Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C8H11NO3 |
Molecular Weight | 169.1778 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC[C@H](O)C1=CC(O)=C(O)C=C1
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
Molecular Formula | C8H11NO3 |
Molecular Weight | 169.1778 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/203202lbl.pdfhttps://www.accessdata.fda.gov/drugsatfda_docs/label/2007/007513Orig1s024lbl.pdfCurator'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
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/203202lbl.pdfhttps://www.accessdata.fda.gov/drugsatfda_docs/label/2007/007513Orig1s024lbl.pdf
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
Sources: http://www.fda.gov/downloads/AdvisoryCommittees/CommitteesMeetingMaterials/Drugs/CardiovascularandRenalDrugsAdvisoryCommittee/UCM292631.pdfhttp://www.caam.rice.edu/~cox/wrap/norepinephrine.pdf
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
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2094118 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6124637 |
2600.0 nM [EC50] | ||
Target ID: CHEMBL229 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26125514 |
9.1 nM [EC50] | ||
Target ID: CHEMBL1867 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25282262 |
128.8 nM [EC50] | ||
Target ID: CHEMBL1942 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18578476 |
61.7 nM [EC50] | ||
Target ID: CHEMBL1916 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18578476 |
794.3 nM [EC50] | ||
Target ID: CHEMBL2331074 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | LEVOPHED Approved UseINDICATIONS: Temporary relief of sleep, emotional, nervous or memory disorders. Launch Date-6.1447681E11 |
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Primary | LEVOPHED Approved UseINDICATIONS: Temporary relief of sleep, emotional, nervous or memory disorders. Launch Date-6.1447681E11 |
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Primary | LEVOPHED Approved UseINDICATIONS: Temporary relief of sleep, emotional, nervous or memory disorders. Launch Date-6.1447681E11 |
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Primary | NORTHERA Approved UseIndicated 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 Date1.39268155E12 |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.4 min |
unknown, intravenous |
NOREPINEPHRINE unknown | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
75% |
unknown, intravenous |
NOREPINEPHRINE unknown | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse 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 n = 85 Health Status: unhealthy Condition: cardiogenic shock Age Group: mean 65.5 years Sex: M+F Population Size: 85 Sources: |
Other AEs: Mean arterial pressure high... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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 n = 85 Health Status: unhealthy Condition: cardiogenic shock Age Group: mean 65.5 years Sex: M+F Population Size: 85 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/9848110/ Page: - |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/9848110/ Page: - |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/9848110/ Page: - |
no |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: - |
yes [Km 10.65 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/9687576/ Page: - |
yes [Km 1900 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/26432838/ Page: - |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/27355037/ Page: - |
yes |
PubMed
Title | Date | PubMed |
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Involvement of noradrenaline transporters in S-nitrosocysteine-stimulated noradrenaline release from rat brain slices: existence of functional Na(+)-independent transporter activity. | 2001 Apr |
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Effect of dexmedetomidine on the release of [3H]-noradrenaline from rat kidney cortex slices: characterization of alpha2-adrenoceptor. | 2001 Apr |
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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 |
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Simvastatin inhibits noradrenaline-induced hypertrophy of cultured neonatal rat cardiomyocytes. | 2001 Jan |
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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 |
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Projections and pathways of VIP- and nNOS-containing airway neurons in ferret trachea. | 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 |
|
N-methyl-D-aspartate receptors mediating hippocampal noradrenaline and striatal dopamine release display differential sensitivity to quinolinic acid, the HIV-1 envelope protein gp120, external pH and protein kinase C inhibition. | 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 |
|
Autoregulation of cerebral blood flow in patients resuscitated from cardiac arrest. | 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 |
|
Interaction of gender and exercise training: vasomotor reactivity of porcine skeletal muscle arteries. | 2001 Jan |
|
Effects of PKC isozyme inhibitors on constrictor responses in the feline pulmonary vascular bed. | 2001 Jan |
|
Reactive oxygen species mediate alpha-adrenergic receptor-stimulated hypertrophy in adult rat ventricular myocytes. | 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 |
|
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 |
|
ANG II potentiates mitogenic effect of norepinephrine in vascular muscle cells: role of FGF-2. | 2001 Jan |
|
Increased alpha(1)- and alpha(2)-adrenoceptor-mediated contractile responses of human skeletal muscle resistance arteries in chronic limb ischemia. | 2001 Jan |
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Myocardial interstitial norepinephrine and dihydroxyphenylglycol levels during ischemia and reperfusion. | 2001 Jan |
|
Vasoactive intestinal peptide: cardiovascular effects. | 2001 Jan |
|
Chromaffin-adrenocortical cell interactions: effects of chromaffin cell activation in adrenal cell cocultures. | 2001 Jan |
|
Reference intervals for glucose, beta-cell polypeptides, and counterregulatory factors during prolonged fasting. | 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 |
|
Dietary restriction in pregnant rats causes gender-related hypertension and vascular dysfunction in offspring. | 2001 Jan 1 |
|
IFN-gamma production by Th1 cells generated from naive CD4+ T cells exposed to norepinephrine. | 2001 Jan 1 |
|
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
Substance Class |
Chemical
Created
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Record UNII |
X4W3ENH1CV
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Record Status |
Validated (UNII)
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13782-8
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2666-6
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27221-1
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24523-3
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2668-2
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N0000007715
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25963-0
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14853-6
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C01CA03
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N0000175570
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505
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CHEMBL1437
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X4W3ENH1CV
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D009638
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DTXSID5023378
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X4W3ENH1CV
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33569
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7772
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Norepinephrine (medication)
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757246
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