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Revision as of 14:18, 24 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 456636462 of page Norfenefrine for the Chem/Drugbox validation project (updated: 'CAS_number').  Latest revision as of 21:31, 10 December 2024 edit Graeme Bartlett (talk | contribs)Administrators249,716 edits more ids 
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{{Short description|Sympathomimetic drug}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Infobox drug
{{Drugbox
| Verifiedfields = changed | Verifiedfields = changed
⚫ | verifiedrevid = 462263073
| Watchedfields = changed
⚫ | verifiedrevid = 408778577
⚫ | IUPAC_name = 3-(2-amino-1-hydroxyethyl)phenol
| image = Norfenefrine.png | image = Norfenefrine.png
| width =
| image2 = (R)-Norfenefrine molecule ball.png
| width2 =
| alt2 = Ball-and-stick model of (R)-Norfenefrine


<!--Clinical data--> <!-- Clinical data -->
| tradename = | tradename =
| Drugs.com = {{drugs.com|international|norfenefrine}} | Drugs.com = {{drugs.com|international|norfenefrine}}
⚫ | pregnancy_category =
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫ | legal_status = Rx-only
| pregnancy_US = <!-- A / B / C / D / X -->
⚫ | routes_of_administration =
⚫ | pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
⚫ | legal_status =
⚫ | routes_of_administration =


<!--Pharmacokinetic data--> <!-- Pharmacokinetic data -->
| bioavailability = | bioavailability =
| protein_bound = | 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>
| metabolism =
| elimination_half-life = | elimination_half-life =
| excretion = | excretion =


<!--Identifiers--> <!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = <!-- blanked - oldvalue: 536-21-0 --> | CAS_number = 536-21-0
| CAS_supplemental = <br />15308-34-6 (])
| ATC_prefix = C01 | ATC_prefix = C01
| ATC_suffix = CA05 | ATC_suffix = CA05
| PubChem = 4538 | PubChem = 4538
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
⚫ | DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4379 | ChemSpiderID = 4379
| UNII_Ref = {{fdacite|changed|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = D2P3M6SRN5 | UNII = D2P3M6SRN5
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D08286 | KEGG = D08286
| ChEBI = 134779
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 358040 | ChEMBL = 358040
⚫ | DrugBank = DB13378
| synonyms = Norfenephrine; Norphenephrine; Norphenylephrine; ''meta''-Norsynephrine; ''meta''-Octopamine; 3-Octopamine; Adrianol; 3,β-Dihydroxyphenethylamine; 3,β-Dihydroxy-β-phenylethylamine


<!--Chemical data--> <!-- Chemical data -->
⚫ | IUPAC_name = 3-(2-Amino-1-hydroxyethyl)phenol
| C=8 | H=11 | N=1 | O=2 | C=8 | H=11 | N=1 | O=2
⚫ | SMILES = OC(c1cc(O)ccc1)CN
| molecular_weight = 153.178 g/mol
⚫ | smiles = OC(c1cc(O)ccc1)CN
| InChI = 1/C8H11NO2/c9-5-8(11)6-2-1-3-7(10)4-6/h1-4,8,10-11H,5,9H2
| InChIKey = LRCXRAABFLIVAI-UHFFFAOYAV
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C8H11NO2/c9-5-8(11)6-2-1-3-7(10)4-6/h1-4,8,10-11H,5,9H2 | StdInChI = 1S/C8H11NO2/c9-5-8(11)6-2-1-3-7(10)4-6/h1-4,8,10-11H,5,9H2
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| StdInChIKey = LRCXRAABFLIVAI-UHFFFAOYSA-N | StdInChIKey = LRCXRAABFLIVAI-UHFFFAOYSA-N
}} }}
<!-- Definition and medical uses -->
'''Norfenefrine''', also known as '''''meta''-octopamine''' or '''norphenylephrine''' and sold under the brand name '''Novadral''' among others, is a ] ] which is used in the treatment of ] (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 ] ] and the ]s, norfenefrine is a ] ] ] and plays a role as a minor ] in the ].<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 ] (low blood pressure).<ref name="Docherty2008" /> It is said to be similarly effective or less effective than ].<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 ] ] and ].<ref name="Elks2014" /><ref name="IndexNominum2000" /> It is said to act predominantly as an ] 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 ] ].<ref name="Elks2014" /><ref name="IndexNominum2000" /> It is an ] of ] (3,4,β-trihydroxyphenethylamine), of ] (3-hydroxyphenethylamine), of ] ((''R'')-β,3-dihydroxy-''N''-methylphenethylamine), of ] (3,β-dihydroxy-''N''-ethylphenethylamine), and of ] (3,β-dihydroxy-N-isopropylphenethylamine), as well as of ] ((1''R'',2''S'')-3,β-dihydroxy-α-methylphenethylamine).<ref name="Elks2014" />

Norfenefrine is used medically as the ] ].<ref name="Elks2014" /><ref name="IndexNominum2000" />

The predicted ] 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 ] 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 ], ], and ].<ref name="IndexNominum2000" />

==References==
{{Reflist}}

{{Cardiac stimulants excluding cardiac glycosides}}
{{Neurotransmitters}}
{{Adrenergic receptor modulators}}
{{TAAR ligands}}
{{Phenethylamines}}

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