General
Preferred name
METHYLENE BLUE
Synonyms
METHYLTHIONINIUM CHLORIDE ()
CI-52015 ()
Tetramethylthionine chloride ()
Basic Blue 9 ()
Basic Blue 9, Tetramethylthionine chloride, methylthioninium chloride, CI-52015 ()
METHYLENE BLUE ANHYDROUS ()
Trx-0014 ()
Cloruro de metiltioninio ()
NSC-617593 ()
Trx0014 ()
Lumeblue (previously known as methylthioninium chloride cosmo) ()
Methylthioninium chloride proveblue ()
Methylthioninium Chloride ()
Urolene Blue ()
NSC-215213 ()
Chlorure de methylthioninium ()
Methylene blue ()
P&D ID
PD008913
CAS
105504-42-5
61-73-4
Tags
available
drug
prodrug
nuisance
Drug indication
colorectal neoplasm
Acquired methemoglobinemia
Drug Status
approved
investigational
Max Phase
4.0
First approval
2011
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
INDICATION Indicated for the treatment of pediatric and adult patients with acquired methemoglobinemia. ; ; Other clinical applications of methylene blue include improvement of hypotension associated with various clinical states, an antiseptic in urinary tract infections, treatment of hypoxia and hyperdynamic circulation in cirrhosis of liver and severe hepatopulmonary syndrome, and treatment of ifofosamide induced neurotoxicity.
METABOLISM Following distribution into tissues, rapidly reduced to leukomethylene blue (leucomethylthioninium chloride).; Metabolism to leucomethylene blue may be less efficient in neonates than in older individuals.
MOA * Main mechanism of action involves inhibition of nitric oxide synthase and guanylate cyclase. ; * In Alzheimers Disease: a mechanistic study found that methylene blue oxidizes cysteine sulfhydryl groups on tau to keep tau monomeric. One preclinical treatment study in tauopathy mice reported anti-inflammatory or neuroprotective effects mediated by the Nrf2/antioxidant response element (ARE); another reported insoluble tau reduction and a learning and memory benefit when given early. ; * In Methemoglobinemia: Methylene Blue acts by reacting within RBC to form leukomethylene blue, which is a reducing agent of oxidized hemoglobin converting the ferric ion (fe+++) back to its oxygen-carrying ferrous state(fe++). ; * As antimalarial agent: Methylene Blue, a specific inhibitor of P.falciparum glutathione reductase has the potential to reverse CQ resistance and it prevents the polymerization of haem into haemozoin similar to 4-amino-quinoline antimalarials. ; * For ifosfamide induced neurotoxicity: Methylene blue functions as an alternate electron acceptor. It acts to reverse the NADH inhibition caused by gluconeogenesis in the liver while blocking the transformation of chloroethylamine into chloroacetaldehyde. In addition, it inhibits various amine oxidase activities, which also prevents the formation of chloroacetaldehyde. ;
DESCRIPTION Methylene blue is an oxidation-reduction agent. Main mechanism of action involves inhibition of nitric oxide synthase and guanylate cyclase. It is used for the treatment of pediatric and adult patients with acquired methemoglobinemia. (Enamine Bioactive Compounds)
DESCRIPTION Methylene Blue (Tetramethylthionine chloride) (IC50 of 1.9 μM) inhibits tau filament formation. And it inhibits soluble guanylyl cyclase. It is also used as a dye in chromoendoscopy. (TargetMol Bioactive Compound Library)
Cell lines
6
Organisms
2
Compound Sets
15
A Collection of Useful Nuisance Compounds (CONS) for Interrogation of Bioassay Integrity
AdooQ Bioactive Compound Library
A16612
ChEMBL Approved Drugs
CHEMBL405110
ChEMBL Drugs
CHEMBL405110
CZ-OPENSCREEN Bioactive Library
DrugBank
DB09241
DrugBank Approved Drugs
DB09241
DrugMAP
DMJAPE7
DrugMAP Approved Drugs
DMJAPE7
DrugMatrix
Enamine Bioactive Compounds
EBC-26786
EU-OPENSCREEN Bioactive Compound Library
EOS102012
Nuisance compounds in cellular assays
Selleckchem Bioactive Compound Library
methylene-blue
TargetMol Bioactive Compound Library
T6888
External IDs
26
Properties
(calculated by RDKit )
Molecular Weight
319.09
Hydrogen Bond Acceptors
3
Hydrogen Bond Donors
0
Rotatable Bonds
1
Ring Count
3
Aromatic Ring Count
1
cLogP
-0.5
TPSA
19.14
Fraction CSP3
0.25
Chiral centers
0.0
Largest ring
6.0
QED
0.44
Structural alerts
4
Singlet oxygen sensitization
Nuisance compounds
aggregator (Aggregator Advisor)
Aggregators
aggregator (ZINC)
Aggregators
AlphaScreen FH
Nuisance compounds
Related compounds
Custom attributes
(extracted from source data)
Pathway
Cytoskeletal Signaling
GPCR/G protein
Immunology/Inflammation
Microbiology/virology
Neuroscience
Nuisance MOA
Singlet oxygen sensitization
Targets
Monoamine oxidase A Microtubule-associated protein tau
Target
Dyes,Guanylate Cyclase,Microtubule Associated
Guanylate Cyclase
Monoamine Oxidase
NO Synthase
Parasite
Tau aggregation
Source data