Methylthioninium

Identification

Name
Methylthioninium
Accession Number
DB08167
Type
Small Molecule
Groups
Experimental, Investigational
Description
Not Available
Structure
Thumb
Synonyms
  • Methylene blue cation
Categories
Not Available
UNII
ZMZ79891ZH
CAS number
7060-82-4
Weight
Average: 284.399
Monoisotopic: 284.122143281
Chemical Formula
C16H18N3S
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)-5λ⁴-phenothiazin-5-ylium
SMILES
CN(C)C1=CC2=[S+]C3=CC(=CC=C3N=C2C=C1)N(C)C

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAcetylcholinesteraseNot AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
4139
PubChem Substance
99444638
ChemSpider
3996
BindingDB
50434369
ChEBI
43830
ChEMBL
CHEMBL191083
HET
MBT
PDB Entries
2yve / 3zyx / 4xyp / 5acm / 5dlp / 5e4t

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2Unknown StatusDiagnosticCancer, Breast1
4Not Yet RecruitingTreatmentUrinary Tract Infections (UTIs)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
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

Taxonomy

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
Benzothiazine / Dialkylarylamine / Tertiary aliphatic/aromatic amine / Benzenoid / Heteroaromatic compound / Secondary ketimine / Tertiary amine / Azacycle / Organic nitrogen compound / Organopnictogen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organic cation (CHEBI:43830) / a dye (CPD0-1625)

Targets

Kind
Protein
Organism
Human
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. [PubMed:10592235]
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. [PubMed:10592235]

Drug created on September 15, 2010 15:29 / Updated on December 01, 2017 16:01