REPAGLINIDE

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Trade Names
Synonyms
Status
Molecule Category Free-form
ATC A10BX02
UNII 668Z8C33LU
EPA CompTox DTXSID3023552

Structure

InChI Key FAEKWTJYAYMJKF-QHCPKHFHSA-N
Smiles CCOc1cc(CC(=O)N[C@@H](CC(C)C)c2ccccc2N2CCCCC2)ccc1C(=O)O
InChI
InChI=1S/C27H36N2O4/c1-4-33-25-17-20(12-13-22(25)27(31)32)18-26(30)28-23(16-19(2)3)21-10-6-7-11-24(21)29-14-8-5-9-15-29/h6-7,10-13,17,19,23H,4-5,8-9,14-16,18H2,1-3H3,(H,28,30)(H,31,32)/t23-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C27H36N2O4
Molecular Weight 452.6
AlogP 5.22
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 10.0
Polar Surface Area 78.87
Molecular species ACID
Aromatic Rings 2.0
Heavy Atoms 33.0

Bioactivity

Mechanism of Action Action Reference
Sulfonylurea receptor 1, Kir6.2 blocker BLOCKER PubMed PubMed PubMed PubMed
Protein: Sulfonylurea receptor 1, Kir6.2
Description: ATP-binding cassette sub-family C member 8
Organism : Homo sapiens
Q09428 ENSG00000006071
Protein: Sulfonylurea receptor 1, Kir6.2
Description: ATP-sensitive inward rectifier potassium channel 11
Organism : Homo sapiens
Q14654 ENSG00000187486
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 42
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- 9200 - - 76
Transporter Electrochemical transporter
- 9200 - - 14
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 22000 - - 35
Transporter Primary active transporter ATP-binding cassette ABCC subfamily
- 106 50 - -
Assay Description Organism Bioactivity Reference
Displacement of [3H]glibenclamide from COS-1 cells expressing Sulfonylurea receptor 1 (SUR-1) Homo sapiens 50.0 nM
In vitro displacement of [3H]glibenclamide (IC50=0.61) from COS-1 cells expressing Sulfonylurea receptor 1 (SUR-1) Homo sapiens 106.0 nM
Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells at 100 uM by confocal microscopy Homo sapiens 76.4 %
Inhibition of norA-mediated ethidium bromide efflux in Staphylococcus aureus SA-1199B harboring grlA A116E mutant at 50 uM after 5 mins by fluorometric analysis Staphylococcus aureus 14.0 %
Inhibition of human recombinant MDR1 expressed in mouse L5178Y cells assessed as inhibition of rhodamine-123 efflux at 10'-4 M preincubated for 10 mins measured after 20 mins by FACS analysis Homo sapiens 35.0 %
Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as reduction in E17-betaG uptake at 20 uM by scintillation counting Homo sapiens 88.4 %
Inhibition of human liver OATP1B3 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E17-betaG uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 83.2 %
Inhibition of human liver OATP2B1 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E3S uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 42.2 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus 15.76 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli -4.96 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 3.14 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 6.11 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 15.61 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 4.01 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans -6.91 %
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 0.78 %
Antidiabetic activity in glucose-treated rat INS1(832/13) cells assessed as increase in insulin release at 1 ug/ml in presence of 3 mM glucose measured after 2 hrs by radioimmunoassay (Rvb = 52.25 +/- 2.15 %) Rattus norvegicus 96.16 %
Antidiabetic activity in glucose-treated rat INS1(832/13) cells assessed as increase in insulin release at 10 ug/ml in presence of 3 mM glucose measured after 2 hrs by radioimmunoassay (Rvb = 52.25 +/- 2.15 %) Rattus norvegicus 99.05 %
Antihyperglycemic activity in alloxan-induced diabetic BALB/c mouse model assessed as reduction in blood glucose level at 10 mg/kg measured after 8 hrs by glucometry analysis relative to control Mus musculus 66.1 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 7.8 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 4.154 %
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 0.08 % 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 0.05 % 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 0.05 % 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 0.08 %

Cross References

Resources Reference
ChEBI 8805
ChEMBL CHEMBL1272
DrugBank DB00912
DrugCentral 2366
FDA SRS 668Z8C33LU
Human Metabolome Database HMDB0015048
Guide to Pharmacology 6841
KEGG C07670
PDB BJX
PharmGKB PA451234
PubChem 65981
SureChEMBL SCHEMBL16137
ZINC ZINC000003798537
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