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Compound Detail

CHEMBL564085

TROLEANDOMYCIN
💊 Approved Drug
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💊 Approved Drug
CO[C@H]1C[C@H](O[C@H]2[C@H](C)[C@@H](O[C@@H]3O[C@H](C)C[C@H](N(C)C)[C@H]3OC(C)=O)[C@@H](C)C[C@@]3(CO3)C(=O)[C@H](C)[C@@H](OC(C)=O)[C@@H](C)[C@@H](C)OC(=O)[C@@H]2C)O[C@@H](C)[C@@H]1OC(C)=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL564085
Name TROLEANDOMYCIN
Phase Approved
Structure Type MOL
InChI Key LQCLVBQBTUVCEQ-QTFUVMRISA-N
Therapeutic ✓ Yes

Known Names

Acetyloleandomycin NSC-108166 Oleandomycin (as troleandomycin) Oleandomycin triacetate ester Triacetyloleandomycin Troleandomicina Troleandomycin Troleandomycine
2
Targets
11
Activities
2
Assay Types
0
PK Parameters
20
Publications
8
Known Names
2
Indications
1
Mechanisms

Molecular Properties

814.0
MW (Da)
3.62
ALogP
16
HBA
0
HBD
184.2
PSA (Ų)
0.19
QED
2
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1969
Availability Discontinued
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -mycin
USAN Year 1968

Extended Properties

Molecular Formula C41H67NO15
MW 813.98
Aromatic Rings 0
Heavy Atoms 57
NP-Likeness 1.38

Mechanism of Action

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

Indications

Bacterial Infections Osteomyelitis

ATC Classification

J01FA08
troleandomycin
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE

Activity Summary

IC50 8 meas. best 5.1
Ki 3 meas. best 4.06

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cytochrome P450 3A4
CHEMBL340
 IC50 5.1 4.658 7998.3 5
ATP-dependent translocase ABCB1
CHEMBL4302
 IC50 4.17 4.1133 68300.0 3
ATP-dependent translocase ABCB1
CHEMBL4302
 Ki 4.06 4.06 87640.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cytochrome P450 3A4 IC50 = 7998.34 nM 5.1 Inhibition of CYP3A4 19128860
Cytochrome P450 3A4 IC50 = 16000.0 nM 4.8 Inhibition of recombinant human Cytochrome P450 3A4 with BFC [7-benzyloxy-4-trif... 12930139
Cytochrome P450 3A4 IC50 = 20000.0 nM 4.7 Inhibition of recombinant human Cytochrome P450 3A4 using BFC [7-benzyloxy-4-tri... 12930139
Cytochrome P450 3A4 IC50 = 33000.0 nM 4.48 Inhibition of recombinant human Cytochrome P450 3A4 with BFC [7-benzyloxy-4-trif... 12930139
Cytochrome P450 3A4 IC50 = 61000.0 nM 4.21 Inhibition of recombinant human Cytochrome P450 3A4 with BFC [7-benzyloxy-4-trif... 12930139
ATP-dependent translocase ABCB1 IC50 = 68300.0 nM 4.17 TP_TRANSPORTER: inhibition of Daunorubicin efflux in NIH-3T3-G185 cells 11716514
ATP-dependent translocase ABCB1 IC50 = 78200.0 nM 4.11 TP_TRANSPORTER: inhibition of LDS-751 efflux in NIH-3T3-G185 cells 11716514
ATP-dependent translocase ABCB1 IC50 = 86300.0 nM 4.06 TP_TRANSPORTER: inhibition of Rhodamine 123 efflux in NIH-3T3-G185 cells 11716514
ATP-dependent translocase ABCB1 Ki = 87640.0 nM 4.06 TP_TRANSPORTER: increase in Vinblastine intracellular accumulation in MDR1-expre... 11961113

Literature References

PubMed DOI Target Context # Activities
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
12930139 10.1021/jm034111v Cytochrome P450 3A4 4
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
11716514 10.1006/bbrc.2001.6000 ATP-dependent translocase ABCB1 3
20014752 10.1021/tx900326k Hepatotoxicity 3
22931300 10.1021/tx300075j Cytochrome P450 3A4 2
11961113 10.1124/mol.61.5.964 ATP-dependent translocase ABCB1 2
12235267 10.1124/jpet.102.037549 ATP-dependent translocase ABCB1 2
22931300 10.1021/tx300075j Liver microsomes 2
37468498 10.1038/s41467-023-40064-9 Mu-type opioid receptor 2
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 Progesterone receptor 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 2
38318365 10.1016/j.isci.2024.108907 Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 1
22931300 10.1021/tx300075j Cytochrome P450 2D6 1

Data from ChEMBL 36 via Core Engine