Methylthioninium
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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
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Methaemoglobinaemia •••••••••••• •••••••••• •••••••• - Contraindications & Blackbox Warnings
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism AAcetylcholinesterase inhibitorHumans UTranscriptional regulator 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. View sample adverse effects data in our new Data Library!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. - 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
- 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
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data4 Completed Treatment Urinary Tract Infection 1 somestatus stop reason just information to hide 3 Completed Diagnostic Breast Cancer 1 somestatus stop reason just information to hide 3 Completed Treatment Dysuria 1 somestatus stop reason just information to hide 2 Completed Diagnostic Breast Cancer 1 somestatus stop reason just information to hide
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
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 162.54115 predictedDeepCCS 1.0 (2019) [M+H]+ 164.89914 predictedDeepCCS 1.0 (2019) [M+Na]+ 171.42911 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsAcetylcholinesterase
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Hydrolyzes rapidly the acetylcholine neurotransmitter released into the synaptic cleft allowing to terminate the signal transduction at the neuromuscular junction. Role in neuronal apoptosis
- Specific Function
- acetylcholine binding
- 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]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
2. DetailsTranscriptional regulator
- Kind
- Protein
- Organism
- Corynebacterium glutamicum (strain ATCC 13032 / DSM 20300 / JCM 1318 / LMG 3730 / NCIMB 10025)
- Pharmacological action
- Unknown
- General Function
- Not Available
- Specific Function
- DNA binding
- 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 August 26, 2024 19:22