Probucol

Probucol
Clinical data
Trade names	Lorelco
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 ;
	(what is this?) (verify)

Probucol, sold under the trade name Lorelco among others, is an anti-hyperlipidemic drug[1] initially developed for the treatment of coronary artery disease. Clinical development was discontinued after it was found that the drug may have the undesired effect of lowering HDL in patients with a previous history of heart disease. It may also cause QT interval prolongation.

Probucol was initially developed in the 1970s by a chemical company to maximize airplane tire longevity.

Mechanism of action

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 form atherosclerotic plaques.

Probucol has also been shown to inhibit ABCA1-dependent cholesterol transport,[3] which may contribute to its known effect of lowering HDL.[4]

References

Yamamoto A (11 December 2008). "A Unique Antilipidemic Drug - Probucol". J. Atheroscler. Thromb. 15 (6): 304–5. doi:10.5551/jat.E621. PMID 19075491. Retrieved 2020-01-29.
"Probucol (Systemic)". Drugs.com. 1998-08-24. Retrieved 2020-01-29.
Favari E, Zanotti I, Zimetti F, Ronda N, Bernini F, Rothblat GH (28 October 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. Retrieved 2020-01-29.
Miida T, Seino U, Miyazaki O, Hanyu O, Hirayama S, Saito T, Ishikawa Y, Akamatsu S, Nakano T, Katsuyuki N, Okazaki M, Okada M (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. Retrieved 2020-01-29.

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[pmid19075491-1] Yamamoto A (11 December 2008). "A Unique Antilipidemic Drug - Probucol". J. Atheroscler. Thromb. 15 (6): 304–5. doi:10.5551/jat.E621. PMID 19075491. Retrieved 2020-01-29.

[2] "Probucol (Systemic)". Drugs.com. 1998-08-24. Retrieved 2020-01-29.

[pmid15514211-3] Favari E, Zanotti I, Zimetti F, Ronda N, Bernini F, Rothblat GH (28 October 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. Retrieved 2020-01-29.

[4] Miida T, Seino U, Miyazaki O, Hanyu O, Hirayama S, Saito T, Ishikawa Y, Akamatsu S, Nakano T, Katsuyuki N, Okazaki M, Okada M (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. Retrieved 2020-01-29.