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Compound Detail

CHEMBL1651956

ALISPORIVIR
🧪 Phase III
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🧪 Phase III
C/C=C/C[C@@H](C)[C@@H](O)[C@H]1C(=O)N[C@@H](CC)C(=O)N(C)[C@H](C)C(=O)N(CC)[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N(C)[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@H](C)C(=O)N(C)[C@@H](CC(C)C)C(=O)N(C)[C@@H](CC(C)C)C(=O)N(C)[C@@H](C(C)C)C(=O)N1C

Basic Information

ChEMBL ID CHEMBL1651956
Name ALISPORIVIR
Phase Phase III
Structure Type BOTH
InChI Key OLROWHGDTNFZBH-XEMWPYQTSA-N

Known Names

(d-meala)3-(etval)4-csa Alisporivir DEB 025 DEB-025 DEB025 DEBIO 025 DEBIO-025 DEBIO025 UNIL 025 UNIL-025 UNIL025
25
Targets
74
Activities
4
Assay Types
4
PK Parameters
20
Publications
11
Known Names
5
Indications
1
Mechanisms

Molecular Properties

1216.7
MW (Da)

Drug Information

Molecule Type Protein
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -vir
USAN Year 2011

Extended Properties

Molecular Formula C63H113N11O12
MW 1216.66

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Cyclophilin A inhibitor INHIBITOR Peptidyl-prolyl cis-trans isomerase A

Indications

Hepatitis C Hepatitis C, Chronic Liver Diseases Severe Acute Respiratory Syndrome Kidney Failure, Chronic

Activity Summary

IC50 48 meas. best 8.15
EC50 21 meas. best 8.4
Kd 4 meas. best 9.0
Ki 1 meas. best 9.47

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Peptidyl-prolyl cis-trans isomerase A
CHEMBL1949
Ki 9.47 9.47 0.3 1
Peptidyl-prolyl cis-trans isomerase B
CHEMBL2075
Kd 9.0 9.0 1.0 1
Peptidyl-prolyl cis-trans isomerase F, mitochondrial
CHEMBL3325306
Kd 9.0 9.0 1.0 1
Peptidyl-prolyl cis-trans isomerase A
CHEMBL1949
Kd 8.66 8.31 2.2 2
Hepatitis C virus
CHEMBL379
EC50 8.4 6.9093 4.0 15
Human immunodeficiency virus 1
CHEMBL378
IC50 8.15 6.92 7.0 26
Nonstructural protein 5A
CHEMBL3307224
EC50 7.8 7.8 15.8 1
Unchecked
CHEMBL612545
EC50 7.8 7.8 15.8 3
RNA-directed RNA polymerase
CHEMBL4296320
EC50 7.8 7.8 15.8 1
Human immunodeficiency virus 2
CHEMBL380
IC50 7.24 6.11 58.0 2
Human immunodeficiency virus 1
CHEMBL378
EC50 7.2 7.2 63.0 1
Bile salt export pump
CHEMBL6020
IC50 6.96 6.96 110.0 1
Solute carrier organic anion transporter family member 1B1
CHEMBL1697668
IC50 6.75 6.425 180.0 2
Solute carrier organic anion transporter family member 1B3
CHEMBL1743121
IC50 6.66 6.66 220.0 1
Hepatitis C virus
CHEMBL379
IC50 6.66 6.66 220.0 1
PBMC
CHEMBL613107
IC50 6.3 6.19 500.0 2
ATP-dependent translocase ABCB1
CHEMBL4302
IC50 6.23 6.23 590.0 1
ADMET
CHEMBL612558
IC50 6.09 6.09 820.0 1
Feline coronavirus
CHEMBL612744
IC50 5.66 5.66 2200.0 1
Broad substrate specificity ATP-binding cassette transporter ABCG2
CHEMBL5393
IC50 5.6 5.6 2500.0 1
Human alphaherpesvirus 3
CHEMBL613132
IC50 5.6 5.6 2500.0 1
SARS-CoV-2
CHEMBL4303835
IC50 5.51 5.51 3100.0 1
Hepatitis B virus
CHEMBL613497
IC50 5.39 5.39 4100.0 1
Human betaherpesvirus 5
CHEMBL371
IC50 5.21 5.13 6100.0 2
SARS-CoV
CHEMBL4303836
IC50 5.11 5.11 7700.0 1
Simian immunodeficiency virus
CHEMBL613499
IC50 5.1 5.1 7970.0 1
NON-PROTEIN TARGET
CHEMBL3879801
IC50 5.08 5.08 8240.0 1
ATP-binding cassette sub-family C member 2
CHEMBL5748
IC50 4.75 4.75 18000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 26888.19 ng.hr.mL-1 Rattus norvegicus
AUC 2798.32 ng.hr.mL-1 Rattus norvegicus
AUC 2664.49 ng.hr.mL-1 Canis lupus familiaris
AUC 486.66 ng.hr.mL-1 Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Peptidyl-prolyl cis-trans isomerase A Ki = 0.34 nM 9.47 Inhibition of human recombinant cyclophilin-associted cis-trans propyl isomerase... 18212100
Peptidyl-prolyl cis-trans isomerase F, mitochondrial Kd = 1.0 nM 9.0 Binding affinity to human cyclophilin F by surface plasmon resonance method 25310383
Peptidyl-prolyl cis-trans isomerase B Kd = 1.0 nM 9.0 Binding affinity to human cyclophilin B by surface plasmon resonance method 25310383
Peptidyl-prolyl cis-trans isomerase A Kd = 2.2 nM 8.66 Binding affinity to human cyclophilin A by surface plasmon resonance method 25310383
Hepatitis C virus EC50 = 4.0 nM 8.4 Antiviral activity against BILN 2061-resistant HCV genotype 1b infected in human... 19104013
Human immunodeficiency virus 1 IC50 = 7.0 nM 8.15 Antiviral activity against APV, ATV, LPV, IDV, NFV, RTV, SQV-resistant HIV-1 106... 18212100
Human immunodeficiency virus 1 IC50 = 8.0 nM 8.1 Antiviral activity against HIV1 subtype A 92RW016 infected in human PBMC assesse... 18212100
Human immunodeficiency virus 1 IC50 = 10.0 nM 8.0 Antiviral activity against HIV1 subtype D 92UG046 infected in human PBMC assesse... 18212100
Human immunodeficiency virus 1 IC50 = 10.0 nM 8.0 Antiviral activity against HIV1 subtype B NL4-3 infected in human PBMC assessed ... 18212100
Peptidyl-prolyl cis-trans isomerase A Kd = 11.0 nM 7.96 Binding affinity to human cyclophilin A by fluorescence polarization assay 24900335
Human immunodeficiency virus 1 IC50 = 12.0 nM 7.92 Antiviral activity against APV, ATV, IDV, LPV, NFV, RTV, SQV, 3TC, FTC, ABC, AZT... 18212100
Human immunodeficiency virus 1 IC50 = 15.0 nM 7.82 Antiviral activity against HIV1 subtype B WEJO infected in human PBMC assessed a... 18212100
Human immunodeficiency virus 1 IC50 = 15.0 nM 7.82 Antiviral activity against HIV1 subtype C 92BR025 infected in human PBMC assesse... 18212100
Human immunodeficiency virus 1 IC50 = 15.0 nM 7.82 Antiviral activity against HIV1 subtype B SF162 infected in human PBMC assessed ... 18212100
Human immunodeficiency virus 1 IC50 = 15.0 nM 7.82 Antiviral activity against HIV1 subtype B JR-CSF infected in human PBMC assessed... 18212100
RNA-directed RNA polymerase EC50 = 15.8 nM 7.8 Inhibition of NS5B S282T mutant in HCV genotype 1b infected in HuH7.5Lcu-Neo cel... 27783522
Human immunodeficiency virus 1 IC50 = 16.0 nM 7.8 Antiviral activity against HIV1 subtype A 92UG037 infected in human PBMC assesse... 18212100
Unchecked EC50 = 15.8 nM 7.8 Inhibition of NS3 R155Q/A156T mutant in HCV genotype 1b infected in HuH7.5Lcu-Ne... 27783522
Unchecked EC50 = 15.8 nM 7.8 Inhibition of NS5A in HCV genotype 1b infected in HuH7.5Lcu-Neo cells assessed a... 27783522
Unchecked EC50 = 15.8 nM 7.8 Inhibition of NS5A D320E/Y321N mutant in HCV genotype 1b infected in HuH7.5Lcu-N... 27783522

Literature References

PubMed DOI Target Context # Activities
18212100 10.1128/aac.01324-07 Human immunodeficiency virus 1 31
19104013 10.1128/aac.00939-08 Hepatitis C virus 16
18212100 10.1128/aac.01324-07 Rattus norvegicus 12
18212100 10.1128/aac.01324-07 ADMET 5
18212100 10.1128/aac.01324-07 NON-PROTEIN TARGET 5
18625766 10.1128/aac.01534-07 Hepatitis C virus 4
18625766 10.1128/aac.01534-07 ADMET 4
19104013 10.1128/aac.00939-08 ADMET 3
18212100 10.1128/aac.01324-07 Human alphaherpesvirus 2 3
18212100 10.1128/aac.01324-07 Human alphaherpesvirus 1 3
25310383 10.1021/jm500862r No relevant target 3
27783522 10.1021/acs.jmedchem.6b01301 Unchecked 3
25310383 10.1021/jm500862r Hepatitis C virus 3
25310383 10.1021/jm500862r Plasma 2
18212100 10.1128/aac.01324-07 Influenza A virus 2
18212100 10.1128/aac.01324-07 Human papillomavirus type 16 2
24900335 10.1021/ml200039u Peptidyl-prolyl cis-trans isomerase A 2
18212100 10.1128/aac.01324-07 Human betaherpesvirus 5 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
25310383 10.1021/jm500862r Solute carrier organic anion transporter family member 1B1 2

Data from ChEMBL 36 via Core Engine