Structure via PubChem · Public domain (PubChem)
pipazethate
Sign in to saveAlso known as D-254, SO-15874, Pipazetate, SK&F-70230-A
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.
Chemical data
- Formula
- C21H25N3O3S
- Molecular weight
- 399.5 g/mol
- IUPAC name
- 2-(2-piperidin-1-ylethoxy)ethyl pyrido[3,2-b][1,4]benzothiazine-10-carboxylate
- SMILES
- C1CCN(CC1)CCOCCOC(=O)N2C3=CC=CC=C3SC4=C2N=CC=C4
- InChIKey
- DTVJXCOMJLLMAK-UHFFFAOYSA-N
- XLogP
- 3.4
- Polar surface area
- 80.2 Ų
- H-bond donors
- 0
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
- Indications
- Cough
via ChEMBL · EBI
Research
24 papers- Pipazethate--acute childhood poisoning.Clinical toxicology · 1977
- Severe Acute Pipazethate HCl Poisoning: A Case Report.Journal of paediatrics and child health · 2026
- Utilization of N-bromosuccinimide for the sensitive spectrophotometric determination of pipazethate HCl as antitussive drug in pure and dosage forms.Annales pharmaceutiques francaises · 2021
- Accidental lethal pipazethate poisoning in a child.Zeitschrift fur Rechtsmedizin. Journal of legal medicine · 1982
- Trial of pipazethate as an antitussive.Clinical pharmacology and therapeutics · 1966
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 399.161663
- Has use
- medication
Show 4 more facts
- defined daily dose
- 80
- chemical formula
- C₂₁H₂₅N₃O₃S
- canonical SMILES
- C1CCN(CC1)CCOCCOC(=O)N2C3=CC=CC=C3SC4=C2N=CC=C4
- subject has role
- antitussive
Sources (3)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- Synthesis
- References
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 It was withdrawn from the US market in 1972 when the manufacturer, Bristol Myers Squibb, failed to produce evidence of efficacy.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.
Excerpted from Wikipedia’s “pipazethate” article, available under the CC BY-SA 4.0 licence.
Available in 5 languages
via Wikidata sitelinks · CC0