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Compound Detail

CHEMBL1829174

FASIGLIFAM
🧪 Phase III
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🧪 Phase III
Cc1cc(OCCCS(C)(=O)=O)cc(C)c1-c1cccc(COc2ccc3c(c2)OC[C@H]3CC(=O)O)c1

Basic Information

ChEMBL ID CHEMBL1829174
Name FASIGLIFAM
Phase Phase III
Structure Type MOL
InChI Key BZCALJIHZVNMGJ-HSZRJFAPSA-N

Known Names

Fasiglifam Fasiglifam hemihydrate Fasiglifam hydrate TAK-875 Tak-875 anhydrous TAK875
9
Targets
50
Activities
4
Assay Types
29
PK Parameters
20
Publications
6
Known Names
2
Indications
1
Mechanisms

Molecular Properties

524.6
MW (Da)
5.31
ALogP
6
HBA
1
HBD
99.1
PSA (Ų)
0.34
QED
2
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product Chemical Probe
USAN Year 2013

Extended Properties

Molecular Formula C29H32O7S
MW 524.64
Aromatic Rings 3
Heavy Atoms 37
NP-Likeness -0.01

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Free fatty acid receptor 1 positive allosteric modulator POSITIVE ALLOSTERIC MODULATOR Free fatty acid receptor 1

Indications

Diabetes Mellitus Diabetes Mellitus, Type 2

Activity Summary

EC50 41 meas. best 9.46
IC50 5 meas. best 5.7
Kd 2 meas. best 8.35
Ki 2 meas. best 8.11

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Free fatty acid receptor 1
CHEMBL4422
EC50 9.46 7.5289 0.3 36
Free fatty acid receptor 1
CHEMBL4422
Kd 8.35 8.135 4.5 2
Free fatty acid receptor 1
CHEMBL4422
Ki 8.11 7.825 7.7 2
Free fatty acid receptor 1
CHEMBL5411
EC50 8.07 8.07 8.6 1
GPR40-Galpha16
CHEMBL5482994
EC50 7.45 7.45 35.8 1
Free fatty acid receptor 1
CHEMBL1795180
EC50 7.44 6.4733 36.0 3
Hepatic sodium/bile acid cotransporter
CHEMBL5287
IC50 5.7 5.7 2000.0 1
Solute carrier organic anion transporter family member 1B1
CHEMBL1697668
IC50 5.64 5.64 2280.0 1
ATP-binding cassette sub-family C member 2
CHEMBL5748
IC50 5.62 5.62 2410.0 1
Solute carrier organic anion transporter family member 1B3
CHEMBL1743121
IC50 4.95 4.95 11200.0 1
Hepatitis B virus
CHEMBL613497
IC50 4.52 4.52 30000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 6514706.71 ng.hr.mL-1 Mus musculus
AUC 10640076.94 ng.hr.mL-1 Mus musculus
AUC 79520.0 ng.hr.mL-1 Rattus norvegicus
AUC 2066000.0 ng.hr.mL-1 Mus musculus
AUC 137326.0 ng.hr.mL-1 Rattus norvegicus
AUC 1064230.0 ng.hr.mL-1 Rattus norvegicus
AUC 255.0 ng.hr.mL-1 Rattus norvegicus
AUC 100300.0 ng.hr.mL-1 Homo sapiens
AUC 7372.0 ng.hr.mL-1 Mus musculus
CL 5.25 uL.min-1.(10^6cells)-1 Homo sapiens
CL 5.5 mL.min-1.g-1 Homo sapiens
CL 10.0 uL.min-1.(10^6cells)-1 Rattus norvegicus
CL 0.6177 mL.min-1.kg-1 Rattus norvegicus
CL 0.4177 mL.min-1.kg-1 Rattus norvegicus
Cmax 12313.21 nM Rattus norvegicus
Cmax 37034.92 nM Rattus norvegicus
Cmax 166571.36 nM Rattus norvegicus
Cmax 75.86 nM Rattus norvegicus
Cmax 10102.17 nM Homo sapiens
Cmax 3490.01 nM Rattus norvegicus
F 36.0 % Rattus norvegicus
T1/2 28.0 hr Homo sapiens
T1/2 4.29 hr Rattus norvegicus
T1/2 3.94 hr Rattus norvegicus
T1/2 4.32 hr Rattus norvegicus
T1/2 2.9 hr Rattus norvegicus
t1/2 - - Rattus norvegicus
Tmax 3.5 hr Rattus norvegicus
Tmax 2.0 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Free fatty acid receptor 1 EC50 = 0.35 nM 9.46 Agonist activity at human recombinant full length GPR40 overexpressed in human H... 27749056
Free fatty acid receptor 1 EC50 = 1.9 nM 8.72 Agonist activity at human GPR40 expressed in HEK293 cells measured after 18 to 2... 27994752
Free fatty acid receptor 1 Kd = 4.5 nM 8.35 Displacement of [3H]-(S)-2-(6-((2',6'-dimethyl-4'-(3-(methylsulfonyl)propoxy)bip... 27749056
Free fatty acid receptor 1 EC50 = 7.7 nM 8.11 Agonist activity at FFAR1 (unknown origin) 36518697
Free fatty acid receptor 1 Ki = 7.7 nM 8.11 Displacement of [3H]-TAK-875 from human recombinant full-length GPR40 expressed ... 27749056
Free fatty acid receptor 1 EC50 = 8.6 nM 8.07 Agonist activity at Prolink-tagged mouse GPR40 fused with EA-tagged beta-arresti... 27749056
Free fatty acid receptor 1 EC50 = 9.333 nM 8.03 Agonist activity at human C-terminal eYFP-tagged FFA1 receptor expressed in HEK-... 27074625
Free fatty acid receptor 1 EC50 = 12.0 nM 7.92 Agonist activity at human recombinant full-length Prolink-tagged GPR40 fused wit... 27749056
Free fatty acid receptor 1 Kd = 11.9 nM 7.92 Binding affinity to human GPR40 expressed in CHO cells by LC-MS analysis 32900194
Free fatty acid receptor 1 EC50 = 14.13 nM 7.85 Agonist activity at human FFA1 receptor expressed in human 1321N1 cells assessed... 21854074
Free fatty acid receptor 1 EC50 = 14.0 nM 7.85 Agonist activity at human GPR40 expressed in CHO cells after 24 hrs by NFAT-luci... 29259758
Free fatty acid receptor 1 EC50 = 14.0 nM 7.85 Agonist activity at FFA1 (unknown origin) 30296685
Free fatty acid receptor 1 EC50 = 14.0 nM 7.85 Agonist activity at FFA1 (unknown origin) 36343410
Free fatty acid receptor 1 EC50 = 16.0 nM 7.8 Agonist activity at human GP40 receptor expressed in CHO cells assessed as incre... 22490067
Free fatty acid receptor 1 EC50 = 19.0 nM 7.72 Agonist activity at human recombinant FFA1 stably expressed in CHO cells assesse... 38039791
Free fatty acid receptor 1 EC50 = 27.0 nM 7.57 Agonist activity at human GPR40 expressed in CHO cells assessed as increase in i... 28277660
Free fatty acid receptor 1 EC50 = 27.5 nM 7.56 Agonist activity at human GPR40 expressed in CHO cells by FLIPR calcium flux ass... 27054485
Free fatty acid receptor 1 Ki = 28.84 nM 7.54 Displacement of 3-(2-Fluoro-4-((2'-methyl-4'-(2-(2-((7-nitrobenzo[c][1,2,5]-oxad... 27074625
Free fatty acid receptor 1 EC50 = 29.6 nM 7.53 Agonist activity at human FFA1 receptor expressed in CHO cells assessed as incre... 26482570
Free fatty acid receptor 1 EC50 = 29.5 nM 7.53 Agonist activity at human GPR40 expressed in HEK293 cells by Fluo4-AM dye based ... 36933395

Literature References

PubMed DOI Target Context # Activities
27749056 10.1021/acs.jmedchem.6b00892 Free fatty acid receptor 1 16
- 10.6019/CHEMBL5058564 Fibroblast 8
30212763 10.1016/j.ejmech.2018.08.075 Free fatty acid receptor 1 7
30392954 10.1016/j.bmc.2018.10.019 Rattus norvegicus 7
28277660 10.1021/acs.jmedchem.6b01357 Free fatty acid receptor 1 6
29366647 10.1016/j.bmcl.2018.01.013 Rattus norvegicus 6
- 10.6019/CHEMBL5209801 Apelin receptor 5
27074625 10.1021/acs.jmedchem.6b00202 Free fatty acid receptor 1 5
- 10.6019/CHEMBL5209801 Type-1 angiotensin II receptor 5
26945112 10.1016/j.ejmech.2016.02.040 Mus musculus 5
- 10.6019/CHEMBL5209801 Sphingosine 1-phosphate receptor 1 5
- 10.6019/CHEMBL5209801 C5a anaphylatoxin chemotactic receptor 1 5
- 10.6019/CHEMBL5209801 Beta-2 adrenergic receptor 5
30655940 10.1021/acsmedchemlett.8b00444 Free fatty acid receptor 1 5
- 10.6019/CHEMBL5209801 CX3C chemokine receptor 1 5
- 10.6019/CHEMBL5209801 Alpha-2A adrenergic receptor 5
- 10.6019/CHEMBL5209801 Glucose-dependent insulinotropic receptor 5
- 10.6019/CHEMBL5209801 N-formyl peptide receptor 2 5
- 10.6019/CHEMBL5209801 Adhesion G-protein coupled receptor F1 5
- 10.6019/CHEMBL5209801 Glucagon-like peptide 1 receptor 5

Data from ChEMBL 36 via Core Engine