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Compound Detail

CHEMBL1237072

DIRITHROMYCIN
💊 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)(O)C[C@@H](C)[C@@H]2N[C@@H](COCCOC)O[C@H]([C@H]2C)[C@]1(C)O

Basic Information

ChEMBL ID CHEMBL1237072
Name DIRITHROMYCIN
Phase Approved
Structure Type MOL
InChI Key WLOHNSSYAXHWNR-DWIOZXRMSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL1201397

Known Names

Dirithromycin Dirithromycine Diritromicina Dynabac LY 237216 LY-237216 NSC-758672
2
Targets
7
Activities
2
Assay Types
0
PK Parameters
20
Publications
7
Known Names
2
Indications
1
Mechanisms

Molecular Properties

835.1
MW (Da)
2.20
ALogP
16
HBA
5
HBD
196.3
PSA (Ų)
0.14
QED
2
Ro5 Violations
12
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1995
Availability Discontinued
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product Prodrug
USAN Stem -mycin
USAN Year 1989

Extended Properties

Molecular Formula C42H78N2O14
MW 835.09
Aromatic Rings 0
Heavy Atoms 58
NP-Likeness 1.41

Mechanism of Action

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

Indications

Bacterial Infections Osteomyelitis

ATC Classification

J01FA13
dirithromycin
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE

Activity Summary

IC50 6 meas. best 5.26
EC50 1 meas. best 6.93

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Streptococcus
CHEMBL612313
EC50 6.93 6.93 117.0 1
Unchecked
CHEMBL612545
IC50 5.26 4.7383 5520.0 6

Activity Data Samples

Top measurements by pChEMBL value

Literature References

PubMed DOI Target Context # Activities
16472241 10.2174/1570163043334794 Hepatotoxicity 18
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
17210767 10.1128/aac.01048-06 Escherichia coli 3
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2
30371064 10.1021/acs.jmedchem.8b01044 PC-3 1
- 10.1101/2020.04.03.023846 SARS-CoV-2 1
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
- 10.1101/2020.04.21.054387 SARS-CoV-2 1
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 1
30371064 10.1021/acs.jmedchem.8b01044 Caco-2 1
30371064 10.1021/acs.jmedchem.8b01044 A549 1
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 1
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B1 1

Data from ChEMBL 36 via Core Engine