| Stereochemistry | ABSOLUTE |
| Molecular Formula | C17H21NO3 |
| Molecular Weight | 287.3535 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCC1=CC=CC2=C1NC3=C2CCO[C@]3(CC)CC(O)=O
InChI
InChIKey=NNYBQONXHNTVIJ-QGZVFWFLSA-N
InChI=1S/C17H21NO3/c1-3-11-6-5-7-12-13-8-9-21-17(4-2,10-14(19)20)16(13)18-15(11)12/h5-7,18H,3-4,8-10H2,1-2H3,(H,19,20)/t17-/m1/s1
| Molecular Formula | C17H21NO3 |
| Molecular Weight | 287.3535 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
R-etodolac (SDX-101) is the non-cyclooxygenase 2-inhibiting R-enantiomer of the non-steroid anti-inflammatory drug etodolac (1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid). The absolute configuration of the enantiomer is R-(-)-etodolac. R-etodolac specifically bound retinoid X receptor (RXRalpha), inhibited RXRalpha transcriptional activity, and induced its degradation by a ubiquitin and proteasome-dependent pathway. In addition R-etodolac can disrupt the beta-catenin signaling pathway. R-etodolac exerts antineoplastic properties. R-etodolac was in phase 2 studies for the treatment of hematologic malignancies however development was discontinued.
CNS Activity
Originator
Approval Year
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
Drug as perpetrator
Drug as victim
Sample Use Guides
Phase 2, multi-center, open label, randomized clinical study for the treatment chronic lymphocytic leukaemia: R-etodolac 600mg tablets + chlorambucil 2mg tablets for 24-26 weeks
Route of Administration:
Oral
R-etodolac induced significant cytotoxicity in MM.1S, U266, RPMI8226, INA-6, and OPM1 MM cell lines with IC50 of 0.49, 1.06, 0.54, 0.22, and 0.47 mM, respectively. R-etodolac also triggers cytotoxicity, with IC50 of 0.62, 0.76 and 0.62 mM, respectively, in Dex-resistant MM.1R, Dox-resistant RPMI-Dox40, and bortezomib-resistant DHL4 cells32. Importantly, R-etodolac does not induce cytotoxicity in PBMCs from 3 healthy volunteers with concentrations as high as 2.5 mM
