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Open Access Articles- Top Results for Butamirate

Butamirate

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Butamirate
File:Butamirate.png
Systematic (IUPAC) name
2-(2-diethylaminoethoxy)ethyl 2-phenylbutanoate
Clinical data
AHFS/Drugs.com International Drug Names
Pharmacokinetic data
Protein binding 98%
Half-life 6 hours
Excretion 90% renal
Identifiers
18109-80-3 7pxY
R05DB13
PubChem CID 28892
ChemSpider 26873 7pxY
UNII M75MZG2236 7pxY
KEGG D07594 7pxY
ChEMBL CHEMBL1332546
Chemical data
Formula C18H29NO3
307.428 g/mol
 14pxY (what is this?)  (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.)

Synthesis

File:Butamirate synthesis.svg
Butamirate synthesis: DE 1151515 ; Heusser, U.S. Patent 3,349,114 (1963, 1967, both to Hommel A.G.).

Prepd by the esterification of phenylethylacetyl chloride with diethylaminoethoxyethanol.

References

  1. ^ Germouty, J.; Weibel, M. A. (1990). "Clinical comparison of butamirate citrate with a codeine-based antitussive agent". Revue medicale de la Suisse romande 110 (11): 983–986. PMID 1980027.  edit
  2. ^ Klein, M.; Musacchio, J. M. (1989). "High affinity dextromethorphan binding sites in guinea pig brain. Effect of sigma ligands and other agents". The Journal of Pharmacology and Experimental Therapeutics 251 (1): 207–215. PMID 2477524.  edit


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