methylthioninium chloride Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
1763 61-73-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • methylthioninium benzalkonium chloride hydrate
  • methylthioninium chloride hydrate
  • methylenum coeruleum
  • methylthioninium chloratum
  • methylene blue
  • methylthioninium chloride
  • aizen methylene blue
  • proveblue
A compound consisting of dark green crystals or crystalline powder, having a bronze-like luster. Solutions in water or alcohol have a deep blue color. Methylene blue is used as a bacteriologic stain and as an indicator. It inhibits GUANYLATE CYCLASE, and has been used to treat cyanide poisoning and to lower levels of METHEMOGLOBIN.
  • Molecular weight: 284.40
  • Formula: C16H18N3S
  • CLOGP: 0.95
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 0
  • TPSA: 19.37
  • ALOGS: -2.93
  • ROTB: 2

Drug dosage:

None

ADMET properties:

None

Approvals:

DateAgencyCompanyOrphan
None FDA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Serotonin syndrome 730.99 37.34 173 1717 24047 46660125
Drug interaction 188.98 37.34 111 1779 202983 46481189
Hyperreflexia 139.04 37.34 34 1856 5220 46678952
Clonus 136.96 37.34 32 1858 4048 46680124
Encephalopathy 107.34 37.34 43 1847 33546 46650626
Agitation 95.71 37.34 46 1844 55369 46628803
Mydriasis 77.32 37.34 25 1865 10528 46673644
Dyskinesia 68.69 37.34 30 1860 28895 46655277
Confusional state 65.49 37.34 53 1837 159839 46524333
Nystagmus 60.74 37.34 18 1872 5681 46678491
Muscle twitching 44.08 37.34 18 1872 14654 46669518
Body temperature increased 43.91 37.34 21 1869 24840 46659332
Hypertonia 42.80 37.34 13 1877 4453 46679719
Vasoplegia syndrome 38.91 37.34 9 1881 1083 46683089
Coma 38.87 37.34 26 1864 58323 46625849

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Serotonin syndrome 686.58 61.27 155 1066 17736 29933521
Drug interaction 210.86 61.27 118 1103 199450 29751807
Vasoplegia syndrome 75.88 61.27 16 1205 1255 29950002
Overdose 62.15 61.27 40 1181 84297 29866960

Pharmacologic Action:

SourceCodeDescription
ATC V03AB17 VARIOUS
ALL OTHER THERAPEUTIC PRODUCTS
ALL OTHER THERAPEUTIC PRODUCTS
Antidotes
ATC V04CG05 VARIOUS
DIAGNOSTIC AGENTS
OTHER DIAGNOSTIC AGENTS
Tests for gastric secretion
MeSH PA D004791 Enzyme Inhibitors
CHEBI has role CHEBI:22586 antioxidants
CHEBI has role CHEBI:33281 antibiotics
CHEBI has role CHEBI:35208 physical tracer
CHEBI has role CHEBI:35469 thymoanaleptics
CHEBI has role CHEBI:37733 bche inhibitor
CHEBI has role CHEBI:38068 antimalarials
CHEBI has role CHEBI:38623 monoamine oxidase inhibitors
CHEBI has role CHEBI:50407 indicateur acide-base
CHEBI has role CHEBI:51217 fluorochromes
CHEBI has role CHEBI:63726 neuroprotective agents
CHEBI has role CHEBI:77178 histological stain
CHEBI has role CHEBI:77307 cardioprotective agents
CHEBI has role CHEBI:78678 gtp diphosphate-lyase (cyclizing; 3',5'-cyclic-gmp-forming) inhibitor

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Methemoglobinemia indication 38959009 DOID:10783
Gastritis contraindication 4556007 DOID:4029
Hypocalcemia contraindication 5291005
Severe chronic ulcerative colitis contraindication 14311001
Disorder of autonomic nervous system contraindication 15241006
Cirrhosis of liver contraindication 19943007 DOID:5082
Hyperphosphatemia contraindication 20165001 DOID:0050459
Glaucoma contraindication 23986001 DOID:1686
Toxic megacolon contraindication 28536002 DOID:1770
Atony of colon contraindication 29479008
Hyperthyroidism contraindication 34486009 DOID:7998
Hypertensive disorder contraindication 38341003 DOID:10763
Hypernatremia contraindication 39355002
Hypovolemic shock contraindication 39419009
Gastrointestinal ulcer contraindication 40845000
Body fluid retention contraindication 43498006
Conduction disorder of the heart contraindication 44808001
Achalasia of esophagus contraindication 45564002 DOID:9164
Chronic heart failure contraindication 48447003
Disorder of cardiovascular system contraindication 49601007 DOID:1287
Vitamin K deficiency contraindication 52675005 DOID:11249
Nasal polyp contraindication 52756005
Paralytic ileus contraindication 55525008 DOID:8442
Acute nephropathy contraindication 58574008
Hepatic failure contraindication 59927004
Blood coagulation disorder contraindication 64779008 DOID:1247
Diabetes mellitus contraindication 73211009 DOID:9351
Factor II deficiency contraindication 73975000
Gastrointestinal hemorrhage contraindication 74474003
Thrombotic thrombocytopenic purpura contraindication 78129009 DOID:10772
Hiatal hernia contraindication 84089009 DOID:12642
Kidney disease contraindication 90708001 DOID:557
Thyrotoxicosis contraindication 90739004 DOID:7997
Hemophilia contraindication 90935002
Myasthenia gravis contraindication 91637004 DOID:437
Anemia due to enzyme deficiency contraindication 111577008
Deficiency of glucose-6-phosphate dehydrogenase contraindication 124134002 DOID:2862
Liver function tests abnormal contraindication 166603001
Gastroesophageal reflux disease contraindication 235595009 DOID:8534
Disease of liver contraindication 235856003 DOID:409
Bladder outflow obstruction contraindication 236645006
Pyloric obstruction contraindication 244815007
Benign prostatic hyperplasia contraindication 266569009
Edema contraindication 267038008
Anemia contraindication 271737000 DOID:2355
Pregnancy, function contraindication 289908002
Cardiovascular event risk contraindication 395112001
Breastfeeding (mother) contraindication 413712001
Disorder of coronary artery contraindication 414024009
Fever greater than 100.4 Fahrenheit contraindication 426000000
Severe dehydration contraindication 450316000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 4.42 Basic
pKa2 3.81 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
50MG/10ML (5MG/ML) PROVAYBLUE PROVEPHARM SAS N204630 April 8, 2016 RX SOLUTION INTRAVENOUS April 8, 2023 FOR TREATMENT OF PEDIATRIC AND ADULT PATIENTS WITH ACQUIRED METHEMOGLOBINEMIA.

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Glutathione reductase, mitochondrial Enzyme IC50 4.80 CHEMBL
Microtubule-associated protein tau Structural IC50 5.72 CHEMBL
Thioredoxin reductase 1, cytoplasmic Enzyme IC50 4.52 CHEMBL
Amine oxidase [flavin-containing] A Enzyme IC50 7.15 CHEMBL
Amine oxidase [flavin-containing] B Enzyme IC50 5.36 CHEMBL
Amyloid beta A4 protein Unclassified IC50 6.26 CHEMBL
iron Inorganic material OTHER SCIENTIFIC LITERATURE SCIENTIFIC LITERATURE
Cruzipain Enzyme IC50 4.26 CHEMBL
Glutathione reductase Enzyme IC50 5.19 CHEMBL

External reference:

IDSource
4018579 VUID
N0000146895 NUI
D02312 KEGG_DRUG
7220-79-3 SECONDARY_CAS_RN
4018579 VANDF
C0025746 UMLSCUI
CHEBI:6872 CHEBI
MBT PDB_CHEM_ID
CHEMBL550495 ChEMBL_ID
CHEMBL191083 ChEMBL_ID
CHEMBL405110 ChEMBL_ID
D008751 MESH_DESCRIPTOR_UI
DB09241 DRUGBANK_ID
T42P99266K UNII
6099 PUBCHEM_CID
6878 RXNORM
1036 MMSL
5090 MMSL
d01128 MMSL
001094 NDDF
002616 NDDF
002877 NDDF
354064008 SNOMEDCT_US
6725000 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
URELLE HUMAN PRESCRIPTION DRUG LABEL 5 0037-6321 TABLET 10.80 mg ORAL Unapproved drug other 12 sections
URIBEL HUMAN PRESCRIPTION DRUG LABEL 5 0076-0111 CAPSULE 10 mg ORAL unapproved drug other 20 sections
Hyophen HUMAN PRESCRIPTION DRUG LABEL 5 0076-0901 TABLET 10.80 mg ORAL unapproved drug other 19 sections
Phosphasal HUMAN PRESCRIPTION DRUG LABEL 5 0076-0902 TABLET 10.80 mg ORAL unapproved drug other 20 sections
Ustell HUMAN PRESCRIPTION DRUG LABEL 5 0076-0903 CAPSULE 10 mg ORAL unapproved drug other 20 sections
Utira-C HUMAN PRESCRIPTION DRUG LABEL 5 0178-0513 TABLET 10.80 mg ORAL unapproved drug other 12 sections
URIBEL HUMAN PRESCRIPTION DRUG LABEL 5 0178-0740 CAPSULE 10 mg ORAL unapproved drug other 21 sections
UROGESIC BLUE HUMAN PRESCRIPTION DRUG LABEL 4 0485-0151 TABLET, COATED 10.80 mg ORAL unapproved drug other 18 sections
UROGESIC BLUE HUMAN PRESCRIPTION DRUG LABEL 4 0485-0151 TABLET, COATED 10.80 mg ORAL unapproved drug other 18 sections
PROVAYBLUE HUMAN PRESCRIPTION DRUG LABEL 1 0517-0125 INJECTION 5 mg INTRAVENOUS NDA 29 sections
PROVAYBLUE HUMAN PRESCRIPTION DRUG LABEL 1 0517-0374 INJECTION 5 mg INTRAVENOUS NDA 29 sections
UroAv-81 HUMAN PRESCRIPTION DRUG LABEL 5 15338-502 TABLET 10.80 mg ORAL unapproved drug other 18 sections
UroAv-B HUMAN PRESCRIPTION DRUG LABEL 5 15338-503 CAPSULE 10 mg ORAL unapproved drug other 18 sections
Methylene Blue HUMAN PRESCRIPTION DRUG LABEL 1 17478-504 INJECTION 10 mg INTRAVENOUS unapproved drug other 15 sections
UroAv-81 HUMAN PRESCRIPTION DRUG LABEL 5 42291-851 TABLET 10.80 mg ORAL unapproved drug other 18 sections
UroAv-B HUMAN PRESCRIPTION DRUG LABEL 5 42291-852 CAPSULE 10 mg ORAL unapproved drug other 18 sections
Hyophen HUMAN PRESCRIPTION DRUG LABEL 5 44523-741 TABLET 10.80 mg ORAL unapproved drug other 19 sections
Phosphasal HUMAN PRESCRIPTION DRUG LABEL 5 44523-742 TABLET 10.80 mg ORAL unapproved drug other 20 sections
Ustell HUMAN PRESCRIPTION DRUG LABEL 5 44523-743 CAPSULE 10 mg ORAL unapproved drug other 20 sections
UrinD/S HUMAN PRESCRIPTION DRUG LABEL 5 54859-701 TABLET 10.80 mg ORAL Unapproved drug other 17 sections
Uro-MP HUMAN PRESCRIPTION DRUG LABEL 5 58657-456 CAPSULE 10 mg ORAL unapproved drug other 18 sections
Uro-458 HUMAN PRESCRIPTION DRUG LABEL 5 58657-458 TABLET 10.80 mg ORAL unapproved drug other 18 sections
Urimar-T HUMAN PRESCRIPTION DRUG LABEL 5 79043-334 TABLET 10.80 mg ORAL Unapproved drug other 19 sections