Metopimazine

Jump to: navigation, search
Metopimazine.png
Metopimazine
Systematic (IUPAC) name
1-(3-[2-(methylsulfonyl)-10H-phenothiazin-10-yl]propyl)piperidine-4-carboxamide
Identifiers
CAS number 14008-44-7
ATC code A04AD05
PubChem 26388
Chemical data
Formula C22H27N3O3S2 
Mol. mass 445.6 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

?

Legal status
Routes  ?

WikiDoc Resources for Metopimazine

Articles

Most recent articles on Metopimazine

Most cited articles on Metopimazine

Review articles on Metopimazine

Articles on Metopimazine in N Eng J Med, Lancet, BMJ

Media

Powerpoint slides on Metopimazine

Images of Metopimazine

Photos of Metopimazine

Podcasts & MP3s on Metopimazine

Videos on Metopimazine

Evidence Based Medicine

Cochrane Collaboration on Metopimazine

Bandolier on Metopimazine

TRIP on Metopimazine

Clinical Trials

Ongoing Trials on Metopimazine at Clinical Trials.gov

Trial results on Metopimazine

Clinical Trials on Metopimazine at Google

Guidelines / Policies / Govt

US National Guidelines Clearinghouse on Metopimazine

NICE Guidance on Metopimazine

NHS PRODIGY Guidance

FDA on Metopimazine

CDC on Metopimazine

Books

Books on Metopimazine

News

Metopimazine in the news

Be alerted to news on Metopimazine

News trends on Metopimazine

Commentary

Blogs on Metopimazine

Definitions

Definitions of Metopimazine

Patient Resources / Community

Patient resources on Metopimazine

Discussion groups on Metopimazine

Patient Handouts on Metopimazine

Directions to Hospitals Treating Metopimazine

Risk calculators and risk factors for Metopimazine

Healthcare Provider Resources

Symptoms of Metopimazine

Causes & Risk Factors for Metopimazine

Diagnostic studies for Metopimazine

Treatment of Metopimazine

Continuing Medical Education (CME)

CME Programs on Metopimazine

International

Metopimazine en Espanol

Metopimazine en Francais

Business

Metopimazine in the Marketplace

Patents on Metopimazine

Experimental / Informatics

List of terms related to Metopimazine

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [3]

Overview

Metopimazine (INN) is a phenothiazine antiemetic.

Synthesis

Metopimazine synthesis:Jacob, R. M.; Robert, J. G.; 1092476 Patent DE via CAMBIA Patent Lens[1] – espacenet[2] (1959).

The reduced basicity of phenothiazine nitrogen requires that even acylation proceed via the anion. The amide (2) from the methyl thioether (2) can be prepared, for example, by sequential reaction with sodium amide and acetic anhydride. Oxidation of that intermediate with peracid proceeds preferentially on the more electron-rich alkyl thioether to give the sulfone; this affords the phenothiazine (3) on hydrolysis of the amide. Complex side chains are most conveniently incorporated in a stepwise fashion. The first step in the present sequence involves reaction of (3) as its anion with 1-bromo-3-chloropropane to give (4). The use of that halide with alkylate piperidine-4-carboxamide (5) affords the antipsychotic agent metopimazine (6).


References


Linked-in.jpg