Butamirate

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Cough suppressant

title: "Butamirate" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["antitussives", "diethylamino-compounds", "carboxylate-esters", "glycol-ethers", "sigma-agonists"] description: "Cough suppressant" topic_path: "general/antitussives" source: "https://en.wikipedia.org/wiki/Butamirate" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Cough suppressant ::

| verifiedrevid = 447812394 | IUPAC_name = 2-(2-diethylaminoethoxy)ethyl 2-phenylbutanoate | image = Butamirate.png | image_class = skin-invert-image

| tradename = Acodeen, Codesin, Pertix, Sinecod, Sinecoden, Sinecodix | Drugs.com = | pregnancy_AU = | pregnancy_US = | legal_AU = | legal_CA = | legal_UK = | legal_US =

| protein_bound = 98% | elimination_half-life = 6 hours | excretion = 90% renal

| CAS_number_Ref = | CAS_number = 18109-80-3 | ATC_prefix = R05 | ATC_suffix = DB13 | PubChem = 28892 | ChEMBL = 1332546 | DrugBank_Ref = | DrugBank = DB13731 | ChemSpiderID_Ref = | ChemSpiderID = 26873 | UNII_Ref = | UNII = M75MZG2236 | KEGG_Ref = | KEGG = D07594

| C=18 | H=29 | N=1 | O=3 | smiles = O=C(OCCOCCN(CC)CC)C(c1ccccc1)CC | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = DDVUMDPCZWBYRA-UHFFFAOYSA-N Butamirate (or brospamin, trade names Acodeen, Codesin, Pertix, Sinecod, Sinecoden, Sinecodix) is a cough suppressant. It has been marketed in Europe and Mexico, but not in the United States.

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.

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.

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.)

File:Oxeladin.png|Oxeladin File:Pentoxyverine skeletal.svg|Pentoxyverine

References

References

  1. (November 1990). "[Clinical comparison of butamirate citrate with a codeine-based antitussive agent]". Revue Médicale de la Suisse Romande.
  2. (1991). "Drugs Available Abroad, 1st Edition". Derwent Publications Ltd..
  3. (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.

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antitussivesdiethylamino-compoundscarboxylate-estersglycol-etherssigma-agonists