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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL550495
CHEMBL550495
Compound Name METHYLENE BLUE
ChEMBL Synonyms METHYLENE BLUE | METHYLTHIONINIUM CHLORIDE | METHYLTHIONINE CHLORIDE | PROVAYBLUE | UROLENE BLUE | METHYLTHIONINE HYDROCHLORIDE
Max Phase 4 (Approved)
Trade Names PROVAYBLUE | UROLENE BLUE
Molecular Formula C16H24ClN3O3S

Additional synonyms for CHEMBL550495 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES O.O.O.[Cl-].CN(C)c1ccc2N=C3C=CC(=[N+](C)C)C=C3Sc2c1
Standard InChI InChI=1S/C16H18N3S.ClH.3H2O/c1-18(2)11-5-7-13-15(9-11)20-16- ...
Download InChI
Standard InChI Key XQAXGZLFSSPBMK-UHFFFAOYSA-M

Sources

  • British National Formulary
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL550495

Molecule Features

CHEMBL550495 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:N Parenteral:Y Topical:N Black Box:N Availability Type:Prescription-only

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Bipolar DisorderD001714EFO:0000289bipolar disorder3ClinicalTrials
MalariaD008288EFO:0001068malaria2ClinicalTrials
Stress Disorders, Post-TraumaticD013313EFO:0001358post-traumatic stress disorder2ClinicalTrials
Wounds and InjuriesD014947EFO:0000546injury2ClinicalTrials
Malaria, FalciparumD016778EFO:0007444Plasmodium falciparum malaria2ClinicalTrials
SepsisD018805HP:0100806sepsis1ClinicalTrials
Tooth DiseasesD014076EFO:1001216tooth disease2ClinicalTrials
DysuriaD053159EFO:0003901dysuria3ClinicalTrials
AbscessD000038EFO:0003030abscess1ClinicalTrials
Glucosephosphate Dehydrogenase DeficiencyD005955EFO:0007287glucosephosphate dehydrogenase deficiency1ClinicalTrials
Shock, SepticD012772EFO:0006834septic shock3ClinicalTrials

Clinical Data

ClinicalTrials.gov METHYLENE BLUE
The Cochrane Collaboration METHYLENE BLUE

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL550495. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL2487 Beta amyloid A4 protein Homo sapiens 1.000
CHEMBL5567 Luciferin 4-monooxygenase Photinus pyralis 1.000
CHEMBL5247 Serine/threonine-protein kinase ILK-1 Homo sapiens 1.000
CHEMBL1293224 Microtubule-associated protein tau Homo sapiens 0.676
CHEMBL4224 Dual specificty protein kinase CLK1 Homo sapiens 0.334
CHEMBL1952 Thymidylate synthase Homo sapiens 0.283



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL2487 Beta amyloid A4 protein Homo sapiens 1.000
CHEMBL5150 Luciferin 4-monooxygenase Photuris pennsylvanica 1.000
CHEMBL5567 Luciferin 4-monooxygenase Photinus pyralis 0.999
CHEMBL5247 Serine/threonine-protein kinase ILK-1 Homo sapiens 0.992
CHEMBL6101 Signal transducer and activator of transcription 1-alpha/beta Homo sapiens 0.773
CHEMBL1293277 Niemann-Pick C1 protein Homo sapiens 0.742
CHEMBL3467 P-glycoprotein 1 Mus musculus 0.360
CHEMBL1293224 Microtubule-associated protein tau Homo sapiens 0.358
CHEMBL5869 Heat shock factor protein 1 Homo sapiens 0.304
CHEMBL6194 Pteridine reductase 1 Leishmania major 0.223

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
284.4 284.1216 2.5 1 19.14 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
3 0 0 3 0 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- 4.88 -.84 -.84 1 20 0.51

Structural Alerts

There are 6 structural alerts for CHEMBL550495. To view alerts please click here.

Compound Cross References

ATC V - VARIOUS
V04 - DIAGNOSTIC AGENTS
V04C - OTHER DIAGNOSTIC AGENTS
V04CG - Tests for gastric secretion
V04CG05 - methylthioninium chloride

V - VARIOUS
V03 - ALL OTHER THERAPEUTIC PRODUCTS
V03A - ALL OTHER THERAPEUTIC PRODUCTS
V03AB - Antidotes
V03AB17 - methylthioninium chloride

ChemSpider ChemSpider:XQAXGZLFSSPBMK-UHFFFAOYSA-M
DailyMed methylene blue
PubChem SID: 144209723 SID: 17388909

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL550495



ACToR 7220-79-3
eMolecules 711545 14089957
EPA CompTox Dashboard DTXSID0025600
FDA SRS T42P99266K
MolPort MolPort-004-963-308 MolPort-039-063-118
PubChem 104827
PubChem: Thomson Pharma 163528845
SureChEMBL SCHEMBL1207311

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/XQAXGZLFSSPBMK-UHFFFAOYSA-M spacer
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