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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 ]<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 ] 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 ].


Oxolamine also has ] activity, which causes a reduction in irritation of the nerve receptors of the ].<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-] systems all rely on ] for providing a preformed N-O linkage. The preparation of the respiratory anti-inflammatory and antitussive agent oxolamine starts by ] of the ] 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 ] leads
to cyclization via imine formation to afford the 1,2,4-oxadiazole. Displacement of the terminal ] with ] gives the corresponding amine oxolamine.


It is mainly used for the treatment of ], ], ], bronchiectasis and ].<ref name=":0" />
]


Oxolamine is not approved in the USA, it may be marketed elsewhere internationally as a cough suppressant. It is listed as a ] in New Zealand legislation. Oxolamine is also approved in Taiwan for the treatment of ].<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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] ]
] ]
] ]


{{respiratory-system-drug-stub}}

Latest revision as of 10:59, 28 December 2023

Cough suppressant Pharmaceutical compound
Oxolamine
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
IUPAC name
  • N,N-diethyl-2-(3-phenyl-1,2,4-oxadiazol-5-yl)ethanamine
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.012.267 Edit this at Wikidata
Chemical and physical data
FormulaC14H19N3O
Molar mass245.326 g·mol
3D model (JSmol)
SMILES
  • n1c(onc1c2ccccc2)CCN(CC)CC
InChI
  • InChI=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
  • Key:IDCHQQSVJAAUQQ-UHFFFAOYSA-N
  (what is this?)  (verify)

Oxolamine is a cough suppressant that is available as a generic drug in many jurisdictions.

Oxolamine also has anti-inflammatory activity, which causes a reduction in irritation of the nerve receptors of the respiratory tract.

It is mainly used for the treatment of pharyngitis, tracheitis, bronchitis, bronchiectasis and pertussis.

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 inflammation.

References

  1. de Groot AC (2022). "3.357 Oxolamine". Systemic Drugs. Monographs in Contact Allergy. Vol. 4 (First ed.). CRC Press. p. 712. ISBN 978-1-00-054991-1.
  2. "Oxolamine". drugs.com. 19 April 2015. Archived from the original on 20 September 2018. Retrieved 23 January 2018.
  3. ^ "NCATS Inxight Drugs — OXOLAMINE CITRATE". drugs.ncats.io. Archived from the original on 2022-09-26. Retrieved 2022-09-26.
  4. "Oxolamine". go.drugbank.com. Archived from the original on 2022-09-26. Retrieved 2022-09-26.
Cough and cold preparations (R05)
Expectorants
Mucolytics
Cough suppressants
Opium alkaloids,
opioids,
and derivatives
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