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^Y
ATC code	R05DB13
PubChem	CID 28892
ChemSpider	26873^Y
UNII	M75MZG2236^Y
KEGG	D07594^Y
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^Y Key:DDVUMDPCZWBYRA-UHFFFAOYSA-N^Y
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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.)

Synthesis

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

↑ 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.

Cough and cold preparations (R05)

Expectorants

Mucolytics

Cough suppressants

Opium alkaloids, opioids, and derivatives	Acetyldihydrocodeine Benzylmorphine Butorphanol Codeine Dextromethorphan Dihydrocodeine Dimemorfan Droxypropine Ethylmorphine Heroin Hydrocodone Hydromorphone Isoaminile Laudanum Levomethadone Levopropoxyphene Methadone Nicocodeine Nicodicodeine Normethadone Noscapine Pholcodine Thebacon Tipepidine

Other	Benzonatate Benproperine Bibenzonium bromide Butamirate Clobutinol Clofedanol Cloperastine Diphenhydramine Dibunate Dimethoxanate Dropropizine Fedrilate Glaucine Levodropropizine Meprotixol Morclofone Nepinalone Oxolamine Oxeladin Pentoxyverine Pipazetate Prenoxdiazine Piperidione Zipeprol

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