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[ CAS No. 59721-29-8 ] {[proInfo.proName]}

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Chemical Structure| 59721-29-8
Chemical Structure| 59721-29-8
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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 [ 59721-29-8 ]

CAS No. :59721-29-8 MDL No. :MFCD00941410
Formula : C21H26N4O8S Boiling Point : -
Linear Structure Formula :- InChI Key :FSEKIHNIDBATFG-UHFFFAOYSA-N
M.W : 494.52 Pubchem ID :5284360
Synonyms :
Camostat mesilate;FOY305;Foipan;Camostat (mesylate);FOY-S980
Chemical Name :4-(2-(2-(Dimethylamino)-2-oxoethoxy)-2-oxoethyl)phenyl 4-guanidinobenzoate methanesulfonate

Calculated chemistry of [ 59721-29-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 34
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.24
Num. rotatable bonds : 11
Num. H-bond acceptors : 9.0
Num. H-bond donors : 4.0
Molar Refractivity : 124.29
TPSA : 197.56 ?2

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -9.0 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.15
Log Po/w (XLOGP3) : 0.45
Log Po/w (WLOGP) : 1.78
Log Po/w (MLOGP) : 1.28
Log Po/w (SILICOS-IT) : 1.36
Consensus Log Po/w : 1.41

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 2.0
Egan : 1.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.72
Solubility : 0.932 mg/ml ; 0.00188 mol/l
Class : Soluble
Log S (Ali) : -4.17
Solubility : 0.0337 mg/ml ; 0.0000681 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.87
Solubility : 0.00666 mg/ml ; 0.0000135 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 4.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.34

Safety of [ 59721-29-8 ]

Signal Word:Danger Class:9
Precautionary Statements:P501-P273-P260-P270-P264-P280-P391-P314-P337+P313-P305+P351+P338-P301+P312+P330 UN#:3077
Hazard Statements:H302-H319-H372-H410 Packing Group:Ⅲ
GHS Pictogram:
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