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Compound Detail

CHEMBL290960

NIFURTIMOX
💊 Approved Drug
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💊 Approved Drug
CC1CS(=O)(=O)CCN1/N=C/c1ccc([N+](=O)[O-])o1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL290960
Name NIFURTIMOX
Phase Approved
Structure Type MOL
InChI Key ARFHIAQFJWUCFH-IZZDOVSWSA-N
Therapeutic ✓ Yes

Known Names

BAY 2502 BAY A2502 BAY-2502 BAY-A2502 BAYER 2502 BAYER-2502 DNDI1613515 Lampit Nifurtimox Nifurtimoxum
20
Targets
229
Activities
3
Assay Types
1
PK Parameters
20
Publications
10
Known Names
6
Indications
1
Mechanisms

Molecular Properties

287.3
MW (Da)
0.64
ALogP
7
HBA
0
HBD
106.0
PSA (Ų)
0.46
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2020
Availability Prescription
Chirality Racemic

Routes of Administration

Oral

Flags

Natural Product
USAN Stem nifur-
USAN Year 2015

Extended Properties

Molecular Formula C10H13N3O5S
MW 287.30
Aromatic Rings 1
Heavy Atoms 19
NP-Likeness -1.28

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
DNA inhibitor INHIBITOR DNA ✓ ✓

Indications

Chagas Disease Chagas Disease Leishmaniasis Trypanosomiasis Trypanosomiasis, African Neuroblastoma

ATC Classification

P01CC01
nifurtimox
Level 1: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
Level 2: ANTIPROTOZOALS

Activity Summary

IC50 186 meas. best 6.96
EC50 42 meas. best 8.4
Ki 1 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Leishmania donovani
CHEMBL367
 EC50 8.4 8.01 4.0 2
Trypanosoma brucei brucei
CHEMBL612851
 EC50 7.24 5.74 57.0 12
Leishmania donovani
CHEMBL367
 IC50 6.96 5.6167 110.0 3
Trypanosoma brucei brucei
CHEMBL612851
 IC50 6.89 5.7636 130.0 25
Trypanosoma cruzi
CHEMBL368
 IC50 6.64 5.3488 230.0 111
Trypanosoma brucei gambiense
CHEMBL613768
 EC50 6.58 6.58 260.0 1
Trypanosoma brucei
CHEMBL612849
 IC50 6.58 5.612 260.0 10
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 6.47 6.01 340.0 2
Unchecked
CHEMBL612545
 IC50 6.22 5.205 600.0 2
Trypanosoma cruzi
CHEMBL368
 EC50 6.16 5.8258 700.0 12
Leishmania amazonensis
CHEMBL612877
 EC50 6.1 6.1 800.0 1
Trypanosoma congolense
CHEMBL4296607
 IC50 5.96 5.96 1100.0 1
Trypanosoma brucei rhodesiense
CHEMBL612348
 IC50 5.84 5.68 1440.0 4
Trypanosoma brucei rhodesiense
CHEMBL612348
 EC50 5.77 5.77 1708.0 1
Trypanosoma brucei
CHEMBL612849
 EC50 5.62 5.1671 2400.0 7
Trypanosoma evansi
CHEMBL1075362
 IC50 5.58 5.58 2600.0 1
Leishmania mexicana
CHEMBL612880
 IC50 5.51 5.51 3100.0 1
Trypanosoma brucei gambiense
CHEMBL613768
 IC50 5.36 5.3433 4400.0 3
Leishmania infantum
CHEMBL612848
 IC50 5.22 5.19 6000.0 6
HeLa
CHEMBL399
 IC50 4.92 4.92 12000.0 1
ADMET
CHEMBL612558
 IC50 4.77 4.77 17000.0 1
L6
CHEMBL614793
 IC50 4.5 4.335 32000.0 2
Rattus norvegicus
CHEMBL376
 IC50 4.5 4.5 32000.0 1
V79
CHEMBL614074
 IC50 4.46 4.46 35000.0 1
Vero
CHEMBL391
 EC50 4.3 4.3 50000.0 1
Vero
CHEMBL391
 IC50 4.19 4.1067 64110.0 3
THP-1
CHEMBL614245
 IC50 4.19 4.19 64800.0 1
HeLa
CHEMBL399
 EC50 4.04 4.04 91200.0 1

Pharmacokinetic Data

Parameter Value Units Species
F 79.0 % Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Leishmania donovani EC50 = 4.0 nM 8.4 Antileishmanial activity against amastigote form of Leishmania donovani assessed... 30234295
Leishmania donovani EC50 = 24.0 nM 7.62 Antileishmanial activity against Leishmania donovani promastigotes assessed as p... 30234295
Trypanosoma brucei brucei EC50 = 57.0 nM 7.24 Antitrypanosomal activity against bloodstream form Trypanosoma brucei brucei 427... 31978782
Leishmania donovani IC50 = 110.0 nM 6.96 Antileishmanial activity against Leishmania donovani LdBOB derived from MHOM/SD/... 34531949
Trypanosoma brucei brucei IC50 = 130.0 nM 6.89 Trypanocidal activity against bloodstream forms of Trypanosoma brucei brucei Lis... 25240098
Trypanosoma brucei brucei IC50 = 130.0 nM 6.89 Antitrypanosomal activity against bloodstream form of Trypanosoma brucei brucei ... 22550999
Trypanosoma brucei brucei IC50 = 130.0 nM 6.89 Antitrypanosomal activity against tetracycline-induced blood-stream Trypanosoma ... 22023653
Trypanosoma cruzi IC50 = 230.0 nM 6.64 DNDI: Inhibition of Chagas Disease parasite Trypanosoma cruzi (Tulahuen LacZ, Cl... -
Trypanosoma cruzi IC50 = 240.0 nM 6.62 Antitrypanosomal activity against Trypanosoma cruzi clone Cl-Brener infected in ... 20679506
Trypanosoma brucei gambiense EC50 = 260.0 nM 6.58 Antimicrobial activity against Trypanosoma brucei gambiense 20439607
Trypanosoma brucei IC50 = 260.0 nM 6.58 Antitrypanosomal activity against Trypanosoma brucei bloodstream form overexpres... 23031595
Trypanosoma cruzi IC50 = 300.0 nM 6.52 Antitrypanosomal activity against Trypanosoma cruzi MHOM/BR/78/Silvio cloneX10/7... 30655943
NON-PROTEIN TARGET EC50 = 340.0 nM 6.47 Antitrypanosomal activity against amastigote stage of Trypanosoma cruzi Y infect... 27318979
Trypanosoma cruzi IC50 = 390.0 nM 6.41 Antitrypanosomal activity against Trypanosoma cruzi Tulahuen CL2 by microdilutio... 15497942
Trypanosoma cruzi IC50 = 390.0 nM 6.41 In vitro anti-protozoal parasite activity against Trypanosoma cruzi TC-1 12781185
Trypanosoma cruzi IC50 = 400.0 nM 6.4 Antitrypanosomal activity against Trypanosoma cruzi Tulahuen amastigote forms in... 30100019
Trypanosoma brucei brucei IC50 = 430.0 nM 6.37 Antiparasitic activity against blood stream form of Trypanosoma brucei brucei ov... 26344593
Trypanosoma brucei brucei IC50 = 430.0 nM 6.37 Antimicrobial activity against bloodstream forms of Trypanosoma brucei brucei ov... 26363868
Trypanosoma cruzi IC50 = 450.0 nM 6.35 Antitrypanosomal activity against Trypanosoma cruzi Sylvio X-10 amastigotes infe... 24749923
Trypanosoma cruzi IC50 = 450.0 nM 6.35 In vitro anti protozoal activity against Trypanosoma cruzi strain Tulahuen CL2 w... 15203133

Literature References

PubMed DOI Target Context # Activities
19446929 10.1016/j.ejmech.2009.04.015 Mus musculus 28
1919589 10.1021/np50074a015 Trypanosoma cruzi 20
406399 10.1021/jm00217a017 Trypanosoma cruzi 20
9554887 10.1021/jm970860z Trypanosoma cruzi 19
15713399 10.1016/j.bmcl.2005.01.002 Trypanosoma cruzi 12
20439607 10.1128/aac.00332-10 Trypanosoma brucei 12
29247858 10.1016/j.ejmech.2017.12.011 Trypanosoma cruzi 11
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
24461296 10.1016/j.bmcl.2013.12.071 Trypanosoma cruzi 10
25899337 10.1016/j.ejmech.2015.03.066 Trypanosoma cruzi 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
21506600 10.1021/jm2002469 Trypanosoma cruzi 8
19616875 10.1016/j.ejmech.2009.06.014 Trypanosoma cruzi 7
16455249 10.1016/j.bmcl.2005.12.087 Trypanosoma cruzi 6
21605926 10.1016/j.ejmech.2011.04.057 Trypanosoma cruzi 6
33479686 10.1039/d0md00073f Leishmania infantum 6
18255195 10.1016/j.ejmech.2007.12.016 Mus musculus 6
18255195 10.1016/j.ejmech.2007.12.016 Trypanosoma cruzi 5
69024 10.1021/jm00216a001 Trypanosoma cruzi 5
28499168 10.1016/j.ejmech.2017.04.075 Trypanosoma cruzi 5

Data from ChEMBL 36 via Core Engine