methylthioninium chloride 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | 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: -1.87
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 0
  • TPSA: 19.37
  • ALOGS: -2.93
  • ROTB: 2
  • Status: OFP
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

None

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
kinase-safety-class ACVR2A,ACVR2B,ACVRL1,AKT1,AKT2,AKT3,ALK,AURKA,AURKB,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK1,CDK4,CDK5,CDK9,CHEK1,CSF1R,DDR1,DYRK1B,EGFR,EIF2AK3,EPHA2,EPHB4,ERBB2,FGFR1,FGFR4,FLT3,GRK1,GRK2,GSK3B,IGF1R,IKBKB,INSR,IRAK1,ITK,JAK1,JAK2,JAK3,KIT,MAP2K6,MAP3K1,MAP3K10,MAP3K11,MAP3K14,MAP3K21,MAP3K3,MAP3K7,MAP3K8,MAP4K1,MAP4K3,MAP4K5,MAPK10,MAPK12,MAPK14,MAPK7,MAPK9,MAPKAPK2,MAPKAPK5,MARK4,MELK,MET,MTOR,NTRK2,PAK4,PDK1,PDK2,PDK4,PDPK1,PIK3CA,PIK3CB,PIK3CD,PIM2,PRKCD,PRKCZ,PRKDC,SGK1,SIK2,SIK3,STK10,STK33,SYK,TEK,TGFBR1,TTK,ULK1,ULK2,ZAP70 90
kinase-selectivity-class AURKA,AXL,BRAF,CDK9,DDR1,DYRK1B,EIF2AK3,EPHB4,ERBB2,GRK2,MAP2K3,MAP2K6,MAP3K7,MAPK10,MAPK12,MAPK7,MAPK8,PDK4,PRKCZ,SGK1,SIK2,STK33,SYK,TEK,TTK 25
pfas-class PFAS structural alert (1 = True, 0 = False) 0

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 1358.36 73.66 301 2767 37586 90587793
Drug interaction 501.11 73.66 223 2845 276230 90349149
Myoglobin urine present 336.51 73.66 51 3017 711 90624668
Toxic encephalopathy 270.60 73.66 62 3006 8637 90616742
Amylase increased 223.09 73.66 51 3017 7021 90618358
Troponin increased 191.16 73.66 51 3017 13230 90612149
Blood creatine phosphokinase increased 186.88 73.66 62 3006 33961 90591418
Blood potassium increased 168.66 73.66 51 3017 20698 90604681
Clonus 162.85 73.66 38 3030 5712 90619667
Blood lactate dehydrogenase increased 157.46 73.66 51 3017 25881 90599498
Hyperreflexia 136.97 73.66 34 3034 6623 90618756
Intentional overdose 131.98 73.66 64 3004 93770 90531609
Encephalopathy 94.53 73.66 41 3027 46403 90578976
Alanine aminotransferase increased 93.51 73.66 55 3013 118283 90507096
Agitation 91.95 73.66 45 3023 67053 90558326
Mydriasis 80.89 73.66 27 3041 14985 90610394
Distributive shock 78.06 73.66 19 3049 3405 90621974

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 640.28 61.27 163 1879 25682 42593611
Drug interaction 164.32 61.27 120 1922 266879 42352414
Drug ineffective 125.96 61.27 151 1891 630046 41989247
Vasoplegia syndrome 117.97 61.27 27 2015 2628 42616665
Shock 76.23 61.27 34 2008 29087 42590206
Hypotension 75.49 61.27 76 1966 257555 42361738
Coma scale abnormal 66.13 61.27 19 2023 4546 42614747
Metabolic acidosis 65.71 61.27 37 2005 51821 42567472
Overdose 65.65 61.27 48 1994 105216 42514077
Compartment syndrome 62.81 61.27 17 2025 3272 42616021

FDA Adverse Event Reporting System (Geriatric)

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 1829.72 63.53 441 4594 58712 110525552
Drug interaction 581.92 63.53 329 4706 499854 110084410
Myoglobin urine present 297.45 63.53 49 4986 871 110583393
Toxic encephalopathy 222.23 63.53 63 4972 15151 110569113
Drug ineffective 172.22 63.53 271 4764 1520269 109063995
Amylase increased 170.05 63.53 49 4986 12470 110571794
Clonus 168.49 63.53 45 4990 8671 110575593
Vasoplegia syndrome 148.63 63.53 37 4998 5402 110578862
Intentional overdose 141.22 63.53 83 4952 132418 110451846
Hyperreflexia 137.21 63.53 39 4996 9446 110574818
Troponin increased 128.39 63.53 49 4986 29717 110554547
Blood potassium increased 126.62 63.53 50 4985 33199 110551065
Blood creatine phosphokinase increased 120.09 63.53 61 4974 73016 110511248
Blood lactate dehydrogenase increased 109.52 63.53 49 4986 44285 110539979
Encephalopathy 103.00 63.53 57 4978 80998 110503266
Hypotension 98.66 63.53 120 4915 523729 110060535
Distributive shock 88.65 63.53 25 5010 5879 110578385
Coma 85.70 63.53 58 4977 117811 110466453
Nystagmus 83.84 63.53 28 5007 11549 110572715
Overdose 82.49 63.53 75 4960 233719 110350545
Methaemoglobinaemia 81.91 63.53 26 5009 9142 110575122
Drug ineffective for unapproved indication 78.10 63.53 52 4983 102786 110481478
Lactic acidosis 77.98 63.53 50 4985 92761 110491503
Shock 74.46 63.53 40 4995 53548 110530716
Toxicity to various agents 71.41 63.53 98 4937 480457 110103807
Agitation 66.76 63.53 49 4986 113002 110471262
Coma scale abnormal 64.41 63.53 22 5013 9704 110574560

FDA Adverse Event Reporting System (Pediatric)

None

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 antioxidant
CHEBI has role CHEBI:33281 antimicrobial agent
CHEBI has role CHEBI:35208 physical tracer
CHEBI has role CHEBI:35469 antidepressant
CHEBI has role CHEBI:35610 antineoplastic agent
CHEBI has role CHEBI:37733 EC 3.1.1.8 (cholinesterase) inhibitor
CHEBI has role CHEBI:38068 antimalarial
CHEBI has role CHEBI:38623 EC 1.4.3.4 (monoamine oxidase) inhibitor
CHEBI has role CHEBI:50407 acid-base indicator
CHEBI has role CHEBI:51217 fluorochrome
CHEBI has role CHEBI:63726 neuroprotective agent
CHEBI has role CHEBI:77178 histological dye
CHEBI has role CHEBI:77307 cardioprotective agent
CHEBI has role CHEBI:78678 EC 4.6.1.2 (guanylate cyclase) inhibitor

Related Drugs by ATC class:

V03AB Antidotes 28 drugs
4-dimethylaminophenolacetylcysteineamyl nitriteandexanet alfaatropinecopper sulfatedimercaprolethanolflumazenilfomepizoleglutathionehydroxocobalamin show all 28 →
V04CG Tests for gastric secretion 5 drugs
betazolecaffeinehistaminepentagastrinsodium benzoate

Drug Use | Suggest Off label Use Form| |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




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

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
10MG/2ML (5MG/ML) PROVAYBLUE PROVEPHARM SAS N204630 July 18, 2019 RX SOLUTION INTRAVENOUS Jan. 8, 2027 INFORMATION ADDED TO THE CLINICAL STUDIES SECTION TO FULFILL A POST-MARKETING REQUIREMENT
50MG/10ML (5MG/ML) PROVAYBLUE PROVEPHARM SAS N204630 April 8, 2016 RX SOLUTION INTRAVENOUS Jan. 8, 2027 INFORMATION ADDED TO THE CLINICAL STUDIES SECTION TO FULFILL A POST-MARKETING REQUIREMENT

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])		Mechanism
action		Bioact sourceMoA source
Amine oxidase [flavin-containing] A Enzyme IC50 7.15 CHEMBL
Glutathione reductase, mitochondrial Enzyme IC50 4.80 CHEMBL
Amine oxidase [flavin-containing] B Enzyme IC50 5.36 CHEMBL
Thioredoxin reductase 1, cytoplasmic Enzyme IC50 4.52 CHEMBL
Microtubule-associated protein tau Structural IC50 5.72 CHEMBL
Amyloid beta A4 protein Membrane other IC50 6.26 CHEMBL
Glutathione reductase Enzyme IC50 5.19 CHEMBL
Cruzipain Enzyme IC50 4.26 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
CHEMBL405110 ChEMBL_ID
CHEMBL550495 ChEMBL_ID
DB09241 DRUGBANK_ID
6099 PUBCHEM_CID
6878 RXNORM
1036 MMSL
5090 MMSL
d01128 MMSL
001094 NDDF
002616 NDDF
002877 NDDF
354064008 SNOMEDCT_US
6725000 SNOMEDCT_US
D008751 MESH_DESCRIPTOR_UI
T42P99266K UNII

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
Methylene blue HUMAN PRESCRIPTION DRUG LABEL 1 0143-9094 INJECTION, SOLUTION 5 mg INTRAVENOUS ANDA 18 sections
URIBEL TABS HUMAN PRESCRIPTION DRUG LABEL 5 0178-0745 TABLET, COATED 10.80 mg ORAL unapproved drug other 13 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 30 sections
PROVAYBLUE HUMAN PRESCRIPTION DRUG LABEL 1 0517-0371 INJECTION 5 mg INTRAVENOUS NDA 30 sections
PROVAYBLUE HUMAN PRESCRIPTION DRUG LABEL 1 0517-0374 INJECTION 5 mg INTRAVENOUS NDA 30 sections
PROVAYBLUE HUMAN PRESCRIPTION DRUG LABEL 1 0517-0381 INJECTION 5 mg INTRAVENOUS NDA 30 sections
Uretron D/S HUMAN PRESCRIPTION DRUG LABEL 5 12539-144 TABLET 10.80 mg ORAL unapproved drug other 20 sections
Methylene Blue HUMAN PRESCRIPTION DRUG LABEL 1 14789-119 INJECTION, SOLUTION 5 mg INTRAVENOUS ANDA 32 sections
Methylene Blue HUMAN PRESCRIPTION DRUG LABEL 1 15243-344 INJECTION, SOLUTION 5 mg INTRAVENOUS ANDA 31 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
URIMAR-T CAPS HUMAN PRESCRIPTION DRUG LABEL 5 28595-224 CAPSULE 10.80 mg ORAL unapproved drug other 19 sections
MB CAPS HUMAN PRESCRIPTION DRUG LABEL 5 28595-299 CAPSULE 10.80 mg ORAL unapproved drug other 18 sections
Methylene Blue HUMAN PRESCRIPTION DRUG LABEL 1 54288-147 INJECTION 10 mg INTRAVENOUS unapproved drug other 13 sections
Methylene Blue HUMAN PRESCRIPTION DRUG LABEL 1 54288-159 INJECTION 10 mg INTRAVENOUS unapproved drug other 13 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-MP HUMAN PRESCRIPTION DRUG LABEL 5 58657-456 CAPSULE 10 mg ORAL unapproved drug other 18 sections
METHYLENE BLUE HUMAN PRESCRIPTION DRUG LABEL 1 68462-698 INJECTION 50 mg INTRAVENOUS ANDA 29 sections
Methylene blue HUMAN PRESCRIPTION DRUG LABEL 1 70121-2715 INJECTION, SOLUTION 5 mg INTRAVENOUS ANDA 28 sections
Methylene blue HUMAN PRESCRIPTION DRUG LABEL 1 70121-2716 INJECTION, SOLUTION 5 mg INTRAVENOUS ANDA 28 sections
METHYLENE BLUE HUMAN PRESCRIPTION DRUG LABEL 1 70700-328 INJECTION 50 mg INTRAVENOUS ANDA 19 sections
Methylene blue HUMAN PRESCRIPTION DRUG LABEL 1 70710-1837 INJECTION 5 mg INTRAVENOUS ANDA 25 sections