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Compound Detail

CHEMBL2359966

QUININE SULFATE
💊 Approved Drug
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💊 Approved Drug
C=C[C@H]1CN2CC[C@H]1C[C@H]2[C@H](O)c1ccnc2ccc(OC)cc12.C=C[C@H]1CN2CC[C@H]1C[C@H]2[C@H](O)c1ccnc2ccc(OC)cc12.O.O.O=S(=O)(O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2359966
Name QUININE SULFATE
Phase Approved
Structure Type MOL
InChI Key ZHNFLHYOFXQIOW-LPYZJUEESA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL170
Active Moiety CHEMBL170

Known Names

Anhydrous quinine sulfate Chininum sulphuricum FEMA NO. 2977 Gls 1200 Gls-1200 GLS1200 NSC-5362 NSC-757298 Qualaquin Quinamm Quinate Quinine hemisulfate anhydrous +7 more
1
Targets
25
Activities
1
Assay Types
0
PK Parameters
15
Publications
19
Known Names
3
Indications
1
Mechanisms

Molecular Properties

324.4
MW (Da)
3.17
ALogP
4
HBA
1
HBD
45.6
PSA (Ų)
0.88
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2005
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning

Extended Properties

Molecular Formula C40H54N4O10S
MW 782.96
Aromatic Rings 2
Heavy Atoms 24
NP-Likeness 0.83

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Ferriprotoporphyrin IX inhibitor INHIBITOR Ferriprotoporphyrin IX ✓ ✓

Indications

Malaria, Falciparum Muscle Cramp Kidney Diseases

Drug Warnings

Black Box Warning
hematological toxicity
Country: United States
Black Box Warning
General Warning
Country: United States

Activity Summary

IC50 25 meas. best 10.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 IC50 10.7 8.7088 0.0 24

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 0.02 nM 10.7 Antiplasmodial activity against Plasmodium falciparum D10 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 0.03 nM 10.52 Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 0.03 nM 10.52 Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 0.04 nM 10.4 Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 0.04 nM 10.4 Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 0.06 nM 10.22 Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr... 19734910
Plasmodium falciparum IC50 = 0.08 nM 10.1 Antiplasmodial activity against Plasmodium falciparum D10 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 0.09 nM 10.05 Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 0.16 nM 9.8 Antiplasmodial activity against Plasmodium falciparum Dd2 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 0.16 nM 9.8 Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 0.17 nM 9.77 Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 0.19 nM 9.72 Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 0.22 nM 9.66 Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr... 19734910
Plasmodium falciparum IC50 = 0.35 nM 9.46 Antiplasmodial activity against Plasmodium falciparum Dd2 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 79.43 nM 7.1 Antiplasmodial activity against Plasmodium falciparum D10 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 100.0 nM 7.0 Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 120.0 nM 6.92 Antiplasmodial activity against multi-drug resistant Plasmodium falciparum K1 in... 24813729
Plasmodium falciparum IC50 = 150.0 nM 6.82 Antiplasmodial activity against drug susceptible Plasmodium falciparum 3D7 NF54 ... 24813729
Plasmodium falciparum IC50 = 158.49 nM 6.8 Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 158.49 nM 6.8 Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR g... 19734910

Literature References

PubMed DOI Target Context # Activities
- 10.5281/zenodo.13943903 ADMET 89
31158845 10.1038/s41586-019-1291-3 ADMET 53
19734910 10.1038/nchembio.215 Plasmodium falciparum 21
24813729 10.1016/j.bmcl.2014.04.070 Plasmodium falciparum 2
17088494 10.1128/aac.00985-06 Histidine-rich protein PFHRP-II 1
18391949 10.1038/nchembio.79 PC-12 1
17417631 10.1038/nchembio873 Unchecked 1
20547797 10.1128/aac.00431-10 Plasmodium falciparum 1
20553011 10.1021/tx1000865 Hepatotoxicity 1
20843939 10.1124/dmd.110.035113 Hepatotoxicity 1
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B1 1
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B3 1
24813729 10.1016/j.bmcl.2014.04.070 ADMET 1
26453006 10.1016/j.bmcl.2015.09.034 Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 1 1
26453006 10.1016/j.bmcl.2015.09.034 Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 2 1

Data from ChEMBL 36 via Core Engine