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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL130
CHEMBL130
Compound Name CHLORAMPHENICOL
ChEMBL Synonyms CHLOROPTIC S.O.P. | ECONOCHLOR | Chloramphenicol Sulfate Salt | AMPHICOL | BROCHLOR | CHLOROFAIR | MYCHEL | TUBILUX INFECTED EYES | Tevcocin | BROLENE ANTIBIOTIC | Kernispray | Mychel-S | OPHTHOCHLOR | CHLOROPTIC | KEMICETINE | Chloramex | Chloramphenicol | OPTOMYCIN | Chlorbiotic | GOLDEN EYE ANTIBIOTIC | CHLOROMYCETIN | SNO PHENICOL | KLORAFECT
Max Phase 4 (Approved)
Withdrawn Yes
Trade Names BROLENE ANTIBIOTIC | AMPHICOL | BROCHLOR | CHLOROFAIR | MYCHEL | TUBILUX INFECTED EYES | Tevcocin | CHLOROMYCETIN | CHLOROPTIC S.O.P. | ECONOCHLOR | CHLORAMPHENICOL | Chlorbiotic | GOLDEN EYE ANTIBIOTIC | Chloramex | OPTOMYCIN | CHLOROPTIC | KEMICETINE | Kernispray | OPHTHOCHLOR | KLORAFECT | SNO PHENICOL
Molecular Formula C11H12Cl2N2O5

Additional synonyms for CHEMBL130 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES OC[C@@H](NC(=O)C(Cl)Cl)[C@H](O)c1ccc(cc1)[N+](=O)[O-]
Standard InChI InChI=1S/C11H12Cl2N2O5/c12-10(13)11(18)14-8(5-16)9(17)6-1-3- ...
Download InChI
Standard InChI Key WIIZWVCIJKGZOK-RKDXNWHRSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • DrugMatrix
  • Open TG-GATEs
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification
  • Withdrawn Drugs

Alternate Forms of Compound in ChEMBL


CHEMBL130

Molecule Features

CHEMBL130 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:Y Parenteral:Y Topical:Y Black Box:Y Availability Type:Withdrawn

Withdrawal Information

Year 2012
Country United States
Reason Bone marrow depression (anemia, thrombocytopenia, and granulocytopenia temporally associated with treatment). Bone marrow toxicities may present as either reversible bone marrow depression, which was dose-related and responsive to drug withdrawal, or as aplastic anemia, which was not dose-related, irreversible, and associated with a high mortality
Class Hematological toxicity

Mechanism of Action

Mechanism of Action ChEMBL Target References
Bacterial 70S ribosome inhibitor Bacterial 70S ribosome PubMed PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
OsteomyelitisD010019EFO:0003102osteomyelitis0ClinicalTrials

Clinical Data

ClinicalTrials.gov CHLORAMPHENICOL
The Cochrane Collaboration CHLORAMPHENICOL

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL130. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL2802 Microbial collagenase Clostridium perfringens (strain 13 / Type A) 1.000
CHEMBL5774 Monoglyceride lipase Mus musculus 0.994
CHEMBL4588 Matrix metalloproteinase 8 Homo sapiens 0.986
CHEMBL3457 Kynurenine 3-monooxygenase Rattus norvegicus 0.973
CHEMBL1075138 Tyrosyl-DNA phosphodiesterase 1 Homo sapiens 0.953
CHEMBL2949 Cyclooxygenase-1 Ovis aries 0.836
CHEMBL6110 Thioredoxin glutathione reductase Schistosoma mansoni 0.831
CHEMBL1997 Equilibrative nucleoside transporter 1 Homo sapiens 0.772
CHEMBL2608 Lysosomal alpha-glucosidase Homo sapiens 0.646
CHEMBL3180 Carboxylesterase 2 Homo sapiens 0.644
CHEMBL5192 Botulinum neurotoxin type A Clostridium botulinum 0.434
CHEMBL3326 Beta-lactamase L1 Stenotrophomonas maltophilia 0.356
CHEMBL3622 Cytochrome P450 2C19 Homo sapiens 0.317
CHEMBL1293231 Nuclear receptor ROR-gamma Mus musculus 0.287
CHEMBL2623 Acyl coenzyme A:cholesterol acyltransferase Oryctolagus cuniculus 0.247



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL2802 Microbial collagenase Clostridium perfringens (strain 13 / Type A) 1.000
CHEMBL3457 Kynurenine 3-monooxygenase Rattus norvegicus 0.996
CHEMBL5774 Monoglyceride lipase Mus musculus 0.984
CHEMBL3902 Glutathione S-transferase Pi Homo sapiens 0.952
CHEMBL5010 Monoacylglycerol lipase ABHD6 Mus musculus 0.949
CHEMBL4588 Matrix metalloproteinase 8 Homo sapiens 0.890
CHEMBL3180 Carboxylesterase 2 Homo sapiens 0.774
CHEMBL4361 Induced myeloid leukemia cell differentiation protein Mcl-1 Homo sapiens 0.472
CHEMBL2949 Cyclooxygenase-1 Ovis aries 0.376
CHEMBL5192 Botulinum neurotoxin type A Clostridium botulinum 0.344
CHEMBL5463 Acid ceramidase Homo sapiens 0.338
CHEMBL3326 Beta-lactamase L1 Stenotrophomonas maltophilia 0.326
CHEMBL1997 Equilibrative nucleoside transporter 1 Homo sapiens 0.309
CHEMBL1075138 Tyrosyl-DNA phosphodiesterase 1 Homo sapiens 0.253
CHEMBL6110 Thioredoxin glutathione reductase Schistosoma mansoni 0.234
CHEMBL2007628 Tyrosine-protein phosphatase non-receptor type 5 Homo sapiens 0.218
CHEMBL3308 Caspase-6 Homo sapiens 0.215

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
323.1 322.0123 0.91 6 112.7 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
5 3 0 7 3 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
11.03 - 1.1 1.1 1 20 0.41

Structural Alerts

There are 12 structural alerts for CHEMBL130. To view alerts please click here.

Compound Cross References

ATC S - SENSORY ORGANS
S02 - OTOLOGICALS
S02A - ANTIINFECTIVES
S02AA - Antiinfectives
S02AA01 - chloramphenicol

J - ANTIINFECTIVES FOR SYSTEMIC USE
J01 - ANTIBACTERIALS FOR SYSTEMIC USE
J01B - AMPHENICOLS
J01BA - Amphenicols
J01BA01 - chloramphenicol

S - SENSORY ORGANS
S01 - OPHTHALMOLOGICALS
S01A - ANTIINFECTIVES
S01AA - Antibiotics
S01AA01 - chloramphenicol

D - DERMATOLOGICALS
D10 - ANTI-ACNE PREPARATIONS
D10A - ANTI-ACNE PREPARATIONS FOR TOPICAL USE
D10AF - Antiinfectives for treatment of acne
D10AF03 - chloramphenicol

S - SENSORY ORGANS
S03 - OPHTHALMOLOGICAL AND OTOLOGICAL PREPARATIONS
S03A - ANTIINFECTIVES
S03AA - Antiinfectives
S03AA08 - chloramphenicol

G - GENITO URINARY SYSTEM AND SEX HORMONES
G01 - GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
G01A - ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
G01AA - Antibiotics
G01AA05 - chloramphenicol

D - DERMATOLOGICALS
D06 - ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
D06A - ANTIBIOTICS FOR TOPICAL USE
D06AX - Other antibiotics for topical use
D06AX02 - chloramphenicol

ChemSpider ChemSpider:WIIZWVCIJKGZOK-RKDXNWHRSA-N
DailyMed chloramphenicol
PubChem SID: 144204859 SID: 144214022 SID: 17389985 SID: 26752873 SID: 47193729 SID: 49734345 SID: 50105494 SID: 69616
Wikipedia Chloramphenicol

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL130



ACToR 137731-90-9 2787-09-9
Atlas chloramphenicol
Brenda 48900 955 139482 48899
ChEBI 17698
ChemicalBook CB3364529
DrugBank DB00446
DrugCentral 589
eMolecules 490388 29538748
EPA CompTox Dashboard DTXSID7020265
FDA SRS 66974FR9Q1
Human Metabolome Database HMDB0014589
IBM Patent System 59107782AAEF696DAE4DE807D51A2D5F
KEGG Ligand C00918
LINCS LSM-5256
Mcule MCULE-5311202412 MCULE-7778960570
Metabolights MTBLC17698
MolPort MolPort-001-794-646
PDBe CLM
PubChem 5959
PubChem: Thomson Pharma 15000217 14801512
Rhea 17698
Selleck Chloramphenicol(Chloromycetin)
SureChEMBL SCHEMBL16111
ZINC ZINC000000113382

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/WIIZWVCIJKGZOK-RKDXNWHRSA-N spacer
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