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
Structure for Methylthioninium (DB08167)
- Weight
- Average: 284.399
Monoisotopic: 284.122143281 - Chemical Formula
- C16H18N3S
- Synonyms
- Methylene blue cation
Pharmacology
- Indication
Not Available
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- Contraindications & Blackbox Warnings
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Not Available
- Mechanism of action
Target Actions Organism UAcetylcholinesterase Not Available Humans UBacterial regulatory protein, TetR family Not Available Corynebacterium 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAlfentanil The risk or severity of serotonin syndrome can be increased when Alfentanil is combined with Methylthioninium. Almotriptan The risk or severity of serotonin syndrome can be increased when Almotriptan is combined with Methylthioninium. Amantadine The risk or severity of serotonin syndrome can be increased when Amantadine is combined with Methylthioninium. Amitriptyline The risk or severity of serotonin syndrome can be increased when Amitriptyline is combined with Methylthioninium. Amitriptylinoxide The risk or severity of serotonin syndrome can be increased when Methylthioninium is combined with Amitriptylinoxide. Amoxapine The risk or severity of serotonin syndrome can be increased when Amoxapine is combined with Methylthioninium. Amphetamine The risk or severity of serotonin syndrome can be increased when Amphetamine is combined with Methylthioninium. Apomorphine The risk or severity of serotonin syndrome can be increased when Apomorphine is combined with Methylthioninium. Aripiprazole The risk or severity of serotonin syndrome can be increased when Aripiprazole is combined with Methylthioninium. Aripiprazole lauroxil The risk or severity of serotonin syndrome can be increased when Methylthioninium is combined with Aripiprazole lauroxil. 
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- 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
- External Links
- PubChem Compound
- 4139
- PubChem Substance
- 99444638
- ChemSpider
- 3996
- BindingDB
- 50434369
- 1546414
- ChEBI
- 43830
- ChEMBL
- CHEMBL191083
- ZINC
- ZINC000012414057
- PDBe Ligand
- MBT
- PDB Entries
- 2yve / 3zyx / 4xyp / 5acm / 5dlp / 5e4t
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Urinary Tract Infection 1 3 Completed Diagnostic Breast Cancer 1 3 Completed Treatment Dysuria 1 2 Completed Diagnostic Breast Cancer 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, solution Intravenous 5 MG/ML Injection, solution Intravenous - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.376 mg/mL ALOGPS logP 2.8 ALOGPS logP 2.61 Chemaxon logS -2.9 ALOGPS pKa (Strongest Basic) 2.44 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 19.37 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 86.98 m3·mol-1 Chemaxon Polarizability 33.11 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.6918 Blood Brain Barrier + 0.9365 Caco-2 permeable + 0.6774 P-glycoprotein substrate Non-substrate 0.6069 P-glycoprotein inhibitor I Non-inhibitor 0.7772 P-glycoprotein inhibitor II Non-inhibitor 0.76 Renal organic cation transporter Non-inhibitor 0.8129 CYP450 2C9 substrate Non-substrate 0.7603 CYP450 2D6 substrate Non-substrate 0.667 CYP450 3A4 substrate Non-substrate 0.5198 CYP450 1A2 substrate Inhibitor 0.797 CYP450 2C9 inhibitor Non-inhibitor 0.8764 CYP450 2D6 inhibitor Inhibitor 0.5982 CYP450 2C19 inhibitor Non-inhibitor 0.5845 CYP450 3A4 inhibitor Non-inhibitor 0.6834 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7705 Ames test AMES toxic 0.9107 Carcinogenicity Non-carcinogens 0.8503 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.5787 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9782 hERG inhibition (predictor II) Inhibitor 0.6063
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
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
- 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
- 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