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Chemical Compound Review

TRIPARANOL     2-(4-chlorophenyl)-1-[4-(2...

Synonyms: Drenaren, Clotrox, Diticyl, Acosterina, Metasclene, ...
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Disease relevance of Metasqualene

  • We show here that treatment with Triparanol, a distal inhibitor of cholesterol biosynthesis, induced patterning defects of the autopod at high frequency, including pre-axial syndactyly and post-axial polydactyly, thus reproducing limb anomalies frequently observed in humans [1].
  • Three of the ten Gli3 mutant mice treated with triparanol, which blocks hedgehog signalling upstream of the Gli transcription factors, developed synovial chondromatosis, compared with eight of ten control mice [2].
  • Diazacholesterol and triparanol induced myotonia in rats achieved by single dose administration [3].
  • Triparanol (Trp) is known to cause clinical features similar to those seen in myotonic dystrophy, including myotonia, cataract and baldness [4].
  • The changes seen were dissimilar to those reported with the most commonly used class of hypolipidaemic agents in the clinic, the hydroxymethyl glutaryl coenzyme A (HMGCoA) reductase inhibitors but were reminiscent of those reported for the hypolipidaemic agent Triparanol. which was predictive of toxicity seen in man [5].

High impact information on Metasqualene

  • We identified a variety of experimental drugs with nanomolar affinity for the human EBP (Ki = 0.5-14 nM) such as MDL28815, AY9944, triparanol, and U18666A [6].
  • Gas liquid chromatography-mass spectrometry (GC-MS) profiling of the sterols in the serum of the dams and in extracted embryos shows that in addition to desmosterol Delta24 reductase inhibition the conversion of Delta8 to Delta7 unsaturated sterols is also blocked by Triparanol [7].
  • The true rate of sterol synthesis in liver cells was determined by measurement of the weight of desmosterol produced over a given time period during incubations in the presence of triparanol [8].
  • Calcium increase in mouse skeletal muscles by triparanol: a drug to induce myotonic dystrophy-like clinical manifestations [4].
  • The sterol inhibitors miconazole, AMO 1618, CCC, and MER 29 increased both the incorporation of (14)C-IPP into artemisinin by cell-free extracts and the production of artemisinin in shoot cultures of ARTEMISIA ANNUA [9].

Chemical compound and disease context of Metasqualene


Anatomical context of Metasqualene


Associations of Metasqualene with other chemical compounds


Gene context of Metasqualene


Analytical, diagnostic and therapeutic context of Metasqualene

  • Treatment with triparanol, an inhibitor of Hedgehog signaling, resulted in a 60% decrease in tumor volume, a 30% decrease in cellularity, and a 20% reduction in proliferation rate [20].


  1. Molecular mechanisms underlying limb anomalies associated with cholesterol deficiency during gestation: implications of Hedgehog signaling. Gofflot, F., Hars, C., Illien, F., Chevy, F., Wolf, C., Picard, J.J., Roux, C. Hum. Mol. Genet. (2003) [Pubmed]
  2. Dysregulation of hedgehog signalling predisposes to synovial chondromatosis. Hopyan, S., Nadesan, P., Yu, C., Wunder, J., Alman, B.A. J. Pathol. (2005) [Pubmed]
  3. Diazacholesterol and triparanol induced myotonia in rats achieved by single dose administration. Dromgoole, S.H., Campion, D.S., Peter, J.B. Exp. Neurol. (1975) [Pubmed]
  4. Calcium increase in mouse skeletal muscles by triparanol: a drug to induce myotonic dystrophy-like clinical manifestations. Takahashi, M.P., Kimura, T., Yanagihara, T., Sakoda, S. Neurosci. Lett. (1999) [Pubmed]
  5. Toxicologic lesions associated with two related inhibitors of oxidosqualene cyclase in the dog and mouse. Pyrah, I.T., Kalinowski, A., Jackson, D., Davies, W., Davis, S., Aldridge, A., Greaves, P. Toxicologic pathology. (2001) [Pubmed]
  6. Pharmacological analysis of sterol delta8-delta7 isomerase proteins with [3H]ifenprodil. Moebius, F.F., Reiter, R.J., Bermoser, K., Glossmann, H., Cho, S.Y., Paik, Y.K. Mol. Pharmacol. (1998) [Pubmed]
  7. Limb malformations of rat fetuses exposed to a distal inhibitor of cholesterol biosynthesis. Chevy, F., Illien, F., Wolf, C., Roux, C. J. Lipid Res. (2002) [Pubmed]
  8. The relationship between the rate of hepatic sterol synthesis and the incorporation of [3H]water. Pullinger, C.R., Gibbons, G.F. J. Lipid Res. (1983) [Pubmed]
  9. Effect of Sterol Inhibitors on the Incorporation of 14C-Isopentenyl Pyrophosphate into Artemisinin by a Cell-Free System from Artemisia annua Tissue Cultures and Plants. Kudakasseril, G.J., Lam, L., Staba, E.J. Planta Med. (1987) [Pubmed]
  10. Desmosterol accumulation in rats with experimental myotonia. Seiler, D., Fiehn, W., Kuhn, E. Zeitschrift für klinische Chemie und klinische Biochemie. (1975) [Pubmed]
  11. Measurement of the absolute rates of cholesterol biosynthesis in isolated rat liver cells. Gibbons, G.F., Pullinger, C.R. Biochem. J. (1977) [Pubmed]
  12. Adrenocortical function of rats under prolonged administration of lipidosis-inducing drugs. Duncker, G., Hartmann, F., Mohr, K. Naunyn Schmiedebergs Arch. Pharmacol. (1982) [Pubmed]
  13. Drug absorption from the small intestine of the triparanol-treated rat in situ. Venho, V.M. Acta pharmacologica et toxicologica. (1976) [Pubmed]
  14. Myeloid bodies formation in triparanol treated cultured cells. Kalina, M., Bubis, J.J. Virchows Archiv. B: Cell pathology. (1975) [Pubmed]
  15. Functional and biochemical evidence of damage to enterocytes induced by triparanol: role of lysosomes and the effect of gluten-free diet. Soulé, J.C., Neale, G., Peters, T.J. Clinical science and molecular medicine. (1976) [Pubmed]
  16. Fatty acid metabolism in Paramecium. Oleic acid metabolism and inhibition of polyunsaturated fatty acid synthesis by triparanol. Rhoads, D.E., Kaneshiro, E.S. Biochim. Biophys. Acta (1984) [Pubmed]
  17. Intestinal absorption of tolfenamic acid at experimental malabsorption states in rats. Senius, K.E., Fendrich, Z., Hradil, J. Arzneimittel-Forschung. (1981) [Pubmed]
  18. Absorption of morphine, butylscopolamine, mecamylamine and phenobarbitone from the small intestine of the triparanol-treated rat in situ. Venho, V.M. Arzneimittel-Forschung. (1975) [Pubmed]
  19. Selective biliary secretion of basal and glucagon-inhibited neutral sterol after triparanol administration. Meyers, W.C., Hanks, J.B., Jakoi, L., Quarfordt, S., Jones, R.S. Surgery (1980) [Pubmed]
  20. Constitutive hedgehog signaling in chondrosarcoma up-regulates tumor cell proliferation. Tiet, T.D., Hopyan, S., Nadesan, P., Gokgoz, N., Poon, R., Lin, A.C., Yan, T., Andrulis, I.L., Alman, B.A., Wunder, J.S. Am. J. Pathol. (2006) [Pubmed]
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