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

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
No information available.
Summary of Clinical Use Click here for help
Clindamycin is used to treat a wide range of bacterial infections. These include bone and joint infections, gynecological infections, intra-abdominal infections, lower respiratory infections, septicemia and skin infections. A combined therapy of clindamycin with fosmidomycin to treat uncomplicated P. falciparum malaria shows promising results, progressing to Phase 3 (NCT00214643). It is also used to treat uncomplicated malaria (particularly useful in areas where chloroquine or multidrug-resistant strains of P. falciparum are found) and as an effective treatment for severe malaria, when used as a combination therapy [6]. It should not be used as a monotherapy for malaria treatment due to a delayed antimalarial effect (see MOA for more details).
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Antibacterial MMOA is reversible binding to the 50S ribosomal subunits to prevent peptide-bond formation by sterically blocking A-site tRNA positioning at the peptidyl-transferase centre (PTC) and thereby inhibiting bacterial protein synthesis [2]. In Plasmodium, pharmacological concentrations of the compound kill the parasite in the lifecycle after treatment starts. It is thought that clindamycin inhibits the production of proteins encoded by the apicoplast genome, leading to a subsequent loss of apicoplast function and a possible explanation for the delayed antimalarial effect [1].
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT00214643 Efficacy of Fosmidomycin-Clindamycin for Treating Malaria in Gabonese Children Phase 3 Interventional Albert Schweitzer Hospital
External links Click here for help