triparanol
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 It was withdrawn in 1962 due to severe adverse effects such as nausea and vomiting, vision loss due to irreversible cataracts, alopecia, skin disorders (e.g., dryness, itching,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. — NCATS
Clinical trial activity
0 trials · 0 clinical orgs · 0 marketing orgs
Indications
Approved for
Mechanism of action
- Delta(24)-sterol reductaseINHIBITOR
DHCR24 inhibitor
Inhibits 24-dehydrocholesterol reductase, which catalyzes the final step of cholesterol biosynthesis, the conversion of desmosterol into cholesterol. This results in tissue accumulation of desmosterol, which in turn is responsible for the side effects of triparanol.
Chemistry & pharmacology
SMILES
CCN(CC)CCOC1=CC=C(C=C1)C(O)(CC2=CC=C(Cl)C=C2)C3=CC=C(C)C=C3- Mol. weight
- 438.001 g/mol
- Lipinski Ro5
- 1 violation(s)
- Rule of 3
- No
- Chirality
- Racemic Mixture
- Inorganic
- No
- Polymer
- No
Oral
No
Parenteral
No
Topical
No
Sources
- WikipediaTriparanol ↗
- NCATS63S8C3RXGS ↗
- ChEMBLCHEMBL187709 ↗
Also known as
- clotrox
- metasclene
- metasqualene
- trianel
- triparanol
- triparanol
- triparanol
- triparanol
- triparanol
- triparanol
- triparin
- tropalin