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Related Concept Videos

Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism01:13

Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism

Carboxylic acids react with alcohols to yield esters via an acid-catalyzed condensation reaction called Fischer esterification. This is a nucleophilic acyl substitution reaction that proceeds via a tetrahedral intermediate, where a water molecule is eliminated as the leaving group.
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview01:20

Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview

The Fischer esterification reaction was developed by the German chemist Emil Fischer in 1895. It is a condensation reaction between carboxylic acids and alcohols in an acidic medium to give esters and water.
Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides01:16

Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides

Naming Acid Halides
The IUPAC and common names of acid halides are derived from the corresponding carboxylic acids, by changing “ic acid” to “yl halide.” For example, as shown below, the IUPAC name ethanoyl chloride is derived from ethanoic acid, and the common name, acetyl chloride, is obtained from acetic acid.
Acid Halides to Esters: Alcoholysis01:12

Acid Halides to Esters: Alcoholysis

Alcoholysis is a nucleophilic acyl substitution reaction in which an alcohol functions as a nucleophile. Acid halides react with alcohol to produce esters. The mechanism proceeds in three steps:
Carboxylic Acid Derivatives: Overview01:15

Carboxylic Acid Derivatives: Overview

Carboxylic acid derivatives are formed by replacing the hydroxyl group of carboxylic acids with a different functional group. The most common carboxylic acid derivatives are:

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Related Experiment Video

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A Strategy for Sensitive, Large Scale Quantitative Metabolomics
14:18

A Strategy for Sensitive, Large Scale Quantitative Metabolomics

Published on: May 27, 2014

Fumaric acid esters.

Martin Rostami Yazdi1, Ulrich Mrowietz

  • 1Psoriasis Center at the Department of Dermatology, University of Kiel, Kiel, Germany.

Clinics in Dermatology
|August 30, 2008
PubMed
Summary
This summary is machine-generated.

Fumaric acid esters (FAEs) effectively treat moderate to severe psoriasis. Dimethylfumarate (DMF), a key component, acts as a prodrug, with its metabolite monomethylfumarate being detected in plasma.

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Area of Science:

  • Dermatology
  • Pharmacology
  • Immunology

Background:

  • Systemic therapy with fumaric acid esters (FAEs) shows efficacy and a favorable safety profile for moderate to severe psoriasis.
  • A specific FAE formulation containing dimethylfumarate (DMF) and monoethylfumarate salts is registered in Germany.
  • DMF is considered the primary active component responsible for the antipsoriatic effects.

Purpose of the Study:

  • To investigate the pharmacokinetics of fumarates in humans.
  • To explore the role of dimethylfumarate (DMF) as a prodrug.
  • To understand the molecular mechanisms underlying FAEs' therapeutic effects in psoriasis.

Main Methods:

  • Clinical studies evaluating FAEs for psoriasis treatment.
  • Pharmacokinetic analysis of fumarate metabolites in human plasma after oral FAE administration.
  • In vitro biological assays to assess DMF's cellular effects.

Main Results:

  • Oral administration of FAEs resulted in the detection of monomethylfumarate as the primary metabolite in human plasma.
  • Evidence suggests DMF acts as a prodrug, with monomethylfumarate being its main active metabolite.
  • DMF demonstrated effects such as inhibition of the nuclear factor kappa B pathway and induction of apoptosis.

Conclusions:

  • FAEs, particularly DMF, are effective systemic treatments for moderate to severe psoriasis.
  • DMF's role as a prodrug for monomethylfumarate is supported by pharmacokinetic data.
  • DMF modulates intracellular glutathione, contributing to its therapeutic actions in psoriasis.