R-(+)-Etomoxir Chemical Properties

Melting point:

32-34°C

Boiling point:

405.0±25.0 °C(Predicted)

Density 

1.163

storage temp. 

Inert atmosphere,2-8°C

solubility 

≥32.7 mg/mL in DMSO; ≥109.6 mg/mL in EtOH; ≥48.3 mg/mL in H2O with gentle warming

form 

Powder

color 

Colorless to light yellow

InChI

InChI=1S/C17H23ClO4/c1-2-20-16(19)17(13-22-17)11-5-3-4-6-12-21-15-9-7-14(18)8-10-15/h7-10H,2-6,11-13H2,1H3/t17-/m1/s1

InChIKey

DZLOHEOHWICNIL-QGZVFWFLSA-N

SMILES

O1C[C@]1(CCCCCCOC1=CC=C(Cl)C=C1)C(OCC)=O

R-(+)-Etomoxir Usage And Synthesis

Description

Etomoxir, or 2[6(4-chlorophenoxy)hexyl]oxirane-2-carboxylate, is an irreversible inhibitor of carnitine palmitoyltransferase-1 (CPT-1) on the outer face of the inner mitochondrial membrane.This prevents the formation of acyl carnitines, a step that is necessary for the transport of fatty acyl chains from the cytosol into the intermembrane space of the mitochondria. This step is essential to the production of ATP from fatty acid oxidation. Etomoxir has also been identified as a direct agonist of PPARα. An off-target effect has been demonstrated at high concentrations of etomoxir on Coenzyme-A (CoA) metabolism.

Application

Etomoxir (R-(+)-Etomoxir) is an irreversible inhibitor of carnitine palmitoyltransferase 1a (CPT-1a), inhibits fatty acid oxidation (FAO) through CPT-1a and inhibits palmitate β-oxidation in human, rat and guinea pig.

Chemical Properties

Colourless Oil

Uses

R-(+)-Etomoxir is an inhibitor of carnitine palmitoyltransferase A (CPT1), which is required for the oexidation of long-chain acyl CoA esters. A strong inhibitor of mitochondrial CPT1 and is a candidate as an anti-diabetic drug

Definition

ChEBI: (2R)-2-[6-(4-chlorophenoxy)hexyl]-2-oxiranecarboxylic acid ethyl ester is an aromatic ether.

Biological Activity

etomoxir is a cell-permeable, irreversible, and stereospecific compound. etomoxir is shown to inhibit carnitine palmitoyltransferase (cpt)-1 and dgat activity in the mitochondria of rat heart h9c2 myoblastic cells at a concentration of 1-80 μm and 40 μm, respectively.

Mechanism of action

R-(+)-Etomoxir (ETO) is a carnitine palmitoyltransferase 1 (CPT1) inhibitor. ETO inhibits oxidative phosphorylation (OxPhos), a mitochondrial electron transport chain (ETC) that generates large amounts of ATP in cells. ETO prevents acylcarnitine formation. It is a step necessary for the translocation of fatty acyl chains from the cytoplasmic lysate to the mitochondrial intermembrane space. This step is essential for the production of ATP from fatty acid oxidation.

R-(+)-Etomoxir(124083-20-1)Related Product Information

• (R)-(+)-Etomoxir sodium salt
• R-(+)-ETOMOXIR
• Etomoxir