Stereochemistry | RACEMIC |
Molecular Formula | C27H32ClNO2 |
Molecular Weight | 438.001 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCN(CC)CCOC1=CC=C(C=C1)C(O)(CC2=CC=C(Cl)C=C2)C3=CC=C(C)C=C3
InChI
InChIKey=SYHDSBBKRLVLFF-UHFFFAOYSA-N
InChI=1S/C27H32ClNO2/c1-4-29(5-2)18-19-31-26-16-12-24(13-17-26)27(30,23-10-6-21(3)7-11-23)20-22-8-14-25(28)15-9-22/h6-17,30H,4-5,18-20H2,1-3H3
Molecular Formula | C27H32ClNO2 |
Molecular Weight | 438.001 |
Charge | 0 |
Count |
MOL RATIO
1 MOL RATIO (average) |
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Triparanol (brand and developmental code names MER/29) is a 24-dehydro cholesterol reductase inhibitor, which is an enzyme involved in the biosynthesis of cholesterol. It has antitumor properties, such as decreasing proliferation and inducing apoptosis in many cancer cell lines and slowing tumor growth in a mouse xenograft model. It can also decrease Hedgehog pathway signaling in cancer cells. Triparanol was the first synthetic cholesterol-lowering drug. It was withdrawn in 1962 due to severe adverse effects such as nausea and vomiting, vision loss due to irreversible cataracts, alopecia, skin disorders (e.g., dryness, itching, peeling, and "fish-scale" texture), and accelerated atherosclerosis and is now considered to be obsolete.
Originator
Approval Year
Doses
AEs
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Tox targets
Sourcing
PubMed
Patents
Sample Use Guides
Lung cancer A549; breast cancer MCF7; hepatocellular carcinoma (liver cancer) HepG2; pancreatic cancer cell line bxpc3; prostate cancer cell line LnCAP; melanoma G361; and normal fibroblast were used for activity evaluation. One day before treatment, cells (5 _ 104) will be plated in 96-wells in growth medium without antibiotics and with reduced serum (2.5%). Cells will be incubated with Triparanol at different concentrations (0.5 and 1 mkM) as indicated with or without cholesterol (5 lM) in the same medium until ready for further analysis. Cells will be treated with Triparanol in 96-well plates for 6–7 days. Cell proliferation was assayed by MTS assay (Promega) according to the manufacturer’s protocol.