Dimethoxanate

Dimethoxanate (trade names Cothera, Cotrane, Atuss, Perlatoss, Tossizid)[1] is a cough suppressant of the phenothiazine class.[2]

Dimethoxanate
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
IUPAC name
  • 2-(2-dimethylaminoethoxy)ethyl phenothiazine-10-carboxylate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard100.006.838
Chemical and physical data
FormulaC19H22N2O3S
Molar mass358.46 g·mol−1
3D model (JSmol)
SMILES
  • O=C(OCCOCCN(C)C)N1c3c(Sc2c1cccc2)cccc3
InChI
  • InChI=1S/C19H22N2O3S/c1-20(2)11-12-23-13-14-24-19(22)21-15-7-3-5-9-17(15)25-18-10-6-4-8-16(18)21/h3-10H,11-14H2,1-2H3 Y
  • Key:OOVJCSPCMCAXEX-UHFFFAOYSA-N Y
  (verify)

It may have analgesic, local anesthetic, and central nervous system depressant effects, but it may also produce nausea and vomiting.[3]

Approval for marketing in the US was withdrawn by the FDA in 1975 due to lack of evidence of efficacy.[4]

It binds to the sigma-1 receptor in the brain with an IC50 of 41 nM.[5]

References
  1. William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia. Elsevier. pp. 1332–3. ISBN 978-0-8155-1856-3.
  2. Parish FA (November 1959). "Clinical evaluation of the antitussive, dimethoxanate". Medical Times. 87: 1488–90. PMID 14430450.
  3. Martín, Alfonso Velasco (2004). "Tratamiento sintomático de la tos y del resfriado común". Farmacología clínica y terapéutica médica. p. 260. ISBN 9788448604271.
  4. Cough Preparation Containing Dimethoxanate Hydrochloride (PDF). Federal Register (Report). 40. December 18, 1975. 75N–0321.
  5. Klein M, Musacchio JM (October 10, 1988). "Dextromethorphan binding sites in the guinea pig brain". Cellular and Molecular Neurobiology. 8 (2): 149–156.
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