phenothiazine

Also known as dibenzothiazine, fenothiazine, thiodiphenylamine, 10H-Phenothiazin, dibenzo-1,4-thiazine

Phenothiazine, abbreviated PTZ, is an organic compound that has the formula S(C6H4)2NH and is related to the thiazine-class of heterocyclic compounds. Derivatives of phenothiazine are highly bioactive and have widespread use.

Chemical data

Formula: C12H9NS
Molecular weight: 199.27 g/mol
IUPAC name: 10H-phenothiazine
SMILES: C1=CC=C2C(=C1)NC3=CC=CC=C3S2
InChIKey: WJFKNYWRSNBZNX-UHFFFAOYSA-N
XLogP: 4.2
Polar surface area: 37.3 Å²
H-bond donors: 1
H-bond acceptors: 2
Formal charge: 0

via PubChem

Research

57,635 papers

Phenothiazine: the seven lives of pharmacology's first lead structure.Drug discovery today · 2011
PHENOTHIAZINE.Bulletin. American Pharmaceutical Association. Committee on National Formulary · 1946
Phenothiazine-associated supraventricular tachycardia.The Australian and New Zealand journal of psychiatry · 1994
[Phenothiazine derivatives].France Medecine · 1957
Phenothiazine as an anthelmintic.Australian veterinary journal · 1945

via PubMed

Wikidata facts

Mass: 199.046

Show 8 more facts

canonical SMILES: C1=CC=C2C(=C1)NC3=CC=CC=C3S2
melting point: 185
NIOSH Pocket Guide ID: 0494
Commons category: Phenothiazine
boiling point: 700
vapor pressure: 0
time-weighted average exposure limit: 5
chemical formula: C₁₂H₉NS

Sources (4)

via Wikidata · CC0

~9 min read

Article

9 sections

Contents

Uses
Phenothiazine-derived drugs
Nondrug applications
Trade names
Former uses
As an anthelminthic
Structure and synthesis
References
External links

The derivatives chlorpromazine and promethazine revolutionized the fields of psychiatry and allergy treatment, respectively. An earlier derivative, methylene blue, was one of the first antimalarial drugs, and derivatives of phenothiazine are currently under investigation as possible anti-infective drugs. Phenothiazine is a prototypical pharmaceutical lead structure in medicinal chemistry.