Butamirate

Cough suppressant
  • R05DB13 (WHO)
Pharmacokinetic dataProtein binding98%Elimination half-life6 hoursExcretion90% renalIdentifiers
  • 2-(2-diethylaminoethoxy)ethyl 2-phenylbutanoate
CAS Number
  • 18109-80-3 checkY
PubChem CID
  • 28892
DrugBank
  • DB13731 checkY
ChemSpider
  • 26873 checkY
UNII
  • M75MZG2236
KEGG
  • D07594 checkY
ChEMBL
  • ChEMBL1332546
CompTox Dashboard (EPA)
  • DTXSID7048403 Edit this at Wikidata
ECHA InfoCard100.038.172 Edit this at WikidataChemical and physical dataFormulaC18H29NO3Molar mass307.434 g·mol−13D model (JSmol)
  • Interactive image
  • O=C(OCCOCCN(CC)CC)C(c1ccccc1)CC
InChI
  • InChI=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 checkY
  • Key:DDVUMDPCZWBYRA-UHFFFAOYSA-N checkY
  (verify)

Butamirate (or brospamin, trade names Acodeen, Codesin, Pertix, Sinecod, Sinecoden, Sinecodix) is a cough suppressant.[1] It has been marketed in Europe and Mexico, but not in the United States.[2]

It is sold in the form of lozenges, syrup, tablets, dragées, or pastilles as the citrate salt. Adverse effects can include nausea, diarrhea, vertigo, and exanthema.[2]

Pharmacology

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.[3]

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.)

See also

References

  1. ^ Germouty J, Weibel MA (November 1990). "[Clinical comparison of butamirate citrate with a codeine-based antitussive agent]". Revue Médicale de la Suisse Romande. 110 (11): 983–6. PMID 1980027.
  2. ^ a b Schlesser JL (1991). Drugs Available Abroad, 1st Edition. Derwent Publications Ltd. pp. 29–30. ISBN 0-8103-7177-4.
  3. ^ Klein M, Musacchio JM (October 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): 207–15. PMID 2477524.
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ExpectorantsMucolyticsCough suppressants
Opium alkaloids,
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