Compound Detail

CHEMBL532

ERYTHROMYCIN

💊 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(=O)[C@H](C)[C@@H](O)[C@]1(C)O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL532
Name	ERYTHROMYCIN
Phase	Approved
Structure Type	MOL
InChI Key	ULGZDMOVFRHVEP-RWJQBGPGSA-N
Therapeutic	✓ Yes

Known Names

A/t/s Akne-mycin Aknemycin plus C-solve-2 E-base E-glades E-mycin E-solve 2 Emgel Eritromicina Ery-tab Eryacne 2 +18 more

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

733.9

MW (Da)

1.79

ALogP

HBA

HBD

193.9

PSA (Å²)

0.24

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1964
Availability	Prescription
Chirality	Single Enantiomer

Routes of Administration

Oral Parenteral Topical

Flags

Natural Product

USAN Stem

-mycin

Extended Properties

Molecular Formula	C37H67NO13
MW	733.94
Aromatic Rings	0
Heavy Atoms	51
NP-Likeness	1.89

Mechanism of Action

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

Indications

Acne Vulgaris Bacterial Infections Eye Infections Infections Whooping Cough Carcinoma, Non-Small-Cell Lung Chlamydia Infections Epidermolysis Bullosa Gastrointestinal Hemorrhage Hematemesis HIV Infections Pneumonia Bulimia Nervosa Colorectal Neoplasms Feeding and Eating Disorders Gastroparesis Pulmonary Disease, Chronic Obstructive Stomach Neoplasms Erectile Dysfunction Hepatitis C

ATC Classification

D10AF02

erythromycin

Level 1: DERMATOLOGICALS

Level 2: ANTI-ACNE PREPARATIONS

D10AF52

erythromycin, combinations

Level 1: DERMATOLOGICALS

Level 2: ANTI-ACNE PREPARATIONS

J01FA01

erythromycin

Level 1: ANTIINFECTIVES FOR SYSTEMIC USE

Level 2: ANTIBACTERIALS FOR SYSTEMIC USE

S01AA17

erythromycin

Level 1: SENSORY ORGANS

Level 2: OPHTHALMOLOGICALS

Activity Summary

IC50 39 meas. best 7.43

EC50 11 meas. best 7.3

Kd 9 meas. best 7.96

Ki 2 meas. best 4.43

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Bacterial 70S ribosome CHEMBL2363135	Kd	7.96	7.7733	11.0	3
Streptococcus pneumoniae CHEMBL347	IC50	7.43	7.2133	37.0	3
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	IC50	7.41	5.91	39.0	2
Motilin receptor CHEMBL2203	IC50	7.36	7.255	43.6	2
Motilin receptor CHEMBL2203	EC50	7.3	6.5333	50.1	6
Escherichia coli CHEMBL354	IC50	7.1	6.2975	80.0	4
Bacterial 70S ribosome CHEMBL2363135	IC50	6.77	5.7417	170.0	6
Cytochrome P450 3A4 CHEMBL340	IC50	6.72	5.64	190.0	3
Staphylococcus aureus CHEMBL352	IC50	6.6	6.6	250.0	1
Micrococcus luteus CHEMBL614421	IC50	6.51	6.51	310.0	1
Oryctolagus cuniculus CHEMBL374	EC50	6.5	6.5	316.2	1
Raoultella planticola CHEMBL613271	IC50	6.46	6.46	350.0	1
Bacillus subtilis CHEMBL359	IC50	6.38	6.38	420.0	1
Unchecked CHEMBL612545	IC50	5.96	5.815	1100.0	2
NON-PROTEIN TARGET CHEMBL3879801	EC50	5.92	5.92	1200.0	1
Motilin receptor CHEMBL5306	EC50	5.92	5.92	1200.0	3
Unchecked CHEMBL612545	Kd	5.21	4.906	6110.0	5
Plasmodium falciparum CHEMBL364	IC50	5.03	4.5833	9400.0	6
Albumin CHEMBL3253	Kd	4.92	4.92	12000.0	1
Motilin receptor CHEMBL2203	Ki	4.43	4.43	37000.0	1
ATP-dependent translocase ABCB1 CHEMBL4302	Ki	4.42	4.42	37790.0	1
Cytochrome P450 1B1 CHEMBL4878	IC50	4.4	4.4	40000.0	1
ATP-dependent translocase ABCB1 CHEMBL2573	IC50	4.37	4.37	43000.0	1
ATP-dependent translocase ABCB1 CHEMBL4302	IC50	4.37	4.37	43000.0	1
Toxoplasma gondii CHEMBL612888	IC50	4.03	4.03	93000.0	1
Aldehyde oxidase CHEMBL3257	IC50	4.01	4.01	96900.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	7700.0	ng.hr.mL-1	Homo sapiens
AUC	4021.4	ng.hr.mL-1	Homo sapiens
AUC	4010.0	ng.hr.mL-1	Homo sapiens
AUC	4852.6	ng.hr.mL-1	Homo sapiens
AUC	4787.4	ng.hr.mL-1	Homo sapiens
CL	5.6	mL.min-1.kg-1	Homo sapiens
CL	5.3	mL.min-1.kg-1	Homo sapiens
CL	5.6	mL.min-1.kg-1	Homo sapiens
CL	73.0	mL.min-1.kg-1	Rattus norvegicus
CL	5.6	mL.min-1.kg-1	Homo sapiens
CL	7.0	mL.min-1.kg-1	Homo sapiens
CL	14.0	mL.min-1.kg-1	Macaca
CL	21.0	mL.min-1.kg-1	Canis lupus familiaris
CL	2.1e-05	mL.min-1.g-1	Homo sapiens
CL	4.483	mL.min-1.kg-1	Canis lupus familiaris
CL	2.376	mL.min-1.kg-1	Canis lupus familiaris
CL	22.38	mL.min-1.kg-1	Rattus norvegicus
CL	17.4	mL.min-1.kg-1	Rattus norvegicus
CL	7.169	mL.min-1.kg-1	Homo sapiens
CL	1.147	mL.min-1.kg-1	Homo sapiens
CL	35.0	uL.min-1.(10^6cells)-1	Rattus norvegicus
CL	26.0	uL.min-1.(10^6cells)-1	Rattus norvegicus
CL	0.021	uL/min	Homo sapiens
CL	225.0	mL.min-1.kg-1	Homo sapiens
CL	23.33	mL.min-1.kg-1	Homo sapiens
Cmax	2725.02	nM	Homo sapiens
Cmax	1592.77	nM	Homo sapiens
Cmax	1519.2	nM	Homo sapiens
Cmax	1120.0	nM	Homo sapiens
F	35.0	%	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Bacterial 70S ribosome	Kd	=	11.0	nM	7.96	Displacement of [14C]ERY from erythromycin-sensitive Escherichia coli BL21 ribos...	17923495
Bacterial 70S ribosome	Kd	=	15.0	nM	7.82	Displacement of [14C]-erythromycin from Escherichia coli K-12 70S ribosome after...	19164155
Bacterial 70S ribosome	Kd	=	29.0	nM	7.54	Displacement of [14C]ERY from erythromycin-sensitive Propionibacterium acnes EG7...	17923495
Streptococcus pneumoniae	IC50	=	37.0	nM	7.43	Antibacterial activity against Streptococcus pneumoniae ATCC BAA1663	32146051
Voltage-gated inwardly rectifying potassium channel KCNH2	IC50	=	39.0	nM	7.41	Inhibition of human ERG expressed in HEK cells	19821563
Motilin receptor	IC50	=	43.65	nM	7.36	Compound was tested for in vitro motilin receptor binding affinity	-
Motilin receptor	EC50	=	50.12	nM	7.3	Agonist activity at human recombinant motilin receptor expressed in CHO cells as...	19191554
Motilin receptor	EC50	=	50.12	nM	7.3	Agonist activity at human recombinant motilin receptor expressed in CHO cells by...	19006669
Streptococcus pneumoniae	IC50	=	51.0	nM	7.29	Antibacterial activity against Streptococcus pneumoniae ATCC 49617	32146051
Motilin receptor	IC50	=	70.79	nM	7.15	Compound was tested for in vitro motilin receptor binding affinity after treatme...	-
Escherichia coli	IC50	=	80.0	nM	7.1	Inhibition of ribosome function in a coupled transcription and translational ass...	16309904
Streptococcus pneumoniae	IC50	=	120.0	nM	6.92	Cell free inhibiting activity against erythromycin-susceptible strain Streptococ...	11708916
Bacterial 70S ribosome	IC50	=	170.0	nM	6.77	Inhibition of ribosomal activity in erythromycin-sensitive Propionibacterium acn...	17923495
Cytochrome P450 3A4	IC50	=	190.0	nM	6.72	Inhibition of human CYP3A4 expressed in Escherichia coli using diethoxyfluoresce...	19191554
Staphylococcus aureus	IC50	=	250.0	nM	6.6	Inhibition of bio-film formation of Staphylococcus aureus MLS16 MTCC 2940 incuba...	26048810
Micrococcus luteus	IC50	=	310.0	nM	6.51	Inhibition of bio-film formation of Micrococcus luteus MTCC 2470 incubated for 2...	26048810
Oryctolagus cuniculus	EC50	=	316.23	nM	6.5	Compound was tested for the in vitro smooth muscle contractile activity	-
Raoultella planticola	IC50	=	350.0	nM	6.46	Inhibition of bio-film formation of Klebsiella planticola MTCC 530 incubated for...	26048810
Motilin receptor	EC50	=	400.0	nM	6.4	In vitro effective concentration towards human motilin receptor	15027861
Bacillus subtilis	IC50	=	420.0	nM	6.38	Inhibition of bio-film formation of Bacillus subtilis MTCC 121 incubated for 24 ...	26048810

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	320
18779354	10.1128/aac.00450-08	Campylobacter jejuni	78
17145801	10.1128/aac.01033-06	Burkholderia pseudomallei	51
20231401	10.1128/aac.01565-09	Staphylococcus epidermidis	51
17353243	10.1128/aac.01411-06	Campylobacter jejuni	40
2231610	10.1021/jm00173a028	Rattus norvegicus	39
19075048	10.1128/aac.01247-08	NON-PROTEIN TARGET	38
20308374	10.1128/aac.01797-09	Streptococcus pneumoniae	36
17060526	10.1128/aac.01016-06	Streptococcus pneumoniae	33
17387155	10.1128/aac.00062-07	Cutibacterium acnes	32
19884376	10.1128/aac.01123-09	Streptococcus pneumoniae	30
19273677	10.1128/aac.01464-08	Streptococcus pneumoniae	27
19546358	10.1128/aac.00206-09	Staphylococcus aureus	27
17325224	10.1128/aac.00187-07	Streptococcus pneumoniae	26
19738026	10.1128/aac.00952-09	NON-PROTEIN TARGET	24
2231610	10.1021/jm00173a028	Mus musculus	24
35839126	10.1021/acs.jmedchem.2c00684	Staphylococcus aureus	24
20498319	10.1128/aac.01756-09	Streptococcus pneumoniae	24
-	10.4172/jbb.1000041	Homo sapiens	23
17353243	10.1128/aac.01411-06	Campylobacter coli	23

Data from ChEMBL 36 via Core Engine