CANDESARTAN CILEXETIL

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Trade Names	ATACAND CANDESARTAN CILEXETIL
Synonyms	Amias Atacand Candesartan Candesartan 1-(((cyclohexyloxy)carbonyl)oxy)ethyl ester Candesartan cilexetil NSC-758697 Ratacand TCV-116
Status
Molecule Category	Free-form
UNII	R85M2X0D68
EPA CompTox	DTXSID5020239


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	GHOSNRCGJFBJIB-UHFFFAOYSA-N
Smiles	CCOc1nc2cccc(C(=O)OC(C)OC(=O)OC3CCCCC3)c2n1Cc1ccc(-c2ccccc2-c2nn[nH]n2)cc1
InChI	InChI=1S/C33H34N6O6/c1-3-42-32-34-28-15-9-14-27(31(40)43-21(2)44-33(41)45-24-10-5-4-6-11-24)29(28)39(32)20-22-16-18-23(19-17-22)25-12-7-8-13-26(25)30-35-37-38-36-30/h7-9,12-19,21,24H,3-6,10-11,20H2,1-2H3,(H,35,36,37,38)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C33H34N6O6
Molecular Weight	610.67
AlogP	6.32
Hydrogen Bond Acceptor	11.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	10.0
Polar Surface Area	143.34
Molecular species	ACID
Aromatic Rings	5.0
Heavy Atoms	45.0

Pharmacology

Mechanism of Action	Action	Reference
Type-1 angiotensin II receptor antagonist	ANTAGONIST	DailyMed


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(%)
Enzyme Protease Cysteine protease Cysteine protease CA clan Cysteine protease C1A family	-	42000	-	-	-
Enzyme Transferase	-	11200	-	-	100
Enzyme	-	5600-9200	-	-	100
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Short peptide receptor (family A GPCR) Angiotensin receptor	-	200	-	-	36-87
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group C Nuclear hormone receptor subfamily 1 group C member 3	4200	-	-	-	-
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides	-	2455	-	1900	11
Unclassified protein	-	16430	-	-	100

Assay Description	Organism	Bioactivity	Reference
Inhibitory activity on AII (100 ng/kg iv)-induced pressor response after administration at 0.1 mg/kg po in conscious male Sprague-Dawley rats at 2 h.	None	80.0 %
Inhibitory activity on AII (100 ng/kg iv)-induced pressor response after administration at 0.1 mg/kg po in conscious male Sprague-Dawley rats at 24 h.	None	36.0 %
Inhibitory activity on AII (100 ng/kg iv)-induced pressor response after administration at 0.1 mg/kg po in conscious male Sprague-Dawley rats at 3 h.	None	87.0 %
Inhibitory activity on AII (100 ng/kg iv)-induced pressor response after administration at 0.1 mg/kg po in conscious male Sprague-Dawley rats at 5 h.	None	82.0 %
Inhibitory activity on AII (100 ng/kg iv)-induced pressor response after administration at 0.1 mg/kg po in conscious male Sprague-Dawley rats at 7 h.	None	75.0 %
Inhibitory activity on AII (100 ng/kg iv)-induced pressor response at 0.1 mg/kg po in conscious male Sprague-Dawley rats at 1 h.	None	76.0 %
Inhibitory effect on AII (100 ng/kg iv)-induced pressor response after administration at 0.1 mg/kg po in conscious male Sprague-Dawley rats at 0.5 h.	None	38.0 %
Antagonist activity at angiotensin AT1 receptor in rabbit aortic strip assessed as inhibition of angiotensin 2-induced contractile response	Oryctolagus cuniculus	200.0 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	10.55 %
pIC50 values for sodium fluorescein (10 uM) uptake in OATP1B1-transfected CHO cells	Cricetulus griseus	724.44 nM
Ki values for sodium fluorescein (10 uM) uptake in OATP1B1-transfected CHO cells	Cricetulus griseus	400.0 nM
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	5.967 %
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	-1.4 %
Inhibition of Nedd8-Ubc12 (unknown origin) assessed as decrease in Ubc12-Nedd8 adduct formation at 50 uM preincubated for 10 mins followed by ATP addition and measured after 30 mins by immunoblot analysis	Homo sapiens	100.0 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	15.29 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	25.64 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	9.656 %
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	-0.21 %		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	-0.11 %		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	0.07 %		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	-0.11 %		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	-0.21 %
Inhibition of NAE (unknown origin)-mediated neddylation assessed as suppression of cullin1-Nedd8 adduct formation at 25 uM preincubated for 10 mins followed by ATP addition and measured after 30 mins by immunoblot analysis relative to control	Homo sapiens	87.8 %

Related Entries

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Cross References

Resources	Reference
ChEBI	3348
ChEMBL	CHEMBL1014
DrugBank	DB00796
DrugCentral	475
FDA SRS	R85M2X0D68
Guide to Pharmacology	8352
KEGG	C07709
PubChem	2540
SureChEMBL	SCHEMBL40831
ZINC	ZINC14255250

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).