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Compound Detail

CHEMBL1136

TELITHROMYCIN
💊 Approved Drug
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💊 Approved Drug
CC[C@H]1OC(=O)[C@H](C)C(=O)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@](C)(OC)C[C@@H](C)C(=O)[C@H](C)[C@H]2N(CCCCn3cnc(-c4cccnc4)c3)C(=O)O[C@]12C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1136
Name TELITHROMYCIN
Phase Approved
Structure Type MOL
InChI Key LJVAJPDWBABPEJ-PNUFFHFMSA-N
Therapeutic ✓ Yes

Known Names

HMR 3647 HMR-3647 HMR3647 Ketek Levviax NSC-758940 Telithromycin Telithromycine Telitromicina
10
Targets
18
Activities
4
Assay Types
30
PK Parameters
20
Publications
9
Known Names
15
Indications
1
Mechanisms

Molecular Properties

812.0
MW (Da)
4.93
ALogP
14
HBA
1
HBD
171.8
PSA (Ų)
0.18
QED
2
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2001
Availability Discontinued
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -mycin
USAN Year 2004

Extended Properties

Molecular Formula C43H65N5O10
MW 812.02
Aromatic Rings 2
Heavy Atoms 58
NP-Likeness 0.71

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Bacterial 70S ribosome inhibitor INHIBITOR Bacterial 70S ribosome ✓ ✓

Indications

Bacterial Infections Bronchitis, Chronic Community-Acquired Infections Infections Pharyngitis Pneumonia Pneumonia, Bacterial Sinusitis Tonsillitis Tonsillitis Asthma Maxillary Sinusitis Otitis Media Otitis Media, Suppurative Scrub Typhus

ATC Classification

J01FA15
telithromycin
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE

Drug Warnings

Black Box Warning
General Warning
Country: United States

Activity Summary

IC50 15 meas. best 6.64
EC50 1 meas.
Kd 1 meas. best 8.19
Ki 1 meas. best 8.62

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cytochrome P450 3A
CHEMBL2364675
 Ki 8.62 8.62 2.4 1
Bacterial 70S ribosome
CHEMBL2363135
 Kd 8.19 8.19 6.4 1
Unchecked
CHEMBL612545
 IC50 6.64 6.05 230.0 2
Plasmodium falciparum
CHEMBL364
 IC50 6.55 5.995 280.0 4
Solute carrier organic anion transporter family member 1B1
CHEMBL1697668
 IC50 5.46 5.46 3467.4 1
Bile salt export pump
CHEMBL6020
 IC50 5.4 5.0733 4000.0 3
Solute carrier organic anion transporter family member 1B3
CHEMBL1743121
 IC50 5.23 5.23 5888.4 1
ATP-binding cassette sub-family C member 4
CHEMBL1743128
 IC50 5.15 5.15 7100.0 1
Cytochrome P450 3A4
CHEMBL340
 IC50 4.93 4.93 11800.0 2
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 4.4 4.4 40000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 2500.0 ng.hr.mL-1 Rattus norvegicus
AUC 48000.0 ng.hr.mL-1 Rattus norvegicus
AUC 24333.33 ng.hr.mL-1 Rattus norvegicus
AUC 3090.0 ng.hr.mL-1 Homo sapiens
AUC 8250.0 ng.hr.mL-1 Homo sapiens
AUC 12500.0 ng.hr.mL-1 Homo sapiens
AUC 9386.95 ng.hr.mL-1 Homo sapiens
AUC 3950.0 ng.hr.mL-1 Rattus norvegicus
AUC 2730.0 ng.hr.mL-1 Rattus norvegicus
AUC 927.0 ng.hr.mL-1 Rattus norvegicus
AUC 897.0 ng.hr.mL-1 Rattus norvegicus
AUC 927.0 ng.hr.mL-1 Rattus norvegicus
AUC 897.0 ng.hr.mL-1 Rattus norvegicus
C(24h) 0.03 mcg/mL Homo sapiens
CL 100.0 mL.min-1.kg-1 Rattus norvegicus
CL 14.0 mL.min-1.kg-1 Homo sapiens
CL 19.4 mL.min-1.kg-1 Rattus norvegicus
CL 15.1 mL.min-1.kg-1 Rattus norvegicus
CL 14.0 mL.min-1.kg-1 Homo sapiens
CL 42.5 mL.min-1.kg-1 Rattus norvegicus
CL 75.9 mL.min-1.kg-1 Rattus norvegicus
CL 362.63 mL.min-1.kg-1 Rattus norvegicus
CL 362.64 mL.min-1.kg-1 Rattus norvegicus
CL 38.4 mL.min-1.kg-1 Homo sapiens
Cmax 6773.23 nM Mus musculus
Cmax 2339.84 nM Homo sapiens
Cmax 6194.43 nM Rattus norvegicus
Cmax 985.2 nM Homo sapiens
Cmax 2339.84 nM Homo sapiens
Cmax 2795.5 nM Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cytochrome P450 3A Ki = 2.4 nM 8.62 Inhibition of CYP3A in human liver microsomes assessed as hydroxymidazolam forma... 19775168
Bacterial 70S ribosome Kd = 6.4 nM 8.19 Binding affinity to Escherichia coli ribosomes after 2 hrs by fluorescence polar... 25221660
Unchecked IC50 = 230.0 nM 6.64 Inhibition of protein synthesis using Escherichia coli S30 extracts preincubated... 24900314
Plasmodium falciparum IC50 = 280.0 nM 6.55 Antiplasmodial activity after 96 hrs against Plasmodium falciparum 3D7 as Malsta... 18056275
Plasmodium falciparum IC50 = 440.0 nM 6.36 Antiplasmodial activity after 120 hrs against Plasmodium falciparum 3D7 as Malst... 18056275
Plasmodium falciparum IC50 = 1040.0 nM 5.98 Antiplasmodial activity after 72 hrs against Plasmodium falciparum 3D7 as Malsta... 18056275
Solute carrier organic anion transporter family member 1B1 IC50 = 3467.37 nM 5.46 pIC50 values for sodium fluorescein (10 uM) uptake in OATP1B1-transfected CHO ce... 23571415
Unchecked IC50 = 3500.0 nM 5.46 Inhibition of human nAChR expressed in human TE671 cells assessed as reduction i... 31644280
Bile salt export pump IC50 = 4000.0 nM 5.4 Inhibition of human BSEP expressed in fall armyworm sf9 cell plasma membrane ves... 20829430
Bile salt export pump IC50 = 5000.0 nM 5.3 Inhibition of human BSEP overexpressed in Sf9 cell membrane vesicles assessed as... 23956101
Solute carrier organic anion transporter family member 1B3 IC50 = 5888.44 nM 5.23 pIC50 values for sodium fluorescein (10 uM) uptake in OATP1B3-transfected CHO ce... 23571415
ATP-binding cassette sub-family C member 4 IC50 = 7100.0 nM 5.15 Inhibition of human MRP4 overexpressed in Sf9 cell membrane vesicles assessed as... 23956101
Plasmodium falciparum IC50 = 8080.0 nM 5.09 Antiplasmodial activity after 48 hrs against Plasmodium falciparum 3D7 as Malsta... 18056275
Cytochrome P450 3A4 IC50 = 11800.0 nM 4.93 Inhibition of CYP3A4 in human liver microsomes assessed as reduction in metaboli... 30852383
Cytochrome P450 3A4 IC50 = 11800.0 nM 4.93 Inhibition of CYP3A4 in human liver microsomes using midazolam as substrate incu... 30925339
Bile salt export pump IC50 = 30000.0 nM 4.52 Inhibition of recombinant human BSEP expressed in baculovirus infected sf9 cell ... 24799086
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 40000.0 nM 4.4 Inhibition of human ERG by patch-clamp assay 19775168

Literature References

PubMed DOI Target Context # Activities
19884376 10.1128/aac.01123-09 Streptococcus pneumoniae 92
17876003 10.1128/aac.00827-07 Streptococcus pneumoniae 53
16509588 10.1021/jm051157a Streptococcus pneumoniae 44
18443117 10.1128/aac.00310-08 Streptococcus pneumoniae 27
18160519 10.1128/aac.01210-07 Rattus norvegicus 16
22153939 10.1016/j.bmcl.2011.10.101 Streptococcus pneumoniae 16
19171799 10.1128/aac.01275-08 Mycolicibacterium smegmatis 16
17908940 10.1128/aac.00971-07 Streptococcus pneumoniae 16
19738026 10.1128/aac.00952-09 Streptococcus pneumoniae 16
18316525 10.1128/aac.01383-07 Streptococcus pneumoniae 15
19884376 10.1128/aac.01123-09 Streptococcus pyogenes 15
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
17938189 10.1128/aac.01229-07 Streptococcus pneumoniae 14
17908940 10.1128/aac.00971-07 Haemophilus influenzae 12
17698631 10.1128/aac.00422-07 Haemophilus influenzae 12
18056275 10.1128/aac.00892-07 Plasmodium falciparum 12
16509588 10.1021/jm051157a Rattus norvegicus 12
18443122 10.1128/aac.01398-07 Streptococcus pneumoniae 12
19307366 10.1128/aac.01531-08 Streptococcus pneumoniae 12
10560728 10.1016/s0960-894x(99)00534-x Mus musculus 12

Data from ChEMBL 36 via Core Engine