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| Trade names | Dipect, Lenopect, Selvignon, Selvigon, Theratuss, Toraxan |
| Other names | Pipazethate; D-254; LG-254; SKF-70230A; SQ-15874 |
| AHFS/Drugs.com | International Drug Names |
| Routes of administration | oral |
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| ECHA InfoCard | 100.016.826 |
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| Formula | C21H25N3O3S |
| Molar mass | 399.51 g·mol−1 |
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Pipazetate (INNTooltip International Nonproprietary Name) (brand namesDipect,Lenopect,Selvigon,Theratuss,Toraxan), orpipazethate (USANTooltip United States Adopted Name), is a 1-azaphenothiazine drug that was briefly marketed as acough suppressant.[1][2] It binds to thesigma-1 receptor with anIC50 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 It was withdrawn from the US market in 1972 when the manufacturer,Bristol Myers Squibb, failed to produce evidence of efficacy.[5] Clinical studies showed that it did not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]
Note: 1-azaphenothiazine is also used for makingProthipendyl &Isothipendyl.
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 ofPipazethate (4).
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