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Compound Detail

CHEMBL964

DISULFIRAM
💊 Approved Drug
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💊 Approved Drug
CCN(CC)C(=S)SSC(=S)N(CC)CC

Basic Information

ChEMBL ID CHEMBL964
Name DISULFIRAM
Phase Approved
Structure Type MOL
InChI Key AUZONCFQVSMFAP-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Antabuse Disulfiram Disulfirame Esperal NSC-25953 ORA-102 ORA102
58
Targets
129
Activities
3
Assay Types
2
PK Parameters
20
Publications
7
Known Names
20
Indications
1
Mechanisms

Molecular Properties

296.6
MW (Da)
3.62
ALogP
4
HBA
0
HBD
6.5
PSA (Ų)
0.57
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1951
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product

Extended Properties

Molecular Formula C10H20N2S4
MW 296.55
Aromatic Rings 0
Heavy Atoms 16
NP-Likeness -0.74

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Aldehyde dehydrogenase inhibitor INHIBITOR Aldehyde dehydrogenase, mitochondrial

Indications

Alcoholism Ectoparasitic Infestations Alcohol-Related Disorders Breast Neoplasms Breast Neoplasms Carcinoma, Non-Small-Cell Lung Cocaine-Related Disorders Cocaine-Related Disorders Glioblastoma Melanoma Melanoma Neoplasms, Germ Cell and Embryonal Opioid-Related Disorders Pancreatic Neoplasms Paraganglioma Severe Acute Respiratory Syndrome Amphetamine-Related Disorders Fatigue HIV Infections Multiple Myeloma

ATC Classification

N07BB01
disulfiram
Level 1: NERVOUS SYSTEM
Level 2: OTHER NERVOUS SYSTEM DRUGS
P03AA04
disulfiram
Level 1: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
Level 2: ECTOPARASITICIDES, INCL. SCABICIDES, INSECTICIDES AND REPELLENTS
P03AA54
disulfiram, combinations
Level 1: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
Level 2: ECTOPARASITICIDES, INCL. SCABICIDES, INSECTICIDES AND REPELLENTS

Drug Warnings

Black Box Warning
General Warning
Country: United States

Activity Summary

IC50 102 meas. best 7.51
Ki 21 meas. best 6.7
EC50 6 meas. best 7.06

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
IC50 7.51 5.3289 31.1 18
Lysyl oxidase homolog 4
CHEMBL4295926
IC50 7.23 7.23 59.0 1
Unchecked
CHEMBL612545
EC50 7.06 6.196 87.0 5
Lysyl oxidase homolog 3
CHEMBL4105989
IC50 7.03 7.03 93.0 1
MCF7
CHEMBL387
IC50 7.0 7.0 100.0 1
Aldehyde dehydrogenase 1A1
CHEMBL3577
IC50 6.89 6.89 130.0 1
Lysyl oxidase homolog 2
CHEMBL3714029
IC50 6.82 6.82 150.0 1
T47D
CHEMBL614361
IC50 6.77 6.77 170.0 1
Adenosine receptor A3
CHEMBL256
Ki 6.7 6.7 201.0 1
Replicase polyprotein 1ab
CHEMBL4523582
IC50 6.66 5.3267 220.0 12
4T1
CHEMBL612589
IC50 6.6 6.6 250.0 1
MDA-MB-231
CHEMBL400
IC50 6.5 6.5 320.0 1
Protein-lysine 6-oxidase
CHEMBL2249
IC50 6.5 6.5 320.0 1
Adenosine receptor A3
CHEMBL256
IC50 6.45 6.45 356.0 1
Monoglyceride lipase
CHEMBL4191
IC50 6.44 6.17 360.0 2
D(3) dopamine receptor
CHEMBL234
Ki 6.43 6.43 368.0 1
Gasdermin-D
CHEMBL4523247
IC50 6.4 6.4 400.0 1
Gasdermin-D
CHEMBL4523446
IC50 6.4 6.4 400.0 1
THP-1
CHEMBL614245
IC50 6.39 5.775 410.0 2
D-3-phosphoglycerate dehydrogenase
CHEMBL2311243
IC50 6.23 6.23 590.0 1
Histone-lysine N-methyltransferase EHMT2
CHEMBL6032
IC50 6.22 6.22 600.0 1
Fructose-1,6-bisphosphatase 1
CHEMBL3975
IC50 6.22 5.88 600.0 9
Carbamate kinase
CHEMBL4802003
IC50 6.22 6.22 600.0 1
Giardia intestinalis
CHEMBL612652
IC50 6.05 6.05 900.0 1
C-C chemokine receptor type 2
CHEMBL4015
Ki 6.02 6.02 954.0 1
D(1A) dopamine receptor
CHEMBL2056
Ki 5.97 5.97 1079.0 1
D(3) dopamine receptor
CHEMBL234
IC50 5.96 5.96 1084.0 1
D(4) dopamine receptor
CHEMBL219
Ki 5.96 5.96 1105.0 1
Mu-type opioid receptor
CHEMBL233
Ki 5.85 5.85 1425.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
Ki 5.83 5.83 1469.0 1
Mitogen-activated protein kinase 3
CHEMBL3385
IC50 5.82 5.82 1510.0 1
Histone-lysine N-methyltransferase EHMT1
CHEMBL6031
IC50 5.8 5.8 1600.0 1
1-acylglycerol-3-phosphate O-acyltransferase ABHD5/Perilipin-5
CHEMBL3885501
IC50 5.79 5.79 1622.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 5.74 5.74 1839.0 1
5-hydroxytryptamine receptor 1B
CHEMBL3459
Ki 5.67 5.67 2145.0 1
D(1A) dopamine receptor
CHEMBL2056
IC50 5.67 5.67 2158.0 1
C-C chemokine receptor type 2
CHEMBL4015
IC50 5.61 5.61 2468.0 1
Kappa-type opioid receptor
CHEMBL237
Ki 5.61 5.61 2441.0 1
Plasmodium falciparum
CHEMBL364
IC50 5.6 5.34 2511.9 5
NACHT, LRR and PYD domains-containing protein 3
CHEMBL3779755
IC50 5.52 5.52 3000.0 1
Transient receptor potential cation channel subfamily A member 1
CHEMBL6007
EC50 5.52 5.52 3000.0 1
D(4) dopamine receptor
CHEMBL219
IC50 5.5 5.5 3150.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
IC50 5.49 5.49 3218.0 1
Aldehyde dehydrogenase, mitochondrial
CHEMBL1935
IC50 5.47 5.47 3400.0 1
Mu-type opioid receptor
CHEMBL233
IC50 5.46 5.46 3511.0 1
Sodium-dependent dopamine transporter
CHEMBL238
Ki 5.43 5.43 3684.0 1
CEM-SS
CHEMBL614548
IC50 5.41 5.41 3900.0 1
Cytochrome P450 1A2
CHEMBL3356
IC50 5.4 5.4 4000.0 1
C-X-C chemokine receptor type 2
CHEMBL2434
Ki 5.38 5.38 4209.0 1
C-C chemokine receptor type 4
CHEMBL2414
Ki 5.36 5.36 4397.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 1848.0 mL.min-1.g-1 Rattus norvegicus
T1/2 0.0125 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 31.1 nM 7.51 Cytotoxicity against patient derived GSC after 96 hrs by CellTiter-Glo assay 30583248
Lysyl oxidase homolog 4 IC50 = 59.0 nM 7.23 Inhibition of recombinant human LOXL4 expressed in baculovirus infected insect c... 30098867
Unchecked EC50 = 87.0 nM 7.06 PUBCHEM_BIOASSAY: High Throughput Screen to Identify Compounds that Suppress the... -
Unchecked EC50 = 91.0 nM 7.04 PUBCHEM_BIOASSAY: High Throughput Screen to Identify Compounds that Suppress the... -
Lysyl oxidase homolog 3 IC50 = 93.0 nM 7.03 Inhibition of recombinant human LOXL3 expressed in CHO cells using diaminopentan... 30098867
MCF7 IC50 = 100.0 nM 7.0 Antiproliferative activity against human MCF7 cells expressing BCA2 and estrogen... 20222671
Unchecked IC50 = 130.0 nM 6.89 Inhibition of Metallo-beta-lactamase NDM-1 (unknown origin) expressed in Escheri... 32707526
Aldehyde dehydrogenase 1A1 IC50 = 130.0 nM 6.89 Inhibition of ALDH1A1 (unknown origin) 33744437
Unchecked IC50 = 130.0 nM 6.89 Inhibition of NDM-1 (unknown origin) 34391033
Lysyl oxidase homolog 2 IC50 = 150.0 nM 6.82 Inhibition of recombinant LOXL2 (unknown origin) expressed in NS0 cells using di... 30098867
T47D IC50 = 170.0 nM 6.77 Antiproliferative activity against human T47D cells expressing BCA2 and estrogen... 20222671
Adenosine receptor A3 Ki = 201.0 nM 6.7 DRUGMATRIX: Adenosine A3 radioligand binding (ligand: AB-MECA) -
Replicase polyprotein 1ab IC50 = 220.0 nM 6.66 SARS-CoV-2 3CL-Pro protease inhibition IC50 determined by FRET kind of response ... -
Unchecked EC50 = 249.0 nM 6.6 PubChem BioAssay. Leishmania major promastigote EC50 determinations. (Class of... -
4T1 IC50 = 250.0 nM 6.6 Anticancer activity against mouse 4T1 cells assessed as cell growth inhibition b... 33650861
Protein-lysine 6-oxidase IC50 = 320.0 nM 6.5 Inhibition of recombinant human LOX expressed in HEK293 cells using diaminopenta... 30098867
MDA-MB-231 IC50 = 320.0 nM 6.5 Antiproliferative activity against human MDA-MB-231 cells expressing BCA2 and ER... 20222671
Adenosine receptor A3 IC50 = 356.0 nM 6.45 DRUGMATRIX: Adenosine A3 radioligand binding (ligand: AB-MECA) -
Monoglyceride lipase IC50 = 360.0 nM 6.44 Inhibition of recombinant human N-terminal His6-tagged and C-terminal Strep-tagg... 27766867
D(3) dopamine receptor Ki = 368.0 nM 6.43 DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1394
- 10.6019/CHEMBL3885881 Rattus norvegicus 405
36948075 10.1016/j.ejmech.2023.115179 Schistosoma mansoni 22
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
29571571 10.1016/j.bmcl.2018.03.023 Staphylococcus aureus 13
36027862 10.1016/j.ejmech.2022.114641 Schistosoma mansoni 12
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
32375478 10.1021/acs.jmedchem.0c00699 Fructose-1,6-bisphosphatase 1 9
29519735 10.1016/j.bmcl.2018.02.043 Histone-lysine N-methyltransferase EHMT2 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
32375478 10.1021/acs.jmedchem.0c00699 Unchecked 8
29519735 10.1016/j.bmcl.2018.02.043 Histone-lysine N-methyltransferase EHMT1 8
36948075 10.1016/j.ejmech.2023.115179 Unchecked 7
29571571 10.1016/j.bmcl.2018.03.023 Staphylococcus epidermidis 5
27311892 10.1016/j.bmcl.2016.04.075 Proteasome Macropain subunit MB1 5
19734910 10.1038/nchembio.215 Plasmodium falciparum 5
29571571 10.1016/j.bmcl.2018.03.023 Bacillus anthracis 4
9207937 10.1021/jm970147+ CEM-SS 4
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 3

Data from ChEMBL 36 via Core Engine