ALISKIREN FUMARATE

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Search structure


Synonyms	Aliskiren fumarate Aliskiren hemifumarate NSC-759185 SPP-100B SPP100 Tekturna
Status
Molecule Category	Mixture
UNII	C8A0P8G029


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

Structure


InChI Key	KLRSDBSKUSSCGU-KRQUFFFQSA-N
Smiles	COCCCOc1cc(C[C@@H](C[C@H](N)[C@@H](O)C[C@H](C(=O)NCC(C)(C)C(N)=O)C(C)C)C(C)C)ccc1OC.COCCCOc1cc(C[C@@H](C[C@H](N)[C@@H](O)C[C@H](C(=O)NCC(C)(C)C(N)=O)C(C)C)C(C)C)ccc1OC.O=C(O)/C=C/C(=O)O
InChI	InChI=1S/2C30H53N3O6.C4H4O4/c21-19(2)22(14-21-10-11-26(38-8)27(15-21)39-13-9-12-37-7)16-24(31)25(34)17-23(20(3)4)28(35)33-18-30(5,6)29(32)36;5-3(6)1-2-4(7)8/h210-11,15,19-20,22-25,34H,9,12-14,16-18,31H2,1-8H3,(H2,32,36)(H,33,35);1-2H,(H,5,6)(H,7,8)/b;;2-1+/t2*22-,23-,24-,25-;/m00./s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C64H110N6O16
Molecular Weight	1219.61
AlogP	3.29
Hydrogen Bond Acceptor	7.0
Hydrogen Bond Donor	4.0
Number of Rotational Bond	19.0
Polar Surface Area	146.13
Molecular species	BASE
Aromatic Rings	1.0
Heavy Atoms	39.0

Bioactivity

Mechanism of Action	Action	Reference
Renin inhibitor	INHIBITOR	DailyMed


Protein: Renin Description: Renin Organism : Homo sapiens P00797 ENSG00000143839

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Protease Aspartic protease Aspartic protease AA clan Aspartic protease A1A subfamily	-	2-3	-	-	-

Assay Description	Organism	Bioactivity	Reference
Inhibition of human recombinant renin compound treated for 10 mins before substrate addition measured after 90 mins by fluorescence method	Homo sapiens	1.5 nM
Inhibition of human plasma renin activity after 60 mins by competitive RIA	Homo sapiens	2.9 nM
Inhibition of cynomolgus monkey plasma renin activity after 60 mins by competitive RIA	Macaca fascicularis	8.0 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	6.99 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	13.56 %
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	0.03 %		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	0.03 %

Cross References

Resources	Reference
ChEBI	53777
ChEMBL	CHEMBL3545059
FDA SRS	C8A0P8G029
SureChEMBL	SCHEMBL187762

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).