237-44. Pubmed
  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
  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
  7. Gilsbach R, Hein L: Presynaptic metabotropic receptors for acetylcholine and adrenaline/noradrenaline. Handb Exp Pharmacol. 2008;(184):261-88. Pubmed

6. Alpha-2C adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Alpha-2C adrenergic receptor P18825 Details

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
  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
  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
  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
  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 Apr 4;. Pubmed
  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
  7. Gilsbach R, Hein L: Presynaptic metabotropic receptors for acetylcholine and adrenaline/noradrenaline. Handb Exp Pharmacol. 2008;(184):261-88. Pubmed

7. Beta-1 adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Beta-1 adrenergic receptor P08588 Details

References:

  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  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
  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. Pubmed
  4. Gilsbach R, Hein L: Presynaptic metabotropic receptors for acetylcholine and adrenaline/noradrenaline. Handb Exp Pharmacol. 2008;(184):261-88. Pubmed

8. Beta-2 adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Beta-2 adrenergic receptor P07550 Details

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
  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
  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
  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
  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
  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
  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. Pubmed
  8. Gilsbach R, Hein L: Presynaptic metabotropic receptors for acetylcholine and adrenaline/noradrenaline. Handb Exp Pharmacol. 2008;(184):261-88. Pubmed

9. Beta-3 adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Beta-3 adrenergic receptor P13945 Details

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
  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
  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
  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
  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
  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

10. Phenylalanine-4-hydroxylase

Kind: protein

Organism: Human

Pharmacological action: no

Actions: inhibitor

Components

Name UniProt ID Details
Phenylalanine-4-hydroxylase P00439 Details

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
  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
  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
  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
  5. Molinoff PB: The regulation of the noradrenergic neuron. J Psychiatr Res. 1974;11:339-45. Pubmed

11. Synaptic vesicular amine transporter

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: binder

Components

Name UniProt ID Details
Synaptic vesicular amine transporter Q05940 Details

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

12. Chromaffin granule amine transporter

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: binder

Components

Name UniProt ID Details
Chromaffin granule amine transporter P54219 Details

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

Enzymes

1. Cytochrome P450 1A2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

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. Epub 2009 Nov 24. Pubmed

Transporters

1. Sodium-dependent noradrenaline transporter

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Sodium-dependent noradrenaline transporter P23975 Details

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
  2. Bonisch H, Bruss M: The norepinephrine transporter in physiology and disease. Handb Exp Pharmacol. 2006;(175):485-524. Pubmed
  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
  4. Gutman DA, Owens MJ: Serotonin and norepinephrine transporter binding profile of SSRIs. Essent Psychopharmacol. 2006;7(1):35-41. Pubmed
  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

2. Solute carrier family 22 member 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 2 O15244 Details

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
  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
  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
  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

3. Solute carrier family 22 member 3

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 3 O75751 Details

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
  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

4. Solute carrier family 22 member 5

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 5 O76082 Details

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
  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

5. Solute carrier family 22 member 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Solute carrier family 22 member 1 O15245 Details

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
  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

6. POU domain, class 5, transcription factor 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
POU domain, class 5, transcription factor 1 Q01860 Details

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. Epub 2010 Apr 6. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:10