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Compound Detail

CHEMBL3545059

ALISKIREN FUMARATE
💊 Approved Drug
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💊 Approved Drug
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
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3545059
Name ALISKIREN FUMARATE
Phase Approved
Structure Type MOL
InChI Key KLRSDBSKUSSCGU-KRQUFFFQSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL1639
Active Moiety CHEMBL1639

Known Names

Aliskiren fumarate Aliskiren fumarate component of amturnide aliskiren hemifumarate Aliskiren fumarate component of raprazo-hct aliskiren hemifumarate Aliskiren fumarate component of rasilamlo aliskiren hemifumarate Aliskiren fumarate component of rasilez-hct aliskiren hemifumarate Aliskiren fumarate component of rasitrio aliskiren hemifumarate Aliskiren fumarate component of sprimeo-hct aliskiren hemifumarate Aliskiren fumarate component of tekamlo aliskiren hemifumarate Aliskiren fumarate component of tekturna hct aliskiren hemifumarate Aliskiren fumarate component of valturna aliskiren hemifumarate Aliskiren hemifumarate Aliskiren hemifumarate component of amturnide +10 more
2
Targets
3
Activities
1
Assay Types
30
PK Parameters
14
Publications
22
Known Names
2
Indications
1
Mechanisms

Molecular Properties

551.8
MW (Da)
3.29
ALogP
7
HBA
4
HBD
146.1
PSA (Ų)
0.19
QED
1
Ro5 Violations
19
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2007
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning First in Class
USAN Stem -kiren
USAN Year 2005

Extended Properties

Molecular Formula C64H110N6O16
MW 1219.61
Aromatic Rings 1
Heavy Atoms 39
NP-Likeness 0.21

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Renin inhibitor INHIBITOR Renin ✓ ✓

Indications

Hypertension Stroke

Drug Warnings

Black Box Warning
teratogenicity
Country: United States

Activity Summary

IC50 3 meas. best 8.82

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Renin
CHEMBL286
 IC50 8.82 8.68 1.5 2
Renin
CHEMBL2046264
 IC50 8.1 8.1 8.0 1

Pharmacokinetic Data

Parameter Value Units Species
Absorption 3.4 % Rattus norvegicus
ALP_CHANGE_TO - - Callithrix jacchus
AUC 31.0 ng.hr.mL-1 Rattus norvegicus
AUC 21.0 ng.hr.mL-1 Rattus norvegicus
AUC 149.0 ng.hr.mL-1 Canis lupus familiaris
AUC 154.0 ng.hr.mL-1 Macaca fascicularis
AUC 21.0 ng.hr.mL-1 Rattus norvegicus
AUC 22000.0 ng.hr.mL-1 Callithrix jacchus
AUC 58100.0 ng.hr.mL-1 Callithrix jacchus
AUC 76400.0 ng.hr.mL-1 Callithrix jacchus
AUC 21300.0 ng.hr.mL-1 Callithrix jacchus
AUC 56200.0 ng.hr.mL-1 Callithrix jacchus
AUC 84000.0 ng.hr.mL-1 Callithrix jacchus
AUC 33900.0 ng.hr.mL-1 Callithrix jacchus
AUC 107000.0 ng.hr.mL-1 Callithrix jacchus
AUC 109000.0 ng.hr.mL-1 Callithrix jacchus
AUC 29000.0 ng.hr.mL-1 Callithrix jacchus
AUC 109000.0 ng.hr.mL-1 Callithrix jacchus
AUC 142000.0 ng.hr.mL-1 Callithrix jacchus
AUC 64000.0 ng.hr.mL-1 Callithrix jacchus
AUC 103000.0 ng.hr.mL-1 Callithrix jacchus
AUC 3884.46 ng.hr.mL-1 Mus musculus
AUC 4982.48 ng.hr.mL-1 Mus musculus
AUC 1660.83 ng.hr.mL-1 Rattus norvegicus
AUC 6952.3 ng.hr.mL-1 Rattus norvegicus
AUC 28.5 ng.hr.mL-1 Homo sapiens
AUC 96.4 ng.hr.mL-1 Homo sapiens
AUC 214.8 ng.hr.mL-1 Homo sapiens
AUC 1193.4 ng.hr.mL-1 Homo sapiens
AUC 46.7 ng.hr.mL-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Renin IC50 = 1.5 nM 8.82 Inhibition of human recombinant renin compound treated for 10 mins before substr... 24900544
Renin IC50 = 2.9 nM 8.54 Inhibition of human plasma renin activity after 60 mins by competitive RIA 24900544
Renin IC50 = 8.0 nM 8.1 Inhibition of cynomolgus monkey plasma renin activity after 60 mins by competiti... 24900544

Literature References

PubMed DOI Target Context # Activities
19457666 10.1016/j.bmcl.2009.04.140 Rattus norvegicus 8
24900262 10.1021/ml200137x Canis familiaris 5
24900262 10.1021/ml200137x Cynomolgus monkey 5
24900262 10.1021/ml200137x Rattus norvegicus 5
17824680 10.1021/jm070316i No relevant target 4
24900544 10.1021/ml300168e Renin 3
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
17824680 10.1021/jm070316i ADMET 1
23956101 10.1093/toxsci/kft176 Bile salt export pump 1
23956101 10.1093/toxsci/kft176 ATP-binding cassette sub-family C member 2 1
23956101 10.1093/toxsci/kft176 ATP-binding cassette sub-family C member 3 1
23956101 10.1093/toxsci/kft176 ATP-binding cassette sub-family C member 4 1
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 1

Data from ChEMBL 36 via Core Engine