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Compound Detail

CHEMBL1544

LIOTHYRONINE
💊 Approved Drug
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💊 Approved Drug
N[C@@H](Cc1cc(I)c(Oc2ccc(O)c(I)c2)c(I)c1)C(=O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1544
Name LIOTHYRONINE
Phase Approved
Structure Type MOL
InChI Key AUYYCJSJGJYCDS-LBPRGKRZSA-N
Therapeutic ✓ Yes

Known Names

3,5,3'-triiodothyronine, l- Cyronine Euthroid-0.5 Euthroid-1 Euthroid-2 Euthroid-3 Levothyroxine sodium related compound liothyronine Liothyronine Liotironina NSC-80203 Rathyronine, (s)- Thyrolar-0.25 +6 more
13
Targets
74
Activities
4
Assay Types
1
PK Parameters
20
Publications
18
Known Names
12
Indications
1
Mechanisms

Molecular Properties

651.0
MW (Da)
3.95
ALogP
4
HBA
3
HBD
92.8
PSA (Ų)
0.43
QED
1
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1956
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral Parenteral

Flags

Black Box Warning Natural Product
USAN Year 1963

Extended Properties

Molecular Formula C15H12I3NO4
MW 650.98
Aromatic Rings 2
Heavy Atoms 23
NP-Likeness 0.63

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Thyroid hormone receptor agonist AGONIST Thyroid hormone receptor ✓ ✓

Indications

Bipolar Disorder Depressive Disorder Depressive Disorder, Major Hypothyroidism Breast Neoplasms Euthyroid Sick Syndromes Shock, Septic Atrial Fibrillation Heart Failure Multiple Sclerosis, Chronic Progressive Multiple Sclerosis, Relapsing-Remitting Gliosarcoma

Activity Summary

EC50 33 meas. best 9.39
IC50 19 meas. best 10.47
Ki 13 meas. best 10.74
Kd 9 meas. best 10.24

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Ki 10.74 9.775 0.0 2
Unchecked
CHEMBL612545
 IC50 10.47 9.6167 0.0 3
Thyroid hormone receptor alpha
CHEMBL1860
 Kd 10.24 10.0575 0.1 4
Thyroid hormone receptor beta
CHEMBL1947
 Ki 10.1 9.162 0.1 5
Thyroid hormone receptor beta
CHEMBL1947
 Kd 10.09 10.0 0.1 4
Thyroid hormone receptor alpha
CHEMBL1860
 Ki 9.66 9.1 0.2 4
Thyroid hormone receptor alpha
CHEMBL1860
 IC50 9.62 9.2433 0.2 3
Thyroid hormone receptor beta
CHEMBL1947
 IC50 9.59 9.3275 0.3 4
Thyroid hormone receptor alpha
CHEMBL1860
 EC50 9.39 8.5986 0.4 14
Unchecked
CHEMBL612545
 EC50 9.3 8.1333 0.5 3
Thyroid hormone receptor beta
CHEMBL1947
 EC50 8.96 8.4036 1.1 11
Prothrombin
CHEMBL204
 EC50 8.92 8.6833 1.2 3
Thyroid hormone receptor beta
CHEMBL3917
 IC50 8.74 7.6 1.8 4
Adenosine receptor A1
CHEMBL226
 Ki 6.62 6.62 239.7 1
Adenosine receptor A1
CHEMBL226
 IC50 6.39 6.39 410.9 1
Peroxisome proliferator-activated receptor gamma
CHEMBL235
 Kd 6.15 6.15 710.0 1
Proliferating cell nuclear antigen
CHEMBL2346488
 IC50 5.44 5.44 3600.0 1
Peroxisome proliferator-activated receptor gamma
CHEMBL235
 EC50 5.24 5.24 5800.0 1
GABA-A receptor; anion channel
CHEMBL1907607
 EC50 5.16 5.16 7000.0 1
Bile salt export pump
CHEMBL6020
 IC50 4.95 4.95 11270.0 1
GABA-A receptor; anion channel
CHEMBL2093872
 IC50 4.64 4.64 23000.0 1
Solute carrier organic anion transporter family member 1C1
CHEMBL2073688
 Ki 4.62 4.62 24200.0 1
Solute carrier organic anion transporter family member 1A4
CHEMBL1781860
 IC50 4.3 4.3 50400.0 1

Pharmacokinetic Data

Parameter Value Units Species
Cmax 108.0 nM Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 0.018 nM 10.74 Displacement of [125I]Triiodothyronine from thyroid hormone receptor in Wistar r... 23403082
Unchecked IC50 = 0.034 nM 10.47 Displacement of [125I]Triiodothyronine from thyroid hormone receptor in Wistar r... 23403082
Thyroid hormone receptor alpha Kd = 0.058 nM 10.24 Displacement of [125I]T3 from human TRalpha receptor 17988877
Thyroid hormone receptor alpha Kd = 0.06 nM 10.22 Binding affinity of compound was determined against Thyroid hormone receptor alp... 12825953
Thyroid hormone receptor beta Ki = 0.08 nM 10.1 Inhibitory activity against [125I]T3 binding to human TRbeta1 receptor 12565933
Thyroid hormone receptor beta Kd = 0.081 nM 10.09 Displacement of [125I]T3 from human TRbeta receptor 17988877
Thyroid hormone receptor beta Kd = 0.087 nM 10.06 Binding affinity of compound was determined against thyroid hormone receptor bet... 12825953
Thyroid hormone receptor alpha Kd = 0.1 nM 10.0 Binding affinity against human Thyroid hormone receptor alpha-1 (hTRalpha1) usin... 12109914
Thyroid hormone receptor beta Kd = 0.1 nM 10.0 Binding affinity against human Thyroid hormone receptor beta 1 (hTRbeta1) using ... 12109914
Thyroid hormone receptor beta Kd = 0.14 nM 9.85 Binding affinity towards thyroid hormone receptor (hTR beta 1) 11597408
Thyroid hormone receptor alpha Kd = 0.17 nM 9.77 Binding affinity towards thyroid hormone receptor (hTR alpha 1) 11597408
Thyroid hormone receptor alpha Ki = 0.22 nM 9.66 Displacement of [125I]T3 from recombinant thyroid hormone receptor alpha express... 17878314
Thyroid hormone receptor alpha IC50 = 0.24 nM 9.62 Inhibitory concentration against cloned human thyroid hormone receptor alpha 1 16099653
Thyroid hormone receptor alpha IC50 = 0.24 nM 9.62 Binding affinity at human thyroid hormone receptor alpha 1 expressed in CHOK1 ce... 17543524
Thyroid hormone receptor beta IC50 = 0.257 nM 9.59 Inhibition of human thyroid hormone receptor beta 1 17524652
Thyroid hormone receptor beta IC50 = 0.26 nM 9.59 Binding affinity at human thyroid hormone receptor beta-1 expressed in CHOK1 cel... 17543524
Thyroid hormone receptor beta IC50 = 0.26 nM 9.59 Inhibitory concentration against cloned human thyroid hormone receptor beta 1 16099653
Thyroid hormone receptor alpha Ki = 0.33 nM 9.48 Displacement of [125I]3,5,3'-triiodo-L-thyronine from His-tagged human recombina... 18975928
Unchecked IC50 = 0.38 nM 9.42 Inhibition of rat thyroid hormone receptor 20875743
Thyroid hormone receptor alpha EC50 = 0.41 nM 9.39 Agonist activity at human thyroid hormone receptor alpha expressed in HEK293 cel... 25305688

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 346
17878314 10.1073/pnas.0702759104 Rattus norvegicus 39
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
- 10.6019/CHEMBL4689842 HEK-293T 10
24290064 10.1016/j.bmc.2013.11.001 Rattus norvegicus 10
31931337 10.1016/j.ejmech.2019.112006 ADMET 9
17878314 10.1073/pnas.0702759104 Mus musculus 8
- 10.6019/CHEMBL4689842 Fibroblast 8
- 10.6019/CHEMBL4689842 U2OS 8
35507418 10.1021/acs.jmedchem.2c00144 Unchecked 8
36799411 10.1021/acs.jmedchem.2c01669 ADMET 5
7861417 10.1021/jm00004a015 Rattus norvegicus 5
24712661 10.1021/jm4019299 Mus musculus 5
17543524 10.1016/j.bmcl.2007.05.049 Rattus norvegicus 5
- 10.6019/CHEMBL4808148 Histone deacetylase 6 4
7861417 10.1021/jm00004a015 Thyroid hormone receptor beta 4
1738147 10.1021/jm00081a017 Rattus norvegicus 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
- 10.6019/CHEMBL5724696 TERT-RPE1 4
10937719 10.1016/s0960-894x(00)00309-7 Rattus norvegicus 4

Data from ChEMBL 36 via Core Engine