Butamirate (original) (raw)

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Cough suppressant

Pharmaceutical compound

Butamirate

Clinical data
Trade names	Acodeen, Codesin, Pertix, Sinecod, Sinecoden, Sinecodix
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 Y
PubChem CID	28892
DrugBank	DB13731 Y
ChemSpider	26873 Y
UNII	M75MZG2236
KEGG	D07594 Y
ChEMBL	ChEMBL1332546
CompTox Dashboard (EPA)	DTXSID7048403
ECHA InfoCard	100.038.172
Chemical and physical data
Formula	C18H29NO3
Molar mass	307.434 g·mol−1
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 YKey:DDVUMDPCZWBYRA-UHFFFAOYSA-N Y
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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]

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.)

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• Cough syrup

• Noscapine

• Codeine; Pholcodine

• Dextromethorphan; Dimemorfan

• Racemorphan; Dextrorphan; Levorphanol

• Pentoxyverine

• Tipepidine

• Cloperastine; Levocloperastine

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.