Oxolamine: Difference between revisions

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{{Short description|Cough suppressant}}
{{Drugbox
{{Drugbox
| Watchedfields = changed
| Verifiedfields = changed
| verifiedrevid = 443480666
| verifiedrevid = 447812881
| IUPAC_name = N,N-diethyl-2-(3-phenyl-1,2,4-oxadiazol-5-yl)ethanamine
| IUPAC_name = N,N-diethyl-2-(3-phenyl-1,2,4-oxadiazol-5-yl)ethanamine
| image = Oxolamine.png
| image = Oxolamine.png


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


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


<!--Identifiers-->
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 959-14-8
| CAS_number = 959-14-8
| ATC_prefix = R05
| ATC_prefix = R05
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| PubChem = 13738
| PubChem = 13738
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| DrugBank = DB13216
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 13143
| ChemSpiderID = 13143
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| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07387
| KEGG = D07387
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1620875


<!--Chemical data-->
<!--Chemical data-->
| C=14 | H=19 | N=3 | O=1
| C=14 | H=19 | N=3 | O=1
| molecular_weight = 245.32 g/mol
| smiles = n1c(onc1c2ccccc2)CCN(CC)CC
| smiles = n1c(onc1c2ccccc2)CCN(CC)CC
| InChI = 1/C14H19N3O/c1-3-17(4-2)11-10-13-15-14(16-18-13)12-8-6-5-7-9-12/h5-9H,3-4,10-11H2,1-2H3
| InChIKey = IDCHQQSVJAAUQQ-UHFFFAOYAF
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C14H19N3O/c1-3-17(4-2)11-10-13-15-14(16-18-13)12-8-6-5-7-9-12/h5-9H,3-4,10-11H2,1-2H3
| StdInChI = 1S/C14H19N3O/c1-3-17(4-2)11-10-13-15-14(16-18-13)12-8-6-5-7-9-12/h5-9H,3-4,10-11H2,1-2H3
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}}
}}


'''Oxolamine''' is a [[cough suppressant]]<ref>{{cite book | vauthors = de Groot AC | chapter = 3.357 Oxolamine |title=Systemic Drugs | series = Monographs in Contact Allergy | volume = 4 |date=2022 |publisher=CRC Press |isbn=978-1-00-054991-1 |page=712 |edition=First}}</ref> that is available as a [[generic drug]] in many jurisdictions.<ref>{{cite web | work = drugs.com | url = https://www.drugs.com/international/oxolamine.html | title = Oxolamine | date = 19 April 2015 | access-date = 23 January 2018 | archive-date = 20 September 2018 | archive-url = https://web.archive.org/web/20180920145016/https://www.drugs.com/international/oxolamine.html | url-status = live }}</ref>
'''Oxolamine''' is a [[cough suppressant]].


Oxolamine also has [[anti-inflammatory]] activity, which causes a reduction in irritation of the nerve receptors of the [[respiratory tract]].<ref name=":0">{{Cite web |title=NCATS Inxight Drugs — OXOLAMINE CITRATE |url=https://drugs.ncats.io/drug/K5X4XBR694 |access-date=2022-09-26 |website=drugs.ncats.io |language=en |archive-date=2022-09-26 |archive-url=https://web.archive.org/web/20220926180401/https://drugs.ncats.io/drug/K5X4XBR694 |url-status=live }}</ref>
==Synthesis==
The syntheses of 1,2,4-[[oxadiazole]] systems all rely on [[hydroxylamine]] for providing a preformed N-O linkage. The preparation of the respiratory anti-inflammatory and antitussive agent oxolamine starts by [[acylation]] of the [[alkoxide]] from the N-hydroxyamidine with 3-chloropropionyl chloride; the presence of the negative charge on oxygen results in the formation of the O-acylated product. Treatment of that intermediate with [[triethylamine]] leads
to cyclization via imine formation to afford the 1,2,4-oxadiazole. Displacement of the terminal [[chlorine]] with [[diethylamine]] gives the corresponding amine oxolamine.


It is mainly used for the treatment of [[pharyngitis]], [[tracheitis]], [[bronchitis]], bronchiectasis and [[pertussis]].<ref name=":0" />
[[File:Oxolamine rxn scheme.png|400px]]


Oxolamine is not approved in the USA, it may be marketed elsewhere internationally as a cough suppressant. It is listed as a [[prescription drug]] in New Zealand legislation. Oxolamine is also approved in Taiwan for the treatment of [[Respiratory tract infection|respiratory tract inflammation]].<ref>{{Cite web |title=Oxolamine |url=https://go.drugbank.com/drugs/DB13216 |access-date=2022-09-26 |website=go.drugbank.com |archive-date=2022-09-26 |archive-url=https://web.archive.org/web/20220926180403/https://go.drugbank.com/drugs/DB13216 |url-status=live }}</ref>
{{Cite patent|DE|1097998}}

==References==
{{reflist}}


{{Cough and cold preparations}}
{{Cough and cold preparations}}
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[[Category:Antitussives]]
[[Category:Antitussives]]
[[Category:Oxadiazoles]]
[[Category:Oxadiazoles]]
[[Category:Amines]]
[[Category:Diethylamino compounds]]


{{respiratory-system-drug-stub}}
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