| Stereochemistry | ABSOLUTE |
| Molecular Formula | C17H23ClO4 |
| Molecular Weight | 326.815 |
| Optical Activity | ( + ) |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCOC(=O)[C@@]2(CCCCCCOC1=CC=C(Cl)C=C1)CO2
InChI
InChIKey=DZLOHEOHWICNIL-QGZVFWFLSA-N
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
Etomoxir is an irreversible inhibitor of carnitine O-palmitoyltransferase (CPT) I. It inhibits fatty acid oxidation and fatty acid and cholesterol synthesis in an enantiomer-selective manner: only the R-enantiomer of etomoxir inhibits fatty acid oxidation, S-enantiomer inhibits fatty acid and cholesterol synthesis but not fatty acid oxidation. Etomoxir was studied for the treatment of congestive heart failure and type II diabetes, however, its development was discontinued.
CNS Activity
Originator
Approval Year
Doses
AEs
Sourcing
PubMed
Sample Use Guides
The ERGO (etomoxir for the recovery of glucose oxidation) study was designed in which etomoxir was tested at a dose of 80 and 40 mg compared with placebo for a period of 6 months in patients with CHF (congestive heart failure).
Route of Administration:
Oral
The apoptotic and chemo-sensitizing action of the fatty acid oxidation inhibitor etomoxir was analyzed in human acute myeloid leukemia cells. Etomoxir caused negligible lethality at concentrations up to 100 µM, but efficaciously cooperated to cause apoptosis with the anti-leukemic agent arsenic trioxide (ATO, Trisenox), and with lower efficacy with other anti-tumour drugs (etoposide, cisplatin), in HL60 cells. Etomoxir-ATO cooperation was also observed in NB4 human acute promyelocytic cells, but not in normal (non-tumour) mitogen-stimulated human peripheral blood lymphocytes. Biochemical determinations in HL60 cells indicated that etomoxir (25-200 µM) dose-dependently inhibited mitochondrial respiration while slightly stimulating glycolysis, and only caused marginal alterations in total ATP content and adenine nucleotide pool distribution.
ACTIVE MOIETY
