General
Preferred name
Methylthioninium
Synonyms
METHYLENE BLUE CHLORIDE HYDRATE ()
METHYLENE BLUE ()
METHYLTHIONINIUM CHLORIDE ()
CI-52015 ()
Tetramethylthionine chloride ()
Basic Blue 9 ()
Methylthionine chloride ()
METHYLENE BLUE CATION ()
3,7-BIS(DIMETHYLAMINO)PHENOTHIAZIN-5-IUM ()
Chemosensitizers ()
Methylene Blue trihydrate ()
Methylene blue (trihydrate) ()
C.I. Basic Blue 9 trihydrate ()
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 ()
DNDI1417128 ()
CI 52015 ()
Provayblue ()
Basic blue 9 trihydrate ()
Lowacryl blue 9 ()
C.i. basic blue 9 ()
Methylenium ceruleum ()
C.I. 52015 ()
NSC-759135 ()
Methylene blue trihydrate ()
Methylene Blue ()
Methylene blue ()
Methylene Blue (hydrate) ()
P&D ID
PD004682
CAS
105504-42-5
61-73-4
26283-09-0
1001913-24-1
7220-79-3
7060-82-4
122965-43-9
Tags
available
prodrug
drug
nuisance
drug candidate
Approved by
FDA
Drug indication
Discovery agent
colorectal neoplasm
Acquired methemoglobinemia
abscess
Drug Status
approved
experimental
investigational
Max Phase
4.0
First approval
2011
2016
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 trihydrate (C.I. Basic Blue 9 trihydrate) is a guanylyl cyclase (sGC), monoamine oxidase A (MAO-A) and NO synthase (NOS) inhibitor. Methylene blue trihydrate is a vasopressor and is often used as a dye in several medical procedures. Methylene blue trihydrate has antinociception, antimalarial, antidepressant and anxiolytic activity effects. Methylene Blue trihydrate has the potential for methemoglobinemias, neurodegenerative disorders and ifosfamide-induced encephalopathytreatment[1][2][3].
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)
DESCRIPTION Methylene Blue trihydrate (Basic blue 9) is a compound consisting of dark green crystals or crystalline powder, having a bronze-like luster. Solutions in water or alcohol have a deep blue color. Methylene Blue trihydrate is used as a bacteriologic stain and as an indicator. It inhibits soluble guanylyl cyclase and has been used to treat cyanide poisoning and to lower levels of methemoglobin. It also inhibits tau filament formation (IC50: 1.9μM). (TargetMol Bioactive Compound Library)
Cell lines
7
Organisms
4
Compound Sets
27
A Collection of Useful Nuisance Compounds (CONS) for Interrogation of Bioassay Integrity
AdooQ Bioactive Compound Library
A16612
Cayman Chemical Bioactives
26095
ChEMBL Approved Drugs
CHEMBL405110
CHEMBL191083
CHEMBL550495
ChEMBL Drugs
CHEMBL405110
CHEMBL191083
CHEMBL550495
CZ-OPENSCREEN Bioactive Library
Drug Repurposing Hub
DrugBank
DB09241
DB08167
DrugBank Approved Drugs
DB09241
DrugCentral
1763
DrugCentral Approved Drugs
1763
DrugMAP
DMJAPE7
DMBIRC6
DMYSG9J
DrugMAP Approved Drugs
DMJAPE7
DrugMatrix
Enamine Bioactive Compounds
EBC-26786
EU-OPENSCREEN Bioactive Compound Library
EOS102012
LSP-MoA library (Laboratory of Systems Pharmacology)
CHEMBL191083
MedChem Express Bioactive Compound Library
HY-B1359
NCATS Inxight Approved Drugs
ZMZ79891ZH
Novartis Chemogenetic Library (NIBR MoA Box)
NPC Screening Collection
Nuisance compounds in cellular assays
ReFrame library
Selleckchem Bioactive Compound Library
methylene-blue
TargetMol Bioactive Compound Library
T6888
T0006
The Spectrum Collection
ZINC Tool Compounds
ZINC000012414057
External IDs
96
Properties
(calculated by RDKit )
Molecular Weight
284.12
Hydrogen Bond Acceptors
3
Hydrogen Bond Donors
0
Rotatable Bonds
2
Ring Count
3
Aromatic Ring Count
3
cLogP
3.86
TPSA
19.37
Fraction CSP3
0.25
Chiral centers
0.0
Largest ring
6.0
QED
0.53
Structural alerts
4
aggregator (Aggregator Advisor)
Aggregators
aggregator (ZINC)
Aggregators
AlphaScreen FH
Nuisance compounds
Singlet oxygen sensitization
Nuisance compounds
Related compounds
Custom attributes
(extracted from source data)
Pathway
Cytoskeletal Signaling
GPCR/G protein
Immunology/Inflammation
Microbiology/virology
Neuroscience
Anti-infection
Neuronal Signaling
MOA
Microtubule Associated inhibitor
Nitric Oxide Production Inhibitors
Tau Aggregation Inhibitors
guanylyl cyclase inhibitor, nitric oxide production inhibitor
Member status
member
Indication
methemoglobinemia
Target
AChE
Guanylate Cyclase
Monoamine Oxidase
NO Synthase
Parasite
Dyes,Guanylate Cyclase,Microtubule Associated
Tau aggregation
Nuisance MOA
Singlet oxygen sensitization
Targets
Monoamine oxidase A Microtubule-associated protein tau
Source data