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Compound Detail

CHEMBL370143

PAROMOMYCIN
💊 Approved Drug
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💊 Approved Drug
NC[C@@H]1O[C@H](O[C@H]2[C@@H](O)[C@H](O[C@@H]3[C@@H](O)[C@H](N)C[C@H](N)[C@H]3O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3N)O[C@@H]2CO)[C@H](N)[C@@H](O)[C@@H]1O

Basic Information

ChEMBL ID CHEMBL370143
Name PAROMOMYCIN
Phase Approved
Structure Type MOL
InChI Key UOZODPSAJZTQNH-LSWIJEOBSA-N
Therapeutic ✓ Yes

Known Names

Aminosidin ANTIBIOTIC 503-3 ANTIBIOTIC SF 767B ANTIBIOTIC SF-767B Catenulin Crestomycin Estomycin Gabromycin Hydroxymycin Monomycin a Neomycin e Paromomicina +7 more
13
Targets
64
Activities
3
Assay Types
1
PK Parameters
20
Publications
19
Known Names
4
Indications

Molecular Properties

615.6
MW (Da)
-8.86
ALogP
19
HBA
13
HBD
347.3
PSA (Ų)
0.11
QED
3
Ro5 Violations
9
Rot. Bonds

Drug Information

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

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -mycin

Extended Properties

Molecular Formula C23H45N5O14
MW 615.63
Aromatic Rings 0
Heavy Atoms 42
NP-Likeness 1.16

Indications

Leishmaniasis, Cutaneous Leishmaniasis, Visceral Leishmaniasis Osteomyelitis

ATC Classification

A07AA06
paromomycin
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: ANTIDIARRHEALS, INTESTINAL ANTIINFLAMMATORY/ANTIINFECTIVE AGENTS

Activity Summary

IC50 33 meas. best 7.48
Kd 24 meas. best 8.3
EC50 7 meas. best 8.3

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
Kd 8.3 5.6971 5.0 7
Leishmania donovani
CHEMBL367
EC50 8.3 7.21 5.0 3
Bacterial 70S ribosome
CHEMBL2363135
IC50 7.48 7.45 33.0 2
Escherichia coli
CHEMBL354
IC50 7.25 7.25 56.0 1
Ribosomal RNA A-site
CHEMBL614640
Kd 7.0 6.7033 100.0 3
No relevant target
CHEMBL2362975
Kd 6.7 6.7 200.0 1
Nucleic Acid
CHEMBL345
Kd 6.4 5.66 400.0 9
Nucleic Acid
CHEMBL345
IC50 6.22 6.22 600.0 1
Cryptosporidium parvum
CHEMBL612855
IC50 6.15 6.15 711.0 1
Leishmania major
CHEMBL612879
EC50 5.4 5.385 3980.0 2
Unchecked
CHEMBL612545
IC50 4.92 4.695 12000.0 4
Leishmania amazonensis
CHEMBL612877
IC50 4.72 4.72 19000.0 1
Leishmania donovani
CHEMBL367
IC50 4.71 4.4714 19700.0 7
Trypanosoma brucei rhodesiense
CHEMBL612348
EC50 4.64 4.64 22700.0 1
Leishmania major
CHEMBL612879
IC50 4.6 4.6 25000.0 1
Leishmania infantum
CHEMBL612848
IC50 4.37 4.184 42410.0 5
Bacillus subtilis
CHEMBL359
Kd 4.3 4.3 50000.0 1
Cryptosporidium parvum
CHEMBL612855
EC50 4.19 4.19 65000.0 1

Pharmacokinetic Data

Parameter Value Units Species
Ka 3.9 10'-5/M Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Leishmania donovani EC50 = 5.0 nM 8.3 Antileishmanial activity against Leishmania donovani promastigotes assessed as p... 30234295
Unchecked Kd = 5.0 nM 8.3 Binding affinity to 5'-fluorescein-tagged Escherichia coli ribosomal A site wt-b... 31610941
Leishmania donovani EC50 = 7.0 nM 8.15 Antileishmanial activity against amastigote form of Leishmania donovani assessed... 30234295
Bacterial 70S ribosome IC50 = 33.0 nM 7.48 Inhibition of Mycobacterium smegmatis wild type ribosomes assessed as inhibition... 34671740
Bacterial 70S ribosome IC50 = 38.0 nM 7.42 Inhibition of Mycobacterium smegmatis wild type ribosomes assessed as inhibition... 31303992
Escherichia coli IC50 = 56.0 nM 7.25 Inhibition of protein translation in Escherichia coli by coupled transcription/t... 19309154
Ribosomal RNA A-site Kd = 100.0 nM 7.0 Dissociation constant against 16S rRNA A-site 16168642
Ribosomal RNA A-site Kd = 200.0 nM 6.7 Binding affinity of aminoglycoside to 16S ribosomal RNA A-site in Escherichia co... 11206440
No relevant target Kd = 200.0 nM 6.7 Dissociation constant of the compound 15293991
Unchecked Kd = 370.0 nM 6.43 Affinity to hairpin A-site 16S rRNA by Electrospray ionization mass spectrometry 17399988
Ribosomal RNA A-site Kd = 390.0 nM 6.41 Binding affinity to bacterial ribosomal A site RNA oligonucleotide 16942021
Nucleic Acid Kd = 400.0 nM 6.4 Tested for binding affinity against RNA construct E 11814798
Nucleic Acid Kd = 440.0 nM 6.36 Dissociation constant for binding to mitochondrial 12S rRNA construct M3 was det... 12127547
Nucleic Acid IC50 = 600.0 nM 6.22 Inhibitory concentration against cell-free bacterial transcription / translation... 16168642
Cryptosporidium parvum IC50 = 711.0 nM 6.15 Antimicrobial activity against Cryptosporidium parvum infected in human HCT-8 ce... 18591280
Unchecked Kd = 980.0 nM 6.01 Affinity to 2-aminopurine labeled hairpin A-site 16S rRNA by Electrospray ioniza... 17399988
Nucleic Acid Kd = 1580.0 nM 5.8 Tested for binding affinity against RNA construct B 11814798
Nucleic Acid Kd = 1640.0 nM 5.79 Tested for binding affinity against RNA construct A 11814798
Nucleic Acid Kd = 1700.0 nM 5.77 Tested for binding affinity against RNA construct D 11814798
Unchecked Kd = 2800.0 nM 5.55 Binding affinity to 5'-fluorescein-tagged human mitochondrial ribosome A site mu... 31610941

Literature References

PubMed DOI Target Context # Activities
26264847 10.1016/j.bmc.2015.07.062 Unchecked 16
17060530 10.1128/aac.00261-06 Bifidobacterium longum 15
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
18591280 10.1128/aac.00207-08 Cryptosporidium parvum 10
17060530 10.1128/aac.00261-06 NON-PROTEIN TARGET 10
17060530 10.1128/aac.00261-06 Bifidobacterium bifidum 10
31610941 10.1016/j.bmc.2019.115121 Unchecked 9
17400454 10.1016/j.bmcl.2007.03.014 Unchecked 8
19309154 10.1021/jm801640k Nucleic Acid 8
17060530 10.1128/aac.00261-06 Bifidobacterium breve 8
29461823 10.1021/acs.jmedchem.7b01581 Leishmania infantum 7
34671740 10.1039/D1MD00214G Unchecked 6
29461823 10.1021/acs.jmedchem.7b01581 Leishmania donovani 6
31303992 10.1039/C9MD00153K Unchecked 6
19104019 10.1128/aac.00388-08 Streptomyces coelicolor 6
23602621 10.1016/j.bmc.2013.03.046 Streptococcus pyogenes 6
17875999 10.1128/aac.00926-07 Escherichia coli 5
22989363 10.1021/jm301172v ADMET 5
11814798 10.1016/s0960-894x(01)00760-0 Nucleic Acid 5
17088492 10.1128/aac.01096-06 Escherichia coli 5

Data from ChEMBL 36 via Core Engine