Butamirate

Butamirate
Clinical data
Trade namesAcodeen, Codesin, Pertix, Sinecod, Sinecoden, Sinecodix
AHFS/Drugs.comInternational Drug Names
ATC code
Pharmacokinetic data
Protein binding98%
Elimination half-life6 hours
Excretion90% renal
Identifiers
IUPAC name
  • 2-(2-diethylaminoethoxy)ethyl 2-phenylbutanoate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.038.172
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Chemical and physical data
FormulaC18H29NO3
Molar mass307.434 g·mol−1
3D model (JSmol)
SMILES
  • 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]

As the citrate salt, it is sold in the form of lozenges, syrup, tablets, dragées, or pastilles. 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. 1 2 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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