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Compound Detail

CHEMBL5201510

FIPRAVIRIMAT
🧪 Phase II
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🧪 Phase II
C=C(C)[C@@H]1CC[C@]2(NCCN3CCS(=O)(=O)CC3)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC=C(C6=CC[C@@](CF)(C(=O)O)CC6)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12

Basic Information

ChEMBL ID CHEMBL5201510
Name FIPRAVIRIMAT
Phase Phase II
Structure Type MOL
InChI Key YFSNREBZTKMFEB-DHGHKPCRSA-N

Known Names

Fipravirimat GSK-3640254 GSK-3640254A GSK3640254 GSK3640254A
3
Targets
37
Activities
3
Assay Types
30
PK Parameters
20
Publications
5
Known Names
1
Indications

Molecular Properties

727.1
MW (Da)
8.40
ALogP
5
HBA
2
HBD
86.7
PSA (Ų)
0.24
QED
2
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer
USAN Stem -vir-
USAN Year 2022

Extended Properties

Molecular Formula C43H67FN2O4S
MW 727.08
Aromatic Rings 0
Heavy Atoms 51
NP-Likeness 1.28

Indications

HIV Infections

Activity Summary

EC50 35 meas. best 8.96
IC50 1 meas. best 5.41
Kd 1 meas. best 8.85

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Human immunodeficiency virus 1
CHEMBL378
EC50 8.96 8.3385 1.1 33
Unchecked
CHEMBL612545
Kd 8.85 8.85 1.4 1
Unchecked
CHEMBL612545
EC50 8.83 7.765 1.5 2
UDP-glucuronosyltransferase 1A1
CHEMBL1287617
IC50 5.41 5.41 3900.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 5074.29 ng.hr.mL-1 Rattus norvegicus
AUC 5357.13 ng.hr.mL-1 Rattus norvegicus
AUC 21739.69 ng.hr.mL-1 Mus musculus
AUC 5380.39 ng.hr.mL-1 Rattus norvegicus
AUC 3126.44 ng.hr.mL-1 Canis lupus familiaris
AUC 5525.81 ng.hr.mL-1 Macaca fascicularis
AUC 5380.39 ng.hr.mL-1 Rattus norvegicus
CL 2.6 mL.min-1.kg-1 Mus musculus
CL 6.5 mL.min-1.kg-1 Rattus norvegicus
CL 0.38 mL.min-1.kg-1 Canis lupus familiaris
CL 1.8 mL.min-1.kg-1 Macaca fascicularis
CL 6.5 mL.min-1.kg-1 Rattus norvegicus
Cmax 2700.0 nM Mus musculus
Cmax 900.0 nM Rattus norvegicus
Cmax 4300.0 nM Canis lupus familiaris
Cmax 800.0 nM Macaca fascicularis
Cmax 900.0 nM Rattus norvegicus
F 91.0 % Mus musculus
F 40.0 % Rattus norvegicus
F 117.0 % Canis lupus familiaris
F 28.0 % Macaca fascicularis
F 40.0 % Rattus norvegicus
MRT 4.9 hr Rattus norvegicus
T1/2 4.6 hr Mus musculus
T1/2 4.0 hr Rattus norvegicus
T1/2 18.7 hr Canis lupus familiaris
T1/2 5.3 hr Macaca fascicularis
T1/2 2.0 hr Homo sapiens
T1/2 2.0 hr Mus musculus
T1/2 2.0 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Human immunodeficiency virus 1 EC50 = 1.1 nM 8.96 Antiviral activity against HIV1 wild type subtype B NL (4 to 3) harbouring V362/... 36044257
Human immunodeficiency virus 1 EC50 = 1.2 nM 8.92 Antiviral activity against HIV1 wild type subtype C NL (4 to 3) transfected in h... 36044257
Unchecked Kd = 1.4 nM 8.85 Binding affinity to HIV1 wild type Gag assessed as dissociation constant 36044257
Unchecked EC50 = 1.48 nM 8.83 HIV Cell Culture Assay: MT-2 cells and 293T cells were obtained from the NIH AID... -
Human immunodeficiency virus 1 EC50 = 1.8 nM 8.74 Antiviral activity against HIV1 harbouring deltaV370/T371A mutant infected in hu... 36044257
Human immunodeficiency virus 1 EC50 = 1.9 nM 8.72 Antiviral activity against HIV1 wild type subtype B NL (4 to 3) transfected in h... 36044257
Human immunodeficiency virus 1 EC50 = 2.0 nM 8.7 Antiviral activity against wild type HIV-1 NLRepRlucP373S harboring V370A mutant... 36441509
Human immunodeficiency virus 1 EC50 = 2.0 nM 8.7 Antiviral activity against HIV1 wild type NL (4 to 3) infected in human MT2 cell... 36044257
Human immunodeficiency virus 1 EC50 = 2.0 nM 8.7 Antiviral activity against HIV 1 harbouring V370A mutant 37583823
Human immunodeficiency virus 1 EC50 = 2.0 nM 8.7 Antiviral activity against wild type HIV-1 NLRepRlucP373S infected in human MT2 ... 36441509
Human immunodeficiency virus 1 EC50 = 2.7 nM 8.57 Antiviral activity against HIV1 NL (4 to 3) harbouring V362I mutant transfected ... 36044257
Human immunodeficiency virus 1 EC50 = 3.0 nM 8.52 Antiviral activity against HIV1 NL (4 to 3) harbouring V362I/deltaV370 mutant tr... 36044257
Human immunodeficiency virus 1 EC50 = 3.0 nM 8.52 Antiviral activity against HIV1 wild type NL (4 to 3) infected in human MT2 cell... 36044257
Human immunodeficiency virus 1 EC50 = 3.0 nM 8.52 Antiviral activity against HIV 1 harbouring R361K/V362I/L363M mutant 37583823
Human immunodeficiency virus 1 EC50 = 3.0 nM 8.52 Antiviral activity against wild type HIV 1 37583823
Human immunodeficiency virus 1 EC50 = 3.0 nM 8.52 Antiviral activity against HIV 1 harbouring deltaV370 mutant 37583823
Human immunodeficiency virus 1 EC50 = 3.0 nM 8.52 Antiviral activity against HIV 1 harbouring V362I/V370 mutant 37583823
Human immunodeficiency virus 1 EC50 = 3.0 nM 8.52 Antiviral activity against wild type HIV-1 NLRepRlucP373S harboring V362I/V370A ... 36441509
Human immunodeficiency virus 1 EC50 = 3.0 nM 8.52 Antiviral activity against HIV1 harbouring V362I/V370A mutant infected in human ... 36044257
Human immunodeficiency virus 1 EC50 = 3.0 nM 8.52 Antiviral activity against wild type HIV-1 NLRepRlucP373S infected in human MT2 ... 36441509

Literature References

Data from ChEMBL 36 via Core Engine