clindamycin   Click here for help

GtoPdb Ligand ID: 10607

Approved drug PDB Ligand Antimalarial Ligand
clindamycin is an approved drug (FDA (1970))
Compound class: Synthetic organic
Comment: Clindamycin is a semisynthetic lincosamide antibiotic with broad-spectrum activity. The compound also has antimalarial activity.
Clindamycin is one of the key access group antibacterials on the World Health Organization's Model List of Essential Medicines (link provided in the Classification table, under the Summary tab below).

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 4
Rotatable bonds 8
Topological polar surface area 127.56
Molecular weight 424.18
XLogP 2
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CCC[C@H]1CN([C@@H](C1)C(=O)N[C@@H]([C@H]1O[C@H](SC)[C@@H]([C@H]([C@H]1O)O)O)[C@@H](Cl)C)C
Isomeric SMILES CCC[C@H]1CN([C@@H](C1)C(=O)N[C@@H]([C@H]1O[C@H](SC)[C@@H]([C@H]([C@H]1O)O)O)[C@@H](Cl)C)C
InChI InChI=1S/C18H33ClN2O5S/c1-5-6-10-7-11(21(3)8-10)17(25)20-12(9(2)19)16-14(23)13(22)15(24)18(26-16)27-4/h9-16,18,22-24H,5-8H2,1-4H3,(H,20,25)/t9-,10+,11-,12+,13-,14+,15+,16+,18+/m0/s1
InChI Key KDLRVYVGXIQJDK-AWPVFWJPSA-N
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
Approved drug? Yes (FDA (1970))
WHO Essential Medicine WHO Essential Medicines List (EML) (22nd List, 2021). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
(2S,4R)-N-[(1S,2S)-2-chloro-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide
International Nonproprietary Names Click here for help
INN number INN
2550 clindamycin
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo 1532
Other databases
CAS Registry No. 18323-44-9 (source: Scifinder)
ChEBI CHEBI:3745
ChEMBL Ligand CHEMBL1753
DrugBank Ligand DB01190
DrugCentral Ligand 678
GtoPdb PubChem SID 404859054
PubChem CID 446598
RCSB PDB Ligand CLY
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Search PubMed clinical trials clindamycin
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UniChem Compound Search for chemical match using the InChIKey KDLRVYVGXIQJDK-AWPVFWJPSA-N
UniChem Connectivity Search for chemical match using the InChIKey KDLRVYVGXIQJDK-AWPVFWJPSA-N
Wikipedia Clindamycin