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Latest revision as of 16:07, 11 January 2025 edit undoArthurfragoso (talk | contribs)Extended confirmed users, Template editors4,951 edits dark mode fix |
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{{short description|Cough suppressant}} |
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{{refimprove|date=June 2011}} |
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{{Drugbox |
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{{Drugbox |
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⚫ |
| verifiedrevid = 447812394 |
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| Watchedfields = changed |
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| verifiedrevid = 444432848 |
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| IUPAC_name = 2-(2-diethylaminoethoxy)ethyl 2-phenylbutanoate |
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| IUPAC_name = 2-(2-diethylaminoethoxy)ethyl 2-phenylbutanoate |
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| image = Butamirate.png |
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| image = Butamirate.png |
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| image_class = skin-invert-image |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| tradename = |
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| tradename = Acodeen, Codesin, Pertix, Sinecod, Sinecoden, Sinecodix |
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| Drugs.com = {{drugs.com|international|butamirate}} |
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| Drugs.com = {{drugs.com|international|butamirate}} |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 18109-80-3 |
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| CAS_number = 18109-80-3 |
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| ATC_prefix = R05 |
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| ATC_prefix = R05 |
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| ATC_suffix = DB13 |
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| ATC_suffix = DB13 |
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| PubChem = 28892 |
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| PubChem = 28892 |
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| ChEMBL = 1332546 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB13731 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 26873 |
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| ChemSpiderID = 26873 |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=18 | H=29 | N=1 | O=3 |
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| C=18 | H=29 | N=1 | O=3 |
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| molecular_weight = 307.428 g/mol |
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| smiles = O=C(OCCOCCN(CC)CC)C(c1ccccc1)CC |
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| smiles = O=C(OCCOCCN(CC)CC)C(c1ccccc1)CC |
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| InChI = 1/C18H29NO3/c1-4-17(16-10-8-7-9-11-16)18(20)22-15-14-21-13-12-19(5-2)6-3/h7-11,17H,4-6,12-15H2,1-3H3 |
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| InChIKey = DDVUMDPCZWBYRA-UHFFFAOYAN |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C18H29NO3/c1-4-17(16-10-8-7-9-11-16)18(20)22-15-14-21-13-12-19(5-2)6-3/h7-11,17H,4-6,12-15H2,1-3H3 |
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| StdInChI = 1S/C18H29NO3/c1-4-17(16-10-8-7-9-11-16)18(20)22-15-14-21-13-12-19(5-2)6-3/h7-11,17H,4-6,12-15H2,1-3H3 |
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| StdInChIKey = DDVUMDPCZWBYRA-UHFFFAOYSA-N |
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| StdInChIKey = DDVUMDPCZWBYRA-UHFFFAOYSA-N |
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}} |
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}} |
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'''Butamirate''' (or '''brospamin''', trade names '''Acodeen''', '''Codesin''', '''Pertix''', '''Sinecod''', '''Sinecoden''', '''Sinecodix''') is a ].<ref>{{cite journal | vauthors = Germouty J, Weibel MA | title = | journal = Revue Médicale de la Suisse Romande | volume = 110 | issue = 11 | pages = 983–6 | date = November 1990 | pmid = 1980027 }}</ref> It has been marketed in Europe and Mexico, but not in the United States.<ref name="abroad">{{cite book |isbn=0-8103-7177-4 |title=Drugs Available Abroad, 1st Edition |pages=29–30 |date=1991 | vauthors = Schlesser JL |publisher=Derwent Publications Ltd.}}</ref> |
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'''Butamirate''' (or '''brospamin''') is an nonaddictive{{Citation needed|date=June 2011}} opioid central ]. It acts on the cough center in the ]. It does not cause respiratory suppression, so should be safer than ].{{Citation needed|date=June 2011}} |
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It is sold in the form of lozenges, syrup, tablets, ]s, or pastilles as the ] salt. Adverse effects can include nausea, diarrhea, vertigo, and ].<ref name="abroad"/> |
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==Pharmacology== |
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A study found it to bind to the cough center in the ], more specifically the ]-binding site in guinea pig brain with high affinity.<ref>{{cite journal | vauthors = Klein M, Musacchio JM | title = High affinity dextromethorphan binding sites in guinea pig brain. Effect of sigma ligands and other agents | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 251 | issue = 1 | pages = 207–15 | date = October 1989 | pmid = 2477524 }}</ref> |
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As a 2-(2-diethylaminoethoxy)ethyl ester, it is chemically related to ] and ], which are in the same class. (Oxeladin has an additional ethyl group in its carboxylic acid, pentoxyverine has both ethyl groups of oxeladin replaced by one cyclopentyl in the same place.) |
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<div class="skin-invert-image"><gallery> |
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File:Oxeladin.png|] |
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File:Pentoxyverine skeletal.svg|] |
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</gallery></div> |
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== See also == |
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* ] |
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* ] |
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* ]; ] |
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* ]; ] |
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* ]; ]; ] |
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* ] |
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* ] |
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* ]; ] |
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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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] |
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] |
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] |
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] |
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] |
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] |
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] |
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] |
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{{respiratory-system-drug-stub}} |
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{{respiratory-system-drug-stub}} |
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] |
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] |
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] |
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] |
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