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{{Short description|Chemical compound}} |
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{{drugbox |
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{{cs1 config|name-list-style=vanc}}{{Drugbox |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| verifiedrevid = 443984387 |
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| UNII = 1E3KG5FWDB |
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| IUPAC_name = 2-(2-dimethylaminoethoxy)ethyl phenothiazine-10-carboxylate |
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| verifiedrevid = 443321035 |
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| image = dimethoxanate.png |
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| IUPAC_name = 2-(2-dimethylaminoethoxy)ethyl phenothiazine-10-carboxylate |
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| image = dimethoxanate.png |
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| width = 150 |
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| width = 150 |
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<!--Clinical data--> |
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| tradename = Atuss, Cothera, Cotrane, Perlatos, Pulmoll, Tussizid |
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| Drugs.com = {{drugs.com|international|dimethoxanate}} |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category = |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = |
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| routes_of_administration = |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| protein_bound = |
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| metabolism = |
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| elimination_half-life = |
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| excretion = |
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<!--Identifiers--> |
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| CAS_number = 477-93-0 |
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| ATC_prefix = R05 |
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| ATC_suffix = DB28 |
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| PubChem = 10610 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 10165 |
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| ChemSpiderID = 10165 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| InChI = 1/C19H22N2O3S/c1-20(2)11-12-23-13-14-24-19(22)21-15-7-3-5-9-17(15)25-18-10-6-4-8-16(18)21/h3-10H,11-14H2,1-2H3 |
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| UNII = 1E3KG5FWDB |
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| InChIKey = OOVJCSPCMCAXEX-UHFFFAOYAU |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D07397 |
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<!--Chemical data--> |
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| C=19 | H=22 | N=2 | O=3 | S=1 |
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| smiles = O=C(OCCOCCN(C)C)N1c3c(Sc2c1cccc2)cccc3 |
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| smiles = O=C(OCCOCCN(C)C)N1c3c(Sc2c1cccc2)cccc3 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = OOVJCSPCMCAXEX-UHFFFAOYSA-N |
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| StdInChIKey = OOVJCSPCMCAXEX-UHFFFAOYSA-N |
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| CAS_number = 477-93-0 |
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| ATC_prefix = R05 |
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| ATC_suffix = DB28 |
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| PubChem = 10610 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D07397 |
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| C=19 | H=22 | N=2 | O=3 | S=1 |
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| molecular_weight = 358.456 g/mol |
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| bioavailability = |
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| metabolism = |
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| elimination_half-life = |
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| excretion = |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category= |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = |
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| routes_of_administration = |
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}} |
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}} |
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'''Dimethoxanate''' (trade names '''Cothera''', '''Cotrane''', '''Atuss''', '''Perlatoss''', '''Tossizid''')<ref>{{cite book |author = William Andrew Publishing |title=Pharmaceutical Manufacturing Encyclopedia |url= https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA1103 |date=22 October 2013 |publisher=Elsevier |isbn=978-0-8155-1856-3 |pages=1332–3 }}</ref> is a ] of the ] class.<ref>{{cite journal | vauthors = Parish FA | title = Clinical evaluation of the antitussive, dimethoxanate | journal = Medical Times | volume = 87 | pages = 1488–90 | date = November 1959 | pmid = 14430450 }}</ref> |
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'''Dimethoxanate''' is a ]. |
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==Side effects== |
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Dimethoxanate may have ], ], and ] effects, but it may also produce nausea and vomiting.<ref>{{cite book |isbn=9788448604271|title=Farmacología clínica y terapéutica médica|last1=Martín|first1=Alfonso Velasco|year=2004|chapter=Tratamiento sintomático de la tos y del resfriado común|page=260|publisher=McGraw-Hill/Interamericana }}</ref> |
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==Pharmacology== |
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It binds to the ] in the brain with an ] of 41 nM.<ref>{{cite journal | vauthors = Klein M, Musacchio JM | title = Dextromethorphan binding sites in the guinea pig brain. | journal = Cellular and Molecular Neurobiology | volume = 8 | issue = 2 | pages = 149–156 | date = October 10, 1988 | doi = 10.1007/BF00711241 | pmid = 3044591 | s2cid = 33844132 }}</ref> |
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==Society and culture== |
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Dimethoxanate was introduced in Austria, Belgium, and France in 1911, and in Italy and Spain in 1963.<ref>{{cite book |isbn=0-8103-7177-4 |title=Drugs Available Abroad, 1st Edition |page=67 |date=1991 | vauthors = Schlesser JL |publisher=Derwent Publications Ltd.}}</ref> |
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Approval for marketing in the US was withdrawn by the ] in 1975 due to lack of evidence of efficacy.<ref>{{cite report |url=https://www.govinfo.gov/content/pkg/FR-1975-12-18/pdf/FR-1975-12-18.pdf |docket=75N–0321 |date=December 18, 1975 |work=Federal Register |volume=40 |issue=244 |title=Cough Preparation Containing Dimethoxanate Hydrochloride}}</ref> |
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==Synthesis== |
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] ('''1''') is reacted with ] to give Phenothiazine-10-carbonyl chloride ('''2'''). Further reaction with 2-(2-(dimethylamino)ethoxy)ethanol ('''3''') completed the synthesis of Dimethoxanate ('''4'''). |
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== References == |
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{{reflist}} |
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{{Cough and cold preparations}} |
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{{Cough and cold preparations}} |
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{{Sigma receptor modulators}} |
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