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Compound Detail

CHEMBL1753

CLINDAMYCIN
💊 Approved Drug
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💊 Approved Drug
CCC[C@@H]1C[C@@H](C(=O)N[C@@H]([C@H]2O[C@H](SC)[C@H](O)[C@@H](O)[C@H]2O)[C@H](C)Cl)N(C)C1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1753
Name CLINDAMYCIN
Phase Approved
Structure Type MOL
InChI Key KDLRVYVGXIQJDK-AWPVFWJPSA-N
Therapeutic ✓ Yes

Known Names

7(s)-chloro-7-deoxylincomycin Chlorodeoxylincomycin Chlorolincomycin Clindamicina Clindamycin Clindamycine U-21,251 U-21251
3
Targets
11
Activities
2
Assay Types
11
PK Parameters
20
Publications
8
Known Names
20
Indications

Molecular Properties

425.0
MW (Da)
0.39
ALogP
7
HBA
4
HBD
102.3
PSA (Ų)
0.44
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1970
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -mycin
USAN Year 1968

Extended Properties

Molecular Formula C18H33ClN2O5S
MW 424.99
Aromatic Rings 0
Heavy Atoms 27
NP-Likeness 0.60

Indications

Acne Vulgaris Bacterial Infections Endometritis Infections Intraabdominal Infections Osteomyelitis Breast Neoplasms Candidiasis, Vulvovaginal Chorioretinitis Hernia Hernia, Ventral Kidney Calculi Malaria Nasal Obstruction Pain Pneumonia, Pneumocystis Skin Diseases Staphylococcal Infections Vaginosis, Bacterial Carcinoma, Non-Small-Cell Lung

ATC Classification

D10AF01
clindamycin
Level 1: DERMATOLOGICALS
Level 2: ANTI-ACNE PREPARATIONS
G01AA10
clindamycin
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
J01FF01
clindamycin
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE

Drug Warnings

Black Box Warning
gastrointestinal toxicity
Country: United States
Black Box Warning
infectious disease
Country: United States
Black Box Warning
misuse
Country: United States

Activity Summary

IC50 10 meas. best 8.89
Ki 1 meas. best 5.57

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 IC50 8.89 8.0429 1.3 7
Bacterial 70S ribosome
CHEMBL2363135
 Ki 5.57 5.57 2700.0 1
Escherichia coli
CHEMBL354
 IC50 4.74 4.74 18100.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 4.5 mL.min-1.kg-1 Homo sapiens
CL 3.9 mL.min-1.kg-1 Homo sapiens
CL 4.5 mL.min-1.kg-1 Homo sapiens
CL 4.5 mL.min-1.kg-1 Homo sapiens
Cmax 5882.49 nM Homo sapiens
Cmax 9411.99 nM Homo sapiens
Fu 0.06 - Homo sapiens
Fu 0.06 - Homo sapiens
Fu 0.1 - Homo sapiens
MRT 2.9 hr Homo sapiens
T1/2 2.1 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 1.3 nM 8.89 Inhibition of Plasmodium falciparum FCK2 growth as [3H]hypoxanthine uptake after... 17060533
Plasmodium falciparum IC50 = 3.12 nM 8.51 Antimalarial activity as 3rd generation ring-stage chloroquine-resistant Plasmod... 17698630
Plasmodium falciparum IC50 = 3.1 nM 8.51 Antimalarial activity against Plasmodium falciparum W2 after 96 hrs 26791529
Plasmodium falciparum IC50 = 8.81 nM 8.05 Antimalarial activity as 3rd generation ring-stage chloroquine-sensitive Plasmod... 17698630
Plasmodium falciparum IC50 = 8.81 nM 8.05 Antiplasmodial activity against sorbitol-synchronized post ring stage plasmodium... 36793432
Plasmodium falciparum IC50 = 11.6 nM 7.94 Antimalarial activity against Plasmodium falciparum clinical isolate after 6 day... 19841147
Plasmodium falciparum IC50 = 450.0 nM 6.35 Antimalarial activity against Plasmodium falciparum 3D7 after 96 hrs 26791529
Bacterial 70S ribosome Ki = 2700.0 nM 5.57 Binding affinity to Escherichia coli ribosomes assessed as apparent inhibition c... 37295615
Escherichia coli IC50 = 18100.0 nM 4.74 Inhibition of protein synthesis in Escherichia coli S30 extracts after 90 mins b... 23786357

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 320
19581457 10.1128/aac.00908-08 NON-PROTEIN TARGET 108
19884376 10.1128/aac.01123-09 Streptococcus pneumoniae 89
20100877 10.1128/aac.01788-09 NON-PROTEIN TARGET 68
20404122 10.1128/aac.01516-09 Staphylococcus aureus 62
17876003 10.1128/aac.00827-07 Streptococcus pneumoniae 50
20308374 10.1128/aac.01797-09 Streptococcus pneumoniae 37
6363698 10.1021/jm00368a020 Mus musculus 34
19188385 10.1128/aac.01619-08 Staphylococcus aureus 34
17387155 10.1128/aac.00062-07 Cutibacterium acnes 33
17060526 10.1128/aac.01016-06 Streptococcus pneumoniae 33
17562807 10.1128/aac.01582-06 Clostridioides difficile 30
35839126 10.1021/acs.jmedchem.2c00684 Staphylococcus aureus 24
19738026 10.1128/aac.00952-09 NON-PROTEIN TARGET 24
18955522 10.1128/aac.00595-08 NON-PROTEIN TARGET 23
20713672 10.1128/aac.00470-10 Staphylococcus aureus 22
17698630 10.1128/aac.00527-07 Plasmodium falciparum 21
20696869 10.1128/aac.00644-10 Mycolicibacterium smegmatis 20
6363698 10.1021/jm00368a020 Staphylococcus aureus 18
17242137 10.1128/aac.01201-06 Staphylococcus aureus 18

Data from ChEMBL 36 via Core Engine