Identification

Summary

Methylthioninium is the phenothiazine cation in methylene blue commonly used to treat methemoglobinemia.

Generic Name
Methylthioninium
DrugBank Accession Number
DB08167
Background

Not Available

Type
Small Molecule
Groups
Experimental, Investigational
Structure
Weight
Average: 284.399
Monoisotopic: 284.122143281
Chemical Formula
C16H18N3S
Synonyms
  • Methylene blue cation

Pharmacology

Indication

Not Available

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Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UAcetylcholinesteraseNot AvailableHumans
UBacterial regulatory protein, TetR familyNot AvailableCorynebacterium glutamicum (strain ATCC 13032 / DSM 20300 / JCM 1318 / LMG 3730 / NCIMB 10025)
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AlfentanilThe risk or severity of serotonin syndrome can be increased when Alfentanil is combined with Methylthioninium.
AlmotriptanThe risk or severity of serotonin syndrome can be increased when Almotriptan is combined with Methylthioninium.
AmantadineThe risk or severity of serotonin syndrome can be increased when Amantadine is combined with Methylthioninium.
AmitriptylineThe risk or severity of serotonin syndrome can be increased when Amitriptyline is combined with Methylthioninium.
AmitriptylinoxideThe risk or severity of serotonin syndrome can be increased when Methylthioninium is combined with Amitriptylinoxide.
AmoxapineThe risk or severity of serotonin syndrome can be increased when Amoxapine is combined with Methylthioninium.
AmphetamineThe risk or severity of serotonin syndrome can be increased when Amphetamine is combined with Methylthioninium.
ApomorphineThe risk or severity of serotonin syndrome can be increased when Apomorphine is combined with Methylthioninium.
AripiprazoleThe risk or severity of serotonin syndrome can be increased when Aripiprazole is combined with Methylthioninium.
Aripiprazole lauroxilThe risk or severity of serotonin syndrome can be increased when Methylthioninium is combined with Aripiprazole lauroxil.
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Food Interactions
Not Available

Products

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Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as benzothiazines. These are organic compounds containing a benzene fused to a thiazine ring (a six-membered ring with four carbon atoms, one nitrogen atom and one sulfur atom).
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzothiazines
Sub Class
Not Available
Direct Parent
Benzothiazines
Alternative Parents
Dialkylarylamines / Benzenoids / Secondary ketimines / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives / Organic cations
Substituents
Amine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Benzothiazine / Dialkylarylamine / Heteroaromatic compound / Hydrocarbon derivative / Organic cation / Organic nitrogen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organic cation (CHEBI:43830) / a dye (CPD0-1625)
Affected organisms
Not Available

Chemical Identifiers

UNII
ZMZ79891ZH
CAS number
7060-82-4
InChI Key
RBTBFTRPCNLSDE-UHFFFAOYSA-N
InChI
InChI=1S/C16H18N3S/c1-18(2)11-5-7-13-15(9-11)20-16-10-12(19(3)4)6-8-14(16)17-13/h5-10H,1-4H3/q+1
IUPAC Name
3,7-bis(dimethylamino)-5lambda4-phenothiazin-5-ylium
SMILES
CN(C)C1=CC2=[S+]C3=CC(=CC=C3N=C2C=C1)N(C)C

References

General References
Not Available
PubChem Compound
4139
PubChem Substance
99444638
ChemSpider
3996
BindingDB
50434369
RxNav
1546414
ChEBI
43830
ChEMBL
CHEMBL191083
ZINC
ZINC000012414057
PDBe Ligand
MBT
PDB Entries
2yve / 3zyx / 4xyp / 5acm / 5dlp / 5e4t

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentUrinary Tract Infection1
3CompletedDiagnosticBreast Cancer1
3CompletedTreatmentDysuria1
2CompletedDiagnosticBreast Cancer1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, solutionIntravenous5 MG/ML
Injection, solutionIntravenous
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.376 mg/mLALOGPS
logP2.8ALOGPS
logP2.61ChemAxon
logS-2.9ALOGPS
pKa (Strongest Basic)2.44ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area19.37 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity86.98 m3·mol-1ChemAxon
Polarizability33.11 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.6918
Blood Brain Barrier+0.9365
Caco-2 permeable+0.6774
P-glycoprotein substrateNon-substrate0.6069
P-glycoprotein inhibitor INon-inhibitor0.7772
P-glycoprotein inhibitor IINon-inhibitor0.76
Renal organic cation transporterNon-inhibitor0.8129
CYP450 2C9 substrateNon-substrate0.7603
CYP450 2D6 substrateNon-substrate0.667
CYP450 3A4 substrateNon-substrate0.5198
CYP450 1A2 substrateInhibitor0.797
CYP450 2C9 inhibitorNon-inhibitor0.8764
CYP450 2D6 inhibitorInhibitor0.5982
CYP450 2C19 inhibitorNon-inhibitor0.5845
CYP450 3A4 inhibitorNon-inhibitor0.6834
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7705
Ames testAMES toxic0.9107
CarcinogenicityNon-carcinogens0.8503
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5787 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9782
hERG inhibition (predictor II)Inhibitor0.6063
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-0090000000-562c1559e4cf7d40a13c
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-0090000000-05faeb4f27f1a84c54a2
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-0090000000-77b5d8e28d6335764623
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-0090000000-c0e7ada3d60537137629
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-0090000000-d93a9ae23e6746b4eb6f
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-014i-0090000000-66627aab76bec0253023

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Serine hydrolase activity
Specific Function
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name
ACHE
Uniprot ID
P22303
Uniprot Name
Acetylcholinesterase
Molecular Weight
67795.525 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Kind
Protein
Organism
Corynebacterium glutamicum (strain ATCC 13032 / DSM 20300 / JCM 1318 / LMG 3730 / NCIMB 10025)
Pharmacological action
Unknown
General Function
Dna binding
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
Q8NMG3
Uniprot Name
Transcriptional regulator
Molecular Weight
20258.72 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at September 15, 2010 21:29 / Updated at June 19, 2021 00:26