clindamycin   

GtoPdb Ligand ID: 10607

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 Organisation's List of Essential Medicines (link provided in the Classification table above).

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
2D Structure
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Physico-chemical Properties
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
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
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
Approved drug? Yes (FDA (1970))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name
(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
INN number INN
2550 clindamycin
Database Links
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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Wikipedia Clindamycin