triparanol

Small moleculeexperimental

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 It was withdrawn in 1962 due to severe adverse effects such as nausea and vomiting, vision loss due to irreversible cataracts, alopecia, skin disorders (e.g., dryness, itching,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

Phase 1
0
Phase 2
0
Phase 3
0
Phase 4
0

Indications

Mechanism of action

  • 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

Loading structure…

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

Also known as

  • clotrox
  • metasclene
  • metasqualene
  • trianel
  • triparanol
  • triparanol
  • triparanol
  • triparanol
  • triparanol
  • triparanol
  • triparin
  • tropalin