Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Norfenefrine: Difference between pages

{{Short description|Sympathomimetic drug}}

{{Infobox drug

| verifiedrevid = 462263073

| width =

| image2 = (R)-Norfenefrine molecule ball.png

| width2 =

| alt2 = Ball-and-stick model of (R)-Norfenefrine

<!-- Clinical data -->

| tradename =

| pregnancy_category =

| legal_status = Rx-only

| routes_of_administration =

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| bioavailability =

| protein_bound =

| metabolism = ''m''-Hydroxymandelic acid<ref name="HengstmannKonenKonen1974">{{cite journal | vauthors = Hengstmann JH, Konen W, Konen C, Eichelbaum M, Dengler HJ | title = The physiological disposition of p-octopamine in man | journal = Naunyn-Schmiedeberg's Archives of Pharmacology | volume = 283 | issue = 1 | pages = 93–106 | year = 1974 | pmid = 4277715 | doi = 10.1007/bf00500148 | s2cid = 35523412 }}</ref><ref name="D'AndreaNorderaPizzolato2010">{{cite journal | vauthors = D'Andrea G, Nordera G, Pizzolato G, Bolner A, Colavito D, Flaibani R, Leon A | title = Trace amine metabolism in Parkinson's disease: low circulating levels of octopamine in early disease stages | journal = Neuroscience Letters | volume = 469 | issue = 3 | pages = 348–351 | date = January 2010 | pmid = 20026245 | doi = 10.1016/j.neulet.2009.12.025 | s2cid = 12797090 }}</ref>

| elimination_half-life =

| excretion =

<!-- Identifiers -->

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 536-21-0

| CAS_supplemental = <br />15308-34-6 ([[hydrochloride]])

| UNII_Ref = {{fdacite|correct|FDA}}

| synonyms = Norfenephrine; Norphenephrine; Norphenylephrine; ''meta''-Norsynephrine; ''meta''-Octopamine; 3-Octopamine; Adrianol; 3,β-Dihydroxyphenethylamine; 3,β-Dihydroxy-β-phenylethylamine

<!-- Chemical data -->

| IUPAC_name = 3-(2-Amino-1-hydroxyethyl)phenol

| SMILES = OC(c1cc(O)ccc1)CN

<!-- Definition and medical uses -->

'''Norfenefrine''', also known as '''''meta''-octopamine''' or '''norphenylephrine''' and sold under the brand name '''Novadral''' among others, is a [[sympathomimetic]] [[medication]] which is used in the treatment of [[hypotension]] (low blood pressure).<ref name="Docherty2008" /><ref name="Elks2014">{{cite book | last=Elks | first=J. | title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies | publisher=Springer US | year=2014 | isbn=978-1-4757-2085-3 | url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA61 | access-date=22 July 2024 | page=61}}</ref><ref name="Macdonald1997">{{cite book | author = Macdonald F | title = Dictionary of Pharmacological Agents | url = https://books.google.com/books?id=DeX7jgInYFMC&pg=PA104 | access-date = 24 April 2012 | year = 1997 | publisher = CRC Press | isbn = 978-0-412-46630-4 | page = 104 }}</ref><ref name="IndexNominum2000">{{cite book | title = Index Nominum 2000: International Drug Directory | url = https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA750 | access-date = 24 April 2012 | year = 2000 | publisher = Taylor & Francis | isbn = 978-3-88763-075-1 | page = 750 }}</ref> Along with its [[structural isomer]] [[octopamine|''p''-octopamine]] and the [[tyramine]]s, norfenefrine is a [[natural product|naturally occurring]] [[endogenous]] [[trace amine]] and plays a role as a minor [[neurotransmitter]] in the [[brain]].<ref name="pmid340613">{{cite journal | vauthors = Danielson TJ, Boulton AA, Robertson HA | title = m-Octopamine, p-octopamine and phenylethanolamine in rat brain: a sensitive, specific assay and the effects of some drugs | journal = Journal of Neurochemistry | volume = 29 | issue = 6 | pages = 1131–1135 | date = December 1977 | pmid = 340613 | doi = 10.1111/j.1471-4159.1977.tb06519.x | s2cid = 26137006 }}</ref>

==Medical uses==

Norfenefrine is used in the treatment of [[hypotension]] (low blood pressure).<ref name="Docherty2008" /> It is said to be similarly effective or less effective than [[midodrine]].<ref name="McTavishGoa1989">{{cite journal | vauthors = McTavish D, Goa KL | title = Midodrine. A review of its pharmacological properties and therapeutic use in orthostatic hypotension and secondary hypotensive disorders | journal = Drugs | volume = 38 | issue = 5 | pages = 757–777 | date = November 1989 | pmid = 2480881 | doi = 10.2165/00003495-198938050-00004 | url = }}</ref><ref name="McClellanWisemanWilde1998">{{cite journal | vauthors = McClellan KJ, Wiseman LR, Wilde MI | title = Midodrine. A review of its therapeutic use in the management of orthostatic hypotension | journal = Drugs Aging | volume = 12 | issue = 1 | pages = 76–86 | date = January 1998 | pmid = 9467688 | doi = 10.2165/00002512-199812010-00007 | url = }}</ref><ref name="MaulePapottiNaso2007">{{cite journal | vauthors = Maule S, Papotti G, Naso D, Magnino C, Testa E, Veglio F | title = Orthostatic hypotension: evaluation and treatment | journal = Cardiovasc Hematol Disord Drug Targets | volume = 7 | issue = 1 | pages = 63–70 | date = March 2007 | pmid = 17346129 | doi = 10.2174/187152907780059029 | url = }}</ref>

==Pharmacology==

===Pharmacodynamics===

Norfenefrine is described as an [[α-adrenergic receptor]] [[agonist]] and [[sympathomimetic agent]].<ref name="Elks2014" /><ref name="IndexNominum2000" /> It is said to act predominantly as an [[alpha-1 adrenergic receptor|α₁-adrenergic receptor]] agonist.<ref name="Docherty2008">{{cite journal | vauthors = Docherty JR | title = Pharmacology of stimulants prohibited by the World Anti-Doping Agency (WADA) | journal = Br J Pharmacol | volume = 154 | issue = 3 | pages = 606–622 | date = June 2008 | pmid = 18500382 | pmc = 2439527 | doi = 10.1038/bjp.2008.124 | url = }}</ref>

==Chemistry==

Norfenefrine, also known as 3,β-dihydroxyphenethylamine, is a [[substituted phenethylamine]] [[chemical derivative|derivative]].<ref name="Elks2014" /><ref name="IndexNominum2000" /> It is an [[structural analog|analogue]] of [[norepinephrine (medication)|norepinephrine]] (3,4,β-trihydroxyphenethylamine), of [[meta-Tyramine|''meta''-tyramine]] (3-hydroxyphenethylamine), of [[phenylephrine]] ((''R'')-β,3-dihydroxy-''N''-methylphenethylamine), of [[etilefrine]] (3,β-dihydroxy-''N''-ethylphenethylamine), and of [[metaterol]] (3,β-dihydroxy-N-isopropylphenethylamine), as well as of [[metaraminol]] ((1''R'',2''S'')-3,β-dihydroxy-α-methylphenethylamine).<ref name="Elks2014" />

Norfenefrine is used medically as the [[hydrochloride]] [[salt (chemistry)|salt]].<ref name="Elks2014" /><ref name="IndexNominum2000" />

The predicted [[partition coefficient|log P]] of norfenefrine is -0.28 to -0.95.<ref name="PubChem">{{cite web | title=Norfenefrine | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/4538 | access-date=31 August 2024}}</ref><ref name="DrugBank">{{cite web | title=Norfenefrine: Uses, Interactions, Mechanism of Action | website=DrugBank Online | date=23 June 2017 | url=https://go.drugbank.com/drugs/DB13378 | access-date=31 August 2024}}</ref><ref name="ChemSpider">{{cite web | title=norfenefrine | website=ChemSpider | date=31 August 2024 | url=https://www.chemspider.com/Chemical-Structure.4379.html | access-date=31 August 2024}}</ref>

==Society and culture==

===Names===

''Norfenefrine'' is the [[generic term|generic name]] of the drug and its {{Abbrlink|INN|International Nonproprietary Name}}.<ref name="Elks2014" /><ref name="IndexNominum2000" /> Synonyms of norfenefrine include ''hydroxyphenylethanolamine'', ''nor-phenylephrine'', and ''m-norsynephrine'', among others.<ref name="Elks2014" /><ref name="IndexNominum2000" /> Brand names of norfenefrine include ''Novadral'', ''A.S. COR'', ''Coritat'', ''Energona'', ''Hypolind'', ''Norfenefrin Ziethen'', and ''Norfenefrin-Ratiopharm'', among others.<ref name="IndexNominum2000" />

===Availability===

Norfenefrine is marketed in [[Europe]], [[Japan]], and [[Mexico]].<ref name="IndexNominum2000" />

==References==

{{Reflist}}

{{Cardiac stimulants excluding cardiac glycosides}}

{{Neurotransmitters}}

{{Adrenergic receptor modulators}}

{{TAAR ligands}}

{{Phenethylamines}}

[[Category:Alpha-adrenergic agonists]]

[[Category:Antihypotensive agents]]

[[Category:Cardiac stimulants]]

[[Category:Norepinephrine-dopamine releasing agents]]

[[Category:Neurotransmitters]]

[[Category:Peripherally selective drugs]]

[[Category:3-Hydroxyphenyl compounds]]

[[Category:Phenylethanolamines]]

[[Category:Sympathomimetics]]

[[Category:TAAR1 agonists]]

[[Category:Trace amines]]