SORBINIL

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Synonyms
Status
Molecule Category UNKNOWN
UNII G4186B906P
EPA CompTox DTXSID0023587

Structure

InChI Key LXANPKRCLVQAOG-NSHDSACASA-N
Smiles O=C1NC(=O)[C@@]2(CCOc3ccc(F)cc32)N1
InChI
InChI=1S/C11H9FN2O3/c12-6-1-2-8-7(5-6)11(3-4-17-8)9(15)13-10(16)14-11/h1-2,5H,3-4H2,(H2,13,14,15,16)/t11-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C11H9FN2O3
Molecular Weight 236.2
AlogP 0.64
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 0.0
Polar Surface Area 67.43
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 17.0

Bioactivity

Mechanism of Action Action Reference
Aldose reductase inhibitor INHIBITOR PubMed PubMed PubMed
Protein: Aldose reductase
Description: Aldo-keto reductase family 1 member B1
Organism : Homo sapiens
P15121 ENSG00000085662
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Oxidoreductase
- 17-8000 - - 36-95
Assay Description Organism Bioactivity Reference
In vitro inhibitory activity against aldehyde reductase 1 (ALR1) from rat kidney. None 29.0 nM
Inhibitory Activity against Human recombinant Aldose Reductase (wild type) None 918.6 nM
In vitro % decrease of aldose reductase measured in isolated partially purified bovine lens preparations at 10e-7 M concentration None 10.0 %
In vitro aldose reductase inhibitory activity measured by NADPH-dependent inhibition of glyceraldehyde reduction in a partially purified bovine lens preparation at 10E-6 M None 45.0 %
In vitro aldose reductase inhibitory activity measured by NADPH-dependent inhibition of glyceraldehyde reduction in a partially purified bovine lens preparation at 10E-7 M None 10.0 %
Inhibition of aldose reductase in partially purified bovine lens preparation at 10e-6 M. None 45.0 %
Inhibition of aldose reductase in partially purified bovine lens preparation at 10e-7 M concentration None 10.0 %
Inhibitory activity against bovine lens aldose reductase Bos taurus 150.0 nM
In vitro inhibitory activity against Aldose reductase isolated from human placenta None 170.0 nM
In vitro inhibitory activity towards human placenta aldose reductase None 500.0 nM
Inhibitory activity against human placental aldose reductase in 30 -70% (NH4)2SO4. None 700.0 nM
Inhibitory activity measured against human placental aldose reductase at a concentration of 10e-5 M None 87.0 %
Inhibitory activity measured against human placental aldose reductase at a concentration of 10e-6 M None 70.0 %
Selectivity ratio measured as the IC50 ratio of aldehyde/aldose reductase values None 36.0 %
In vitro inhibition of rabbit lens aldose reductase. Oryctolagus cuniculus 67.0 nM
Tested in vitro for inhibitory activity against partially purified aldose reductase from male rabbit lens Oryctolagus cuniculus 250.0 nM
In vitro inhibition of rabbit lens aldose reductase at 10e-4 M. Oryctolagus cuniculus 95.0 %
In vitro inhibition of rabbit lens aldose reductase at 10e-5 M. Oryctolagus cuniculus 95.0 %
In vitro inhibition of rabbit lens aldose reductase at 10e-6 M. Oryctolagus cuniculus 80.0 %
Inhibition of crude aldose reductase of rat lens Rattus norvegicus 17.0 nM
Compound was tested for inhibitory concentration against rat lens aldose reductase (uncompetitive inhibition type) None 17.0 nM
Compound was tested for its ability to inhibit crude aldose reductase obtained from rat lens None 20.0 nM
Concentration required to produce 50% inhibition of aldose reductase enzyme (the literature IC50 value for sorbinil is 0.07 uM) None 73.0 nM
In vitro inhibitory activity against aldose reductase (ALR2) from rat lens extraction. None 500.0 nM In vitro inhibitory activity against aldose reductase (ALR2) from rat lens extraction. None 650.0 nM
In vitro inhibitory activity of compound against rat lens aldose reductase None 250.0 nM
Inhibition of aldose reductase from rat lens. Value ranges from 0.07 - 1.2 None 230.0 nM
Inhibitory activity against rat lens aldose reductase None 200.0 nM
Inhibitory activity measured against rat lens aldose reductase using 3-pyridinecarboxaldehyde as substrate None 280.0 nM
Inhibitory activity against aldose reductase in rat lens None 190.0 nM
Inhibitory concentration to aldose reductase (ALR-2) obtained from rat lens None 650.0 nM
Inhibitory concentration against aldose reductase obtained from rat lens None 180.0 nM
Tested for in vitro inhibition activity against rat Aldose reductase (AR) None 900.0 nM
The compound was tested for the inhibition of Aldose reductase in rat lens assay. None 70.0 nM
In vitro inhibition of Aldose reductase (AR) from rat lens (RL) Rattus norvegicus 100.0 nM
In vitro inhibitory activity against aldose reductase of rat lens at 2.5x10E-7 M concentration None 48.0 %
In vitro percentage inhibition of rat lens aldose reductase at 10E-6 M concentration None 49.0 %
Inhibition of rat lens aldose reductase at 50 uM Rattus norvegicus 82.0 %
In vitro inhibitory activity against L-Hexonate Dehydrogenase (L-HDH) from rat kidney (RK) Rattus norvegicus 990.0 nM
Inhibition of human placental aldose reductase (HPAR) activity with glyceraldehyde as substrate None 120.0 nM
Inhibitory activity against human placental aldose reductase (HPAR) with glyceraldehyde as substrate None 500.0 nM
In vivo galactitol inhibitory activity measured by its ability to inhibit galactitol accumulation in sciatic nerve at 4 mg/Kg/day Rattus norvegicus 55.0 %
Compound was evaluated in vivo for the inhibition of sorbitol accumulation administered orally at a dose of 0.25 mg/kg. Rattus norvegicus 40.1 %
Compound was evaluated in vivo for the inhibition of sorbitol accumulation administered orally at a dose of 0.75 mg/kg. None 71.2 %
In vivo inhibition of galactitol accumulation in diaphragm of rat at 4 mg/kg/day Rattus norvegicus 69.0 %
In vivo inhibition of galactitol accumulation in sciatic nerves of rat at 4 mg/kg/day Rattus norvegicus 55.0 %
In vivo inhibition of galactitol accumulation in the diaphragm of rat at a dose of 4 mg/kg/day Rattus norvegicus 69.0 %
In vivo inhibition of galactitol accumulation in the sciatic nerves of rat at a dose of 4 mg/kg/day Rattus norvegicus 55.0 %
In vivo inhibition of sorbitol accumulation in rat sciatic nerves at 10e-5 M concentration Rattus norvegicus 96.0 %
In vivo inhibition of sorbitol accumulation in rat sciatic nerves at 10e-6 M concentration Rattus norvegicus 27.0 %
In vivo inhibition of sorbitol accumulation in rat sciatic nerves at 5*10e-6 M concentration Rattus norvegicus 74.0 %
In vitro inhibition of sorbitol accumulation was measured in rat sciatic nerves incubated in the presence of 50 mM glucose at 10e-5 M concentration Rattus norvegicus 96.0 %
In vitro inhibition of sorbitol accumulation was measured in rat sciatic nerves incubated in the presence of 50 mM glucose at 10e-6 M concentration Rattus norvegicus 27.0 %
In vivo galactitol inhibitory activity measured by its ability to inhibit galactitol accumulation in diaphragm at 4 mg/Kg/day Rattus norvegicus 69.0 %
In vivo galactitol inhibitory activity measured by its ability to inhibit galactitol accumulation in lens at 4 mg/Kg/day Rattus norvegicus 20.0 %
Tested in vivo for ability to inhibit sorbitol formation in the lens of a streptozotocinized rat model after oral administration at the dose of 0.15 mg/Kg Rattus norvegicus 12.3 %
Tested in vivo for ability to inhibit sorbitol formation in the lens of a streptozotocinized rat model after oral administration at the dose of 0.75 mg/Kg Rattus norvegicus 44.2 %
Tested in vivo for ability to inhibit sorbitol formation in the lens of a streptozotocinized rat model after oral administration at the dose of 1.5 mg/Kg Rattus norvegicus 73.4 %
Tested in vivo for ability to inhibit sorbitol formation in the lens of a streptozotocinized rat model after oral administration at the dose of 2.5 mg/Kg Rattus norvegicus 38.1 %
Tested in vivo for ability to inhibit sorbitol formation in the nerve of a streptozotocinized rat model after oral administration at the dose of 0.15 mg/Kg Rattus norvegicus 29.0 %
Tested in vivo for ability to inhibit sorbitol formation in the nerve of a streptozotocinized rat model after oral administration at the dose of 0.75 mg/kg Rattus norvegicus 72.7 %
Tested in vivo for ability to inhibit sorbitol formation in the nerve of a streptozotocinized rat model after oral administration at the dose of 1.5 mg/Kg Rattus norvegicus 90.9 %
Tested in vivo for ability to inhibit sorbitol formation in the nerve of a streptozotocinized rat model after oral administration at the dose of 2.5 mg/Kg Rattus norvegicus 50.0 %
Compound was evaluated in vivo for percent inhibition of polyol accumulation at a dose of 15 mg/kg per day Rattus norvegicus 90.2 %
Compound was evaluated in vivo for percent inhibition of polyol accumulation at a dose of 3 mg/kg per day. Rattus norvegicus 69.3 %
In vitro inhibitory activity against human recombinant Aldose reductase in streptozotocin diabetic rat at 50 mg/kg None 140.0 nM
Inhibitory concentration against rat ALR2 aldose reductase Rattus norvegicus 900.0 nM
In vitro inhibitroy concentration against Aldose reductase incubated at 24 degree C for 15 minutes in pH 7.0 Homo sapiens 140.0 nM
Inhibition of human recombinant aldose reductase Homo sapiens 910.0 nM
Inhibition of aldose reductase in rat lenses Rattus norvegicus 249.0 nM
Inhibition of aldose reductase in Fischer-344 rat lens homogenate by spectrometric analysis Rattus norvegicus 250.0 nM
Inhibition of aldose reductase None 70.0 nM
Inhibition of Albino rat eye lens ALR2 assessed as NADPH oxidation by spectrophotometry Rattus norvegicus 620.0 nM
Inhibition of aldose reductase None 249.0 nM
Inhibition of N-terminal 6His-tagged human aldose reductase expressed in Escherichia coli BL21(DE3) mediated NADPH linked pyridine-3-aldehyde reduction Homo sapiens 550.0 nM
Inhibition of Fischer-344 rat lens ALR2 at 0.25 uM Rattus norvegicus 44.7 %
Inhibition of rat lens ALR2 Rattus norvegicus 250.0 nM
Inhibition of Fischer-344 rat lens ALR2 using D-glycuronate as substrate by spectrophotometry Rattus norvegicus 250.0 nM
Inhibition of partially purified Fischer-344 rat lens ALR2 using D,L-glyceraldehyde as substrate assessed as NADPH consumption by spectrophotometry Rattus norvegicus 250.0 nM
Inhibition of AKR1B1 in mouse RAW264.7 cells assessed as inhibition of sorbitol accumulation after 24 hrs by colorimetric assay Mus musculus 44.0 %
Inhibition of Fischer-344 rat lens ALR2 using D, L-glyceraldehyde as substrate by spectrophotometry Rattus norvegicus 250.0 nM
Inhibition of rat lenses ALR2 using DL-glyceraldehyde as substrate preincubated for 10 mins followed by substrate addition measured for 4 mins Rattus norvegicus 430.0 nM
Inhibition of Fischer-344 rat lens ALR2 Rattus norvegicus 250.0 nM
Inhibition of Sprague-Dawley rat kidney ALR1 using sodium D-glucuronate as substrate by spectrophotometric method Rattus norvegicus 29.0 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens -4.62 %
Inhibition of human recombinant ALR2 expressed in Escherichia coli using DL-glyceraldehyde as substrate and NADPH at 50 uM preincubated for 5 mins followed by substrate addition and measured after 30 mins at 2 mins interval by spectrophotometry relative to control Homo sapiens 87.36 %
Inhibition of human recombinant ALR2 expressed in Escherichia coli using DL-glyceraldehyde as substrate and NADPH preincubated for 5 mins followed by substrate addition and measured after 30 mins at 2 mins interval by spectrophotometry relative to control Homo sapiens 750.0 nM
Inhibition of rat kidney ALR1 using DL-glyceraldehyde as substrate and NADPH at 50 uM preincubated for 5 mins followed by substrate addition and measured for 30 mins at 2 mins interval by spectrophotometry relative to control Rattus norvegicus 87.84 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 18.78 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.13 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.13 %
Inhibition of human recombinant AKR1B1 assessed as D,L-glyceraldehyde reduction pretreated with 0.3M DMSO followed by compound addition by DMSO-perturbation assay Homo sapiens 971.0 nM

Cross References

Resources Reference
ChEBI 102029
ChEMBL CHEMBL266497
DrugBank DB02712
FDA SRS G4186B906P
Guide to Pharmacology 7415
PDB SBI
PubChem 337359
SureChEMBL SCHEMBL48877
ZINC ZINC000000002070
CONTENTS