Probucol

Probucol
Clinical data
Other names	2,6-di-tert-butyl-4-({2-[(3,5-di-tert-butyl-4-hydroxyphenyl)sulfanyl]propan-2-yl}sulfanyl)phenol
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a611037
ATC code	C10AX02 (WHO) ;
Identifiers
	IUPAC name 4,4'-[Propane-2,2-diylbis(thio)]bis(2,6-di-tert-butylphenol);
CAS Number	23288-49-5 ;
PubChem CID	4912;
IUPHAR/BPS	7277;
DrugBank	DB01599 ;
ChemSpider	4743 ;
UNII	P3CTH044XJ;
KEGG	D00476 ;
ChEBI	CHEBI:8427 ;
ChEMBL	ChEMBL608 ;
CompTox Dashboard (EPA)	DTXSID2045440 ;
ECHA InfoCard	100.041.404
Chemical and physical data
Formula	C31H48O2S2
Molar mass	516.84 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES S(c1cc(c(O)c(c1)C(C)(C)C)C(C)(C)C)C(Sc2cc(c(O)c(c2)C(C)(C)C)C(C)(C)C)(C)C;
	InChI InChI=1S/C31H48O2S2/c1-27(2,3)21-15-19(16-22(25(21)32)28(4,5)6)34-31(13,14)35-20-17-23(29(7,8)9)26(33)24(18-20)30(10,11)12/h15-18,32-33H,1-14H3 ; Key:FYPMFJGVHOHGLL-UHFFFAOYSA-N ;
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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

Yamamoto A (December 2008). "A Unique Antilipidemic Drug - Probucol". J. Atheroscler. Thromb. 15 (6): 304–5. doi:10.5551/jat.E621. PMID 19075491.
"Probucol. Drugs.com web site
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.
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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[pmid19075491-1] Yamamoto A (December 2008). "A Unique Antilipidemic Drug - Probucol". J. Atheroscler. Thromb. 15 (6): 304–5. doi:10.5551/jat.E621. PMID 19075491.

[2] "Probucol. Drugs.com web site

[pmid15514211-3] 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.