chloramphenicol   Click here for help

GtoPdb Ligand ID: 10901

Synonyms: Brolene® | chloromycetin
Approved drug PDB Ligand
chloramphenicol is an approved drug (FDA (1959))
Compound class: Synthetic organic
Comment: Chloramphenicol is a semisynthetic, broad-spectrum antibacterial derived from Streptomyces venequelae. Its activity is primarily bacteriostatic.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 3
Rotatable bonds 7
Topological polar surface area 112.7
Molecular weight 322.01
XLogP 0.69
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES OC[C@H]([C@@H](c1ccc(cc1)[N+](=O)[O-])O)NC(=O)C(Cl)Cl
Isomeric SMILES OC[C@H]([C@@H](c1ccc(cc1)[N+](=O)[O-])O)NC(=O)C(Cl)Cl
InChI InChI=1S/C11H12Cl2N2O5/c12-10(13)11(18)14-8(5-16)9(17)6-1-3-7(4-2-6)15(19)20/h1-4,8-10,16-17H,5H2,(H,14,18)/t8-,9-/m1/s1
InChI Key WIIZWVCIJKGZOK-RKDXNWHRSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1959))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide
International Nonproprietary Names Click here for help
INN number INN
977 chloramphenicol
Synonyms Click here for help
Brolene® | chloromycetin
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo
GPCRdb Ligand chloramphenicol
Other databases
BindingDB Ligand 23447
CAS Registry No. 56-75-7 (source: WHO INN record)
ChEMBL Ligand CHEMBL130
DrugBank Ligand DB00446
DrugCentral Ligand 589
GtoPdb PubChem SID 405560342
PubChem CID 5959
RCSB PDB Ligand CLM
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UniChem Compound Search for chemical match using the InChIKey WIIZWVCIJKGZOK-RKDXNWHRSA-N
UniChem Connectivity Search for chemical match using the InChIKey WIIZWVCIJKGZOK-RKDXNWHRSA-N