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Compound Detail

CHEMBL467058

LANINAMIVIR OCTANOATE
💊 Approved Drug
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💊 Approved Drug
CCCCCCCC(=O)OC[C@@H](O)[C@@H](OC)[C@@H]1OC(C(=O)O)=C[C@H](NC(=N)N)[C@H]1NC(C)=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL467058
Name LANINAMIVIR OCTANOATE
Phase Approved
Structure Type MOL
InChI Key UKTIJASCFRNWCB-RMIBSVFLSA-N
Active Moiety CHEMBL466246

Known Names

Cs-8958 Laninamivir octanoate Laninamivir octanoic acid ester R-118958
2
Targets
58
Activities
1
Assay Types
17
PK Parameters
14
Publications
4
Known Names
2
Indications
2
Mechanisms

Molecular Properties

472.5
MW (Da)
-0.01
ALogP
8
HBA
6
HBD
193.3
PSA (Ų)
0.09
QED
1
Ro5 Violations
14
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2010
Availability Unknown
Chirality Single Enantiomer

Routes of Administration

Topical

Flags

Natural Product Prodrug
USAN Stem -vir

Extended Properties

Molecular Formula C21H36N4O8
MW 472.54
Aromatic Rings 0
Heavy Atoms 33
NP-Likeness 0.99

Mechanism of Action

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

Indications

Influenza, Human Asthma

Activity Summary

IC50 58 meas. best 7.41

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Neuraminidase
CHEMBL6135
 IC50 7.41 6.5703 39.2 35
Unchecked
CHEMBL612545
 IC50 5.46 5.0917 3500.0 23

Pharmacokinetic Data

Parameter Value Units Species
AUC 152.63 ng.hr.mL-1 Mus musculus
AUC 11151.94 ng.hr.mL-1 Mus musculus
AUClast 4480.0 pmol.hr/g Mus musculus
Cmax - - Mus musculus
Cmax 242.0 nM Mus musculus
Cmax 1760.0 pmol/g Mus musculus
Cmax 20400.0 nM Mus musculus
F 3.5 % Mustela putorius furo
T1/2 0.833 hr Mus musculus
T1/2 0.6 hr Mus musculus
T1/2 1.3 hr Mus musculus
T1/2 1.1 hr Mus musculus
Tmax - - Mus musculus
Tmax 0.5 hr Mus musculus
Tmax 0.5 hr Mus musculus
Tmax 0.033 hr Mus musculus
Tmax 3.0 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Neuraminidase IC50 = 39.2 nM 7.41 Inhibition of Influenza A virus (A/Saitama/80/2003(H3N2)) neuraminidase after 30... 18955520
Neuraminidase IC50 = 46.6 nM 7.33 Inhibition of Influenza A virus (A/Yamagata/2/2002(H3N2)) neuraminidase after 30... 18955520
Neuraminidase IC50 = 56.6 nM 7.25 Inhibition of Influenza A virus (A/Yamagata/1/2002(H3N2)) neuraminidase after 30... 18955520
Neuraminidase IC50 = 63.3 nM 7.2 Inhibition of Influenza A virus (A/Saitama/07/2006(H3N2)) neuraminidase after 30... 18955520
Neuraminidase IC50 = 64.2 nM 7.19 Inhibition of Influenza A virus (A/Shiga/5/2002(H3N2)) neuraminidase after 30 mi... 18955520
Neuraminidase IC50 = 69.1 nM 7.16 Inhibition of Influenza A virus (A/Hiroshima/52/2005(H3N2)) neuraminidase after ... 18955520
Neuraminidase IC50 = 114.0 nM 6.94 Inhibition of Influenza A virus (A/Wyoming/03/2003(H3N2)) neuraminidase after 30... 18955520
Neuraminidase IC50 = 128.0 nM 6.89 Inhibition of Influenza A virus (A/Singapore/1/1957(H2N2)) neuraminidase after 3... 18955520
Neuraminidase IC50 = 129.0 nM 6.89 Inhibition of Influenza A virus (A/Osaka/56/2004(H3N2)) neuraminidase after 30 m... 18955520
Neuraminidase IC50 = 131.0 nM 6.88 Inhibition of Influenza A virus (A/Tokushima/1/2005(H3N2)) neuraminidase after 3... 18955520
Neuraminidase IC50 = 135.0 nM 6.87 Inhibition of Influenza A virus (A/California/07/2004(H3N2)) neuraminidase after... 18955520
Neuraminidase IC50 = 136.0 nM 6.87 Inhibition of Influenza A virus (A/New York/55/2004(H3N2)) neuraminidase after 3... 18955520
Neuraminidase IC50 = 142.0 nM 6.85 Inhibition of Influenza A virus (A/seal/Massachusetts/1/1980(H7N7)) neuraminidas... 18955520
Neuraminidase IC50 = 157.0 nM 6.8 Inhibition of Influenza A virus (A/Wellington/1/2004(H3N2)) neuraminidase after ... 18955520
Neuraminidase IC50 = 164.0 nM 6.79 Inhibition of Influenza A virus (A/Aichi/2/1968(H3N2)) neuraminidase after 30 mi... 18955520
Neuraminidase IC50 = 187.0 nM 6.73 Inhibition of Influenza A virus (A/Wisconsin/67/2005(H3N2)) neuraminidase after ... 18955520
Neuraminidase IC50 = 221.0 nM 6.66 Inhibition of Influenza A virus (A/Kitakyushu/159/1993(H3N2)) neuraminidase afte... 18955520
Neuraminidase IC50 = 262.0 nM 6.58 Inhibition of Influenza A virus (A/duck/England/1/1956(H11N6)) neuraminidase aft... 18955520
Neuraminidase IC50 = 276.0 nM 6.56 Inhibition of Influenza A virus (A/R(duck/Mongolia/54/01-duck/Mongolia/47/01)(H5... 18955520
Neuraminidase IC50 = 356.0 nM 6.45 Inhibition of Influenza A virus (A/duck/Memphis/546/1974(H11N9)) neuraminidase a... 18955520

Literature References

PubMed DOI Target Context # Activities
18955520 10.1128/aac.00333-08 Neuraminidase 35
20047917 10.1128/aac.01311-09 Influenza A virus 24
18955520 10.1128/aac.00333-08 Unchecked 23
19687241 10.1128/aac.00731-09 ADMET 9
23091189 10.1124/dmd.112.048280 ADMET 9
20047917 10.1128/aac.01311-09 Influenza B virus 7
23091189 10.1124/dmd.112.048280 Plasma 4
23091189 10.1124/dmd.112.048280 Lung 4
19687241 10.1128/aac.00731-09 Lung 3
19414262 10.1016/j.bmcl.2009.04.067 Influenza A virus 2
18955520 10.1128/aac.00333-08 Influenza A virus 2
23091189 10.1124/dmd.112.048280 No relevant target 2
35196598 10.1016/j.ejmech.2022.114189 ADMET 2
36055001 10.1016/j.ejmech.2022.114711 ADMET 1

Data from ChEMBL 36 via Core Engine