Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Probucol
- DrugBank Accession Number
- DB01599
- Background
A drug used to lower LDL and HDL cholesterol yet has little effect on serum-triglyceride or VLDL cholesterol. (From Martindale, The Extra Pharmacopoeia, 30th ed, p993).
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Probucol (DB01599)
- Weight
- Average: 516.842
Monoisotopic: 516.30957216 - Chemical Formula
- C31H48O2S2
- Synonyms
- 4,4'- (Isopropylidenedithio)bis(2,6-di-tert-butylphenol)
- Acetone bis(3,5-di-tert-butyl-4-hydroxyphenyl) mercaptole
- Biphenabid
- Bisbid
- Bisphenabid
- Probucol
- Probucolum
- External IDs
- DH-581
Pharmacology
- Indication
Used to lower LDL and HDL cholesterol.
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Probucol lowers cholesterol levels by increasing LDL (low-density lipoprotein) breakdown. Additionally, probucol may inhibit cholesterol synthesis and delay cholesterol absorption. Probucol is a powerful antioxidant drug normally used to prevent vascular disease caused by the free radicals in the body.
- Mechanism of action
Probucol lowers serum cholesterol by increasing the fractional rate of low-density lipoprotein (LDL) catabolism in the final metabolic pathway for cholesterol elimination from the body. This drug may also act to inhibit the initial stages of cholesterol synthesis and act to inhibit the absorption of cholesterol from the diet. Recent information suggests that probucol may inhibit the oxidation and tissue deposition of LDL cholesterol, thereby inhibiting atherogenesis. It appears to inhibits ABCA1-mediated cellular lipid efflux.
Target Actions Organism APhospholipid-transporting ATPase ABCA1 inhibitorHumans ULiver carboxylesterase 1 Not Available Humans - Absorption
Absorption from the gastrointestinal tract is limited and variable (about 7%).
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Ranges from 12 hours to more than 500 hours, the longest half-life probably being in adipose tissue.
- Clearance
Not Available
- Adverse Effects
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Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcrivastine The risk or severity of QTc prolongation can be increased when Acrivastine is combined with Probucol. Adenosine The risk or severity of QTc prolongation can be increased when Adenosine is combined with Probucol. Ajmaline The risk or severity of QTc prolongation can be increased when Ajmaline is combined with Probucol. Albuterol The risk or severity of QTc prolongation can be increased when Salbutamol is combined with Probucol. Alfuzosin The risk or severity of QTc prolongation can be increased when Alfuzosin is combined with Probucol. - Food Interactions
- Take with food. Food increases bioavailability.
Products
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- Lesterol / Lurselle / Serterol / Sinlestal / Superlipid
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Lorelco Tablet 250 mg Oral Sanofi Aventis 1995-12-31 2009-04-03 Canada 
Categories
- ATC Codes
- C10AX02 — Probucol
- Drug Categories
- Anticholesteremic Agents
- Antioxidants
- Benzene Derivatives
- Biological Factors
- Compounds used in a research, industrial, or household setting
- Hypolipidemic Agents
- Lipid Modifying Agents
- Lipid Modifying Agents, Plain
- Lipid Regulating Agents
- Moderate Risk QTc-Prolonging Agents
- Phenols
- Protective Agents
- QTc Prolonging Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Phenylpropanes
- Direct Parent
- Phenylpropanes
- Alternative Parents
- Thiophenol ethers / Phenols / Dithioketals / Alkylarylthioethers / Sulfenyl compounds / Organooxygen compounds / Hydrocarbon derivatives
- Substituents
- Alkylarylthioether / Aromatic homomonocyclic compound / Aryl thioether / Dithioketal / Hydrocarbon derivative / Organic oxygen compound / Organooxygen compound / Organosulfur compound / Phenol / Phenylpropane
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- polyphenol, dithioketal (CHEBI:8427)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- P3CTH044XJ
- CAS number
- 23288-49-5
- InChI Key
- FYPMFJGVHOHGLL-UHFFFAOYSA-N
- 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
- IUPAC Name
- 2,6-di-tert-butyl-4-({2-[(3,5-di-tert-butyl-4-hydroxyphenyl)sulfanyl]propan-2-yl}sulfanyl)phenol
- SMILES
- CC(C)(SC1=CC(=C(O)C(=C1)C(C)(C)C)C(C)(C)C)SC1=CC(=C(O)C(=C1)C(C)(C)C)C(C)(C)C
References
- Synthesis Reference
Claudio Giordano, Giuseppe Barreca, "Process for preparing an intermediate useful in the syntheis of probucol." U.S. Patent US5157156, issued July, 1988.
US5157156- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015537
- KEGG Drug
- D00476
- KEGG Compound
- C07373
- PubChem Compound
- 4912
- PubChem Substance
- 46508876
- ChemSpider
- 4743
- BindingDB
- 50007260
- 8699
- ChEBI
- 8427
- ChEMBL
- CHEMBL608
- ZINC
- ZINC000001530755
- Therapeutic Targets Database
- DAP000916
- PharmGKB
- PA451107
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Probucol
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data4 Completed Health Services Research Healthy Volunteers (HV) 1 somestatus stop reason just information to hide 4 Completed Treatment Arteriosclerosis Obliterans / Type 2 Diabetes Mellitus 1 somestatus stop reason just information to hide 4 Completed Treatment Atherosclerosis Cerebral Infarction 1 somestatus stop reason just information to hide 4 Completed Treatment Chronic Nephropathy 1 somestatus stop reason just information to hide 4 Completed Treatment Diabetic Nephropathy 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Gallipot
- Letco Medical Inc.
- Dosage Forms
Form Route Strength Tablet Oral 250 mg Tablet Oral - Prices
Unit description Cost Unit Probucol powder 2.45USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 125 °C PhysProp - Predicted Properties
Property Value Source Water Solubility 4.18e-05 mg/mL ALOGPS logP 8.92 ALOGPS logP 10.57 Chemaxon logS -7.1 ALOGPS pKa (Strongest Acidic) 10.29 Chemaxon pKa (Strongest Basic) -5.1 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 40.46 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 159.26 m3·mol-1 Chemaxon Polarizability 62.35 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.992 Blood Brain Barrier + 0.8118 Caco-2 permeable + 0.778 P-glycoprotein substrate Non-substrate 0.6117 P-glycoprotein inhibitor I Non-inhibitor 0.8088 P-glycoprotein inhibitor II Non-inhibitor 0.8381 Renal organic cation transporter Non-inhibitor 0.868 CYP450 2C9 substrate Non-substrate 0.6651 CYP450 2D6 substrate Non-substrate 0.6765 CYP450 3A4 substrate Substrate 0.5288 CYP450 1A2 substrate Non-inhibitor 0.8029 CYP450 2C9 inhibitor Non-inhibitor 0.8098 CYP450 2D6 inhibitor Non-inhibitor 0.9232 CYP450 2C19 inhibitor Non-inhibitor 0.7852 CYP450 3A4 inhibitor Non-inhibitor 0.7851 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8793 Ames test Non AMES toxic 0.9398 Carcinogenicity Non-carcinogens 0.6603 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 1.9829 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9868 hERG inhibition (predictor II) Non-inhibitor 0.7771
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 256.488568 predictedDarkChem Lite v0.1.0 [M-H]- 257.835168 predictedDarkChem Lite v0.1.0 [M-H]- 230.1628 predictedDeepCCS 1.0 (2019) [M+H]+ 256.873368 predictedDarkChem Lite v0.1.0 [M+H]+ 258.547868 predictedDarkChem Lite v0.1.0 [M+H]+ 232.55836 predictedDeepCCS 1.0 (2019) [M+Na]+ 256.472468 predictedDarkChem Lite v0.1.0 [M+Na]+ 257.122168 predictedDarkChem Lite v0.1.0 [M+Na]+ 238.47133 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Catalyzes the translocation of specific phospholipids from the cytoplasmic to the extracellular/lumenal leaflet of membrane coupled to the hydrolysis of ATP (PubMed:24097981, PubMed:35974019). Thereby, participates in phospholipid transfer to apolipoproteins to form nascent high density lipoproteins/HDLs (PubMed:14754908). Transports preferentially phosphatidylcholine over phosphatidylserine (PubMed:24097981). May play a similar role in the efflux of intracellular cholesterol to apolipoproteins and the formation of nascent high density lipoproteins/HDLs (PubMed:10533863, PubMed:14754908, PubMed:24097981, PubMed:35974019). Translocates phospholipids from the outer face of the plasma membrane and forces it through its gateway and annulus into an elongated hydrophobic tunnel in its extracellular domain (PubMed:35974019)
- Specific Function
- Abc-type transporter activity
- Gene Name
- ABCA1
- Uniprot ID
- O95477
- Uniprot Name
- Phospholipid-transporting ATPase ABCA1
- Molecular Weight
- 254299.89 Da
References
- Favari E, Zanotti I, Zimetti F, Ronda N, Bernini F, Rothblat GH: Probucol inhibits ABCA1-mediated cellular lipid efflux. Arterioscler Thromb Vasc Biol. 2004 Dec;24(12):2345-50. Epub 2004 Oct 28. [Article]
- Yamamoto A: A uniqe antilipidemic drug--probucol. J Atheroscler Thromb. 2008 Dec;15(6):304-5. Epub 2008 Dec 11. [Article]
- de la Llera-Moya M, Drazul-Schrader D, Asztalos BF, Cuchel M, Rader DJ, Rothblat GH: The ability to promote efflux via ABCA1 determines the capacity of serum specimens with similar high-density lipoprotein cholesterol to remove cholesterol from macrophages. Arterioscler Thromb Vasc Biol. 2010 Apr;30(4):796-801. doi: 10.1161/ATVBAHA.109.199158. Epub 2010 Jan 14. [Article]
- Sirtori CR, Manzoni C, Lovati MR: Mechanisms of lipid-lowering agents. Cardiology. 1991;78(3):226-35. [Article]
- Shichiri M, Takanezawa Y, Rotzoll DE, Yoshida Y, Kokubu T, Ueda K, Tamai H, Arai H: ATP-binding cassette transporter A1 is involved in hepatic alpha-tocopherol secretion. J Nutr Biochem. 2010 May;21(5):451-6. doi: 10.1016/j.jnutbio.2009.02.002. Epub 2009 May 7. [Article]
- Arakawa R, Tsujita M, Iwamoto N, Ito-Ohsumi C, Lu R, Wu CA, Shimizu K, Aotsuka T, Kanazawa H, Abe-Dohmae S, Yokoyama S: Pharmacological inhibition of ABCA1 degradation increases HDL biogenesis and exhibits antiatherogenesis. J Lipid Res. 2009 Nov;50(11):2299-305. doi: 10.1194/jlr.M900122-JLR200. Epub 2009 May 20. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs (PubMed:18762277, PubMed:7980644, PubMed:9169443, PubMed:9490062). Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester (PubMed:18762277, PubMed:7980644, PubMed:9169443, PubMed:9490062). Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine (PubMed:7980644). Catalyzes the transesterification of cocaine to form cocaethylene (PubMed:7980644). Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate (PubMed:7980644). Converts monoacylglycerides to free fatty acids and glycerol. Hydrolyzes of 2-arachidonoylglycerol and prostaglandins (PubMed:21049984). Hydrolyzes cellular cholesteryl esters to free cholesterols and promotes reverse cholesterol transport (RCT) by facilitating both the initial and final steps in the process (PubMed:11015575, PubMed:16024911, PubMed:16971496, PubMed:18762277). First of all, allows free cholesterol efflux from macrophages to extracellular cholesterol acceptors and secondly, releases free cholesterol from lipoprotein-delivered cholesteryl esters in the liver for bile acid synthesis or direct secretion into the bile (PubMed:16971496, PubMed:18599737, PubMed:18762277)
- Specific Function
- Carboxylesterase activity
- Gene Name
- CES1
- Uniprot ID
- P23141
- Uniprot Name
- Liver carboxylesterase 1
- Molecular Weight
- 62520.62 Da
References
- Jeon SM, Park YB, Kwon OS, Huh TL, Lee WH, Do KM, Park T, Choi MS: Vitamin E supplementation alters HDL-cholesterol concentration and paraoxonase activity in rabbits fed high-cholesterol diet: comparison with probucol. J Biochem Mol Toxicol. 2005;19(5):336-46. [Article]
Drug created at August 29, 2007 18:43 / Updated at February 21, 2021 18:51