Structure via PubChem · Public domain (PubChem)
probucol
Sign in to saveAlso known as DH-581, Acetone bis(3,5-di-tert-butyl-4-hydroxyphenyl) mercaptole, 4,4'- (Isopropylidenedithio)bis(2,6-di-tert-butylphenol), Bisbid, Bisphenabid, Biphenabid, Probucolum, Lorelco
Probucol, sold under the trade name Lorelco among others, is an lipid-lowering agent initially developed for the treatment of coronary artery disease. Clinical use was discontinued in some countries after it was found that the drug may have the undesired effect of lowering HDL-C in patients with a previous history of heart disease. It may also cause QT interval prolongation.
Key facts
- Drug.Verifiedfields
- changed
- Drug.verifiedrevid
- 464214831
- Drug.IUPAC_name
- 4,4'-[Propane-2,2-diylbis(thio)]bis(2,6-di-tert-butylphenol)
- Drug.image
- Probucol.svg
- Drug.image_class
- skin-invert-image
- Drug.tradename
- Lorelco
- Drug.MedlinePlus
- a611037
- Drug.metabolism
- minimally renal
- Drug.elimination_half life
- 50-62 h initial, 98 h steady-state
- Drug.excretion
- fecal (84%), urinary (1.9%)
- Drug.IUPHAR_ligand
- 7277
- Drug.CAS_number
- 23288-49-5
- Drug.ATC_prefix
- C10
- Drug.ATC_suffix
- AX02
- Drug.PubChem
- 4912
- Drug.DrugBank
- DB01599
- Drug.ChemSpiderID
- 4743
- Drug.UNII
- P3CTH044XJ
via Wikipedia infobox
Chemical data
- Formula
- C31H48O2S2
- Molecular weight
- 516.8 g/mol
- IUPAC name
- 2,6-ditert-butyl-4-[2-(3,5-ditert-butyl-4-hydroxyphenyl)sulfanylpropan-2-ylsulfanyl]phenol
- SMILES
- CC(C)(C)C1=CC(=CC(=C1O)C(C)(C)C)SC(C)(C)SC2=CC(=C(C(=C2)C(C)(C)C)O)C(C)(C)C
- InChIKey
- FYPMFJGVHOHGLL-UHFFFAOYSA-N
- XLogP
- 11.3
- Polar surface area
- 91.1 Ų
- H-bond donors
- 2
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
Withdrawn- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1977
- Admin. routes
- oral
- Indications
- diabetic nephropathy, cardiovascular disease, peripheral arterial disease, hyperlipidemia
via ChEMBL · EBI
Research
2,056 papers- Probucol.Current atherosclerosis reports · 2000
- Research and Progress of Probucol in Nonalcoholic Fatty Liver Disease.Mini reviews in medicinal chemistry · 2023
- Probucol-bile acid nanoparticles: a novel approach and promising solution to prevent cellular oxidative stress in sensorineural hearing loss.Journal of drug targeting · 2024
- Did we abandon probucol too soon?Current opinion in lipidology · 2015
- Probucol: pharmacology and clinical application.Journal of clinical pharmacology · 1990
via PubMed
Wikidata facts
- Subclass of
- bisphenol
- Mass
- 516.309573
- Has use
- medication
Show 9 more facts
- significant drug interaction
- thioridazine
- chemical formula
- C₃₁H₄₈O₂S₂
- World Health Organisation international non-proprietary name
- probucol
- medical condition treated
- coronary artery disease
- canonical SMILES
- CC(C)(C)C1=CC(=CC(=C1O)C(C)(C)C)SC(C)(C)SC2=CC(=C(C(=C2)C(C)(C)C)O)C(C)(C)C
- subject has role
- antioxidant
- found in taxon
- Penicillium citrinum
- physically interacts with
- ATP binding cassette subfamily A member 1
- Commons category
- Probucol
Sources (5)
via Wikidata · CC0
~5 min read
Encyclopedic overview
9 sectionsContents
- Medical uses
- Adverse effects
- Drug interactions
- Mechanism of action
- Pharmacokinetics
- Research
- Analogues
- Society and culture
- References
{{Infobox drug | Verifiedfields = changed | verifiedrevid = 464214831 | IUPAC_name = 4,4'-[Propane-2,2-diylbis(thio)]bis(2,6-di-tert-butylphenol) | image = Probucol.svg | image_class = skin-invert-image
| pronounce = | tradename = Lorelco | Drugs.com = | MedlinePlus = a611037 | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration =
Excerpted from Wikipedia’s “probucol” article, available under the CC BY-SA 4.0 licence.
Available in 9 languages
via Wikidata sitelinks · CC0