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

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(O)=C(O)C=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

-6.1447681E11
Primary
LEVOPHED

Approved Use

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

Launch Date

-6.1447681E11
Primary
LEVOPHED

Approved Use

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

Launch Date

-6.1447681E11
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

1.39268155E12
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
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...
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
n = 85
Health Status: unhealthy
Condition: cardiogenic shock
Age Group: mean 65.5 years
Sex: M+F
Population Size: 85
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
Effect of dexmedetomidine on the release of [3H]-noradrenaline from rat kidney cortex slices: characterization of alpha2-adrenoceptor.
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
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
Levels of circulating CD8(+) T lymphocytes, natural killer cells, and eosinophils increase upon acute psychosocial stress in patients with atopic dermatitis.
2001 Jan
Acute gastrointestinal manifestations associated with use of crack.
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
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
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
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
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sun Dec 18 19:36:58 UTC 2022
Edited
by admin
on Sun Dec 18 19:36:58 UTC 2022
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
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
NORTHERA
Brand 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 Sun Dec 18 19:37:02 UTC 2022 , Edited by admin on Sun Dec 18 19:37:02 UTC 2022
EU-Orphan Drug EU/3/07/465
Created by admin on Sun Dec 18 19:37:02 UTC 2022 , Edited by admin on Sun Dec 18 19:37:02 UTC 2022
WHO-ATC C01CA27
Created by admin on Sun Dec 18 19:37:02 UTC 2022 , Edited by admin on Sun Dec 18 19:37:02 UTC 2022
EU-Orphan Drug EU/3/07/466
Created by admin on Sun Dec 18 19:37:02 UTC 2022 , Edited by admin on Sun Dec 18 19:37:02 UTC 2022
NCI_THESAURUS C38149
Created by admin on Sun Dec 18 19:37:02 UTC 2022 , Edited by admin on Sun Dec 18 19:37:02 UTC 2022
Code System Code Type Description
USAN
UU-114
Created by admin on Sun Dec 18 19:37:02 UTC 2022 , Edited by admin on Sun Dec 18 19:37:02 UTC 2022
PRIMARY
DRUG CENTRAL
971
Created by admin on Sun Dec 18 19:37:02 UTC 2022 , Edited by admin on Sun Dec 18 19:37:02 UTC 2022
PRIMARY
DAILYMED
J7A92W69L7
Created by admin on Sun Dec 18 19:37:02 UTC 2022 , Edited by admin on Sun Dec 18 19:37:02 UTC 2022
PRIMARY
WIKIPEDIA
L-DOPS
Created by admin on Sun Dec 18 19:37:02 UTC 2022 , Edited by admin on Sun Dec 18 19:37:02 UTC 2022
PRIMARY
MESH
D015103
Created by admin on Sun Dec 18 19:37:02 UTC 2022 , Edited by admin on Sun Dec 18 19:37:02 UTC 2022
PRIMARY
CHEBI
60568
Created by admin on Sun Dec 18 19:37:02 UTC 2022 , Edited by admin on Sun Dec 18 19:37:02 UTC 2022
PRIMARY
NCI_THESAURUS
C73266
Created by admin on Sun Dec 18 19:37:02 UTC 2022 , Edited by admin on Sun Dec 18 19:37:02 UTC 2022
PRIMARY
RXCUI
1489913
Created by admin on Sun Dec 18 19:37:02 UTC 2022 , Edited by admin on Sun Dec 18 19:37:02 UTC 2022
PRIMARY RxNorm
EPA CompTox
DTXSID6046422
Created by admin on Sun Dec 18 19:37:02 UTC 2022 , Edited by admin on Sun Dec 18 19:37:02 UTC 2022
PRIMARY
NDF-RT
N0000178478
Created by admin on Sun Dec 18 19:37:02 UTC 2022 , Edited by admin on Sun Dec 18 19:37:02 UTC 2022
PRIMARY Increased Blood Pressure [PE]
CAS
23651-95-8
Created by admin on Sun Dec 18 19:37:02 UTC 2022 , Edited by admin on Sun Dec 18 19:37:02 UTC 2022
PRIMARY
IUPHAR
7391
Created by admin on Sun Dec 18 19:37:02 UTC 2022 , Edited by admin on Sun Dec 18 19:37:02 UTC 2022
PRIMARY
FDA UNII
J7A92W69L7
Created by admin on Sun Dec 18 19:37:02 UTC 2022 , Edited by admin on Sun Dec 18 19:37:02 UTC 2022
PRIMARY
ChEMBL
CHEMBL2103827
Created by admin on Sun Dec 18 19:37:02 UTC 2022 , Edited by admin on Sun Dec 18 19:37:02 UTC 2022
PRIMARY
PUBCHEM
92974
Created by admin on Sun Dec 18 19:37:02 UTC 2022 , Edited by admin on Sun Dec 18 19:37:02 UTC 2022
PRIMARY
DRUG BANK
DB06262
Created by admin on Sun Dec 18 19:37:02 UTC 2022 , Edited by admin on Sun Dec 18 19:37:02 UTC 2022
PRIMARY
EVMPD
SUB06420MIG
Created by admin on Sun Dec 18 19:37:02 UTC 2022 , Edited by admin on Sun Dec 18 19:37:02 UTC 2022
PRIMARY
MERCK INDEX
M4774
Created by admin on Sun Dec 18 19:37:02 UTC 2022 , Edited by admin on Sun Dec 18 19:37:02 UTC 2022
PRIMARY Merck Index
INN
6120
Created by admin on Sun Dec 18 19:37:02 UTC 2022 , Edited by admin on Sun Dec 18 19:37:02 UTC 2022
PRIMARY
CHEBI
31524
Created by admin on Sun Dec 18 19:37:02 UTC 2022 , Edited by admin on Sun Dec 18 19:37:02 UTC 2022
PRIMARY
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Tmax PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC