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Compound Detail

CHEMBL405110

METHYLENE BLUE ANHYDROUS
💊 Approved Drug
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💊 Approved Drug
CN(C)c1ccc2nc3ccc(N(C)C)cc3[s+]c2c1.[Cl-]
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL405110
Name METHYLENE BLUE ANHYDROUS
Phase Approved
Structure Type MOL
InChI Key CXKWCBBOMKCUKX-UHFFFAOYSA-M
Therapeutic ✓ Yes
Parent Compound CHEMBL191083
Active Moiety CHEMBL549963

Known Names

Chlorure de methylthioninium Cloruro de metiltioninio Lumeblue (previously known as methylthioninium chloride cosmo) Methylene blue anhydrous Methylthioninium chloride Methylthioninium chloride proveblue NSC-215213 NSC-617593 Trx-0014 Trx0014 Urolene blue
23
Targets
73
Activities
3
Assay Types
2
PK Parameters
20
Publications
11
Known Names
4
Indications
1
Mechanisms

Molecular Properties

284.4
MW (Da)
2.50
ALogP
3
HBA
0
HBD
19.1
PSA (Ų)
0.51
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2011
Availability Unknown
Chirality Achiral

Flags

Natural Product Prodrug

Extended Properties

Molecular Formula C16H18ClN3S
MW 319.86
Aromatic Rings 1
Heavy Atoms 20
NP-Likeness -1.55

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Soluble guanylate cyclase inhibitor INHIBITOR Soluble guanylate cyclase ✓ ✓

Indications

Colonoscopy Colorectal Neoplasms Methemoglobinemia Alzheimer Disease

ATC Classification

V03AB17
methylthioninium chloride
Level 1: VARIOUS
Level 2: ALL OTHER THERAPEUTIC PRODUCTS
V04CG05
methylthioninium chloride
Level 1: VARIOUS
Level 2: DIAGNOSTIC AGENTS

Activity Summary

IC50 50 meas. best 8.92
EC50 20 meas. best 8.19
Kd 3 meas. best 6.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium vivax
CHEMBL613013
 IC50 8.92 8.92 1.2 1
Plasmodium falciparum
CHEMBL364
 IC50 8.8 7.1506 1.6 16
Plasmodium falciparum
CHEMBL364
 EC50 8.19 7.515 6.5 4
Unchecked
CHEMBL612545
 EC50 7.37 5.8217 43.0 6
Amine oxidase [flavin-containing] A
CHEMBL1951
 IC50 7.16 7.16 70.0 1
Lymphocyte
CHEMBL5314318
 EC50 7.06 7.06 88.0 1
Microtubule-associated protein tau
CHEMBL1293224
 EC50 6.89 6.56 130.0 2
Calf thymus DNA
CHEMBL612514
 Kd 6.7 6.7 200.0 1
quadruplex DNA
CHEMBL3832742
 Kd 6.7 6.7 200.0 1
Amyloid-beta precursor protein
CHEMBL2487
 IC50 6.3 6.3 500.0 1
Unchecked
CHEMBL612545
 IC50 6.21 4.9925 610.0 12
Peroxisome proliferator-activated receptor gamma/Nuclear receptor coactivator 2
CHEMBL2095163
 EC50 6.13 6.13 742.0 1
Peroxisome proliferator-activated receptor gamma/Nuclear receptor coactivator 1
CHEMBL2095162
 EC50 6.02 6.02 958.0 1
FM3A
CHEMBL614297
 EC50 5.96 5.96 1100.0 1
Microtubule-associated protein tau
CHEMBL1293224
 IC50 5.85 5.3875 1400.0 4
Peroxisome proliferator-activated receptor gamma/Nuclear receptor coactivator 3
CHEMBL2095161
 EC50 5.51 5.51 3056.0 1
B16-F10
CHEMBL612656
 IC50 5.26 5.205 5480.0 2
HepG2
CHEMBL395
 IC50 5.22 5.22 6000.0 1
Glutathione reductase
CHEMBL5061
 IC50 5.19 5.19 6400.0 1
HT-29
CHEMBL384
 IC50 5.04 5.04 9200.0 1
MCF7
CHEMBL387
 IC50 4.98 4.905 10580.0 2
Apoptotic protease-activating factor 1
CHEMBL1795093
 IC50 4.81 4.81 15500.0 1
Glutathione reductase, mitochondrial
CHEMBL2755
 IC50 4.8 4.795 16000.0 2
Unchecked
CHEMBL612545
 Kd 4.55 4.55 28200.0 1
Thioredoxin reductase 1, cytoplasmic
CHEMBL1927
 IC50 4.52 4.52 30000.0 1
Protein RecA
CHEMBL1741171
 EC50 4.52 4.52 30000.0 1
Cruzipain
CHEMBL3563
 IC50 4.26 4.165 55000.0 2

Pharmacokinetic Data

Parameter Value Units Species
T1/2 5.0 hr Rattus norvegicus
T1/2 18.3 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium vivax IC50 = 1.2 nM 8.92 Antiplasmodial activity against Plasmodium vivax assessed as parasitic growth in... 37236020
Plasmodium falciparum IC50 = 1.6 nM 8.8 Antiplasmodial activity against Plasmodium falciparum FCR-3 assessed as plasmodi... 37236020
Plasmodium falciparum IC50 = 5.4 nM 8.27 Antiparasitic activity against chloroquine-sensitive Plasmodium falciparum by [3... 18260613
Plasmodium falciparum EC50 = 6.5 nM 8.19 Antiplasmodial activity after 42 hrs against chloroquine-resistant Plasmodium fa... 17967916
Plasmodium falciparum IC50 = 8.0 nM 8.1 Antimalarial activity against Plasmodium falciparum K1 infected in RBC assessed ... 23837878
Plasmodium falciparum EC50 = 17.0 nM 7.77 In vitro antimalarial activity against chloroquine-sensitive Plasmodium falcipar... 11855978
Plasmodium falciparum IC50 = 20.0 nM 7.7 Antimalarial activity against Plasmodium falciparum 3D7 infected in RBC assessed... 23837878
Plasmodium falciparum IC50 = 30.0 nM 7.52 Gametocytocidal activity against Plasmodium falciparum 3D7 elo1-pfs16-CBG99 late... 29571157
Plasmodium falciparum IC50 = 30.0 nM 7.52 Antimalarial activity against trophozoite stage of Plasmodium falciparum 3D7 inf... 23837878
Unchecked EC50 = 43.0 nM 7.37 Inhibition of erastin-induced cell death in FRDA patient-derived fibroblast asse... 33214825
Amine oxidase [flavin-containing] A IC50 = 70.0 nM 7.16 Inhibition of recombinant human MAO-A expressed in baculovirus infected BTI inse... 28456030
Plasmodium falciparum EC50 = 74.7 nM 7.13 Antiplasmodial activity against synchronous gametocyte early stage of Plasmodium... 32959656
Unchecked EC50 = 75.0 nM 7.12 Cytoprotective activity against BSO-treated human Friedreich's ataxia fibroblast... 29773347
Lymphocyte EC50 = 88.0 nM 7.06 Anti-ferroptotic activity in FRDA patient-derived Lymphocyte assessed as reducti... 33214825
Plasmodium falciparum IC50 = 95.0 nM 7.02 Antimalarial activity against Plasmodium falciparum NF54 early gametocytes trans... 31938463
Plasmodium falciparum EC50 = 107.2 nM 6.97 Antiplasmodial activity against synchronous gametocyte late stage of Plasmodium ... 32959656
Microtubule-associated protein tau EC50 = 130.0 nM 6.89 Inhibition of tau-tau binding (unknown origin) assessed as increase in dissolved... 30884327
Plasmodium falciparum IC50 = 140.0 nM 6.85 Anti-plasmodial activity against chloroquine-sensitive Plasmodium falciparum NF5... 28094524
Plasmodium falciparum IC50 = 140.0 nM 6.85 Antiplasmodial activity against immature stage gametocytes Plasmodium falciparum... 38628794
Plasmodium falciparum IC50 = 140.0 nM 6.85 Antiplasmodial activity against asexual stage (IV/V) Plasmodium falciparum NF54 ... 33844521

Literature References

PubMed DOI Target Context # Activities
29773347 10.1016/j.bmc.2018.05.005 Unchecked 26
17967916 10.1128/aac.00773-07 Unchecked 20
21875807 10.1016/j.bmcl.2011.08.015 CHO 12
29519734 10.1016/j.bmcl.2018.02.041 Escherichia coli 11
28927904 10.1016/j.bmc.2017.08.021 Unchecked 10
30288223 10.1039/C8MD00274F GM16216 9
30288223 10.1039/C8MD00274F GM15850 9
29519734 10.1016/j.bmcl.2018.02.041 Acinetobacter baumannii 9
19506059 10.1128/aac.00371-09 Salmonella enterica 8
32505848 10.1016/j.ejmech.2020.112341 Staphylococcus aureus 7
20426472 10.1021/jm100254w No relevant target 7
23837878 10.1021/jm400656s Plasmodium falciparum 6
18207412 10.1016/j.bmc.2007.12.052 L929 6
32828429 10.1016/j.bmc.2020.115667 Microtubule-associated protein tau 6
32505848 10.1016/j.ejmech.2020.112341 Unchecked 5
33214825 10.1021/acsmedchemlett.0c00293 Unchecked 5
21803586 10.1016/j.bmc.2011.07.016 Unchecked 5
17967916 10.1128/aac.00773-07 Glutathione reductase, mitochondrial 4
17967916 10.1128/aac.00773-07 Thioredoxin reductase 1, cytoplasmic 4
17967916 10.1128/aac.00773-07 Dihydrolipoyl dehydrogenase, mitochondrial 4

Data from ChEMBL 36 via Core Engine