Pipazetate

Pipazetate (INN) (brand names Dipect, Lenopect, Selvigon, Theratuss, Toraxan), or pipazethate (USAN), is a pyridobenzthiazine cough suppressant, closely related to the phenothiazine class.[1][2] It binds to the sigma-1 receptor with an IC50 value of 190 nM.[3] It also has local anesthetic action, and in large doses can produce seizures.[4]

Pipazetate
Clinical data
Trade namesDipect, Lenopect, Selvignon, Selvigon, Theratuss, Toraxan
Other namesPipazethate; D-254; LG-254; SKF-70230A; SQ-15874
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
IUPAC name
  • 2-(2-piperidin-1-ylethoxy)ethyl 10H-pyrido[3,2-b][1,4]benzothiazine-10-carboxylate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard100.016.826
Chemical and physical data
FormulaC21H25N3O3S
Molar mass399.51 g·mol−1
3D model (JSmol)
SMILES
  • O=C(OCCOCCN1CCCCC1)N3c4c(Sc2c3nccc2)cccc4
InChI
  • InChI=1S/C21H25N3O3S/c25-21(27-16-15-26-14-13-23-11-4-1-5-12-23)24-17-7-2-3-8-18(17)28-19-9-6-10-22-20(19)24/h2-3,6-10H,1,4-5,11-16H2 Y
  • Key:DTVJXCOMJLLMAK-UHFFFAOYSA-N Y
  (verify)

As the brand name Theratuss, it was withdrawn from the US market in 1972 when the manufacturer, E.R. Squibb and Sons, failed to produce evidence of efficacy.[5] Clinical studies showed that it did not decrease cough frequency at recommended dosages.[6]

Side effects, which are infrequent, include nausea, vomiting, drowsiness, fatigue, rash, and tachycardia.[6]

References
  1. Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 985–. ISBN 978-1-4757-2085-3.
  2. Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 1418–. ISBN 978-3-88763-075-1.
  3. Klein M, Musacchio JM (October 10, 1988). "Dextromethorphan binding sites in the guinea pig brain". Cellular and Molecular Neurobiology. 8 (2): 149–156. doi:10.1007/BF00711241. PMID 3044591. S2CID 33844132.
  4. Martín, Alfonso Velasco (2004). "Tratamiento sintomático de la tos y del resfriado común". Farmacología clínica y terapéutica médica. p. 259. ISBN 9788448604271.
  5. Certain Preparations Containing Dihyprylone or Pipazethate Hydrochloride; Notice of Withdrawal of Approval of New-Drug Applications (PDF). Federal Register (Report). 37. August 5, 1972. p. 15887. FDC–D–458.
  6. Council on Drugs (1971). AMA Drug Evaluations (Report). Chicago: American Medical Association. p. 360–3. LCCN 75147249. Retrieved April 5, 2021.



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