Compound Detail

CHEMBL1624

LEVOTHYROXINE

💊 Approved Drug

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💊 Approved Drug

N[C@@H](Cc1cc(I)c(Oc2cc(I)c(O)c(I)c2)c(I)c1)C(=O)O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL1624
Name	LEVOTHYROXINE
Phase	Approved
Structure Type	MOL
InChI Key	XUIIKFGFIJCVMT-LBPRGKRZSA-N
Therapeutic	✓ Yes

Known Names

L-thyroxine Levothyroxin Levothyroxine NSC-36397 SK&F 1-6528 Synthetic levothyroxine Thyroxine Thyroxine, l-

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

776.9

MW (Da)

4.56

ALogP

HBA

HBD

92.8

PSA (Å²)

0.39

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1982
Availability	Prescription
Chirality	Single Enantiomer

Routes of Administration

Oral Parenteral

Flags

Black Box Warning Natural Product

USAN Year

1963

Extended Properties

Molecular Formula	C15H11I4NO4
MW	776.87
Aromatic Rings	2
Heavy Atoms	24
NP-Likeness	0.60

Indications

Congenital Hypothyroidism Hypothyroidism Lipid Metabolism Disorders Bipolar Disorder Graves Disease Diabetes Mellitus Infections Pregnancy

Activity Summary

IC50 10 meas. best 5.66

EC50 6 meas. best 7.72

Kd 2 meas. best 6.4

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Thyroid hormone receptor alpha CHEMBL1860	EC50	7.72	7.72	19.0	1
Thyroid hormone receptor beta CHEMBL1947	EC50	6.62	6.62	240.0	1
Peroxisome proliferator-activated receptor gamma CHEMBL235	Kd	6.4	6.4	400.0	1
Retinoic acid receptor RXR-alpha CHEMBL2061	Kd	6.03	6.03	930.0	1
Transthyretin CHEMBL3194	IC50	5.66	5.49	2187.8	4
UDP-glucuronosyltransferase 1A1 CHEMBL1287617	IC50	5.31	5.28	4900.0	2
Bile acid receptor CHEMBL2047	IC50	5.11	5.11	7860.0	1
Solute carrier organic anion transporter family member 4C1 CHEMBL2073690	IC50	5.1	5.1	8000.0	1
Unchecked CHEMBL612545	IC50	4.98	4.98	10500.0	1
Nuclear receptor subfamily 1 group I member 2 CHEMBL3401	EC50	4.95	4.475	11200.0	2
Peroxisome proliferator-activated receptor gamma CHEMBL235	EC50	4.92	4.92	12000.0	1
Retinoic acid receptor RXR-alpha CHEMBL2061	EC50	4.81	4.81	15400.0	1
Malate dehydrogenase, mitochondrial CHEMBL5917	IC50	4.36	4.36	43600.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Thyroid hormone receptor alpha	EC50	=	19.0	nM	7.72	Agonist activity at THRalpha (unknown origin) incubated for 14 to 16 hrs by dual...	32356658
Thyroid hormone receptor beta	EC50	=	240.0	nM	6.62	Agonist activity at THRbeta (unknown origin) incubated for 14 to 16 hrs by dual ...	32356658
Peroxisome proliferator-activated receptor gamma	Kd	=	400.0	nM	6.4	Binding affinity to recombinant PPARgamma LBD (unknown origin) by isothermal tit...	32356658
Retinoic acid receptor RXR-alpha	Kd	=	930.0	nM	6.03	Binding affinity to RXRalpha LBD (unknown origin) by isothermal titration calori...	32356658
Transthyretin	IC50	=	2200.0	nM	5.66	Stabilization of recombinant human wild type TTR expressed in Escherichia coli B...	27020050
Transthyretin	IC50	=	2187.76	nM	5.66	Stabilization of recombinant human wild type TTR expressed in Escherichia coli B...	27020050
Transthyretin	IC50	=	2200.0	nM	5.66	In vitro evaluation of inhibitory activity against WT-TTR: In vitro evaluation o...	-
UDP-glucuronosyltransferase 1A1	IC50	=	4900.0	nM	5.31	Inhibition of human recombinant UGT1A1 expressed in HEK293 cells assessed as red...	21030469
UDP-glucuronosyltransferase 1A1	IC50	=	5600.0	nM	5.25	Inhibition of human recombinant UGT1A1 expressed in HEK293 cells assessed as red...	21030469
Bile acid receptor	IC50	=	7860.0	nM	5.11	Antagonist activity at human GTS-tagged FXR after 20 mins by TR-FRET assay	23688559
Solute carrier organic anion transporter family member 4C1	IC50	=	8000.0	nM	5.1	TP_TRANSPORTER: inhibition of Triiodothyronine uptake in OATP4C1-expressing MDCK...	14993604
Transthyretin	IC50	=	10500.0	nM	4.98	Inhibition of TTR mediated fibrillogenesis assessed as acid-induced protein aggr...	19651509
Unchecked	IC50	=	10500.0	nM	4.98	Inhibition of human recombinant TTR Y78F mutant-mediated fibrillogenesis after 3...	24147937
Nuclear receptor subfamily 1 group I member 2	EC50	=	11200.0	nM	4.95	Competitive binding affinity to human PXR LBD (111 to 434) by TR-FRET assay	20966043
Peroxisome proliferator-activated receptor gamma	EC50	=	12000.0	nM	4.92	Agonist activity at recombinant human pFA-CMV fused PPARgamma expressed in HEK29...	32356658
Retinoic acid receptor RXR-alpha	EC50	=	15400.0	nM	4.81	Agonist activity at recombinant human pFA-CMV fused RXRalpha LBD expressed in HE...	32356658
Malate dehydrogenase, mitochondrial	IC50	=	43600.0	nM	4.36	Inhibition of MDH2 (unknown origin)	28991459
Nuclear receptor subfamily 1 group I member 2	EC50	=	100000.0	nM	4.0	Activation of human PXR expressed in human HepG2 (DPX-2) cells assessed as induc...	20966043

Literature References

PubMed	DOI	Target Context	# Activities
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
32356658	10.1021/acs.jmedchem.9b02150	Peroxisome proliferator-activated receptor gamma	13
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
37930268	10.1021/acs.jmedchem.3c01026	ADMET	10
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
20966043	10.1124/dmd.110.035105	Nuclear receptor subfamily 1 group I member 2	6
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
32356658	10.1021/acs.jmedchem.9b02150	Retinoic acid receptor RXR-alpha	4
19651509	10.1016/j.bmcl.2009.03.004	Transthyretin	3
37468498	10.1038/s41467-023-40064-9	Nuclear receptor subfamily 1 group I member 2	3
7381861	10.1021/jm00179a024	Unchecked	3
20014752	10.1021/tx900326k	Hepatotoxicity	3
12871948	10.1074/jbc.m300909200	Monocarboxylate transporter 8	3
32356658	10.1021/acs.jmedchem.9b02150	ADMET	3
11561088	-	Solute carrier organic anion transporter family member 1A3	3
27020050	10.1016/j.ejmech.2016.02.074	Transthyretin	3
21030469	10.1124/dmd.110.035030	UDP-glucuronosyltransferase 1A1	2
818381	10.1021/jm00227a004	Rattus norvegicus	2
23688559	10.1016/j.bmc.2013.04.069	Nuclear receptor subfamily 1 group I member 2	2
3009810	10.1021/jm00155a010	Transthyretin	2

Data from ChEMBL 36 via Core Engine