Probucol

Probucol
Systematic (IUPAC) name
4,4'-[propane-2,2-diylbis(thio)]bis(2,6-di-tert-butylphenol)
Clinical data
AHFS/Drugs.com Micromedex Detailed Consumer Information
MedlinePlus a611037
Identifiers
CAS Number 23288-49-5 YesY
ATC code C10AX02 (WHO)
PubChem CID 4912
IUPHAR/BPS 7277
DrugBank DB01599 YesY
ChemSpider 4743 YesY
UNII P3CTH044XJ YesY
KEGG D00476 YesY
ChEBI CHEBI:8427 N
ChEMBL CHEMBL608 YesY
Synonyms 2,6-di-tert-butyl-4-({2-[(3,5-di-tert-butyl-4-hydroxyphenyl)sulfanyl]propan-2-yl}sulfanyl)phenol
Chemical data
Formula C31H48O2S2
Molar mass 516.844 g/mol
 NYesY (what is this?)  (verify)

Probucol is an anti-hyperlipidemic drug[1] initially developed in the treatment of coronary artery disease.

However, clinical trials were stopped after it was found that it may lower HDL in patients with a previous history of heart disease.

Probucol was initially developed in the 1970s by a chemical company to maximize airplane tire longevity. Probucol is associated with QT interval prolongation.

Mechanism

Probucol lowers the level of cholesterol in the bloodstream by increasing the rate of LDL catabolism. Additionally, probucol may inhibit cholesterol synthesis and delay cholesterol absorption.[2] Probucol is a powerful antioxidant which inhibits the oxidation of cholesterol in LDLs; this slows the formation of foam cells, which contribute to atherosclerotic plaques.

It is believed to act at ABCA1.[3]

It also lowers levels of HDL.[4]

References

  1. Yamamoto A (December 2008). "A Uniqe Antilipidemic Drug - Probucol". J. Atheroscler. Thromb. 15 (6): 304–5. doi:10.5551/jat.E621. PMID 19075491.
  2. "Probucol. Drugs.com web site.
  3. Favari E, Zanotti I, Zimetti F, Ronda N, Bernini F, Rothblat GH (December 2004). "Probucol inhibits ABCA1-mediated cellular lipid efflux". Arterioscler. Thromb. Vasc. Biol. 24 (12): 2345–50. doi:10.1161/01.ATV.0000148706.15947.8a. PMID 15514211.
  4. Miida T, Seino U, Miyazaki O, et al. (October 2008). "Probucol markedly reduces HDL phospholipids and elevated prebeta1-HDL without delayed conversion into alpha-migrating HDL: putative role of angiopoietin-like protein 3 in probucol-induced HDL remodeling". Atherosclerosis 200 (2): 329–35. doi:10.1016/j.atherosclerosis.2007.12.031. PMID 18279878.



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