Butamirate

Butamirate
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	R05DB13 (WHO) ;
Pharmacokinetic data
Protein binding	98%
Elimination half-life	6 hours
Excretion	90% renal
Identifiers
	IUPAC name 2-(2-diethylaminoethoxy)ethyl 2-phenylbutanoate;
CAS Number	18109-80-3 ;
PubChem CID	28892;
ChemSpider	26873 ;
UNII	M75MZG2236;
KEGG	D07594 ;
ChEMBL	CHEMBL1332546;
ECHA InfoCard	100.038.172
Chemical and physical data
Formula	C18H29NO3
Molar mass	307.428 g/mol
3D model (JSmol)	Interactive image;
	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.)

References

↑ 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.
↑ 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.

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[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.