Compound Detail

CHEMBL2218877

ERYTHROMYCIN ESTOLATE

💊 Approved Drug

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💊 Approved Drug

CCC(=O)O[C@H]1[C@H](O[C@@H]2[C@@H](C)[C@H](O[C@H]3C[C@@](C)(OC)[C@@H](O)[C@H](C)O3)[C@@H](C)C(=O)O[C@H](CC)[C@@](C)(O)[C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@]2(C)O)O[C@H](C)C[C@@H]1N(C)C.CCCCCCCCCCCCOS(=O)(=O)O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL2218877
Name	ERYTHROMYCIN ESTOLATE
Phase	Approved
Structure Type	MOL
InChI Key	AWMFUEJKWXESNL-JZBHMOKNSA-N
Therapeutic	✓ Yes
Parent Compound	CHEMBL2220427
Active Moiety	CHEMBL2220427

Known Names

Erythromycin (as estolate) Erythromycin estolate Erythromycin estolate component of ilosone sulfa Erythromycin estorate Erythromycin lauryl sulfate, propionyl Erythromycin propionate lauryl sulfate Ilosone NSC-263364 Propionyl erythromycin lauryl sulfate

5

Targets

9

Activities

2

Assay Types

1

PK Parameters

14

Publications

9

Known Names

1

Mechanisms

Molecular Properties

790.0

MW (Da)

2.75

ALogP

15

HBA

4

HBD

200.0

PSA (Å²)

0.25

QED

2

Ro5 Violations

9

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1967
Availability	Withdrawn
Chirality	Single Enantiomer

Routes of Administration

Oral

Flags

Withdrawn Natural Product

USAN Stem	-mycin
USAN Year	1962

Extended Properties

Molecular Formula	C52H97NO18S
MW	1056.40
Aromatic Rings	0
Heavy Atoms	55
NP-Likeness	1.83

Mechanism of Action

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

Drug Warnings

Withdrawn

hepatotoxicity

Severe cholestatic hepatitis and jaundice

Country: Mauritius; Bangladesh; Sweden Year: 1982

Withdrawn

General Warning

Harmful

Country: Mauritius; Bangladesh; Sweden Year: 1982

Withdrawn

hepatotoxicity

Hepatotoxicity

Country: Mauritius; Bangladesh; Sweden Year: 1982

Withdrawn

hepatotoxicity

Hepatotoxicity

Country: Mauritius; Bangladesh; Sweden Year: 1982

Withdrawn

hepatotoxicity

Severe cholestatic hepatitis and jaundice

Country: Mauritius; Bangladesh; Sweden Year: 1982

Activity Summary

IC50 7 meas. best 7.18

Ki 2 meas. best 5.63

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Liver CHEMBL613642	IC50	7.18	7.18	65.8	1
Solute carrier organic anion transporter family member 1B3 CHEMBL1743121	Ki	5.63	5.63	2350.0	1
Solute carrier organic anion transporter family member 1B1 CHEMBL1697668	Ki	5.62	5.62	2410.0	1
Solute carrier organic anion transporter family member 1B3 CHEMBL1743121	IC50	5.51	5.51	3090.3	1
Bile salt export pump CHEMBL6020	IC50	5.39	5.0567	4100.0	3
Solute carrier organic anion transporter family member 1B1 CHEMBL1697668	IC50	5.36	5.36	4365.2	1
Bile salt export pump CHEMBL2073674	IC50	4.94	4.94	11400.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
Cmax	4196.0	nM	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Liver	IC50	=	65.8	nM	7.18	Induction of mitochondrial dysfunction in Sprague-Dawley rat liver mitochondria ...	24799086
Solute carrier organic anion transporter family member 1B3	Ki	=	2350.0	nM	5.63	Ki values for sodium fluorescein (10 uM) uptake in OATP1B3-transfected CHO cells	23571415
Solute carrier organic anion transporter family member 1B1	Ki	=	2410.0	nM	5.62	Ki values for sodium fluorescein (10 uM) uptake in OATP1B1-transfected CHO cells	23571415
Solute carrier organic anion transporter family member 1B3	IC50	=	3090.3	nM	5.51	pIC50 values for sodium fluorescein (10 uM) uptake in OATP1B3-transfected CHO ce...	23571415
Bile salt export pump	IC50	=	4100.0	nM	5.39	Inhibition of human BSEP expressed in plasma membrane vesicles of Sf21 cells ass...	21965623
Solute carrier organic anion transporter family member 1B1	IC50	=	4365.16	nM	5.36	pIC50 values for sodium fluorescein (10 uM) uptake in OATP1B1-transfected CHO ce...	23571415
Bile salt export pump	IC50	=	11400.0	nM	4.94	Inhibition of Sprague-Dawley rat Bsep expressed in plasma membrane vesicles of S...	21965623
Bile salt export pump	IC50	=	13000.0	nM	4.89	Inhibition of human BSEP expressed in fall armyworm sf9 cell plasma membrane ves...	20829430
Bile salt export pump	IC50	=	13000.0	nM	4.89	Inhibition of recombinant human BSEP expressed in baculovirus infected sf9 cell ...	24799086

Literature References

PubMed	DOI	Target Context	# Activities
20014752	10.1021/tx900326k	Hepatotoxicity	3
23571415	10.1124/mol.112.084152	Solute carrier organic anion transporter family member 1B3	3
23571415	10.1124/mol.112.084152	Solute carrier organic anion transporter family member 1B1	3
21965623	10.1124/dmd.111.040758	Bile salt export pump	2
24799086	10.1002/hep.27206	Homo sapiens	2
-	10.6019/CHEMBL4495565	SARS-CoV-2	2
20553011	10.1021/tx1000865	Hepatotoxicity	1
20843939	10.1124/dmd.110.035113	Hepatotoxicity	1
21965623	10.1124/dmd.111.040758	Plasma	1
20829430	10.1093/toxsci/kfq269	Bile salt export pump	1
24799086	10.1002/hep.27206	Bile salt export pump	1
24799086	10.1002/hep.27206	Liver	1
-	10.21203/rs.3.rs-23951/v1	SARS-CoV-2	1
-	10.6019/CHEMBL4495564	Replicase polyprotein 1ab	1

Data from ChEMBL 36 via Core Engine