Page last updated: 2024-12-05

norfenefrine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Norfenefrine is a synthetic catecholamine with structural similarities to norepinephrine. It is a potent vasoconstrictor and has been investigated for its potential therapeutic applications in the treatment of various conditions, including nasal congestion and hypotension. The compound is typically synthesized through chemical modifications of existing catecholamines, involving reactions like alkylation and reduction. Studies have shown that norfenefrine can exert its effects by activating alpha-adrenergic receptors, leading to vasoconstriction and increased blood pressure. Its vasoconstrictive properties have made it a subject of research for potential use in nasal decongestants. However, its therapeutic potential remains under investigation due to its potential side effects and limited clinical data. The study of norfenefrine is driven by its unique pharmacological profile and its potential to offer alternative therapeutic options for conditions where vasoconstriction is desired.'

norfenefrine: RN given refers to cpd without isomeric designation; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID4538
CHEMBL ID358040
CHEBI ID134779
SCHEMBL ID153494
MeSH IDM0046779

Synonyms (78)

Synonym
norfenefrinum
unii-d2p3m6srn5
3-13-00-02235 (beilstein handbook reference)
norfenefrina
d2p3m6srn5 ,
norfenefrine
benzenemethanol, .alpha.-(aminomethyl)-3-hydroxy-
norfenefrine [inn]
norfenefrina [inn-spanish]
norfenefrinum [inn-latin]
alpha-(aminomethyl)-m-hydroxybenzyl alcohol
m-octopamine
norphenephrine
1-(3'-hydroxyphenyl)-2-aminoethanol
benzyl alcohol, alpha-(aminomethyl)-m-hydroxy-, (+-)-
1-(m-hydroxyphenyl)-2-aminoethanol
(+-)-norphenylephrine
norphenylephrine
benzyl alcohol, alpha-(aminomethyl)-m-hydroxy-
metacardiol
normetol
brn 1211018
normetasympathol
dl-m-octopamine
(+-)-alpha-(aminomethyl)-m-hydroxybenzyl alcohol
1-(3-hydroxyphenyl)-1-hydroxy-2-aminoethane
norenol
benzenemethanol, alpha-(aminomethyl)-3-hydroxy-, (+-)-
r,s-norphenylephrine
m-hydroxyphenylethanolamine
einecs 208-626-8
OPREA1_016194
wv 569 [as hydrochloride]
3-(2-amino-1-hydroxyethyl)phenol
STK503797
CHEBI:134779
CHEMBL358040
norfenefrine (inn)
536-21-0
D08286
2-amino-1-(3-hydroxyphenyl)ethan-1-ol
AKOS005171592
3-(2-amino-1-hydroxy-ethyl)-phenol
AM100918
wv569 free base
.alpha.-(aminomethyl)-3-hydroxybenzene methanol
norfenefrine [mi]
(1rs)-2-amino-1-(3-hydroxyphenyl)ethanol
.alpha.-(aminomethyl)-m-hydroxybenzyl alcohol.
.alpha.-(aminoethyl)-m-hydroxybenzyl alcohol
etilefrine hydrochloride impurity c [ep impurity]
wv-569 free base
norfenefrine [who-dd]
SCHEMBL153494
BBL028398
dl-[2-hydroxy-2-(3-hydroxyphenyl)ethyl]amine
dl-norphenylephrine
3-[(1rs)-2-amino-1-hydroxyethyl]phenol
DTXSID3048314
NCGC00167553-02
(.+/-.)-norfenefrine
zondel (salt/mix)
.alpha.-(aminomethyl)-m-hydroxybenzyl alcohol
benzyl alcohol, .alpha.-(aminomethyl)-m-hydroxy-
3-(2-amino-1-hydroxyethyl)phenol #
novadral (salt/mix)
sr-01000944512
SR-01000944512-1
norphenylephrine hydrochloride, pharmaceutical secondary standard; certified reference material
norfenefrin
DB13378
Q12746348
FS-4505
normezaton; norphenephrine
benzenemethanol, a-(aminomethyl)-3-hydroxy-, hydrochloride, (a+/-)-
CS-0013711
HY-B1711
EN300-96556

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" From the dose-response relationships after parenteral and oral administration a relative enteral efficacy of 50-80% was established, which corresponds well with bioavailability data."( Haemodynamic effects of amezinium in man.
Kessel, R; Lang, E; Neugebauer, G; Wilsmann, K, 1981
)
0.26

Dosage Studied

ExcerptRelevanceReference
" Treatment was administered during 3-24 weeks at a daily dosage of 90 mg."( Norfenefrine in the treatment of female urinary stress incontinence assessed by one-hour pad weighing test.
Alexander, N; Diernaes, E; Rix, P; Sørensen, T, 1989
)
1.72
" In a preceding dose finding study equipotent dosage of the substances used was confirmed."( [Hemodynamic effects following bolus administration of different vasopressive agents for blood pressure stabilization during peridural anesthesia].
Boldt, J; Börner, U; Brähler, A; Hempelmann, G; Müller, H; Stoyanov, M, 1985
)
0.27
" From the dose-response relationships after parenteral and oral administration a relative enteral efficacy of 50-80% was established, which corresponds well with bioavailability data."( Haemodynamic effects of amezinium in man.
Kessel, R; Lang, E; Neugebauer, G; Wilsmann, K, 1981
)
0.26
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
phenolsOrganic aromatic compounds having one or more hydroxy groups attached to a benzene or other arene ring.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (2)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
GLS proteinHomo sapiens (human)Potency25.11890.35487.935539.8107AID624170
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
POU domain, class 2, transcription factor 1Homo sapiens (human)Km994.10002.10005.39008.6000AID1769498
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (4)

Processvia Protein(s)Taxonomy
negative regulation of DNA-templated transcriptionPOU domain, class 2, transcription factor 1Homo sapiens (human)
negative regulation of DNA-templated transcriptionPOU domain, class 2, transcription factor 1Homo sapiens (human)
positive regulation of transcription by RNA polymerase IIPOU domain, class 2, transcription factor 1Homo sapiens (human)
positive regulation of miRNA transcriptionPOU domain, class 2, transcription factor 1Homo sapiens (human)
regulation of transcription by RNA polymerase IIPOU domain, class 2, transcription factor 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (7)

Processvia Protein(s)Taxonomy
RNA polymerase II cis-regulatory region sequence-specific DNA bindingPOU domain, class 2, transcription factor 1Homo sapiens (human)
RNA polymerase II core promoter sequence-specific DNA bindingPOU domain, class 2, transcription factor 1Homo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificPOU domain, class 2, transcription factor 1Homo sapiens (human)
DNA-binding transcription activator activity, RNA polymerase II-specificPOU domain, class 2, transcription factor 1Homo sapiens (human)
DNA bindingPOU domain, class 2, transcription factor 1Homo sapiens (human)
protein bindingPOU domain, class 2, transcription factor 1Homo sapiens (human)
sequence-specific DNA bindingPOU domain, class 2, transcription factor 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
nucleusPOU domain, class 2, transcription factor 1Homo sapiens (human)
nucleoplasmPOU domain, class 2, transcription factor 1Homo sapiens (human)
endoplasmic reticulumPOU domain, class 2, transcription factor 1Homo sapiens (human)
intracellular membrane-bounded organellePOU domain, class 2, transcription factor 1Homo sapiens (human)
chromatinPOU domain, class 2, transcription factor 1Homo sapiens (human)
RNA polymerase II transcription regulator complexPOU domain, class 2, transcription factor 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (8)

Assay IDTitleYearJournalArticle
AID504749qHTS profiling for inhibitors of Plasmodium falciparum proliferation2011Science (New York, N.Y.), Aug-05, Volume: 333, Issue:6043
Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets.
AID230399Ratio of maximum contraction of rat aorta elicited versus that elicited by noradrenaline (defined as intrinsic activity)1980Journal of medicinal chemistry, Jul, Volume: 23, Issue:7
Synthesis and structure-activity relationships among alpha-adrenergic receptor agonists of the phenylethanolamine type.
AID129460Bronchosecretory activity measured as tracheal secretion of phenol red in mouse after oral administration1987Journal of medicinal chemistry, Mar, Volume: 30, Issue:3
2-[(3-Pyridinylmethyl)thio]pyrimidine derivatives: new bronchosecretolytic agents.
AID33254Binding affinity to alpha adrenergic receptors in rat aorta1980Journal of medicinal chemistry, Jul, Volume: 23, Issue:7
Synthesis and structure-activity relationships among alpha-adrenergic receptor agonists of the phenylethanolamine type.
AID1769499Substrate activity at human OCT1 expressed in HEK293 cells assessed as increase in compound uptake by measuring Vmax incubated for 2 mins by LC-MS/MS analysis2021Journal of medicinal chemistry, 03-11, Volume: 64, Issue:5
Identification of Novel High-Affinity Substrates of OCT1 Using Machine Learning-Guided Virtual Screening and Experimental Validation.
AID1769501Ratio of drug uptake in human OCT1 expressing HEK293 cells at 2.5 uM to drug uptake in empty vector transfected human HEK293 cells at 2.5 uM2021Journal of medicinal chemistry, 03-11, Volume: 64, Issue:5
Identification of Novel High-Affinity Substrates of OCT1 Using Machine Learning-Guided Virtual Screening and Experimental Validation.
AID1769498Substrate activity at human OCT1 expressed in HEK293 cells assessed as increase in compound uptake by measuring Km incubated for 2 mins by LC-MS/MS analysis2021Journal of medicinal chemistry, 03-11, Volume: 64, Issue:5
Identification of Novel High-Affinity Substrates of OCT1 Using Machine Learning-Guided Virtual Screening and Experimental Validation.
AID1769500Substrate activity at human OCT1 expressed in HEK293 cells assessed as increase in compound uptake by measuring intrinsic clearance incubated for 2 mins by LC-MS/MS analysis2021Journal of medicinal chemistry, 03-11, Volume: 64, Issue:5
Identification of Novel High-Affinity Substrates of OCT1 Using Machine Learning-Guided Virtual Screening and Experimental Validation.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (86)

TimeframeStudies, This Drug (%)All Drugs %
pre-199063 (73.26)18.7374
1990's9 (10.47)18.2507
2000's9 (10.47)29.6817
2010's4 (4.65)24.3611
2020's1 (1.16)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 29.30

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index29.30 (24.57)
Research Supply Index4.62 (2.92)
Research Growth Index4.25 (4.65)
Search Engine Demand Index39.34 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (29.30)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials11 (12.22%)5.53%
Reviews2 (2.22%)6.00%
Case Studies3 (3.33%)4.05%
Observational0 (0.00%)0.25%
Other74 (82.22%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]