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Compound Detail

CHEMBL3608680

FEZOLINETANT
💊 Approved Drug
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💊 Approved Drug
Cc1nsc(-c2nnc3n2CCN(C(=O)c2ccc(F)cc2)[C@@H]3C)n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3608680
Name FEZOLINETANT
Phase Approved
Structure Type MOL
InChI Key PPSNFPASKFYPMN-SECBINFHSA-N
Therapeutic ✓ Yes

Known Names

A-2693 A2693 AS-3472693-00 AS3472693-00 ES-256364 ESN-364 Esn364 Fezolinetant Veoza Veozah
7
Targets
19
Activities
2
Assay Types
23
PK Parameters
20
Publications
10
Known Names
3
Indications
1
Mechanisms

Molecular Properties

358.4
MW (Da)
2.46
ALogP
7
HBA
0
HBD
76.8
PSA (Ų)
0.70
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2023
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning First in Class
USAN Stem -tant
USAN Year 2020

Extended Properties

Molecular Formula C16H15FN6OS
MW 358.40
Aromatic Rings 3
Heavy Atoms 25
NP-Likeness -1.87

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Neurokinin 3 receptor antagonist ANTAGONIST Neuromedin-K receptor ✓ ✓

Indications

Hot Flashes Kidney Diseases Liver Diseases

ATC Classification

G02CX06
fezolinetant
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: OTHER GYNECOLOGICALS

Drug Warnings

Black Box Warning
hepatotoxicity
Country: United States
Black Box Warning
cardiotoxicity
Country: United States
Black Box Warning
teratogenicity
Country: United States
Black Box Warning
immune system toxicity
Country: United States

Activity Summary

IC50 12 meas. best 7.75
Ki 7 meas. best 7.64

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Neuromedin-K receptor
CHEMBL4429
 IC50 7.75 7.3683 18.0 6
Neuromedin-K receptor
CHEMBL4429
 Ki 7.64 7.632 23.0 5
Unchecked
CHEMBL612545
 Ki 7.6 7.6 25.0 1
Neuromedin-K receptor
CHEMBL3154
 Ki 6.66 6.66 219.0 1
Cytochrome P450 2C9
CHEMBL3397
 IC50 4.38 4.38 42000.0 1
Cytochrome P450 2C19
CHEMBL3622
 IC50 4.32 4.32 48000.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 4.16 4.16 70000.0 3
Cytochrome P450 3A4
CHEMBL340
 IC50 4.05 4.05 90000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 5592.0 ng.hr.mL-1 Rattus norvegicus
AUC 31641.0 ng.hr.mL-1 Rattus norvegicus
CL 1.5 min/ml/kg Rattus norvegicus
CL 3.17 min/ml/kg Macaca mulatta
CL 6.8 mL.min-1.kg-1 Rattus norvegicus
CL 13.5 mL.min-1.kg-1 Homo sapiens
CL 2.933 mL.min-1.kg-1 Rattus norvegicus
Cmax 4933.04 nM Rattus norvegicus
Cmax 10128.35 nM Rattus norvegicus
F 62.5 % Rattus norvegicus
F 107.0 % Macaca mulatta
F 113.0 % Rattus norvegicus
Fu 0.639 - Rattus norvegicus
Fu 0.532 - Macaca mulatta
Fu 0.525 - Rattus norvegicus
T1/2 4.65 hr Rattus norvegicus
T1/2 5.4 hr Macaca mulatta
T1/2 2.94 hr Rattus norvegicus
T1/2 3.72 hr Rattus norvegicus
Tmax 2.5 hr Rattus norvegicus
Tmax 1.5 hr Macaca mulatta
Tmax 1.83 hr Rattus norvegicus
Vd 0.751 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Neuromedin-K receptor IC50 = 18.0 nM 7.75 Aequorin Assay with Human NK-3 Receptor: Changes in intracellular calcium levels... -
Neuromedin-K receptor IC50 = 18.0 nM 7.75 Aequorin Assay with Human NK-3 Receptor: Changes in intracellular calcium levels... -
Neuromedin-K receptor IC50 = 18.0 nM 7.75 Functional Assay: Chinese Hamster Ovary recombinant cells expressing the human N... -
Neuromedin-K receptor IC50 = 19.95 nM 7.7 Antagonist activity against human recombinant NK3R expressed in CHO cells by aeq... 26191358
Neuromedin-K receptor Ki = 23.0 nM 7.64 Competitive Binding Assays: The affinity of compounds of the invention for the h... -
Neuromedin-K receptor Ki = 23.0 nM 7.64 Binding Competition Assay: Human NK-3: The ability of compounds of the invention... -
Neuromedin-K receptor Ki = 23.0 nM 7.64 Competitive Binding Assays NK-3 receptor: The affinity of compounds of the inven... -
Neuromedin-K receptor Ki = 23.0 nM 7.64 Competitive Binding Assay: The affinity of compounds of the invention for the hu... -
Unchecked Ki = 25.0 nM 7.6 Binding affinity to monkey NK3R 26191358
Neuromedin-K receptor Ki = 25.12 nM 7.6 Binding affinity to human recombinant NK3R by radioligand binding assay 26191358
Neuromedin-K receptor IC50 = 109.78 nM 6.96 Displacement of [3H]-SB-222200 from recombinant human NK3R expressed in CHO-K1 c... 37247507
Neuromedin-K receptor Ki = 219.0 nM 6.66 Binding affinity to rat NK3R 26191358
Neuromedin-K receptor IC50 = 500.83 nM 6.3 Antagonist activity at human NK3R expressed in HEK293T cells assessed as reducti... 37247507
Cytochrome P450 2C9 IC50 = 42000.0 nM 4.38 Inhibition of CYP2C9 (unknown origin) 26191358
Cytochrome P450 2C19 IC50 = 48000.0 nM 4.32 Inhibition of CYP2C19 (unknown origin) 26191358
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 70000.0 nM 4.16 hERG Inhibition Assay: The human ether-a-go-go related gene (hERG) encodes the i... -
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 70000.0 nM 4.16 hERG Inhibition Assay: The human ether-a-go-go related gene (hERG) encodes the i... -
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 70000.0 nM 4.16 Inhibition Assay: The hERG inhibition study aims at quantifying the in vitro eff... -
Cytochrome P450 3A4 IC50 = 90000.0 nM 4.05 Inhibition of CYP3A4 (unknown origin) 26191358

Literature References

PubMed DOI Target Context # Activities
37247507 10.1016/j.ejmech.2023.115486 ADMET 18
26191358 10.1021/acsmedchemlett.5b00117 Rattus norvegicus 10
26191358 10.1021/acsmedchemlett.5b00117 Rhesus monkey 9
26191358 10.1021/acsmedchemlett.5b00117 ADMET 7
26191358 10.1021/acsmedchemlett.5b00117 Plasma 4
26191358 10.1021/acsmedchemlett.5b00117 Caco-2 3
26191358 10.1021/acsmedchemlett.5b00117 Neuromedin-K receptor 3
26191358 10.1021/acsmedchemlett.5b00117 Brain 2
37247507 10.1016/j.ejmech.2023.115486 Neuromedin-K receptor 2
26191358 10.1021/acsmedchemlett.5b00117 Cytochrome P450 1A2 1
26191358 10.1021/acsmedchemlett.5b00117 Voltage-gated inwardly rectifying potassium channel KCNH2 1
26191358 10.1021/acsmedchemlett.5b00117 Cytochrome P450 2C19 1
26191358 10.1021/acsmedchemlett.5b00117 Cytochrome P450 2C9 1
26191358 10.1021/acsmedchemlett.5b00117 Cytochrome P450 3A4 1
26191358 10.1021/acsmedchemlett.5b00117 Cytochrome P450 2D6 1
26191358 10.1021/acsmedchemlett.5b00117 Unchecked 1
26191358 10.1021/acsmedchemlett.5b00117 Cynomolgus monkey 1
26191358 10.1021/acsmedchemlett.5b00117 Oryctolagus cuniculus 1
26191358 10.1021/acsmedchemlett.5b00117 Salmonella typhimurium 1
37247507 10.1016/j.ejmech.2023.115486 Voltage-gated inwardly rectifying potassium channel KCNH2 1

Data from ChEMBL 36 via Core Engine