U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C8H11NO3
Molecular Weight 169.1782
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NOREPINEPHRINE

SMILES

c1cc(c(cc1[C@]([H])(CN)O)O)O

InChI

InChIKey=SFLSHLFXELFNJZ-QMMMGPOBSA-N
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

HIDE SMILES / InChI

Description
Curator's Comment:: description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/?term=17214596; http://www.ncbi.nlm.nih.gov/pubmed/?term=18368304

Norepinephrine (l-arterenol/Levarterenol or l-norepinephrine) is a sympathomimetic catecholamine with multiple roles including as a hormone and a neurotransmitter. As a stress hormone, norepinephrine affects parts of the brain where attention and responding actions are controlled. Along with epinephrine, norepinephrine also underlies the fight-or-flight response, directly increasing heart rate, triggering the release of glucose from energy stores, and increasing blood flow to skeletal muscle. Norepinephrine can also suppress neuroinflammation when released diffusely in the brain from the locus ceruleus. Norepinephrine may be used for blood pressure control in certain acute hypotensive states (e.g., pheochromocytomectomy, sympathectomy, poliomyelitis, spinal anesthesia, myocardial infarction, septicemia, blood transfusion, and drug reactions) and as an adjunct in the treatment of cardiac arrest and profound hypotension. Norepinephrine performs its action by being released into the synaptic cleft, where it acts on adrenergic receptors, followed by the signal termination, either by degradation of norepinephrine, or by uptake by surrounding cells. Prolonged administration of any potent vasopressor may result in plasma volume depletion which should be continuously corrected by appropriate fluid and electrolyte replacement therapy.If plasma volumes are not corrected, hypotension may recur when Norepinephrine is discontinued, or blood pressure may be maintained at the risk of severe peripheral and visceral vasoconstriction (e.g., decreased renal perfusion)with diminution in blood flow and tissue perfusion with subsequent tissue hypoxia and lactic acidosis and possible ischemic injury. Gangrene of extremities has been rarely reported. Overdoses or conventional doses in hypersensitive persons (e.g., hyperthyroid patients) cause severe hypertension with violent headache, photophobia, stabbing retrosternal pain, pallor, intense sweating, and vomiting.

CNS Activity

Curator's Comment:: In the brain, norepinephrine is produced in closely packed brain cell neurons or nuclei that are small yet exert powerful effects on other brain areas.

Originator

Sources: http://www.businesswire.com/news/home/20140218006891/en/Chelsea-Therapeutics-Announces-FDA-Accelerated-Approval-NORTHERA%E2%84%A2Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales (1932), 111, 884-6.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
LEVOPHED

Approved Use

INDICATIONS: ​Temporary relief of sleep, emotional, nervous or memory disorders.

Launch Date

-614476800000
Primary
LEVOPHED

Approved Use

INDICATIONS: ​Temporary relief of sleep, emotional, nervous or memory disorders.

Launch Date

-614476800000
Primary
LEVOPHED

Approved Use

INDICATIONS: ​Temporary relief of sleep, emotional, nervous or memory disorders.

Launch Date

-614476800000
Primary
NORTHERA

Approved Use

Indicated for the treatment of orthostatic dizziness, lightheadedness, or the “feeling that you are about to black out” in adult patients with symptomatic neurogenic orthostatic hypotension (NOH) caused by primary autonomic failure [Parkinson's disease (PD), multiple system atrophy and pure autonomic failure], dopamine beta-hydroxylase deficiency, and non-diabetic autonomic neuropathy.

Launch Date

1392681600000
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.4 min
unknown, intravenous
NOREPINEPHRINE unknown
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
75%
unknown, intravenous
NOREPINEPHRINE unknown
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
0.6 ug/kg/min single, intravenous
Highest studied dose
Dose: 0.6 ug/kg/min
Route: intravenous
Route: single
Dose: 0.6 ug/kg/min
Sources:
unhealthy, mean 65.5 years
Health Status: unhealthy
Age Group: mean 65.5 years
Sex: M+F
Sources:
Other AEs: Mean arterial pressure high...
Other AEs:
Mean arterial pressure high (7.2%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Mean arterial pressure high 7.2%
0.6 ug/kg/min single, intravenous
Highest studied dose
Dose: 0.6 ug/kg/min
Route: intravenous
Route: single
Dose: 0.6 ug/kg/min
Sources:
unhealthy, mean 65.5 years
Health Status: unhealthy
Age Group: mean 65.5 years
Sex: M+F
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer







Drug as perpetrator​

Drug as perpetrator​

Drug as victim

Drug as victim

Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Involvement of noradrenaline transporters in S-nitrosocysteine-stimulated noradrenaline release from rat brain slices: existence of functional Na(+)-independent transporter activity.
2001 Apr
alpha(1B) adrenergic receptors in gonadotrophin-releasing hormone neurones: relation to Transport-P.
2001 Jan
Chronic treatment with reboxetine by osmotic pumps facilitates its effect on extracellular noradrenaline and may desensitize alpha(2)-adrenoceptors in the prefrontal cortex.
2001 Jan
Simvastatin inhibits noradrenaline-induced hypertrophy of cultured neonatal rat cardiomyocytes.
2001 Jan
Beta-adrenoceptor stimulation attenuates the hypertrophic effect of alpha-adrenoceptor stimulation in adult rat ventricular cardiomyocytes.
2001 Jan
Ambulatory norepinephrine treatment of severe autonomic orthostatic hypotension.
2001 Jan
Contrasting clinical properties and exercise responses in obese and lean hypertensive patients.
2001 Jan
Arterial remodeling in chronic sinoaortic-denervated rats.
2001 Jan
Reversal of Haemorrhagic Shock in Rats by Tetrahydroaminoacridine.
2001 Jan
Modulatory effect of protein kinase C activator on contractility of rat vas deferens.
2001 Jan
Hormonal responses to exercise in chronic fatigue syndrome.
2001 Jan
Monoamine compounds in cerebrospinal fluid of healthy subjects punctured without preceding strict bed rest: a pilot study.
2001 Jan
Differences in central noradrenergic and behavioural responses of Maudsley non-reactive and Maudsley reactive inbred rats on exposure to an aversive novel environment.
2001 Jan
Antagonism of Rho-kinase stimulates rat penile erection via a nitric oxide-independent pathway.
2001 Jan
Efferent arteriole tubuloglomerular feedback in the renal nephron.
2001 Jan
Alteration of catecholamines in pheochromocytoma (PC12) cells in vitro by the metabolites of chlorotriazine herbicide.
2001 Jan
Effects of human pregnancy on cardiac autonomic function above and below the ventilatory threshold.
2001 Jan
Ventricular activation during sympathetic imbalance and its computational reconstruction.
2001 Jan
Dorsomedial medulla is more susceptible than rostral ventrolateral medulla to hypoxic insult in cats.
2001 Jan
Interaction of gender and exercise training: vasomotor reactivity of porcine skeletal muscle arteries.
2001 Jan
Catecholamine responses to alpha-adrenergic blockade during exercise in women acutely exposed to altitude.
2001 Jan
Alteration of humoral and peripheral vascular responses during graded exercise in heart failure.
2001 Jan
Effects of PKC isozyme inhibitors on constrictor responses in the feline pulmonary vascular bed.
2001 Jan
Neurotransmitter release from bovine adrenal chromaffin cells is modulated by capacitative Ca(2+)entry driven by depleted internal Ca(2+)stores.
2001 Jan
Reactive oxygen species mediate alpha-adrenergic receptor-stimulated hypertrophy in adult rat ventricular myocytes.
2001 Jan
Catecholaminergic regulation of Na-K-Cl cotransport in pigmented ciliary epithelium: differences between PE and NPE.
2001 Jan
The antidepressant-sensitive dopamine transporter in Drosophila melanogaster: a primordial carrier for catecholamines.
2001 Jan
Neonatal catecholamine levels and neurodevelopmental outcome: a cohort study.
2001 Jan
In vitro reconstitution of fish melanophore pigment aggregation.
2001 Jan
Differential alterations in cardiac adrenergic signaling in chronic hypoxia or norepinephrine infusion.
2001 Jan
A single bout of exercise induces beta-adrenergic desensitization in human adipose tissue.
2001 Jan
Substance P and NPY differentially potentiate ATP and adrenergic stimulated vasopressin and oxytocin release.
2001 Jan
Chronic type IV phosphodiesterase inhibition protects glomerular filtration rate and renal and mesenteric blood flow in a zymosan-induced model of multiple organ dysfunction syndrome treated with norepinephrine.
2001 Jan
Correlation between the release of the sympathetic neurotransmitter ATP and soluble nucleotidases from the guinea pig vas deferens.
2001 Jan
Melatonin potentiates NE-induced vasoconstriction without augmenting cytosolic calcium concentration.
2001 Jan
Vagosympathetic interactions in ischemia-induced myocardial norepinephrine and acetylcholine release.
2001 Jan
ANG II potentiates mitogenic effect of norepinephrine in vascular muscle cells: role of FGF-2.
2001 Jan
Inducible and neuronal nitric oxide synthase involvement in lipopolysaccharide-induced sphincteric dysfunction.
2001 Jan
Characterization of extracellular dopamine clearance in the medial prefrontal cortex: role of monoamine uptake and monoamine oxidase inhibition.
2001 Jan 1
Potentiation by aminoethylisothiourea of the extra-cellular Ca(2+) component of norepinephrine-induced contraction in rat femoral arteries.
2001 Jan 1
IFN-gamma production by Th1 cells generated from naive CD4+ T cells exposed to norepinephrine.
2001 Jan 1
The effects of phosphodiesterase inhibition on cyclic GMP and cyclic AMP accumulation in the hippocampus of the rat.
2001 Jan 12
Changes in sensitivity of cholinoceptors and adrenoceptors during transhemispheric cortical reorganisation in rat SmI.
2001 Jan 12
Nitric oxide synthase activity in peripheral polymorphonuclear leukocytes in patients with chronic congestive heart failure.
2001 Jan 15
Upregulation of immunoreactive angiotensin II release and angiotensinogen mRNA expression by high-frequency preganglionic stimulation at the canine cardiac sympathetic ganglia.
2001 Jan 19
Estrogen modulates norepinephrine-induced accumulation of adenosine cyclic monophosphate in a subpopulation of immortalized luteinizing hormone-releasing hormone secreting neurons from the mouse hypothalamus.
2001 Jan 26
A proposed pathological model in the hippocampus of subjects with schizophrenia.
2001 Jan-Feb
Effect of amlodipine on cardiopulmonary performance in volunteers.
2001 Jan-Feb
L-Dihydroxyphenylserine (L-DOPS): a norepinephrine prodrug.
2006 Fall-Winter
Droxidopa, an oral norepinephrine precursor, improves hemodynamic and renal alterations of portal hypertensive rats.
2012 Nov
Patents

Sample Use Guides

The recommended starting dose is 100 mg, taken orally three times daily: upon arising in the morning, at midday, and in the late afternoon at least 3 hours prior to bedtime (to reduce the potential for supine hypertension during sleep). Administer consistently, either with food or without food. Take capsule whole. Titrate to symptomatic response, in increments of 100 mg three times daily every 2448 hours up to a maximum dose of 600 mg three times daily (i.e., a maximum total daily dose of 1800 mg).
Route of Administration: Oral
Name Type Language
NOREPINEPHRINE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
NORADRENALINE
MART.  
Common Name English
NORADRENALINE [MART.]
Common Name English
NOREPINEPHRINE [WHO-DD]
Common Name English
ADRENALINE TARTRATE IMPURITY B [EP]
Common Name English
NOREPINEPHRINE [MI]
Common Name English
(-)-NORADRENALINE
Common Name English
NSC-757246
Code English
(-)-.ALPHA.-(AMINOMETHYL)-3,4-DIHYDROXYBENZYL ALCOHOL
Systematic Name English
NORADRENALINE [JAN]
Common Name English
NOREPINEPHRINE [INN]
Common Name English
1,2-BENZENEDIOL, 4-(2-AMINO-1-HYDROXYETHYL)-, (R)-(R-(R*,R*))-2,3-DIHYDROXYBUTANEDIOATE
Common Name English
NOR ADRENALIN
Brand Name English
NOREPINEPHRINE [HSDB]
Common Name English
NOREPINEPHRINE [VANDF]
Common Name English
Classification Tree Code System Code
LOINC 13782-8
Created by admin on Fri Jun 25 21:48:19 UTC 2021 , Edited by admin on Fri Jun 25 21:48:19 UTC 2021
LOINC 44837-3
Created by admin on Fri Jun 25 21:48:19 UTC 2021 , Edited by admin on Fri Jun 25 21:48:19 UTC 2021
LOINC 49552-3
Created by admin on Fri Jun 25 21:48:19 UTC 2021 , Edited by admin on Fri Jun 25 21:48:19 UTC 2021
LOINC 14852-8
Created by admin on Fri Jun 25 21:48:19 UTC 2021 , Edited by admin on Fri Jun 25 21:48:19 UTC 2021
WHO-VATC QC01CA03
Created by admin on Fri Jun 25 21:48:19 UTC 2021 , Edited by admin on Fri Jun 25 21:48:19 UTC 2021
LOINC 2666-6
Created by admin on Fri Jun 25 21:48:19 UTC 2021 , Edited by admin on Fri Jun 25 21:48:19 UTC 2021
LOINC 27221-1
Created by admin on Fri Jun 25 21:48:19 UTC 2021 , Edited by admin on Fri Jun 25 21:48:19 UTC 2021
LOINC 16111-7
Created by admin on Fri Jun 25 21:48:19 UTC 2021 , Edited by admin on Fri Jun 25 21:48:19 UTC 2021
LOINC 44341-6
Created by admin on Fri Jun 25 21:48:19 UTC 2021 , Edited by admin on Fri Jun 25 21:48:19 UTC 2021
LOINC 24523-3
Created by admin on Fri Jun 25 21:48:19 UTC 2021 , Edited by admin on Fri Jun 25 21:48:19 UTC 2021
LOINC 13735-6
Created by admin on Fri Jun 25 21:48:19 UTC 2021 , Edited by admin on Fri Jun 25 21:48:19 UTC 2021
LOINC 32549-8
Created by admin on Fri Jun 25 21:48:19 UTC 2021 , Edited by admin on Fri Jun 25 21:48:19 UTC 2021
LOINC 2668-2
Created by admin on Fri Jun 25 21:48:19 UTC 2021 , Edited by admin on Fri Jun 25 21:48:19 UTC 2021
NDF-RT N0000007715
Created by admin on Fri Jun 25 21:48:19 UTC 2021 , Edited by admin on Fri Jun 25 21:48:19 UTC 2021
LOINC 25963-0
Created by admin on Fri Jun 25 21:48:19 UTC 2021 , Edited by admin on Fri Jun 25 21:48:19 UTC 2021
LOINC 2667-4
Created by admin on Fri Jun 25 21:48:19 UTC 2021 , Edited by admin on Fri Jun 25 21:48:19 UTC 2021
LOINC 27977-8
Created by admin on Fri Jun 25 21:48:19 UTC 2021 , Edited by admin on Fri Jun 25 21:48:19 UTC 2021
LOINC 14854-4
Created by admin on Fri Jun 25 21:48:19 UTC 2021 , Edited by admin on Fri Jun 25 21:48:19 UTC 2021
LOINC 14853-6
Created by admin on Fri Jun 25 21:48:19 UTC 2021 , Edited by admin on Fri Jun 25 21:48:19 UTC 2021
WHO-ATC C01CA03
Created by admin on Fri Jun 25 21:48:19 UTC 2021 , Edited by admin on Fri Jun 25 21:48:19 UTC 2021
NDF-RT N0000175570
Created by admin on Fri Jun 25 21:48:19 UTC 2021 , Edited by admin on Fri Jun 25 21:48:19 UTC 2021
Code System Code Type Description
IUPHAR
505
Created by admin on Fri Jun 25 21:48:19 UTC 2021 , Edited by admin on Fri Jun 25 21:48:19 UTC 2021
PRIMARY
ChEMBL
CHEMBL1437
Created by admin on Fri Jun 25 21:48:19 UTC 2021 , Edited by admin on Fri Jun 25 21:48:19 UTC 2021
PRIMARY
FDA UNII
X4W3ENH1CV
Created by admin on Fri Jun 25 21:48:19 UTC 2021 , Edited by admin on Fri Jun 25 21:48:19 UTC 2021
PRIMARY
MESH
D009638
Created by admin on Fri Jun 25 21:48:19 UTC 2021 , Edited by admin on Fri Jun 25 21:48:19 UTC 2021
PRIMARY
EPA CompTox
51-41-2
Created by admin on Fri Jun 25 21:48:19 UTC 2021 , Edited by admin on Fri Jun 25 21:48:19 UTC 2021
PRIMARY
EVMPD
SUB09360MIG
Created by admin on Fri Jun 25 21:48:19 UTC 2021 , Edited by admin on Fri Jun 25 21:48:19 UTC 2021
PRIMARY
HSDB
7772
Created by admin on Fri Jun 25 21:48:19 UTC 2021 , Edited by admin on Fri Jun 25 21:48:19 UTC 2021
PRIMARY
INN
33
Created by admin on Fri Jun 25 21:48:19 UTC 2021 , Edited by admin on Fri Jun 25 21:48:19 UTC 2021
PRIMARY
DRUG CENTRAL
1960
Created by admin on Fri Jun 25 21:48:19 UTC 2021 , Edited by admin on Fri Jun 25 21:48:19 UTC 2021
PRIMARY
CAS
51-41-2
Created by admin on Fri Jun 25 21:48:19 UTC 2021 , Edited by admin on Fri Jun 25 21:48:19 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-096-6
Created by admin on Fri Jun 25 21:48:19 UTC 2021 , Edited by admin on Fri Jun 25 21:48:19 UTC 2021
PRIMARY
WIKIPEDIA
NOREPINEPHRINE
Created by admin on Fri Jun 25 21:48:19 UTC 2021 , Edited by admin on Fri Jun 25 21:48:19 UTC 2021
PRIMARY
DRUG BANK
DB00368
Created by admin on Fri Jun 25 21:48:19 UTC 2021 , Edited by admin on Fri Jun 25 21:48:19 UTC 2021
PRIMARY
MERCK INDEX
M8054
Created by admin on Fri Jun 25 21:48:19 UTC 2021 , Edited by admin on Fri Jun 25 21:48:19 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C2321
Created by admin on Fri Jun 25 21:48:19 UTC 2021 , Edited by admin on Fri Jun 25 21:48:19 UTC 2021
PRIMARY
PUBCHEM
439260
Created by admin on Fri Jun 25 21:48:19 UTC 2021 , Edited by admin on Fri Jun 25 21:48:19 UTC 2021
PRIMARY
LACTMED
Norepinephrine
Created by admin on Fri Jun 25 21:48:19 UTC 2021 , Edited by admin on Fri Jun 25 21:48:19 UTC 2021
PRIMARY
RXCUI
7512
Created by admin on Fri Jun 25 21:48:19 UTC 2021 , Edited by admin on Fri Jun 25 21:48:19 UTC 2021
PRIMARY RxNorm