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Compound Detail

CHEMBL130

CHLORAMPHENICOL
💊 Approved Drug
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💊 Approved Drug
O=C(N[C@H](CO)[C@H](O)c1ccc([N+](=O)[O-])cc1)C(Cl)Cl

Basic Information

ChEMBL ID CHEMBL130
Name CHLORAMPHENICOL
Phase Approved
Structure Type MOL
InChI Key WIIZWVCIJKGZOK-RKDXNWHRSA-N
Therapeutic ✓ Yes

Known Names

9-hydroxy-9-phenylxanthene 9-phenyl-9h-xanthen-9-ol Amphicol Brochlor Brolene antibiotic Chloramex Chloramphenicol Chloramphenicol component of chloromycetin hydrocortisone Chloramphenicol component of chloromyxin Chloramphenicol component of chloroptic-p s.o.p. Chloramphenicol component of elase-chloromycetin Chloramphenicol component of ophthocort +18 more
20
Targets
60
Activities
3
Assay Types
15
PK Parameters
20
Publications
30
Known Names
4
Indications
1
Mechanisms

Molecular Properties

323.1
MW (Da)
0.91
ALogP
5
HBA
3
HBD
112.7
PSA (Ų)
0.41
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1950
Availability Withdrawn
Chirality Single Enantiomer

Routes of Administration

Oral Parenteral Topical

Flags

Withdrawn Natural Product

Extended Properties

Molecular Formula C11H12Cl2N2O5
MW 323.13
Aromatic Rings 1
Heavy Atoms 20
NP-Likeness -0.11

Mechanism of Action

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

Indications

Acne Vulgaris Bacterial Infections Eye Infections Osteomyelitis

ATC Classification

D06AX02
chloramphenicol
Level 1: DERMATOLOGICALS
Level 2: ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
D10AF03
chloramphenicol
Level 1: DERMATOLOGICALS
Level 2: ANTI-ACNE PREPARATIONS
G01AA05
chloramphenicol
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
J01BA01
chloramphenicol
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE
S01AA01
chloramphenicol
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS
S02AA01
chloramphenicol
Level 1: SENSORY ORGANS
Level 2: OTOLOGICALS
S03AA08
chloramphenicol
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICAL AND OTOLOGICAL PREPARATIONS

Drug Warnings

Withdrawn
hematological toxicity
Bone marrow depression (anemia, thrombocytopenia, and granulocytopenia temporally associated with treatment). Bone marrow toxicities may present as either reversible bone marrow depression, which was ...
Country: United States   Year: 2012

Activity Summary

IC50 41 meas. best 6.37
EC50 11 meas. best 6.01
Ki 8 meas. best 6.16

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bacterial 70S ribosome
CHEMBL2363135
IC50 6.37 6.37 430.0 1
Staphylococcus aureus
CHEMBL352
IC50 6.37 5.3088 430.0 8
Escherichia coli
CHEMBL354
Ki 6.16 6.16 700.0 1
Unchecked
CHEMBL612545
Ki 6.06 5.93 880.0 2
Streptokinase A
CHEMBL1293228
EC50 6.01 6.01 973.0 1
Cutibacterium acnes
CHEMBL612639
IC50 6.0 6.0 1000.0 1
Klebsiella pneumoniae subsp. pneumoniae
CHEMBL613207
EC50 5.85 5.85 1400.0 1
Bacillus subtilis
CHEMBL359
IC50 5.84 5.18 1450.0 3
Escherichia coli
CHEMBL354
IC50 5.82 5.226 1500.0 10
Unchecked
CHEMBL612545
IC50 5.8 5.109 1570.0 10
Streptococcus sp. 'group A'
CHEMBL612389
EC50 5.74 5.74 1837.0 1
Enterococcus faecium
CHEMBL357
EC50 5.68 5.68 2100.0 1
Enterobacter cloacae
CHEMBL349
EC50 5.66 5.66 2200.0 1
Staphylococcus aureus
CHEMBL352
EC50 5.66 5.65 2200.0 2
Mammaliicoccus lentus
CHEMBL613149
IC50 5.64 5.64 2300.0 1
Streptococcus
CHEMBL612313
EC50 5.59 5.59 2548.0 1
Xanthomonas campestris
CHEMBL612276
IC50 5.44 5.44 3600.0 1
Methionine--tRNA ligase, mitochondrial
CHEMBL4739700
EC50 5.1 5.1 7900.0 1
Cytochrome P450 3A4
CHEMBL340
Ki 4.97 4.97 10600.0 1
Plasmodium falciparum
CHEMBL364
IC50 4.95 4.95 11200.0 1
Pseudomonas aeruginosa
CHEMBL348
EC50 4.8 4.8 16000.0 1
Candida albicans
CHEMBL366
IC50 4.65 4.65 22500.0 1
Pseudomonas aeruginosa
CHEMBL348
IC50 4.65 4.605 22500.0 2
Acinetobacter baumannii
CHEMBL614425
EC50 4.19 4.19 65000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 2.4 mL.min-1.kg-1 Homo sapiens
CL 2.2 mL.min-1.kg-1 Homo sapiens
CL 2.4 mL.min-1.kg-1 Homo sapiens
CL 2.4 mL.min-1.kg-1 Homo sapiens
CL 69.18 uL.min-1.(10^6cells)-1 Rattus norvegicus
F 79.0 % Homo sapiens
F 69.0 % Homo sapiens
F 82.0 % Homo sapiens
Fu 0.47 - -
Fu 0.225 - -
Fu 0.47 - Homo sapiens
Fu 0.34 - Homo sapiens
Fu 0.34 - Homo sapiens
MRT 6.5 hr Homo sapiens
T1/2 4.6 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Staphylococcus aureus IC50 = 430.0 nM 6.37 Antibacterial activity against Staphylococcus aureus ATCC 25923 assessed as grow... 25927817
Bacterial 70S ribosome IC50 = 430.0 nM 6.37 Displacement of [3H]chloramphenicol from 70S ribosomal complex in Staphylococcus... 18663023
Escherichia coli Ki = 700.0 nM 6.16 Tested for inhibition of puromycin reaction and reported as equilibrium constant... 8246222
Unchecked Ki = 880.0 nM 6.06 Inhibition of Escherichia coli K-12 70S ribosome poly(U)-programmed ribosome (co... 26001343
Streptokinase A EC50 = 973.0 nM 6.01 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Iden... -
Cutibacterium acnes IC50 = 1000.0 nM 6.0 Antibacterial activity against Propionibacterium acnes DSM 1897 after 48 hrs by ... 20545334
Klebsiella pneumoniae subsp. pneumoniae EC50 = 1400.0 nM 5.85 Antibacterial activity against multidrug resistant Klebsiella pneumoniae subsp. ... 27184767
Bacillus subtilis IC50 = 1450.0 nM 5.84 Antimicrobial activity against Bacillus subtilis DSM 347 incubated for 5 hrs by ... 22775474
Escherichia coli IC50 = 1500.0 nM 5.82 Inhibition of protein synthesis in Escherichia coli S30 extracts by coupled tran... 16890435
Escherichia coli IC50 = 1500.0 nM 5.82 Inhibition of protein synthesis in Escherichia coli by coupled transcription-tra... 17188860
Unchecked IC50 = 1570.0 nM 5.8 PUBCHEM_BIOASSAY: A counter screen for small molecule screen for inhibitors of t... -
Unchecked Ki = 1600.0 nM 5.8 Evaluated for the inhibition constant determined from the Dixon and slope vs. in... 7005448
Streptococcus sp. 'group A' EC50 = 1837.0 nM 5.74 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Iden... -
Escherichia coli IC50 = 2000.0 nM 5.7 Antibacterial activity against Escherichia coli BL21(DE3) expressing delta-tolC ... 26001343
Enterococcus faecium EC50 = 2100.0 nM 5.68 Antibacterial activity against multidrug resistant Enterococcus faecium NCTC 717... 27184767
Enterobacter cloacae EC50 = 2200.0 nM 5.66 Antibacterial activity against multidrug resistant Enterobacter cloacae subsp. c... 27184767
Staphylococcus aureus EC50 = 2200.0 nM 5.66 Antibacterial activity against multidrug resistant Staphylococcus aureus subsp. ... 27184767
Staphylococcus aureus EC50 = 2300.0 nM 5.64 Antibacterial activity against methicillin resistant Staphylococcus aureus subsp... 27184767
Mammaliicoccus lentus IC50 = 2300.0 nM 5.64 Antibacterial activity against Staphylococcus lentus DSM 6672 after 48 hrs by mi... 20545334
Streptococcus EC50 = 2548.0 nM 5.59 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Response HTS to Identify... -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1406
- 10.6019/CHEMBL3885881 Rattus norvegicus 320
19164140 10.1128/aac.00822-08 Klebsiella aerogenes 62
17043131 10.1128/aac.00600-06 Salmonella typhimurium 44
18443112 10.1128/aac.00084-08 Salmonella typhimurium 41
23587426 10.1016/j.bmcl.2013.03.078 Staphylococcus aureus 40
20713660 10.1128/aac.00009-10 Pseudomonas aeruginosa 36
19164140 10.1128/aac.00822-08 Klebsiella pneumoniae 34
20211899 10.1128/aac.01420-09 Escherichia coli 28
18474583 10.1128/aac.01107-07 Pseudomonas aeruginosa 25
25219900 10.1016/j.bmcl.2014.08.047 Staphylococcus aureus 25
35839126 10.1021/acs.jmedchem.2c00684 Staphylococcus aureus 24
20696869 10.1128/aac.00644-10 Mycolicibacterium smegmatis 20
19029332 10.1128/aac.00870-08 Escherichia coli 19
35168113 10.1016/j.ejmech.2022.114158 ADMET 18
17404009 10.1128/aac.01066-06 Staphylococcus aureus 18
19029325 10.1128/aac.00754-08 Enterococcus faecalis 18
20679507 10.1128/aac.01607-09 Klebsiella pneumoniae 17
15808482 10.1016/j.bmcl.2005.02.029 Pseudomonas aeruginosa 17
17220404 10.1128/aac.01128-06 Escherichia coli 17

Data from ChEMBL 36 via Core Engine