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Compound Detail

CHEMBL2103837

TAFAMIDIS
💊 Approved Drug
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💊 Approved Drug
O=C(O)c1ccc2nc(-c3cc(Cl)cc(Cl)c3)oc2c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2103837
Name TAFAMIDIS
Phase Approved
Structure Type MOL
InChI Key TXEIIPDJKFWEEC-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

FX-1005 FX-1006 FX1006 Tafamidis Vyndamax
3
Targets
34
Activities
4
Assay Types
18
PK Parameters
20
Publications
5
Known Names
4
Indications
1
Mechanisms

Molecular Properties

308.1
MW (Da)
4.50
ALogP
3
HBA
1
HBD
63.3
PSA (Ų)
0.76
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2011
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Natural Product First in Class
USAN Stem -amidis
USAN Year 2009

Extended Properties

Molecular Formula C14H7Cl2NO3
MW 308.12
Aromatic Rings 3
Heavy Atoms 20
NP-Likeness -1.27

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Transthyretin stabiliser STABILISER Transthyretin ✓ ✓

Indications

Amyloidosis Amyloidosis, Familial Cardiomyopathies Amyloid Neuropathies, Familial

ATC Classification

N07XX08
tafamidis
Level 1: NERVOUS SYSTEM
Level 2: OTHER NERVOUS SYSTEM DRUGS

Activity Summary

Kd 16 meas. best 8.52
IC50 12 meas. best 6.39
EC50 5 meas. best 8.57
Ki 1 meas. best 5.51

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Transthyretin
CHEMBL3194
 EC50 8.57 7.63 2.7 4
Transthyretin
CHEMBL3194
 Kd 8.52 6.9479 3.0 14
Transthyretin
CHEMBL3194
 IC50 6.39 5.5573 410.0 11
Unchecked
CHEMBL612545
 IC50 6.01 6.01 981.0 1
Albumin
CHEMBL3253
 Kd 5.64 5.62 2300.0 2
Transthyretin
CHEMBL3194
 Ki 5.51 5.51 3100.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 4334.0 ng.hr.mL-1 Rattus norvegicus
AUC 1714.0 ng.hr.mL-1 Rattus norvegicus
AUC 956.0 ng.hr.mL-1 Rattus norvegicus
AUC 2363.0 ng.hr.mL-1 Rattus norvegicus
AUC 1500.0 ng.hr.mL-1 Rattus norvegicus
CL 38.7 mL.min-1.kg-1 Rattus norvegicus
CL 0.3833 mL.min-1.kg-1 Rattus norvegicus
CL 0.09934 mL.min-1.kg-1 Rattus norvegicus
Cmax 20000.0 nM Homo sapiens
Cmax 1742.83 nM Rattus norvegicus
Cmax 529.01 nM Rattus norvegicus
Cmax 1684.41 nM Rattus norvegicus
F 55.8 % Rattus norvegicus
F 63.5 % Rattus norvegicus
Fu 0.0051 - Rattus norvegicus
T1/2 12.0 hr Rattus norvegicus
Tmax 8.0 hr Rattus norvegicus
Tmax 4.0 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Transthyretin EC50 = 2.7 nM 8.57 Inhibition of TTR V30M mutant (unknown origin) 36155354
Transthyretin EC50 = 2.7 nM 8.57 Inhibition of TTR V122I mutant (unknown origin) 36155354
Transthyretin EC50 = 2.7 nM 8.57 Inhibition of wild type TTR (unknown origin) 36155354
Transthyretin Kd = 3.0 nM 8.52 Binding affinity to wild type TTR (unknown origin) assessed as Kd1 by isothermal... 32914975
Transthyretin Kd = 4.4 nM 8.36 Binding affinity to transthyretin (unknown origin) by ITC method 30133284
Transthyretin Kd = 9.3 nM 8.03 Binding affinity to recombinant human wild type TTR expressed in Escherichia col... 27020050
Transthyretin Kd = 9.9 nM 8.0 Binding affinity to first binding site of wild type TTR (unknown origin) assesse... 36306808
Transthyretin Kd = 138.0 nM 6.86 Binding affinity to TTR V30M mutant (unknown origin) assessed as dissociation co... 38670538
Transthyretin Kd = 200.0 nM 6.7 Binding affinity to TTR V30M mutant (unknown origin) by isothermal titration cal... 34547896
Transthyretin Kd = 260.0 nM 6.58 Binding affinity to N-terminal hexa-histidine tagged TTR V30M mutant (unknown or... 37910439
Transthyretin Kd = 260.0 nM 6.58 Binding affinity to second binding site of wild type TTR (unknown origin) assess... 36306808
Transthyretin Kd = 278.0 nM 6.56 Binding affinity to wild type TTR (unknown origin) assessed as Kd2 by isothermal... 32914975
Transthyretin Kd = 278.0 nM 6.56 Binding affinity to wild type TTR (unknown origin) assessed as equilibrium disso... 28920684
Transthyretin Kd = 274.0 nM 6.56 Binding affinity to recombinant human wild type TTR expressed in Escherichia col... 27020050
Transthyretin Kd = 370.0 nM 6.43 Competitive binding affinity to human wild type TTR expressed in Escherichia col... 28920684
Transthyretin IC50 = 410.0 nM 6.39 Binding affinity to human plasma TTR tetramer assessed as displacement of diclof... 34138572
Unchecked IC50 = 981.0 nM 6.01 Disruption of retional-induced bacterially expressed MBP-tagged RBP4-TTR (unknow... 34138572
Transthyretin Kd = 1050.0 nM 5.98 Stabilization of wild type human transthyretin expressed in Escherichia coli BL2... 32124607
Transthyretin IC50 = 1550.0 nM 5.81 Inhibition of wild type TTR (unknown origin) assessed as inhibition of acid-medi... 27541261
Transthyretin IC50 = 1620.0 nM 5.79 Inhibition of TTR V30M mutant (unknown origin) assessed as inhibition of acid-me... 27541261

Literature References

PubMed DOI Target Context # Activities
31393717 10.1021/acs.jmedchem.9b01037 Transthyretin 37
30133284 10.1021/acs.jmedchem.8b00817 Transthyretin 18
34225167 10.1016/j.bmc.2021.116292 ADMET 15
34547896 10.1021/acs.jmedchem.1c00823 Transthyretin 11
38670538 10.1021/acs.jmedchem.3c02286 ADMET 8
36306808 10.1021/acs.jmedchem.2c01195 Transthyretin 8
27020050 10.1016/j.ejmech.2016.02.074 Transthyretin 7
37910439 10.1021/acs.jmedchem.3c01698 Transthyretin 7
27541261 10.1016/j.ejmech.2016.08.003 Transthyretin 7
36749109 10.1021/acs.jmedchem.2c01926 Transthyretin 7
28920684 10.1021/acs.jmedchem.7b00952 Transthyretin 6
33062181 10.1021/acsmedchemlett.9b00688 Unchecked 6
38670538 10.1021/acs.jmedchem.3c02286 Transthyretin 5
34890995 10.1016/j.bmc.2021.116550 Transthyretin 5
30133284 10.1021/acs.jmedchem.8b00817 Albumin 4
34138572 10.1021/acs.jmedchem.1c00099 Transthyretin 4
32124607 10.1021/acs.jmedchem.9b01970 Transthyretin 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
36155354 10.1016/j.ejmech.2022.114742 Transthyretin 3
- 10.6019/CHEMBL4808148 Histone deacetylase 6 3

Data from ChEMBL 36 via Core Engine