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.
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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
Bioactivity Comments
Clindamycin, like a number of other antibiotics including azithromycin and doxycycline, kills the malaria parasite in the lifecycle after treatment starts [1]. Consistent with this slow clinical action, the results provided in the table below show that clindamycin is more potent in vitro against erythrocytic stage parasites when assessed two asexual life cycles after the initiation of treatment.
Whole organism assay data
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MOA/likely target Sp. Assay description Type Action Value Parameter Concentration range (M) Reference
Unknown MOA PfW2 Ring formation assay (96 hours) - - 8.5 pIC50 - 1
pIC50 8.5 (IC50 3.12x10-9 M) FACS analysis following 96 hours in culture (third-generation rings) [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA Pf3D7 Ring formation assay (96 hours) - - 8.1 pIC50 - 1
pIC50 8.1 (IC50 8.81x10-9 M) FACS analysis following 96 hours in culture (third-generation rings) [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA Pf3D7 Ring formation assay (48 hours) - - <4.0 pIC50 - 1
pIC50 <4.0 (IC50 >1x10-4 M) FACS analysis following 48 hours in culture (second-generation rings) [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA PfW2 Ring formation assay (48 hours) - - <4.0 pIC50 - 1
pIC50 <4.0 (IC50 >1x10-4 M) FACS analysis following 48 hours in culture (second-generation rings) [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)