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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/007513Orig1s024lbl.pdfhttp://www.accessdata.fda.gov/drugsatfda_docs/label/2014/203202lbl.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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/007513Orig1s024lbl.pdfhttp://www.accessdata.fda.gov/drugsatfda_docs/label/2014/203202lbl.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
Droxidopa (Northera, Chelsea Therapeutics) is a synthetic catecholamino acid precursor of norepinephrine indicated for the treatment of orthostatic dizziness or lightheadedness in adult patients with symptomatic neurogenic orthostatic hypotension (NOH) caused by primary autonomic failure, dopamine beta-hydroxylase deficiency, and non-diabetic autonomic neuropathy. Droxidopa was approved as oral therapy in February 2014 under the FDA’s accelerated approval program. Droxidopa is directly metabolized to norepinephrine by dopadecarboxylase. The specific mechanism of action of the drug is not known completely, but it is supposed to exert the pharmacological effects through norepinephrine and not through the parent molecule or other metabolites. It increases blood flow to the brain by stimulating peripheral arterial and venous vasoconstriction.
CNS Activity
Sources: http://www.caam.rice.edu/~cox/wrap/norepinephrine.pdfhttp://www.fda.gov/downloads/AdvisoryCommittees/CommitteesMeetingMaterials/Drugs/CardiovascularandRenalDrugsAdvisoryCommittee/UCM292631.pdf
Curator's Comment: Droxidopa, a prodrug, is converted mostly peripherally, but also centrally (as it passes through the blood brain barrier) into norepinephrine (NE).
Originator
Sources: Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales (1932), 111, 884-6.http://www.businesswire.com/news/home/20140218006891/en/Chelsea-Therapeutics-Announces-FDA-Accelerated-Approval-NORTHERA%E2%84%A2
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 |
---|---|---|
Diuresis and improved renal hemodynamics produced by prostaglandin E1 in the dog with norepinephrine-induced acute renal failure. | 1975 Jul-Aug |
|
Selective activation of beta3-adrenoceptors by octopamine: comparative studies in mammalian fat cells. | 1999 Apr |
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Modulation of extracellular superoxide dismutase expression by angiotensin II and hypertension. | 1999 Jul 9 |
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alpha2C adrenoceptors inhibit adenylyl cyclase in mouse striatum: potential activation by dopamine. | 1999 Jun |
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Nitroprusside inhibits thermal hyperalgesia induced by noradrenaline in capsaicin-treated skin. | 1999 Mar |
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Does acute volume overloading in the setting of left ventricular dysfunction and pulmonary hypertension affect the defibrillation threshold? | 1999 May |
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Hemodynamic effects of milrinone during weaning from cardiopulmonary bypass: comparison of patients with a low and high prebypass cardiac index. | 2000 Aug |
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Regulation of the human norepinephrine transporter by cocaine and amphetamine. | 2000 Dec |
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Comitogenic effect of catecholamines on rat cardiac fibroblasts in culture. | 2000 Nov |
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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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Effects of brucine, a plant alkaloid, on M(1) muscarinic receptors and alpha(1)-adrenoceptors in the rabbit vas deferens preparation. | 2001 Apr |
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Plasma catecholamine and cardiovascular responses to physostigmine in Alzheimer's disease and aging. | 2001 Feb |
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alpha(1B) adrenergic receptors in gonadotrophin-releasing hormone neurones: relation to Transport-P. | 2001 Jan |
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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 |
|
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 |
|
Dorsomedial medulla is more susceptible than rostral ventrolateral medulla to hypoxic insult in cats. | 2001 Jan |
|
In vitro reconstitution of fish melanophore pigment aggregation. | 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 |
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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 |
|
Reference intervals for glucose, beta-cell polypeptides, and counterregulatory factors during prolonged fasting. | 2001 Jan |
|
Vatanidipine hydrochloride: a new long-lasting antihypertensive agent. | 2001 Jan |
|
Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin. | 2001 Jan |
|
Neuroendocrine responses to experimentally-induced psychological stress in healthy humans. | 2001 Jan |
|
Effects of chronic antidepressant treatments on 5-HT and NA transporters in rat brain: an autoradiographic study. | 2001 Jan |
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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 |
|
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 |
|
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
Acute Hypotension. Initial: 8-12 mcg/min IV infusion; titrate to effect; Maintenance: 2-4 mcg/min IV infusion
Cardiac Arrest. Initial: 8-12 mcg/min IV infusion; titrate to effect; Maintenance: 2-4 mcg/min IV infusion
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27650061
Human umbilical vein endothelial cell line (ECV-304, Shanghai Institute of Cell Biology, Chinese Academy of Science) were used for activity evaluation. Cells were conventionally cultured with modified alpha-MEM containing 10% fetal bovine serum Before all the manipulation experiments, the ECV-304 (VECs) were shifted to serum-free medium (normal medium) and then divided into three groups as follows. Control group was cultured in normal medium in which 0 mol/L NE (Norepinephrine) was detecteded using the NE ELISA kit. NE+Inhibitor group was cultured in normal medium added with 10^-7 mol/L NE (Harcest Pharmaceutical CO,. Shanghai, China) and NE blocker Amitriptyline hydrochloride (10-6 mol/L). NE+Isotype group was cultured in normal medium added with 10^-7 mol/L NE (Norepinephrine) and a negative isotype of NE blocker Amitriptyline hydrochloride. The dose of NE utilized in the experiments was determined in advance through titration. It was selected to approximate the normal concentration in vivo. After 24 h of culture, the supernatant from each group was collected to measure SDF-1 using an ELISA kit (Human CXCL12/SDF-1 alpha Quantikine ELISA Kit; R&D Systems, USA) according to the manufacturer’s protocol. Similarly, the cells from the cell culture were collected for Western blotting analysis. First, proteins were extracted from the cells using the M-PER mammalian protein extraction reagent (Thermo Fisher Scientific, Hudson, USA). Then, the proteins were resolved on a NuPAGE gel and transferred to nylon membranes. After blocking with 7% fat-free dry milk for 2 h, the membranes were incubated with polyclonal rabbit anti-human SDF-1, JNK or p-JNK antibodies (1:200; Santa Cruz) at 4C overnight. After incubation with horseradish peroxidase-conjugated IgG (Santa Cruz) for 1 h, the membranes were treated with chemiluminescent substrate (Thermo) to visualize the protein bands.
Substance Class |
Chemical
Created
by
admin
on
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Wed Jul 05 22:42:30 UTC 2023
by
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on
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Record UNII |
X4W3ENH1CV
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Record Status |
Validated (UNII)
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Record Version |
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CHEMBL1437
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Norepinephrine (medication)
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TARGET -> AGONIST |
SHORT-ACTING
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SHORT-ACTING
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SHORT-ACTING
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METABOLITE -> PARENT | |||
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CHROMATOGRAPHIC PURITY (TLC)
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CHROMATOGRAPHIC PURITY (HPLC/UV)
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CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY |