title: How many drugs are catecholics.
abstract: By examination of the 8659 drugs recorded in the Comprehensive Medicinal Chemistry (CMC) database, 78 catecholics (including five pyrogallolics) were identified, of which 17 are currently prescribed by FDA. Through analyzing the substituent patterns, ClogPs and O-H bond dissociation enthalpies (BDEs) of the catecholic drugs, some molecular features that may benefit circumventing the toxicity of catecholics were revealed: i) strong electron-donating substituents are excluded; ii) ClogP 3; iii) an energy penalty exists for quinone formation. Besides, the present analyses also suggest that the clinical usage and dosage of currently prescribed catecholic drugs are of importance in designing or screening catecholic antioxidants.
authors.affiliation: Shandong Provincial Research Center for Bioinformatic Engineering and Technique, Center for Advanced Study, Shandong University of Technology, Zibo 255049, PR China.
authors.forename: Da-Peng
authors.initials: DP
authors.lastname: Yang
authors.forename: Hong-Fang
authors.initials: HF
authors.lastname: Ji
authors.forename: Guang-Yan
authors.initials: GY
authors.lastname: Tang
authors.forename: Wei
authors.initials: W
authors.lastname: Ren
authors.forename: Hong-Yu
authors.initials: HY
authors.lastname: Zhang
mesh_terms: D000975:Antioxidants / Q000737:chemistry; D002396:Catechols / Q000737:chemistry*; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D019992:Databases as Topic; D015195:Drug Design; D004353:Drug Evaluation, Preclinical; D005609:Free Radicals; D006859:Hydrogen / Q000737:chemistry; D006860:Hydrogen Bonding; D008956:Models, Chemical; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry; D013816:Thermodynamics
chemical_list: D000975:Antioxidants; D002396:Catechols; D005609:Free Radicals; D006859:Hydrogen; D010100:Oxygen