CHLOROQUINE

Search structure
Synonyms:
Status: Approved (1949)
Entry Type: Small molecule
Molecule Category: Parent
ATC: P01BA01
UNII: 886U3H6UFF

Structure
InChI Key WHTVZRBIWZFKQO-UHFFFAOYSA-N
Smile CCN(CC)CCCC(C)Nc1ccnc2cc(Cl)ccc12
InChI
InChI=1S/C18H26ClN3/c1-4-22(5-2)12-6-7-14(3)21-17-10-11-20-18-13-15(19)8-9-16(17)18/h8-11,13-14H,4-7,12H2,1-3H3,(H,20,21)

Physicochemical Descriptors

Property Name Value
Molecular Formula C18H26ClN3
Molecular Weight 319.88
AlogP 4.81
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 8.0
Polar Surface Area 28.16
Molecular species BASE
Aromatic Rings 2.0
Heavy Atoms 22.0

Pharmacology

Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2B Cytochrome P450 2B6
- - - - 112-134
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C19
- - - - 111-113
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9
- - - - 114-128
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2D Cytochrome P450 2D6
- - - - 90-99
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- 349945.17 - - 102-110
Enzyme Hydrolase
- 4073802778041.12 - -
Enzyme Kinase Protein Kinase Atypical protein kinase group Atypical protein kinase PIKK family Atypical protein kinase FRAP subfamily
- 270-270 - - -
Enzyme Kinase Protein Kinase CMGC protein kinase group CMGC protein kinase CDK family
- 150000 - - -
Enzyme Oxidoreductase
- 0.01-0.01 - - -
Enzyme Protease Aspartic protease Aspartic protease AA clan Aspartic protease A1A subfamily
- 7000-12700 - - -
Enzyme Protease Metallo protease Metallo protease MAE clan Metallo protease M27 family
- - - - 6
Enzyme Protease Metallo protease Metallo protease MAE clan Metallo protease M2 family
- 1130 - - -
Enzyme Transferase
- 554000 - - -
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- 2500-2511.89 - 3162.28-7500 39-71
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Chemokine receptor CXC chemokine receptor
6500 - - - -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Acetylcholine receptor
- - - 21877.62 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Adrenergic receptor
- - - 10000 -
Membrane receptor Toll-like and Il-1 receptors
- - - - 23.4
Membrane receptor
6500 7000-12800 - 10000 19.6-56.7
Other cytosolic protein
- 76.5-2560000000 - - 86.25-86.6
Surface antigen
4000 - - - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 4 Nuclear hormone receptor subfamily 4 group A Nuclear hormone receptor subfamily 4 group A member 2
47000-50000 - - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - - 46
Transporter Primary active transporter ATP-binding cassette ABCC subfamily
- 103900 - - -
Unclassified protein
- 160 2100 - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Malaria 4 D008288 ClinicalTrials
Glioblastoma 3 D005909 ClinicalTrials
Arthritis, Rheumatoid 3 D001172 ClinicalTrials
Pregnancy 3 D011247 ClinicalTrials
Malaria, Vivax 3 D016780 ClinicalTrials
Malaria, Falciparum 3 D016778 ClinicalTrials
Severe Acute Respiratory Syndrome 3 D045169 ClinicalTrials
Lupus Erythematosus, Systemic 2 D008180 ClinicalTrials
Brain Diseases 2 D001927 ClinicalTrials
HIV Infections 2 D015658 ClinicalTrials
Acquired Immunodeficiency Syndrome 2 D000163 ClinicalTrials
Multiple Myeloma 2 D009101 ClinicalTrials
Influenza, Human 2 D007251 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Anemia, Sickle Cell 2 D000755 ClinicalTrials
Neoplasms 1 D009369 ClinicalTrials
Gliosarcoma 1 D018316 ClinicalTrials
Pancreatic Neoplasms 1 D010190 ClinicalTrials
Severe Dengue 1 D019595 ClinicalTrials
Carcinoma, Intraductal, Noninfiltrating 1 D002285 ClinicalTrials
Small Cell Lung Carcinoma 1 D055752 ClinicalTrials

Related Entries

Scaffolds

Salt
Salt
Salt
UNKNOWN

Cross References

Resources Reference
CAS NUMBER 54-05-7
ChEBI 3638
ChEMBL CHEMBL76
DrugBank DB00608
DrugCentral 607
EPA CompTox DTXSID2040446
FDA SRS 886U3H6UFF
Human Metabolome Database HMDB14746
Guide to Pharmacology 5535
KEGG C07625
PharmGKB PA448948
PubChem 2719
SureChEMBL SCHEMBL8933
CONTENTS