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{{drugbox
{{Drugbox
| IUPAC_name       = 2-(2-diethylaminoethoxy)ethyl 2-phenylbutanoate
| verifiedrevid = 447812394
| image             = Butamirate.png
| IUPAC_name = 2-(2-diethylaminoethoxy)ethyl 2-phenylbutanoate
| CAS_number        = 18109-80-3
| image = Butamirate.png
| ATC_prefix        = R05
 
| ATC_suffix        = DB13
<!--Clinical data-->
| PubChem          = 28892
| tradename =
| DrugBank          =  
| Drugs.com = {{drugs.com|international|butamirate}}
| C=18|H=29|N=1|O=3
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| molecular_weight = 307.428 g/mol
| pregnancy_US = <!-- A / B            / C / D / X -->
| bioavailability  =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| protein_bound     = 98%
| legal_CA = <!--            / Schedule I, II, III, IV, V, VI, VII, VIII -->
| metabolism        =
| legal_UK = <!-- GSL        / P      / POM / CD / Class A, B, C -->
| legal_US = <!-- OTC                  / Rx-only / Schedule I, II, III, IV, V -->
 
<!--Pharmacokinetic data-->
| protein_bound = 98%
| elimination_half-life = 6 hours
| elimination_half-life = 6 hours
| excretion         = 90% renal
| excretion = 90% renal
| pregnancy_AU      =  <!-- A / B1 / B2 / B3 / C / D / X -->
 
| pregnancy_US      = <!-- A / B            / C / D / X -->
<!--Identifiers-->
| pregnancy_category=
| CAS_number_Ref = {{cascite|correct|??}}
| legal_AU          = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| CAS_number = 18109-80-3
| legal_CA          =  <!--             / Schedule I, II, III, IV, V, VI, VII, VIII -->
| ATC_prefix = R05
| legal_UK          = <!-- GSL        / P      / POM / CD / Class A, B, C -->
| ATC_suffix = DB13
| legal_US          =  <!-- OTC                  / Rx-only  / Schedule I, II, III, IV, V -->
| PubChem = 28892
| legal_status      =  
| ChEMBL = 1332546
| routes_of_administration =  
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 26873
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = M75MZG2236
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07594
 
<!--Chemical data-->
| C=18 | H=29 | N=1 | O=3
| molecular_weight = 307.428 g/mol
| smiles = O=C(OCCOCCN(CC)CC)C(c1ccccc1)CC
| 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
| InChIKey = DDVUMDPCZWBYRA-UHFFFAOYAN
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = DDVUMDPCZWBYRA-UHFFFAOYSA-N
}}
}}
'''Butamirate''' (or '''brospamin''') is a non-opioid central [[cough suppressant]]. It acts on the cough center in the [[medulla oblongata]]. It does noc cause respiratory suppression, so should be safer than [[codeine]].
'''Butamirate''' (or '''brospamin''') is a [[cough suppressant]].<ref>{{cite pmid|1980027}}</ref>
 
A study found it to bind to the cough center in the [[medulla oblongata]], more specifically the [[dextromethorphan]]-binding site in guinea pig brain with high affinity.<ref>{{cite pmid|2477524}}</ref>
 
As a 2-(2-diethylaminoethoxy)ethyl ester it is chemically related to [[oxeladin]] and [[pentoxyverine]], 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.)


{{pharmacology-stub}}
<gallery>
File:Oxeladin.png|[[Oxeladin]]
File:Pentoxyverine skeletal.svg|[[Pentoxyverine]]
</gallery>


==References==
{{reflist}}


{{Cough and cold preparations}}
{{Cough and cold preparations}}
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[[Category:Antitussives]]
[[Category:Antitussives]]
[[Category:Amines]]
[[Category:Amines]]
[[Category:Carboxylate esters]]
[[Category:Butyrates]]
[[Category:Ethers]]
 
 
{{respiratory-system-drug-stub}}

Revision as of 13:44, 13 April 2015

Butamirate
File:Butamirate.png
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Pharmacokinetic data
Protein binding98%
Elimination half-life6 hours
Excretion90% renal
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC18H29NO3
Molar mass307.428 g/mol
3D model (JSmol)
  (verify)

Butamirate (or brospamin) is a cough suppressant.[1]

A study found it to bind to the cough center in the medulla oblongata, more specifically the dextromethorphan-binding site in guinea pig brain with high affinity.[2]

As a 2-(2-diethylaminoethoxy)ethyl ester it is chemically related to oxeladin and pentoxyverine, 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.)

References

  1. ↑ PMID 1980027 (PMID 1980027)
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  2. ↑ PMID 2477524 (PMID 2477524)
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Template:Cough and cold preparations


Template:Respiratory-system-drug-stub

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