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Compound Detail

CHEMBL1741

CLARITHROMYCIN
💊 Approved Drug
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💊 Approved Drug
CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[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](O)[C@]1(C)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1741
Name CLARITHROMYCIN
Phase Approved
Structure Type MOL
InChI Key AGOYDEPGAOXOCK-KCBOHYOISA-N
Therapeutic ✓ Yes

Known Names

6-o-methylerythromycin A-56268 ABBOTT-56268 Biaxin Biaxin xl Biaxin xl pac Clarie xl Clarithromycin Clarithromycin component of prevpac Clarithromycin extended release Clarithromycin identity Clarithromycine +18 more
9
Targets
21
Activities
3
Assay Types
30
PK Parameters
20
Publications
30
Known Names
20
Indications
1
Mechanisms

Molecular Properties

748.0
MW (Da)
2.44
ALogP
14
HBA
4
HBD
182.9
PSA (Ų)
0.27
QED
2
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1991
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -mycin
USAN Year 1988

Extended Properties

Molecular Formula C38H69NO13
MW 747.96
Aromatic Rings 0
Heavy Atoms 52
NP-Likeness 1.77

Mechanism of Action

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

Indications

Bacterial Infections Bronchitis, Chronic Duodenal Ulcer Infections Maxillary Sinusitis Otitis Media Pharyngitis Pneumonia Sinusitis Tonsillitis Asthma Bronchiolitis Obliterans Bronchopulmonary Dysplasia Crohn Disease Gastritis Heart Diseases Helicobacter Infections Hemorrhage Lymphoma, Non-Hodgkin Multiple Myeloma

ATC Classification

J01FA09
clarithromycin
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE

Activity Summary

IC50 19 meas. best 7.05
Kd 1 meas. best 9.19
Ki 1 meas. best 5.26

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
GABA-A receptor; anion channel
CHEMBL1907607
 Kd 9.19 9.19 0.6 1
Streptococcus pneumoniae
CHEMBL347
 IC50 7.05 7.05 90.0 1
Solute carrier organic anion transporter family member 1B1
CHEMBL1697668
 IC50 5.51 5.51 3090.3 1
Solute carrier organic anion transporter family member 1B3
CHEMBL1743121
 IC50 5.48 5.48 3311.3 1
ATP-dependent translocase ABCB1
CHEMBL4302
 IC50 5.42 4.6586 3800.0 7
Cytochrome P450 3A4
CHEMBL340
 Ki 5.26 5.26 5490.0 1
Unchecked
CHEMBL612545
 IC50 4.53 4.405 29650.0 2
Toxoplasma gondii
CHEMBL612888
 IC50 4.51 4.51 31000.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 4.48 4.302 33113.1 5

Pharmacokinetic Data

Parameter Value Units Species
AUC 1310.0 ng.hr.mL-1 Mus musculus
AUC 30380.0 ng.hr.mL-1 Mus musculus
AUC 1767.0 ng.hr.mL-1 Mus musculus
AUC 18900.0 ng.hr.mL-1 Homo sapiens
AUC 2420.0 ng.hr.mL-1 Homo sapiens
AUC 2220.0 ng.hr.mL-1 Homo sapiens
AUC 26810.0 ng.hr.mL-1 Homo sapiens
AUC 920.0 ng.hr.mL-1 Homo sapiens
AUC 840.0 ng.hr.mL-1 Homo sapiens
AUC 10590.0 ng.hr.mL-1 Homo sapiens
AUC 480.0 ng.hr.mL-1 Homo sapiens
AUC 350.0 ng.hr.mL-1 Homo sapiens
AUC 4450.0 ng.hr.mL-1 Homo sapiens
AUC 290.0 ng.hr.mL-1 Homo sapiens
AUC 240.0 ng.hr.mL-1 Homo sapiens
AUC 3630.0 ng.hr.mL-1 Homo sapiens
AUC 7520.0 ng.hr.mL-1 Homo sapiens
AUC 6530.0 ng.hr.mL-1 Staphylococcus aureus
AUC 36645.02 ng.hr.mL-1 Homo sapiens
AUC 58485.51 ng.hr.mL-1 Homo sapiens
AUC 37615.92 ng.hr.mL-1 Homo sapiens
AUC 60796.12 ng.hr.mL-1 Homo sapiens
CL 37.2 L/hr Homo sapiens
CL 18.7 L/hr Homo sapiens
CL 4.7 mL.min-1.kg-1 Homo sapiens
CL 7.3 mL.min-1.kg-1 Homo sapiens
CL 7.3 mL.min-1.kg-1 Homo sapiens
CL 68.0 uL.min-1.(10^6cells)-1 Rattus norvegicus
CL 46.0 uL.min-1.(10^6cells)-1 Rattus norvegicus
Cmax 1617.73 nM Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
GABA-A receptor; anion channel Kd = 0.64 nM 9.19 Displacement of [3H]FMZ from GABA-A receptor in rat brain assessed as Kd of [3H]... 27563397
Streptococcus pneumoniae IC50 = 90.0 nM 7.05 Cell free inhibiting activity against Streptococcus pneumoniae 5635(Wild type ri... 11708916
Solute carrier organic anion transporter family member 1B1 IC50 = 3090.3 nM 5.51 pIC50 values for sodium fluorescein (10 uM) uptake in OATP1B1-transfected CHO ce... 23571415
Solute carrier organic anion transporter family member 1B3 IC50 = 3311.31 nM 5.48 pIC50 values for sodium fluorescein (10 uM) uptake in OATP1B3-transfected CHO ce... 23571415
ATP-dependent translocase ABCB1 IC50 = 3800.0 nM 5.42 TP_TRANSPORTER: inhibition of Daunorubicin efflux in NIH-3T3-G185 cells 11716514
Cytochrome P450 3A4 Ki = 5490.0 nM 5.26 Mechanism based inhibition of human cytochrome P450 3A4 16248836
ATP-dependent translocase ABCB1 IC50 = 7200.0 nM 5.14 TP_TRANSPORTER: inhibition of LDS-751 efflux in NIH-3T3-G185 cells 11716514
ATP-dependent translocase ABCB1 IC50 = 15100.0 nM 4.82 TP_TRANSPORTER: inhibition of Rhodamine 123 efflux in NIH-3T3-G185 cells 11716514
ATP-dependent translocase ABCB1 IC50 = 23800.0 nM 4.62 TP_TRANSPORTER: inhibition of Tetramethylrosamine efflux in NIH-3T3-G185 cells 11716514
Unchecked IC50 = 29650.0 nM 4.53 PUBCHEM_BIOASSAY: A counter screen for small molecule screen for inhibitors of t... -
Toxoplasma gondii IC50 = 31000.0 nM 4.51 Antiparasitic activity against Toxoplasma gondii 2F-1 expressing yellow fluoresc... 21428405
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 33113.11 nM 4.48 Inhibition of K+ channel activity in mammalian cells expressing HERG Kv11.1 12873512
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 46000.0 nM 4.34 Inhibitory concentration against IKr potassium channel 15324906
ATP-dependent translocase ABCB1 IC50 = 50200.0 nM 4.3 TP_TRANSPORTER: inhibition of JC-1 efflux in NIH-3T3-G185 cells 11716514
Unchecked IC50 = 51990.0 nM 4.28 PUBCHEM_BIOASSAY: A small molecule screen for inhibitors of the PhoP region in S... -
ATP-dependent translocase ABCB1 IC50 = 56100.0 nM 4.25 TP_TRANSPORTER: inhibition of Calcein-AM efflux in NIH-3T3-G185 cells 11716514
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 58884.37 nM 4.23 Inhibition of human Potassium channel HERG expressed in mammalian cells 12873512
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 58884.37 nM 4.23 Inhibitory concentration against potassium channel HERG 15911273
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 58884.37 nM 4.23 Inhibition of human ERG expressed in CHO cells by whole cell patch clamp techniq... 18448342
ATP-dependent translocase ABCB1 IC50 = 86700.0 nM 4.06 TP_TRANSPORTER: inhibition of Fluo-3-AM efflux in NIH-3T3-G185 cells 11716514

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 436
19171799 10.1128/aac.01275-08 Mycobacteroides abscessus 171
19884376 10.1128/aac.01123-09 Streptococcus pneumoniae 89
17876003 10.1128/aac.00827-07 Streptococcus pneumoniae 50
17606673 10.1128/aac.00532-07 Homo sapiens 48
19307366 10.1128/aac.01531-08 Streptococcus pneumoniae 43
19075048 10.1128/aac.01247-08 NON-PROTEIN TARGET 38
19332671 10.1128/aac.01424-08 Coxiella burnetii 30
17116666 10.1128/aac.01150-06 Streptococcus pneumoniae 28
19738019 10.1128/aac.00724-09 NON-PROTEIN TARGET 28
19546358 10.1128/aac.00206-09 Staphylococcus aureus 27
20231401 10.1128/aac.01565-09 Staphylococcus epidermidis 24
20855744 10.1128/aac.00553-10 Chlamydia trachomatis 21
18070962 10.1128/aac.00375-07 Escherichia coli 19
- 10.1007/s00044-012-0429-8 Helicobacter pylori 19
16472241 10.2174/1570163043334794 Hepatotoxicity 18
18591267 10.1128/aac.00405-08 Escherichia coli 16
18809936 10.1128/aac.00596-08 Streptococcus sp. 'group B' 16
20479195 10.1128/aac.01439-09 Escherichia coli 16
18591267 10.1128/aac.00405-08 Acinetobacter baumannii 16

Data from ChEMBL 36 via Core Engine