Details of the Drug

General Information of Drug (ID: DMOUC09)

Drug Name
Norepinephrine
Synonyms
norepinephrine; L-Noradrenaline; Levarterenol; 51-41-2; L-Norepinephrine; Levophed; (-)-Norepinephrine; L-arterenol; (R)-Noradrenaline; (R)-Norepinephrine; Levonor; Levonorepinephrine; Adrenor; Aktamin; Levonoradrenaline; Sympathin E; (R)-(-)-Norepinephrine; 4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diol; Noradrenalin; Norepirenamine; norepinephrinum; Noradrenalinum; Levoarterenol; Norartrinal; Nor-Epirenan; L-3,4-dihydroxyphenylethanolamine; Levarterenolo; Noreinefrina; Norepinefrina; Norepinephrinum; Levarterenolo [DCIT]; Nor adrenalin; Noradrenalina [Italian]; Norepinephrine Noradrenalin; LT03330026; ALBB-006229; Nor adrenalin (TN); Noradrenaline (JP15); Noreinefrina [INN-Spanish]; Norepinephrine (INN); Norepinephrine [INN:JAN]; Norepinephrinum [INN-Latin]; Norepinephrine l-Tartrate (1:1); D-(-)-Noradrenaline; D53D5E3A-2360-4CA9-8031-6C2CD4062FD5; L-alpha-(aminomethyl)-3,4-dihydroxybenzyl alcohol; L-1-(3,4-Dihydroxyphenyl)-2-aminoethanol; L-2-Amino-1-(3,4-dihydroxyphenyl)ethanol; (-)-(R)-Norepinephrine; (-)-Arterenol free base; (-)-alpha-(Aminomethyl)protocatechuyl alcohol; (R)-4-(2-Amino-1-hydroxyethyl)-1,2-benzenediol; 1,2-Benzenediol, 4-(2-amino-1-hydroxyethyl)-, (R)-(9CI); 4-[(1R)-2-Amino-1-hydroxyethyl]-1,2-benzenediol; Ecteinascidins
Indication
Disease Entry ICD 11 Status REF
Alopecia ED70 Approved [1]
Bronchiectasis CA24 Approved [1]
Bronchitis CA20 Approved [1]
Chronic fatigue syndrome 8E49 Approved [1]
Depression 6A70-6A7Z Approved [1]
Psychosexual disorder N.A. Approved [1]
Pulmonary emphysema CA21.Z Approved [1]
Pure autonomic failure N.A. Approved [1]
Radiodermatitis N.A. Approved [1]
Sepsis 1G40-1G41 Approved [2]
Severe asthma CA23 Approved [1]
Asthma CA23 Investigative [1]
⏷ Show the Full List of Indication(s)
Therapeutic Class
Vasoconstrictor Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 169.18
Logarithm of the Partition Coefficient (xlogp) -1.2
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 4
Hydrogen Bond Acceptor Count (hbondacc) 4
Chemical Identifiers
Formula
C8H11NO3
IUPAC Name
4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diol
Canonical SMILES
C1=CC(=C(C=C1[C@H](CN)O)O)O
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
InChIKey
SFLSHLFXELFNJZ-QMMMGPOBSA-N
Cross-matching ID
PubChem CID
439260
ChEBI ID
CHEBI:18357
CAS Number
51-41-2
DrugBank ID
DB00368
TTD ID
D07MOX
VARIDT ID
DR00268
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Adrenergic receptor beta-1 (ADRB1) TTR6W5O ADRB1_HUMAN Stimulator [3]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Sodium- and chloride-dependent glycine transporter 2 (SLC6A5) DTE8R17 SC6A5_HUMAN Substrate [4]
Vesicular amine transporter 2 (SLC18A2) DTT7VPB VMAT2_HUMAN Substrate [5]
Vesicular amine transporter 1 (SLC18A1) DTM953D VMAT1_HUMAN Substrate [5]
Sodium-dependent noradrenaline transporter (SLC6A2) DT9JBVI SC6A2_HUMAN Substrate [6]
Organic cation transporter 3 (SLC22A3) DT6201N S22A3_HUMAN Substrate [7]
Organic cation transporter 1 (SLC22A1) DTT79CX S22A1_HUMAN Substrate [8]
Organic cation transporter 2 (SLC22A2) DT9IDPW S22A2_HUMAN Substrate [7]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
72 kDa type IV collagenase (MMP2) OT5NIWA2 MMP2_HUMAN Gene/Protein Processing [9]
Alpha-1A adrenergic receptor (ADRA1A) OTUIWCL5 ADA1A_HUMAN Protein Interaction/Cellular Processes [10]
Alpha-1D adrenergic receptor (ADRA1D) OTW2CD1O ADA1D_HUMAN Protein Interaction/Cellular Processes [11]
Amine oxidase A (MAOA) OT8NIWMQ AOFA_HUMAN Regulation of Drug Effects [12]
Beta-2 adrenergic receptor (ADRB2) OTSDOX4Q ADRB2_HUMAN Protein Interaction/Cellular Processes [9]
C-C motif chemokine 5 (CCL5) OTSCA5CK CCL5_HUMAN Protein Interaction/Cellular Processes [13]
Cannabinoid receptor 1 (CNR1) OTEALO6G CNR1_HUMAN Gene/Protein Processing [14]
Catechol O-methyltransferase (COMT) OTPWKTQG COMT_HUMAN Biotransformations [15]
Equilibrative nucleoside transporter 4 (SLC29A4) OTWTZXMX S29A4_HUMAN Regulation of Drug Effects [16]
Heme oxygenase 1 (HMOX1) OTC1W6UX HMOX1_HUMAN Gene/Protein Processing [9]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Norepinephrine (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Methylene blue DMJAPE7 Moderate Additive hypertensive effects by the combination of Norepinephrine and Methylene blue. Acquired methaemoglobinaemia [3A93] [17]
Droxidopa DM5YF4M Moderate Additive hypertensive effects by the combination of Norepinephrine and Droxidopa. Autonomic nervous system disorder [8D87] [18]
Linezolid DMGFPU2 Major Increased risk of hyperpyrexia by the combination of Norepinephrine and Linezolid. Bacterial infection [1A00-1C4Z] [19]
Levomilnacipran DMV26S8 Moderate Increased risk of rapid heart rate by the combination of Norepinephrine and Levomilnacipran. Chronic pain [MG30] [20]
Selegiline DM6034S Moderate Additive hypertensive effects by the combination of Norepinephrine and Selegiline. Depression [6A70-6A7Z] [17]
Duloxetine DM9BI7M Moderate Increased risk of rapid heart rate by the combination of Norepinephrine and Duloxetine. Depression [6A70-6A7Z] [20]
Isocarboxazid DMAF1NB Moderate Additive hypertensive effects by the combination of Norepinephrine and Isocarboxazid. Depression [6A70-6A7Z] [17]
Milnacipran DMBFE74 Moderate Increased risk of rapid heart rate by the combination of Norepinephrine and Milnacipran. Depression [6A70-6A7Z] [21]
Tranylcypromine DMGB5RE Moderate Additive hypertensive effects by the combination of Norepinephrine and Tranylcypromine. Depression [6A70-6A7Z] [17]
Desvenlafaxine DMHD4PE Moderate Increased risk of rapid heart rate by the combination of Norepinephrine and Desvenlafaxine. Depression [6A70-6A7Z] [20]
Phenelzine DMHIDUE Moderate Additive hypertensive effects by the combination of Norepinephrine and Phenelzine. Depression [6A70-6A7Z] [17]
Ergotamine DMKR3C5 Major Additive hypertensive effects by the combination of Norepinephrine and Ergotamine. Headache [8A80-8A84] [22]
Procarbazine DMIK367 Moderate Additive hypertensive effects by the combination of Norepinephrine and Procarbazine. Hodgkin lymphoma [2B30] [17]
Sibutramine DMFJTDI Moderate Increased risk of rapid heart rate by the combination of Norepinephrine and Sibutramine. Obesity [5B80-5B81] [23]
Opicapone DM1BKA6 Moderate Decreased metabolism of Norepinephrine caused by Opicapone mediated inhibition of non-CYP450 enzyme. Parkinsonism [8A00] [24]
Rasagiline DM3WKQ4 Moderate Additive hypertensive effects by the combination of Norepinephrine and Rasagiline. Parkinsonism [8A00] [17]
Entacapone DMLBVKQ Moderate Decreased metabolism of Norepinephrine caused by Entacapone mediated inhibition of non-CYP450 enzyme. Parkinsonism [8A00] [24]
Ergonovine DM0VEC1 Major Additive hypertensive effects by the combination of Norepinephrine and Ergonovine. Postpartum haemorrhage [JA43] [22]
⏷ Show the Full List of 18 DDI Information of This Drug

References

1 Norepinephrine FDA Label
2 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 505).
3 Impact of exogenous beta-adrenergic receptor stimulation on hepatosplanchnic oxygen kinetics and metabolic activity in septic shock. Crit Care Med. 1999 Feb;27(2):325-31.
4 SLC6A2 Gene (Protein Coding).
5 SLC18: Vesicular neurotransmitter transporters for monoamines and acetylcholine. Mol Aspects Med. 2013 Apr-Jun;34(2-3):360-72.
6 Chronic depolarization stimulates norepinephrine transporter expression via catecholamines. J Neurochem. 2006 May;97(4):1044-51.
7 Differential pharmacological in vitro properties of organic cation transporters and regional distribution in rat brain. Neuropharmacology. 2006 Jun;50(8):941-52.
8 Organic cation transporters and their pharmacokinetic and pharmacodynamic consequences. Drug Metab Pharmacokinet. 2008;23(4):243-53.
9 Quercetin-3-O-glucuronide inhibits noradrenaline-promoted invasion of MDA-MB-231 human breast cancer cells by blocking ?-adrenergic signaling. Arch Biochem Biophys. 2014 Sep 1;557:18-27. doi: 10.1016/j.abb.2014.05.030. Epub 2014 Jun 11.
10 The alpha 1-adrenergic receptor that mediates smooth muscle contraction in human prostate has the pharmacological properties of the cloned human alpha 1c subtype. Mol Pharmacol. 1994 Apr;45(4):703-8.
11 Chromatography studies on bio-affinity of nine ligands of alpha1-adrenoceptor to alpha1D subtypes overexpressed in cell membrane. Sci China C Life Sci. 2004 Aug;47(4):376-81. doi: 10.1360/03yc0109.
12 Association between monoamine oxidase A activity in human male skin fibroblasts and genotype of the MAOA promoter-associated variable number tandem repeat. Hum Genet. 1999 Dec;105(6):542-51. doi: 10.1007/s004399900183.
13 Norepinephrine induces calcium spikes and proinflammatory actions in human hepatic stellate cells. Am J Physiol Gastrointest Liver Physiol. 2006 Nov;291(5):G877-84. doi: 10.1152/ajpgi.00537.2005. Epub 2006 Jun 15.
14 Cannabinoid Type 1 Receptors Are Upregulated During Acute Activation of Brown Adipose Tissue. Diabetes. 2018 Jul;67(7):1226-1236. doi: 10.2337/db17-1366. Epub 2018 Apr 12.
15 Molecular mechanisms controlling the rate and specificity of catechol O-methylation by human soluble catechol O-methyltransferase. Mol Pharmacol. 2001 Feb;59(2):393-402. doi: 10.1124/mol.59.2.393.
16 Selective transport of monoamine neurotransmitters by human plasma membrane monoamine transporter and organic cation transporter 3. J Pharmacol Exp Ther. 2010 Dec;335(3):743-53. doi: 10.1124/jpet.110.170142. Epub 2010 Sep 21.
17 Ban TA "Drug interactions with psychoactive drugs." Dis Nerv Syst 36 (1975): 164-6. [PMID: 1116424]
18 Product Information. Northera (droxidopa). Chelsea Therapeutics Inc, Charlotte, NC.
19 Hendershot PE, Antal EJ, Welshman IR, Batts DH, Hopkins NK "Linezolid: pharmacokinetic and pharmacodynamic evaluation of coadministration with pseudoephedrine HCl, phenylpropanolamine HCl, and dextromethorpan HBr." J Clin Pharmacol 41 (2001): 563-72. [PMID: 11361053]
20 Product Information. Cymbalta (duloxetine). Lilly, Eli and Company, Indianapolis, IN.
21 Cerner Multum, Inc. "Australian Product Information.".
22 Barthel W, Glusa E, Koth W "Interactions of dihydroergotamine with etilefrine in human leg veins in vitro and in situ." Int J Clin Pharmacol Ther Toxicol 25 (1987): 63-9. [PMID: 2881898]
23 Product Information. Meridia (sibutramine). Knoll Pharmaceutical Company, Whippany, NJ.
24 Illi A, Sundberg S, Ojala-Karlsson P, Korhonen P, Scheinin M, Gordin A "The effect of entacapone on the disposition and hemodynamic effects of intravenous isoproterenol and epinephrine." Clin Pharmacol Ther 58 (1995): 221-7. [PMID: 7648772]