Butamirate

Butamirate

Systematic (IUPAC) name
2-(2-diethylaminoethoxy)ethyl 2-phenylbutanoate
Clinical data
AHFS/Drugs.com	International Drug Names
Pharmacokinetic data
Protein binding	98%
Biological half-life	6 hours
Excretion	90% renal
Identifiers
CAS Number	18109-80-3
ATC code	R05DB13 (WHO)
PubChem	CID 28892
ChemSpider	26873
UNII	M75MZG2236
KEGG	D07594
ChEMBL	CHEMBL1332546
Chemical data
Formula	C18H29NO3
Molar mass	307.428 g/mol
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 Key:DDVUMDPCZWBYRA-UHFFFAOYSA-N
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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.)

• 

  Oxeladin

• 

  Pentoxyverine

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.
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.