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Pipazetate

Chemical compound

Pipazetate
Summary

Chemical compound

| Drugs.com =

| elimination_half-life =

Pipazetate () (brand names Dipect, Lenopect, Selvigon, Theratuss, Toraxan), or pipazethate (), is a 1-azaphenothiazine drug that was briefly marketed as a cough suppressant. It binds to the sigma-1 receptor with an IC50 value of 190 nM. It also has local anesthetic action, and in large doses can produce seizures.

As the brand name Theratuss, it was approved by the FDA in 1962, on evidence of safety only. It was withdrawn from the US market in 1972 when the manufacturer, Bristol Myers Squibb, failed to produce evidence of efficacy. Clinical studies showed that it did not decrease cough frequency at recommended dosages.

Infrequent side effects include nausea, vomiting, drowsiness, fatigue, rash, tachycardia and seizures.

Synthesis

Note: 1-azaphenothiazine is also used for making Prothipendyl & Isothipendyl.

0527298}} (1997 to Meda Pharma GmbH and Co KG).</ref>

The reaction of 1-azaphenothiazine [261-96-1] (1) with phosgene gives 1-azaphenothiazine-10-carbonyl chloride [94231-78-4] (2). The reaction of this reactive intermediate with 2-[2-(piperidyl)ethoxy]ethanol [3603-43-8] (3) gives the ester, thus completing the synthesis of Pipazethate (4).

References

References

  1. (14 November 2014). "The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies". Springer.
  2. (2000). "Index Nominum 2000: International Drug Directory". Taylor & Francis.
  3. (October 10, 1988). "Dextromethorphan binding sites in the guinea pig brain.". Cellular and Molecular Neurobiology.
  4. (2004). "Farmacología clínica y terapéutica médica".
  5. (August 5, 1972). "Certain Preparations Containing Dihyprylone or Pipazethate Hydrochloride; Notice of Withdrawal of Approval of New-Drug Applications". Federal Register.
  6. Council on Drugs. (1971). "AMA Drug Evaluations". [[American Medical Association]].
  7. Schuler, Wilhelm A.; Klebe, Hans; Schlichtegroll, Ansgar V. (1964). "Synthesen von 4-Aza-phenothiazinen, II. Derivate der 4-Aza-phenothiazin-10-carbonsäure". Justus Liebigs Annalen der Chemie. 673 (1): 102–112. doi:10.1002/jlac.19646730114.
  8. Schuler Wilhelm Alfons, {{US patent. 2989529 (1961 to Degussa).
  9. Bernd Dr. Lehmann & Bernhard Petrat, {{Cite patent. EP. 0527298 (1997 to Meda Pharma GmbH and Co KG).
Wikipedia Source

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antitussives sigma-receptor-modulators pyridobenzthiazines 1-piperidinyl-compounds carbamates ethers withdrawn-drugs ethanolamines
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