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Compound Detail

CHEMBL3291398

LEFAMULIN
💊 Approved Drug
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💊 Approved Drug
C=C[C@]1(C)C[C@@H](OC(=O)CS[C@@H]2CC[C@@H](N)C[C@H]2O)[C@]2(C)[C@H](C)CC[C@]3(CCC(=O)[C@H]32)[C@@H](C)[C@@H]1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3291398
Name LEFAMULIN
Phase Approved
Structure Type MOL
InChI Key KPVIXBKIJXZQJX-FCEONZPQSA-N
Therapeutic ✓ Yes

Known Names

BC-3781 Lefamulin Lefamulina Lefamuline
5
Targets
11
Activities
3
Assay Types
12
PK Parameters
20
Publications
4
Known Names
3
Indications

Molecular Properties

507.7
MW (Da)
3.87
ALogP
7
HBA
3
HBD
109.8
PSA (Ų)
0.38
QED
1
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2019
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral Parenteral

Flags

Natural Product
USAN Stem -mulin
USAN Year 2014

Extended Properties

Molecular Formula C28H45NO5S
MW 507.74
Aromatic Rings 0
Heavy Atoms 35
NP-Likeness 1.83

Indications

Bacterial Infections Pneumonia Cystic Fibrosis

ATC Classification

J01XX12
lefamulin
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE

Activity Summary

IC50 8 meas. best 6.12
EC50 2 meas. best 6.69
Ki 1 meas. best 6.07

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Wolbachia
CHEMBL4630676
 EC50 6.69 6.675 205.0 2
Cytochrome P450 3A4
CHEMBL340
 IC50 6.12 5.5375 750.0 4
Cytochrome P450 3A4
CHEMBL340
 Ki 6.07 6.07 860.0 1
ATP-dependent translocase ABCB1
CHEMBL4302
 IC50 4.47 4.47 34100.0 1
Unchecked
CHEMBL612545
 IC50 4.37 4.37 43000.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 4.11 4.11 78200.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 275.0 ng.hr.mL-1 Rattus norvegicus
CL 121.67 mL.min-1.kg-1 Rattus norvegicus
CL 4.0 mL.min-1.g-1 Mus musculus
CL 478.0 mL.min-1.kg-1 Mus musculus
CL 1455.0 mL.min-1.kg-1 Homo sapiens
CL 359.0 mL.min-1.kg-1 Sus scrofa domesticus
Fu 0.218 - Mus musculus
MRT 3.8 hr Rattus norvegicus
T1/2 4.4 hr Rattus norvegicus
T1/2 0.1917 hr Mus musculus
T1/2 0.07167 hr Homo sapiens
T1/2 0.255 hr Sus scrofa domesticus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Wolbachia EC50 = 205.0 nM 6.69 Antimicrobial activity against Wolbachia pipientis infected in Asian tiger mosqu... 30730745
Wolbachia EC50 = 220.0 nM 6.66 Antimicrobial activity against Wolbachia wMel infected in Drosophila melanogaste... 30730745
Cytochrome P450 3A4 IC50 = 750.0 nM 6.12 Inhibition of human CYP3A4 incubated for 60 mins by red fluorescent-probe-based ... 38385364
Cytochrome P450 3A4 Ki = 860.0 nM 6.07 Inhibition of CYP3A4 in pooled human liver microsomes using midazolam as substra... 38385364
Cytochrome P450 3A4 IC50 = 4430.0 nM 5.35 Inhibition of CYP3A4 in human liver microsomes using testosterone as substrate a... 24874438
Cytochrome P450 3A4 IC50 = 4460.0 nM 5.35 Inhibition of CYP3A4 in pooled human liver microsomes using testosterone as subs... 38385364
Cytochrome P450 3A4 IC50 = 4650.0 nM 5.33 Inhibition of CYP3A4 in human liver microsomes using midazolam as substrate afte... 24874438
ATP-dependent translocase ABCB1 IC50 = 34100.0 nM 4.47 Inhibition of P-gp in human Caco-2 cells using digoxin as substrate 38385364
Unchecked IC50 = 43000.0 nM 4.37 Inhibition of P-gp efflux in MDCKII-MDR1 cells using calcein-AM as substrate ass... 38385364
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 78200.0 nM 4.11 Inhibition of K+ ion channel activity of hERG 38385364

Literature References

PubMed DOI Target Context # Activities
38385364 10.1021/acs.jmedchem.3c02153 Unchecked 23
38385364 10.1021/acs.jmedchem.3c02153 ADMET 15
39106659 10.1016/j.ejmech.2024.116745 Staphylococcus aureus 9
24874438 10.1021/jm500312x Staphylococcus aureus 6
38385364 10.1021/acs.jmedchem.3c02153 Staphylococcus aureus 6
39106659 10.1016/j.ejmech.2024.116745 Streptococcus pneumoniae 5
24874438 10.1021/jm500312x Rattus norvegicus 5
39106659 10.1016/j.ejmech.2024.116745 Staphylococcus epidermidis 5
32014384 10.1016/j.bmcl.2020.126969 Staphylococcus epidermidis 4
39106659 10.1016/j.ejmech.2024.116745 ADMET 3
30730745 10.1021/acs.jmedchem.8b01854 ADMET 3
38385364 10.1021/acs.jmedchem.3c02153 Voltage-gated inwardly rectifying potassium channel KCNH2 3
38385364 10.1021/acs.jmedchem.3c02153 Cytochrome P450 3A4 3
38385364 10.1021/acs.jmedchem.3c02153 Enterococcus faecium 2
39106659 10.1016/j.ejmech.2024.116745 Enterococcus faecalis 2
32014384 10.1016/j.bmcl.2020.126969 Staphylococcus aureus 2
30730745 10.1021/acs.jmedchem.8b01854 Wolbachia 2
24874438 10.1021/jm500312x Cytochrome P450 3A4 2
38503168 10.1016/j.ejmech.2024.116313 Staphylococcus 1
24874438 10.1021/jm500312x Cytochrome P450 2D6 1

Data from ChEMBL 36 via Core Engine