VALSARTAN

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Trade Names
Synonyms
Status
Molecule Category Free-form
ATC C09CA03
UNII 80M03YXJ7I

Structure

InChI Key ACWBQPMHZXGDFX-QFIPXVFZSA-N
Smiles CCCCC(=O)N(Cc1ccc(-c2ccccc2-c2nnn[nH]2)cc1)[C@H](C(=O)O)C(C)C
InChI
InChI=1S/C24H29N5O3/c1-4-5-10-21(30)29(22(16(2)3)24(31)32)15-17-11-13-18(14-12-17)19-8-6-7-9-20(19)23-25-27-28-26-23/h6-9,11-14,16,22H,4-5,10,15H2,1-3H3,(H,31,32)(H,25,26,27,28)/t22-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C24H29N5O3
Molecular Weight 435.53
AlogP 4.16
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 10.0
Polar Surface Area 112.07
Molecular species ACID
Aromatic Rings 3.0
Heavy Atoms 32.0

Bioactivity

Mechanism of Action Action Reference
Type-1 angiotensin II receptor antagonist ANTAGONIST FDA
Protein: Type-1 angiotensin II receptor
Description: Type-1 angiotensin II receptor
Organism : Homo sapiens
P30556 ENSG00000144891
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Adhesion
- - 100000 - -
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Short peptide receptor (family A GPCR) Angiotensin receptor
- 2 - 3-4700 -
Membrane receptor
- 2 100000 3-4700 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 34-56
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 31070 - - -
Assay Description Organism Bioactivity Reference
Binding affinity for rat angiotensin II receptor, type 1 None 1.9 nM
Inhibitory activity against Angiotensin II receptor, type 1 in rat aortic membrane None 2.7 nM
Tested for inhibition of Angiotensin II receptor, type 1 in the absence of bovine serum albumin (BSA) None 2.7 nM
Tested for inhibition of Angiotensin II-induced pressor response in rabbit aorta Oryctolagus cuniculus 1.4 nM
Compound was tested for its antagonistic activity against angiotensin II-induced contractions in rabbit aorta Oryctolagus cuniculus 1.4 nM
Tested for inhibition of Angiotensin II-induced pressor response in pithed rat model after 10 mg/kg peroral administration Rattus norvegicus 97.0 %
Displacement of [125I]Sar1,Ile8-Ang2 from AT1 receptor in Wistar rat hepatic membrane Rattus norvegicus 3.4 nM
Antagonist activity at angiotensin AT1 receptor in rat aorta Rattus norvegicus 2.7 nM
Displacement of [I125]angiotensin2 from AT1 receptor in Sprague-Dawley rat VSMC after 2.5 hrs by gamma spectrophotometry Rattus norvegicus 2.64 nM Displacement of [I125]angiotensin2 from AT1 receptor in Sprague-Dawley rat VSMC after 2.5 hrs by gamma spectrophotometry Rattus norvegicus 2.22 nM
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 62.2 %
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 33.7 %
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 12.3 %
Displacement of [125I]Angiotensin-2 from angiotensin AT1 receptor in Sprague-Dawley rat VSMC after 60 mins by gamma counting Rattus norvegicus 2.08 nM Displacement of [125I]Angiotensin-2 from angiotensin AT1 receptor in Sprague-Dawley rat VSMC after 60 mins by gamma counting Rattus norvegicus 2.64 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 67.47 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 56.31 %
Time dependent inhibition of CYP1A2 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2B6 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2C9 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2C19 in human liver microsomes at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2D6 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP3A4 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2C8 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Displacement of [125I-Sar1-Ile8]-Ang2 from human angiotensin 2 receptor type 1 receptor expressed in HEK293 cells after 1 hr by gamma counting analysis Homo sapiens 3.0 nM
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 14.82 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 3.3 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 7.53 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 30.1 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 5.64 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 3.96 %
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 -1.97 %
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 -4.0 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 15.63 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 11.09 %
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 -0.12 % 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 0.07 % 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 -0.12 % 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 0.07 %
Displacement of [125-I]-[Sar1, AngII from AT1R (unknown origin) expressed in Escherichia coli BL 21 (DE3) incubated for 2 hrs by radioimmunoassay Homo sapiens 7.4 nM

Environmental Exposure

Environmental Exposure Map
Countries
Croatia
Czech Republic
Germany
Hungary
Romania
Serbia
Slovenia

Cross References

Resources Reference
ChEBI 9927
ChEMBL CHEMBL1069
DrugBank DB00177
DrugCentral 2806
FDA SRS 80M03YXJ7I
Human Metabolome Database HMDB0014323
Guide to Pharmacology 593
PharmGKB PA451848
PubChem 60846
SureChEMBL SCHEMBL2542
ZINC ZINC000003875259
CONTENTS