Pipazetate

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Pipazetate
File:Pipazethate.png
Clinical data
Trade namesDipect, Lenopect, Selvignon, Selvigon, Theratuss, Toraxan
Other namesPipazethate; D-254; LG-254; SKF-70230A; SQ-15874
AHFS/Drugs.comInternational Drug Names
Routes of
administration		oral
ATC code
Legal status
Legal status
  • ?
Identifiers
  • 2-(2-piperidin-1-ylethoxy)ethyl 10H-pyrido[3,2-b][1,4]benzothiazine-10-carboxylate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
E number{{#property:P628}}
CompTox Dashboard (EPA)
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Chemical and physical data
FormulaC21H25N3O3S
Molar mass399.51 g·mol−1
3D model (JSmol)
  • O=C(OCCOCCN1CCCCC1)N3c4c(Sc2c3nccc2)cccc4
  • 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 checkY
  • Key:DTVJXCOMJLLMAK-UHFFFAOYSA-N checkY
  (verify)

Pipazetate (INNTooltip International Nonproprietary Name) (brand names Dipect, Lenopect, Selvigon, Theratuss, Toraxan), or pipazethate (USANTooltip United States Adopted Name), is a 1-azaphenothiazine drug that was briefly marketed as a cough suppressant.[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]

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 It was withdrawn from the US market in 1972 when the manufacturer, Bristol Myers Squibb, failed to produce evidence of efficacy.[5] Clinical studies showed that it did not decrease cough frequency at recommended dosages.[6]

Infrequent side effects include nausea, vomiting, drowsiness, fatigue, rash, tachycardia and seizures.[6]

Synthesis

[edit | edit source]

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

File:Pipazethate synthesis.svg
Thieme Synthesis:[7] Patent:[8] Revised:[9]

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

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  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, U.S. patent 2,989,529 (1961 to Degussa).
  9. ^ Bernd Dr. Lehmann & Bernhard Petrat, EP 0527298  (1997 to Meda Pharma GmbH and Co KG).


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