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beclobrate (Beclipur / beclobrate / Turec)

✓ Approved

Siegfried Holding AG · Small Molecule · Small Molecule

What is beclobrate?

beclobrate is a small molecule developed by Siegfried Holding AG. It is approved for therapeutic indications.

Drug Profile

Brand NamesBeclipur, beclobrate, Turec
CompanySiegfried Holding AG
Drug ClassSmall Molecule
StatusApproved
Sources: ClinicalTrials.gov, Siegfried Holding AG

Therapeutic Indications

beclobrate is developed for 2 unique indications across 1 therapeutic area.

Therapeutic AreaConditionPhase
Vascular disordersArteriosclerosis✓ Approved
Vascular disordersThrombosis✓ Approved

Related Research Articles

PubMedAngewandte Chemie (International ed. in English)2025-10-06

Nickel-Catalyzed O-Alkylisourea-Enabled Electrochemical Radical C(sp3)-C(sp2) Cross-Coupling.

Yan Yonggang Y, Xiong Weikang W, Li Shasha S, Wang Zhenhua Z et al.

The development of efficient methods to employ naturally abundant alcohol derivatives as C(sp3) precursors for deoxygenative carbon-carbon (C-C) cross-coupling holds significant value for expanding sp3-enriched chemical space. While progress has been made in this area, the field lacks readily accessible, bench-stable alkylation reagents capable of undergoing reductive activation to generate alkyl radicals. Herein, we report an electroreductive nickel-catalyzed system for efficient C(sp3)-C(sp2) radical cross-coupling between aryl electrophiles (halides, triflates, tosylates, and boronic acids) and O-alkylisoureas as radical progenitors. This protocol demonstrates broad substrate scope with good functional group compatibility. Its synthetic utility is highlighted through the preparation of beclobrate analogs and bifonazole, as well as late-stage functionalization of bioactive compounds. Mechanistic investigations support a radical cross-coupling pathway for this transformation.

PMID 41047531
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PubMedOrganic letters2022-04-27

Pd-Catalyzed Cross-Coupling of Sb-Aryl Stibines with Halogenomethyl Arenes to Give Unsymmetirc Diarylmethanes.

Zhang Dejiang D, Xu Zhi Z, Tang Ting T, Le Liyuan L et al.

Herein, we describe a general method for the synthesis of unsymmetric diarylmethanes from (hetero)aryl methyl halides and Sb-aryl stibines. This protocol shows a broad substrate scope and a good functional group tolerance. Drug molecules, including beclobrate 3al and bifemelane 3as, and drug derivatives, including celecoxib 3p, ibuprofen 3ao, and probenecid 3ap, were efficiently synthesized on a gram scale. The possible mechanism is proposed on the basis of the results of control experiments.

PMID 35471895
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PubMedMicrobial drug resistance (Larchmont, N.Y.)2021-05-14

In Silico Evaluation of Human Cathelicidin LL-37 as a Novel Therapeutic Inhibitor of Panton-Valentine Leukocidin Toxin of Methicillin-Resistant Staphylococcus aureus.

Toor Himanshu G HG, Banerjee Devjani I DI, Chauhan Jenabhai B JB

Incidence of drug resistance in clinical isolates of methicillin-resistant Staphylococcus aureus (MRSA) is attributed to its diverse repertoire of virulence factors. Of these virulence determinants, Panton-Valentine Leukocidin (PVL) has been experimentally validated as a prospective drug target due to its conspicuous and comprehensive role in nosocomial infections. This study encompassed an in silico approach to elucidate the antimicrobial potentiality of human cathelicidin LL-37 against PVL toxin of MRSA. Molecular docking studies of LL-37 and its segments with the PVL toxin subunits LukS and LukF were carried out using PatchDock server and the results were refined using FireDock server. The paramount ligand-receptor combination was selected and analyzed based on diverse parametric attributes and compared with the commercial inhibitors of PVL viz. Andrimid, Beclobrate, Beta-sitosterol, Diathymosulfone, and Probucol to determine the most potent inhibitor among them. Our results elucidated that the interaction of LL-37 with the LukS subunit of PVL toxin (minimum global energy of -61.82 kcal/mol) depicted 34 molecular interactions, while the commercial PVL inhibitors depicted fewer and insubstantial interactions. SWISS-ADME (Absorption, Distribution, Metabolism, and Excretion) and ToxinPred analysis of LL-37 further corroborated its null potency of toxicity in systemic milieu. The results obtained may credit this study as basis for the development of LL-37 as a potential inhibitor against virulent MRSA toxins, thereby exalting the treatment regimes for nosocomial infections in health care facilities worldwide.

PMID 33983855
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PubMedOrganic & biomolecular chemistry2017-09-28

B(C6F5)3 catalysed reduction of para-quinone methides and fuchsones to access unsymmetrical diaryl- and triarylmethanes: elaboration to beclobrate.

Mahesh Sriram S, Vijaya Anand Ramasamy R

A mild and efficient method for the synthesis of unsymmetrical diaryl- and triarylmethanes through a B(C6F5)3 catalyzed reduction of para-quinone methides and fuchsones respectively, using the Hantzsch ester as a reducing source has been developed. Detailed mechanistic investigations revealed that the reaction actually proceeds through a Lewis acid-base pair complex derived from B(C6F5)3 and the Hantzsch ester.

PMID 28949362
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PubMedArzneimittel-Forschung1993-01-01

Pharmacokinetics of beclobric acid enantiomers and their conjugates after single and multiple oral dosage of racemic beclobrate.

Mayer S S, Spahn-Langguth H H, Gikalov I I, Mutschler E E

The chiral lipid regulating agent beclobrate (CAS 55937-99-0), which was marketed as racemate, is - like clofibrate - rapidly hydrolyzed to beclobric acid immediately after absorption. Pharmacokinetic data were only available for the total concentration, but not for the two enantiomers. Therefore, the pharmacokinetics of (-)- and (+)-beclobric acid were studied in 8 healthy male volunteers after a single 100 mg dose of rac-beclobrate and under steady state conditions, i.e. after repetitive dosage of 100 mg beclobrate once daily for 8 days. After oral administration unchanged beclobrate was not detected in plasma. Distinct differences were found in the pharmacokinetic parameters of the two beclobric acid enantiomers. The maximum plasma concentrations and the AUC values of the (+)-enantiomer exceeded those of the (-)-enantiomer nearly 2 fold. Beclobric acid, the active metabolite, is converted to an acyl glucuronide. The diastereomeric glucuronides were detected in the plasma of all volunteers, but the differences in the pharmacokinetics were not as evident as for beclobric acid enantiomers. A comparison of the measured steady-state beclobric acid enantiomer concentration and those simulated on the basis of the parameters (open two-compartment model) obtained for a single beclobrate dose showed that the accumulation factor is slightly but nevertheless significantly higher than predicted.

PMID 8447845
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PubMedChirality1993-01-01

In vitro and in vivo irreversible plasma protein binding of beclobric acid enantiomers.

Mayer S S, Mutschler E E, Benet L Z LZ, Sphahn-Langguth H H

Acyl glucuronides are known to be labile conjugates, which undergo hydrolysis and bind irreversibly to proteins. The lipid-regulating agent (+/-)-beclobrate is immediately converted to the free acid after oral administration. Further metabolism leads to formation of the corresponding diastereomeric acyl glucuronides. Beclobric acid glucuronides were quantified by indirect measurement with an HPLC method based on chiral fluorescent derivatization of the carboxylic acid and subsequent normal-phase chromatography. The renal clearance of unchanged drug is low, with almost all drug excreted into urine as glucuronic acid conjugates. Beclobric acid glucuronide is also detectable in plasma. In vitro degradation studies with beclobric acid glucuronide (at a concentration of 5 microM in 150 mM phosphate buffer pH 7.4) exhibited a minor tendency for acyl migration and hydrolysis, i.e., a higher stability than has been observed for the acyl glucuronides of most other drugs. The in vitro degradation half-lives of the two beclobric acid beta-1-O-acyl glucuronides were 22.7 and 25.7 h. After incubation with pooled plasma and human serum albumin in buffer pH 7.4 irreversible binding was measured in vitro. No significant difference between the two enantiomers was detected with respect to the magnitude of in vitro irreversible binding. In 3 healthy male volunteers the extent of irreversible binding of both beclobric acid enantiomers to plasma proteins was investigated after single and multiple oral doses of racemic beclobrate (100 mg once daily). Irreversible binding of both enantiomers was observed in all volunteers. The adduct densities for (-)- and (+)-beclobric acid after single 100 mg beclobrate doses were 0.147 x 10(-4) and 0.177 x 10(-4) mol/mol protein. Multiple dosing increased irreversible binding 3- to 4-fold.

PMID 8338721
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