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[ CAS No. 23828-92-4 ] {[proInfo.proName]}

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Chemical Structure| 23828-92-4
Chemical Structure| 23828-92-4
Structure of 23828-92-4 * Storage: {[proInfo.prStorage]}

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Frauke Assmus ; Jean-Sélim Driouich ; Rana Abdelnabi , et al. DOI: PubMed ID:

Abstract: In the absence of drugs to treat or prevent COVID-19, drug repurposing can be a valuable strategy. Despite a substantial number of clinical trials, drug repurposing did not deliver on its promise. While success was observed with some repurposed drugs (e.g., remdesivir, dexamethasone, tocilizumab, baricitinib), others failed to show clinical efficacy. One reason is the lack of clear translational processes based on adequate preclinical profiling before clinical evaluation. Combined with limitations of existing in vitro and in vivo models, there is a need for a systematic approach to urgent antiviral drug development in the context of a global pandemic. We implemented a methodology to test repurposed and experimental drugs to generate robust preclinical evidence for further clinical development. This translational drug development platform comprises in vitro, ex vivo, and in vivo models of SARS-CoV-2, along with pharmacokinetic modeling and simulation approaches to evaluate exposure levels in plasma and target organs. Here, we provide examples of identified repurposed antiviral drugs tested within our multidisciplinary collaboration to highlight lessons learned in urgent antiviral drug development during the COVID-19 pandemic. Our data confirm the importance of assessing in vitro and in vivo potency in multiple assays to boost the translatability of pre-clinical data. The value of pharmacokinetic modeling and simulations for compound prioritization is also discussed. We advocate the need for a standardized translational drug development platform for mild-to-moderate COVID-19 to generate preclinical evidence in support of clinical trials. We propose clear prerequisites for progression of drug candidates for repurposing into clinical trials. Further research is needed to gain a deeper understanding of the scope and limitations of the presented translational drug development platform.

Keywords: COVID-19 ; drug repurposing ; translational medicine ; pandemics ; clinical trials

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Product Details of [ 23828-92-4 ]

CAS No. :23828-92-4 MDL No. :MFCD00078932
Formula : C13H19Br2ClN2O Boiling Point : -
Linear Structure Formula :- InChI Key :QNVKOSLOVOTXKF-UHFFFAOYSA-N
M.W : 414.56 Pubchem ID :108013
Synonyms :
NA-872 hydrochloride;Ambroxol (hydrochloride);Mucosolvan;Ebromin;Duramucal;Ambro-Puren Ambrobeta;Ambril;Abrohexal;NA 872;Ambroxol HCl
Chemical Name :trans-4-((2-Amino-3,5-dibromobenzyl)amino)cyclohexanol hydrochloride

Calculated chemistry of [ 23828-92-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.54
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 3.0
Molar Refractivity : 88.87
TPSA : 58.28 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.39 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 3.44
Log Po/w (WLOGP) : 3.85
Log Po/w (MLOGP) : 2.95
Log Po/w (SILICOS-IT) : 2.87
Consensus Log Po/w : 2.62

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.61
Solubility : 0.0101 mg/ml ; 0.0000244 mol/l
Class : Moderately soluble
Log S (Ali) : -4.34
Solubility : 0.0187 mg/ml ; 0.0000452 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.77
Solubility : 0.00704 mg/ml ; 0.000017 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.78

Safety of [ 23828-92-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:
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[ 23828-92-4 ]

Chemical Structure| 18683-91-5

A233160[ 18683-91-5 ]

rel-(1r,4r)-4-((2-Amino-3,5-dibromobenzyl)amino)cyclohexan-1-ol

Reason: Free-Salt

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