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Compound Detail

CHEMBL1454

LEVAMISOLE
💊 Approved Drug
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💊 Approved Drug
c1ccc([C@H]2CN3CCSC3=N2)cc1

Basic Information

ChEMBL ID CHEMBL1454
Name LEVAMISOLE
Phase Approved
Structure Type MOL
InChI Key HLFSDGLLUJUHTE-SNVBAGLBSA-N
Therapeutic ✓ Yes

Known Names

Levamisol Levamisole TCMDC-125847 Tetramisole, (s)-
7
Targets
27
Activities
3
Assay Types
30
PK Parameters
20
Publications
4
Known Names
5
Indications

Molecular Properties

204.3
MW (Da)
2.15
ALogP
3
HBA
0
HBD
15.6
PSA (Ų)
0.70
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1990
Availability Withdrawn
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Withdrawn Natural Product
USAN Year 1970

Extended Properties

Molecular Formula C11H12N2S
MW 204.30
Aromatic Rings 1
Heavy Atoms 14
NP-Likeness -0.47

Indications

Helminthiasis Carcinoma, Hepatocellular Severe Acute Respiratory Syndrome Acne Vulgaris Anemia, Aplastic

ATC Classification

P02CE01
levamisole
Level 1: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
Level 2: ANTHELMINTICS

Drug Warnings

Withdrawn
neurotoxicity
Adverse effects that cause encephalitis and mortality
Country: Vietnam; China   Year: 2000
Withdrawn
neurotoxicity
leukoencephalopathy
Country: Vietnam; China   Year: 2000
Withdrawn
General Warning
Adverse effects that cause encephalitis and mortality
Country: Vietnam; China   Year: 2000
Withdrawn
immune system toxicity
Adverse effects that cause encephalitis and mortality
Country: Vietnam; China   Year: 2000

Activity Summary

IC50 17 meas. best 5.36
Ki 7 meas. best 5.74
EC50 3 meas. best 6.68

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Nippostrongylus brasiliensis
CHEMBL613822
EC50 6.68 6.68 210.0 1
Alkaline phosphatase, tissue-nonspecific isozyme
CHEMBL2406894
Ki 5.74 5.74 1810.0 1
Unchecked
CHEMBL612545
Ki 5.57 4.6125 2703.0 4
Unchecked
CHEMBL612545
IC50 5.36 4.6967 4392.0 6
Haemonchus contortus
CHEMBL613144
EC50 4.82 4.785 15000.0 2
Alkaline phosphatase, tissue-nonspecific isozyme
CHEMBL5979
Ki 4.8 4.8 16000.0 1
Alkaline phosphatase, tissue-nonspecific isozyme
CHEMBL2406894
IC50 4.72 4.72 19210.0 3
Alkaline phosphatase, tissue-nonspecific isozyme
CHEMBL5979
IC50 4.72 4.7033 19200.0 3
Intestinal-type alkaline phosphatase
CHEMBL5573
IC50 4.69 4.69 20210.0 1
NON-PROTEIN TARGET
CHEMBL3879801
IC50 4.02 4.02 96000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 8940.0 ng.hr.mL-1 Canis lupus familiaris
AUC 12200.0 ng.hr.mL-1 Canis lupus familiaris
AUC 18100.0 ng.hr.mL-1 Canis lupus familiaris
AUC 3070.0 ng.hr.mL-1 Homo sapiens
AUC 3070.0 ng.hr.mL-1 Homo sapiens
AUC 3070.0 ng.hr.mL-1 Homo sapiens
CL 8.92 mL.min-1.kg-1 Canis lupus familiaris
CL 7.56 mL.min-1.kg-1 Homo sapiens
CL 8.25 mL.min-1.kg-1 Homo sapiens
CL 8.04 mL.min-1.kg-1 Homo sapiens
CL 1.5 L/hr Homo sapiens
CL 1.86 L/hr Homo sapiens
CL 1.75 L/hr Homo sapiens
Cmax 9691.63 nM Canis lupus familiaris
Cmax 16299.56 nM Canis lupus familiaris
Cmax 4013.71 nM Homo sapiens
Cmax 3289.28 nM Homo sapiens
Cmax 3509.54 nM Homo sapiens
F 44.0 % Canis lupus familiaris
F 64.0 % Canis lupus familiaris
F 64.7 % Homo sapiens
F 61.5 % Homo sapiens
F 62.5 % Homo sapiens
T1/2 5.6 hr Homo sapiens
T1/2 6.0 hr Not specified
T1/2 1.6 hr Canis lupus familiaris
T1/2 1.3 hr Canis lupus familiaris
T1/2 1.8 hr Canis lupus familiaris
T1/2 5.9 hr Homo sapiens
T1/2 5.4 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Nippostrongylus brasiliensis EC50 = 210.0 nM 6.68 Anthelmintic activity against Nippostrongylus brasiliensis 11754610
Alkaline phosphatase, tissue-nonspecific isozyme Ki = 1810.0 nM 5.74 Inhibition of bovine kidney non-specific alkaline phosphatase using CDP-star che... 25865133
Unchecked Ki = 2703.0 nM 5.57 DRUGMATRIX: Sigma2 radioligand binding (ligand: [3H] Ifenprodil) -
Unchecked IC50 = 4392.0 nM 5.36 DRUGMATRIX: Sigma2 radioligand binding (ligand: [3H] Ifenprodil) -
Unchecked IC50 = 13300.0 nM 4.88 Inhibition of alkaline phosphatase 22853994
Haemonchus contortus EC50 = 15000.0 nM 4.82 In vitro anthelmintic activity against Haemonchus contortus after 24 hr of incub... 15225722
Alkaline phosphatase, tissue-nonspecific isozyme Ki = 16000.0 nM 4.8 Inhibition of TNSALP 19038545
Haemonchus contortus EC50 = 18000.0 nM 4.75 In vitro anthelmintic activity against Haemonchus contortus after 2 hr of incuba... 15225722
Alkaline phosphatase, tissue-nonspecific isozyme IC50 = 19210.0 nM 4.72 Inhibition of bovine kidney non-specific alkaline phosphatase using CDP-star che... 25865133
Alkaline phosphatase, tissue-nonspecific isozyme IC50 = 19210.0 nM 4.72 Inhibition of bovine TNAP using CDP-star as substrate preincubated for 5 to 7 mi... 27907877
Alkaline phosphatase, tissue-nonspecific isozyme IC50 = 19200.0 nM 4.72 Inhibition of human TNAP expressed in COS7 cells preincubated for 5 to 7 mins fo... 29268128
Unchecked IC50 = 19210.0 nM 4.72 Inhibition of bovine kidney TNAP 32386855
Alkaline phosphatase, tissue-nonspecific isozyme IC50 = 19210.0 nM 4.72 Inhibition of bovine TNAP using CDP-star as substrate preincubated with enzyme f... 38911171
Alkaline phosphatase, tissue-nonspecific isozyme IC50 = 20200.0 nM 4.7 Inhibition of human TNAP expressed in African green monkey COS7 cell membranes u... 30296687
Intestinal-type alkaline phosphatase IC50 = 20210.0 nM 4.69 Inhibition of human IAP using CDP-star as substrate pretreated for 10 mins follo... 28288318
Alkaline phosphatase, tissue-nonspecific isozyme IC50 = 20210.0 nM 4.69 Inhibition of human TNAP expressed in COS7 cells using CDP-star as substrate pre... 30015078
Unchecked IC50 = 23200.0 nM 4.63 Inhibition of porcine kidney TNAP assessed as para nitrophenylphosphate conversi... 24183741
Unchecked Ki = 30500.0 nM 4.52 Uncompetitive inhibition of porcine kidney TNAP assessed as para nitrophenylphos... 24183741
Unchecked IC50 = 41000.0 nM 4.39 Inhibition of porcine kidney TNAP using para-nitrophenylphosphate as substrate p... 26860736
Unchecked Ki = 47000.0 nM 4.33 Inhibition of porcine kidney TNAP using para-nitrophenylphosphate as substrate p... 26860736

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 405
31158845 10.1038/s41586-019-1291-3 ADMET 73
- 10.5281/zenodo.13943903 ADMET 71
7005449 10.1021/jm00186a015 Mus musculus 36
22393119 10.1124/dmd.112.045021 Homo sapiens 26
28284807 10.1016/j.bmcl.2017.02.046 Mus musculus 22
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22393119 10.1124/dmd.112.045021 Canis familiaris 16
27474926 10.1016/j.ejmech.2016.07.026 Mus musculus 12
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
4032421 10.1021/jm00147a008 Rattus norvegicus 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
24183741 10.1016/j.bmc.2013.09.053 Unchecked 7
27474926 10.1016/j.ejmech.2016.07.026 NON-PROTEIN TARGET 6
16165359 10.1016/j.bmcl.2005.07.044 Haemonchus contortus 4
6690686 10.1021/jm00367a014 Rattus norvegicus 4
20485427 10.1038/nature09107 Plasmodium falciparum 4
27376493 10.1016/j.ejmech.2016.06.044 NON-PROTEIN TARGET 3
1710256 10.1021/np50070a033 Nippostrongylus brasiliensis 3
2033588 10.1021/jm00109a015 Heligmosomoides polygyrus 3

Data from ChEMBL 36 via Core Engine