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Compound Detail

CHEMBL4078293

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O=[N+]([O-])c1cn2c(n1)OC[C@H](Oc1ccc(OC(F)(F)F)cc1)C2

Basic Information

ChEMBL ID CHEMBL4078293
Phase Preclinical
Structure Type MOL
InChI Key IXUWKDINJWESQG-SNVBAGLBSA-N
9
Targets
24
Activities
1
Assay Types
20
PK Parameters
20
Publications
0
Known Names

Molecular Properties

345.2
MW (Da)
2.53
ALogP
7
HBA
0
HBD
88.7
PSA (Ų)
0.62
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C13H10F3N3O5
MW 345.23
Aromatic Rings 2
Heavy Atoms 24
NP-Likeness -0.58

Activity Summary

IC50 24 meas. best 6.82

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Trypanosoma cruzi
CHEMBL368
IC50 6.82 6.38 150.0 3
Leishmania donovani
CHEMBL367
IC50 6.72 6.3371 190.0 7
Leishmania panamensis
CHEMBL612882
IC50 6.47 6.47 340.0 1
Leishmania infantum
CHEMBL612848
IC50 6.29 5.9375 510.0 8
Leishmania mexicana
CHEMBL612880
IC50 5.93 5.93 1170.0 1
Leishmania tropica
CHEMBL612881
IC50 5.8 5.8 1570.0 1
Leishmania major
CHEMBL612879
IC50 5.63 5.63 2340.0 1
Leishmania aethiopica
CHEMBL612651
IC50 5.5 5.5 3170.0 1
Leishmania amazonensis
CHEMBL612877
IC50 5.33 5.33 4680.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 272000.0 ng.hr.mL-1 Mus musculus
AUC 1510.0 ng.hr.mL-1 Rattus norvegicus
AUC 80600.0 ng.hr.mL-1 Rattus norvegicus
AUC 420.0 ng.hr.mL-1 Mesocricetus auratus
AUC 11200.0 ng.hr.mL-1 Mesocricetus auratus
CL 11.0 mL.min-1.kg-1 Rattus norvegicus
CL 81.0 mL.min-1.kg-1 Mesocricetus auratus
Cmax 60829.01 nM Mus musculus
Cmax 15062.42 nM Rattus norvegicus
Cmax 6082.9 nM Mesocricetus auratus
F 100.0 % Rattus norvegicus
F 100.0 % Mesocricetus auratus
T1/2 7.8 hr Mus musculus
T1/2 3.0 hr Rattus norvegicus
t1/2 - - Rattus norvegicus
T1/2 1.4 hr Mesocricetus auratus
T1/2 2.2 hr Mesocricetus auratus
Tmax 5.3 hr Mus musculus
Tmax 6.7 hr Rattus norvegicus
Tmax 3.3 hr Mesocricetus auratus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Trypanosoma cruzi IC50 = 150.0 nM 6.82 Antitrypanosomal activity against Trypanosoma cruzi infected in human MRC5 cells... 29461823
Leishmania donovani IC50 = 190.0 nM 6.72 Antileishmanial activity against Leishmania donovani amastigotes expressing Luc ... 29461823
Leishmania donovani IC50 = 190.0 nM 6.72 Antileishmanial activity against Leishmania donovani isolate GR265 after 3 to 5 ... 29461823
Leishmania donovani IC50 = 220.0 nM 6.66 Antileishmanial activity against Leishmania donovani MHOM/IN/80/DD8 amastigotes ... 29461823
Leishmania donovani IC50 = 330.0 nM 6.48 Antileishmanial activity against Leishmania donovani MHOM/ET/67/HU3 amastigotes ... 29461823
Leishmania panamensis IC50 = 340.0 nM 6.47 Antileishmanial activity against Leishmania panamensis MHOM/PA/67/Boyton after 3... 29461823
Trypanosoma cruzi IC50 = 400.0 nM 6.4 Antitrypanosomal activity against Trypanosoma cruzi Tulahuen strain C2C4 amastig... 33007723
Leishmania infantum IC50 = 510.0 nM 6.29 Antileishmanial activity against Leishmania infantum MHOM/MA/67/ITMAP263 amastig... 29461823
Leishmania infantum IC50 = 530.0 nM 6.28 Antileishmanial activity against Leishmania infantum amastigotes infected in mou... 29461823
Leishmania donovani IC50 = 570.0 nM 6.24 Antileishmanial activity against Leishmania donovani isolate SUKA001 after 3 to ... 29461823
Leishmania infantum IC50 = 590.0 nM 6.23 Antileishmanial activity against miltefosine resistant Leishmania infantum MHOM/... 29461823
Leishmania infantum IC50 = 750.0 nM 6.12 Antileishmanial activity against Leishmania infantum isolate L3034 after 3 to 5 ... 29461823
Leishmania mexicana IC50 = 1170.0 nM 5.93 Antileishmanial activity against Leishmania mexicana MNYC/BZ/62/M379 after 3 to ... 29461823
Trypanosoma cruzi IC50 = 1200.0 nM 5.92 Antitrypanosomal activity against Trypanosoma cruzi Tulahuen strain C2C4 amastig... 33007723
Leishmania infantum IC50 = 1230.0 nM 5.91 Antileishmanial activity against Leishmania infantum isolate MCAN/BR/2002/BH400 ... 29461823
Leishmania donovani IC50 = 1340.0 nM 5.87 Antileishmanial activity against sodium stibogluconate resistant Leishmania dono... 29461823
Leishmania tropica IC50 = 1570.0 nM 5.8 Antileishmanial activity against Leishmania tropica isolate Anwari after 3 to 5 ... 29461823
Leishmania infantum IC50 = 1770.0 nM 5.75 Antileishmanial activity against Leishmania infantum isolate LEM5695 after 3 to ... 29461823
Leishmania donovani IC50 = 2160.0 nM 5.67 Antileishmanial activity against Leishmania donovani MHOM/SD/62/ISCL2D amastigot... 29461823
Leishmania infantum IC50 = 2220.0 nM 5.65 Antileishmanial activity against Leishmania infantum isolate LEM3323 after 3 to ... 29461823

Literature References

PubMed DOI Target Context # Activities
29461823 10.1021/acs.jmedchem.7b01581 Leishmania infantum 17
29461823 10.1021/acs.jmedchem.7b01581 Leishmania donovani 12
29461823 10.1021/acs.jmedchem.7b01581 Rattus norvegicus 10
29461823 10.1021/acs.jmedchem.7b01581 Syrian golden hamster 10
33007723 10.1016/j.ejmech.2020.112849 Trypanosoma cruzi 9
33007723 10.1016/j.ejmech.2020.112849 Unchecked 4
29461823 10.1021/acs.jmedchem.7b01581 Salmonella typhimurium 4
29461823 10.1021/acs.jmedchem.7b01581 ADMET 4
29461823 10.1021/acs.jmedchem.7b01581 Mus musculus 4
29461823 10.1021/acs.jmedchem.7b01581 Plasma 3
29461823 10.1021/acs.jmedchem.7b01581 No relevant target 3
29461823 10.1021/acs.jmedchem.7b01581 Liver 2
29461823 10.1021/acs.jmedchem.7b01581 Mycobacterium tuberculosis 2
29461823 10.1021/acs.jmedchem.7b01581 Trypanosoma brucei 1
29461823 10.1021/acs.jmedchem.7b01581 Trypanosoma cruzi 1
29461823 10.1021/acs.jmedchem.7b01581 MRC5 1
29461823 10.1021/acs.jmedchem.7b01581 Voltage-gated inwardly rectifying potassium channel KCNH2 1
29461823 10.1021/acs.jmedchem.7b01581 Cytochrome P450 3A4 1
33007723 10.1016/j.ejmech.2020.112849 No relevant target 1
29461823 10.1021/acs.jmedchem.7b01581 Leishmania amazonensis 1

Data from ChEMBL 36 via Core Engine