U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ABSOLUTE
Molecular Formula C9H11NO5
Molecular Weight 213.1873
Optical Activity ( - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DROXIDOPA

SMILES

N[C@@H]([C@H](O)C1=CC=C(O)C(O)=C1)C(O)=O

InChI

InChIKey=QXWYKJLNLSIPIN-JGVFFNPUSA-N
InChI=1S/C9H11NO5/c10-7(9(14)15)8(13)4-1-2-5(11)6(12)3-4/h1-3,7-8,11-13H,10H2,(H,14,15)/t7-,8+/m0/s1

HIDE SMILES / InChI

Molecular Formula C9H11NO5
Molecular Weight 213.1873
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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

1950
Primary
LEVOPHED

Approved Use

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

Launch Date

1950
Primary
LEVOPHED

Approved Use

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

Launch Date

1950
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

2014
T1/2

T1/2

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

Funbound

ValueDoseCo-administeredAnalytePopulation
75%
unknown, intravenous
NOREPINEPHRINE plasma
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
The influence of kynurenine, neopterin, and norepinephrine on tubular epithelial cells and alveolar fibroblasts.
1999
Characterization of human recombinant alpha(2A)-adrenoceptors expressed in Chinese hamster lung cells using intracellular Ca(2+) changes: evidence for cross-talk between recombinant alpha(2A)- and native alpha(1)-adrenoceptors.
2000 Apr
Hemodynamic effects of milrinone during weaning from cardiopulmonary bypass: comparison of patients with a low and high prebypass cardiac index.
2000 Aug
Regulation of the human norepinephrine transporter by cocaine and amphetamine.
2000 Dec
Differential remodeling of the left and right heart after norepinephrine treatment in rats: studies on cytokines and collagen.
2000 Feb
Inhibition of protein phosphatase 1 induces apoptosis in neonatal rat cardiac myocytes: role of adrenergic receptor stimulation.
2000 Oct
Near fatal case of atrio-ventricular block induced by amitriptyline at therapeutic dose.
2000 Sep
Effect of dexmedetomidine on the release of [3H]-noradrenaline from rat kidney cortex slices: characterization of alpha2-adrenoceptor.
2001 Apr
Plasma catecholamine and cardiovascular responses to physostigmine in Alzheimer's disease and aging.
2001 Feb
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
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
Effects of human pregnancy on cardiac autonomic function above and below the ventilatory threshold.
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
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
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
Effects of nicotine and cotinine on porcine arterial endothelial cell function.
2001 Jan
The mechanism of resveratrol-induced vasorelaxation differs in the mesenteric resistance arteries of lean and obese rats.
2001 Jan
The noradrenergic alpha2 agonist clonidine modulates behavioural and neuroanatomical correlates of human attentional orienting and alerting.
2001 Jan
Effects of chronic antidepressant treatments on 5-HT and NA transporters in rat brain: an autoradiographic study.
2001 Jan
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
Diacylglycerol kinase theta is translocated and phosphoinositide 3-kinase-dependently activated by noradrenaline but not angiotensin II in intact small arteries.
2001 Jan 1
The effects of phosphodiesterase inhibition on cyclic GMP and cyclic AMP accumulation in the hippocampus of the rat.
2001 Jan 12
Nitric oxide synthase activity in peripheral polymorphonuclear leukocytes in patients with chronic congestive heart failure.
2001 Jan 15
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
Dialysate dihydroxyphenylglycol as a window for in situ axoplasmic norepinephrine disposition.
2001 Mar
Low temperature prevents potentiation of norepinephrine release by phenylephrine.
2001 Mar
Determination of residues in the norepinephrine transporter that are critical for tricyclic antidepressant affinity.
2001 Mar 16
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
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Wed Apr 02 08:41:30 GMT 2025
Edited
by admin
on Wed Apr 02 08:41:30 GMT 2025
Record UNII
J7A92W69L7
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DROXIDOPA
DASH   INN   JAN   MART.   MI   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
NORTHERA
Preferred Name English
droxidopa [INN]
Common Name English
DOPS
Code English
DROXIDOPA [VANDF]
Common Name English
(-)-(2S,3R)-2-AMINO-3-(3,4-DIHYDROXYPHENYL)-3-HYDROXYPROPANOIC ACID
Systematic Name English
DROXIDOPA [MI]
Common Name English
DROXIDOPA [ORANGE BOOK]
Common Name English
L-THREO-DOPS
Common Name English
THREO-3,4-DIHYDROXYPHENYLSERINE, L-
Common Name English
Droxidopa [WHO-DD]
Common Name English
DROXIDOPA [USAN]
Common Name English
L-TYROSINE, .BETA.,3-DIHYDROXY-, (.BETA.R)-
Common Name English
L-DOPS
Code English
DROXIDOPA [JAN]
Common Name English
DROXIDOPA [MART.]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 229506
Created by admin on Wed Apr 02 08:41:31 GMT 2025 , Edited by admin on Wed Apr 02 08:41:31 GMT 2025
EU-Orphan Drug EU/3/07/465
Created by admin on Wed Apr 02 08:41:31 GMT 2025 , Edited by admin on Wed Apr 02 08:41:31 GMT 2025
WHO-ATC C01CA27
Created by admin on Wed Apr 02 08:41:31 GMT 2025 , Edited by admin on Wed Apr 02 08:41:31 GMT 2025
EU-Orphan Drug EU/3/07/466
Created by admin on Wed Apr 02 08:41:31 GMT 2025 , Edited by admin on Wed Apr 02 08:41:31 GMT 2025
NCI_THESAURUS C38149
Created by admin on Wed Apr 02 08:41:31 GMT 2025 , Edited by admin on Wed Apr 02 08:41:31 GMT 2025
Code System Code Type Description
USAN
UU-114
Created by admin on Wed Apr 02 08:41:31 GMT 2025 , Edited by admin on Wed Apr 02 08:41:31 GMT 2025
PRIMARY
DRUG CENTRAL
971
Created by admin on Wed Apr 02 08:41:31 GMT 2025 , Edited by admin on Wed Apr 02 08:41:31 GMT 2025
PRIMARY
DAILYMED
J7A92W69L7
Created by admin on Wed Apr 02 08:41:31 GMT 2025 , Edited by admin on Wed Apr 02 08:41:31 GMT 2025
PRIMARY
WIKIPEDIA
L-DOPS
Created by admin on Wed Apr 02 08:41:31 GMT 2025 , Edited by admin on Wed Apr 02 08:41:31 GMT 2025
PRIMARY
MESH
D015103
Created by admin on Wed Apr 02 08:41:31 GMT 2025 , Edited by admin on Wed Apr 02 08:41:31 GMT 2025
PRIMARY
CHEBI
60568
Created by admin on Wed Apr 02 08:41:31 GMT 2025 , Edited by admin on Wed Apr 02 08:41:31 GMT 2025
PRIMARY
NCI_THESAURUS
C73266
Created by admin on Wed Apr 02 08:41:31 GMT 2025 , Edited by admin on Wed Apr 02 08:41:31 GMT 2025
PRIMARY
RXCUI
1489913
Created by admin on Wed Apr 02 08:41:31 GMT 2025 , Edited by admin on Wed Apr 02 08:41:31 GMT 2025
PRIMARY RxNorm
SMS_ID
100000081029
Created by admin on Wed Apr 02 08:41:31 GMT 2025 , Edited by admin on Wed Apr 02 08:41:31 GMT 2025
PRIMARY
EPA CompTox
DTXSID6046422
Created by admin on Wed Apr 02 08:41:31 GMT 2025 , Edited by admin on Wed Apr 02 08:41:31 GMT 2025
PRIMARY
NDF-RT
N0000178478
Created by admin on Wed Apr 02 08:41:31 GMT 2025 , Edited by admin on Wed Apr 02 08:41:31 GMT 2025
PRIMARY Increased Blood Pressure [PE]
CAS
23651-95-8
Created by admin on Wed Apr 02 08:41:31 GMT 2025 , Edited by admin on Wed Apr 02 08:41:31 GMT 2025
PRIMARY
IUPHAR
7391
Created by admin on Wed Apr 02 08:41:31 GMT 2025 , Edited by admin on Wed Apr 02 08:41:31 GMT 2025
PRIMARY
FDA UNII
J7A92W69L7
Created by admin on Wed Apr 02 08:41:31 GMT 2025 , Edited by admin on Wed Apr 02 08:41:31 GMT 2025
PRIMARY
ChEMBL
CHEMBL2103827
Created by admin on Wed Apr 02 08:41:31 GMT 2025 , Edited by admin on Wed Apr 02 08:41:31 GMT 2025
PRIMARY
PUBCHEM
92974
Created by admin on Wed Apr 02 08:41:31 GMT 2025 , Edited by admin on Wed Apr 02 08:41:31 GMT 2025
PRIMARY
DRUG BANK
DB06262
Created by admin on Wed Apr 02 08:41:31 GMT 2025 , Edited by admin on Wed Apr 02 08:41:31 GMT 2025
PRIMARY
EVMPD
SUB06420MIG
Created by admin on Wed Apr 02 08:41:31 GMT 2025 , Edited by admin on Wed Apr 02 08:41:31 GMT 2025
PRIMARY
MERCK INDEX
m4774
Created by admin on Wed Apr 02 08:41:31 GMT 2025 , Edited by admin on Wed Apr 02 08:41:31 GMT 2025
PRIMARY Merck Index
INN
6120
Created by admin on Wed Apr 02 08:41:31 GMT 2025 , Edited by admin on Wed Apr 02 08:41:31 GMT 2025
PRIMARY
CHEBI
31524
Created by admin on Wed Apr 02 08:41:31 GMT 2025 , Edited by admin on Wed Apr 02 08:41:31 GMT 2025
PRIMARY
Related Record Type Details
TARGET -> AGONIST
TARGET -> AGONIST
TARGET -> AGONIST
BINDER->LIGAND
BINDING
TARGET -> AGONIST
METABOLIC ENZYME -> SUBSTRATE
RACEMATE -> ENANTIOMER
METABOLIC ENZYME -> SUBSTRATE
TARGET -> INHIBITOR
TARGET -> INHIBITOR
TARGET -> AGONIST
TARGET -> AGONIST
TARGET -> AGONIST
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METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE INACTIVE -> PARENT
METABOLITE -> PARENT
MAJOR
METABOLITE -> PARENT
METABOLITE ACTIVE -> PRODRUG
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Tmax PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC