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Identification
- Summary
Methylene blue is an oxidation-reduction agent used for the treatment of pediatric and adult patients with acquired methemoglobinemia.
- Brand Names
- Hyophen, Phosphasal, Provayblue, Proveblue, Urelle, Uribel, Urimar Reformulated Oct 2013, Urin DS, Urogesic Blue Reformulated Apr 2012, Ustell
- Generic Name
- Methylene blue
- DrugBank Accession Number
- DB09241
- Background
Methylene blue is an oxidation-reduction agent. The intravenous form of methylene blue is approved by the FDA for the treatment of pediatric and adult patients with acquired methemoglobinemia. Historically, it has been widely used in Africa to treat malaria, but now it disappeared when chloroquine (CQ) and other drugs entered the market. Its use as an urinary tract antiseptic has also been investigated.
Methylthioninium chloride (INN, or methylene blue, proposed trade name Rember) is an investigational drug being developed by the University of Aberdeen and TauRx Therapeutics that has been shown in early clinical trials to be an inhibitor of Tau protein aggregation. The drug is of potential interest for the treatment of patients with Alzheimer's disease.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Methylene blue (DB09241)
- Weight
- Average: 319.85
Monoisotopic: 319.0909965 - Chemical Formula
- C16H18ClN3S
- Synonyms
- Azul de metileno
- Basic Blue 9
- C.I. basic blue 9
- Chlorure de méthylthioninium
- Cloruro de metiltioninio
- Lowacryl blue 9
- Methylene blue
- Methylene blue anhydrous
- Methylenium ceruleum
- Methylthioninii chloridum
- Methylthioninium chloride
- Solvent blue 8
- Swiss blue
- External IDs
- C.I. 52015
- CI 52015
- CI-52015
- NSC-617593
- TRX-0014
- TRX0014
Pharmacology
- Indication
Indicated for the treatment of pediatric and adult patients with acquired methemoglobinemia.
Other clinical applications of methylene blue include improvement of hypotension associated with various clinical states, an antiseptic in urinary tract infections, treatment of hypoxia and hyperdynamic circulation in cirrhosis of liver and severe hepatopulmonary syndrome, and treatment of ifofosamide induced neurotoxicity.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination for symptomatic treatment of Cystitis Combination Product in combination with: Potassium nitrate (DB11090), Methenamine (DB06799) ••• ••• ••••••• •••••• Treatment of Methaemoglobinaemia •••••••••••• •••••• •••••••• •••••••••• •••••••• Used in combination for symptomatic treatment of Nephritis Combination Product in combination with: Methenamine (DB06799), Potassium nitrate (DB11090) ••• ••• ••••••• •••••• Used in combination for symptomatic treatment of Urethritis Combination Product in combination with: Methenamine (DB06799), Potassium nitrate (DB11090) ••• ••• ••••••• •••••• Used in combination to treat Urinary tract inflammation Combination Product in combination with: Potassium nitrate (DB11090) ••• ••• •••••• - Associated Therapies
- Contraindications & Blackbox Warnings
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Not Available
- Mechanism of action
- Main mechanism of action involves inhibition of nitric oxide synthase and guanylate cyclase.
- In Alzheimers Disease: a mechanistic study found that methylene blue oxidizes cysteine sulfhydryl groups on tau to keep tau monomeric. One preclinical treatment study in tauopathy mice reported anti-inflammatory or neuroprotective effects mediated by the Nrf2/antioxidant response element (ARE); another reported insoluble tau reduction and a learning and memory benefit when given early.
- In Methemoglobinemia: Methylene Blue acts by reacting within RBC to form leukomethylene blue, which is a reducing agent of oxidized hemoglobin converting the ferric ion (fe+++) back to its oxygen-carrying ferrous state(fe++).
- As antimalarial agent: Methylene Blue, a specific inhibitor of P.falciparum glutathione reductase has the potential to reverse CQ resistance and it prevents the polymerization of haem into haemozoin similar to 4-amino-quinoline antimalarials.
- For ifosfamide induced neurotoxicity: Methylene blue functions as an alternate electron acceptor. It acts to reverse the NADH inhibition caused by gluconeogenesis in the liver while blocking the transformation of chloroethylamine into chloroacetaldehyde. In addition, it inhibits various amine oxidase activities, which also prevents the formation of chloroacetaldehyde.
Target Actions Organism AGuanylate cyclase soluble subunit alpha-2 inhibitorHumans ANitric oxide synthase 1 inhibitorHumans - Absorption
Not Available
- Volume of distribution
10 mg/kg (in rats).
- Protein binding
Methylene blue was reported to bind strongly to rabbit plasma (71–77% of bound drug).
- Metabolism
Following distribution into tissues, rapidly reduced to leukomethylene blue (leucomethylthioninium chloride). Metabolism to leucomethylene blue may be less efficient in neonates than in older individuals.
- Route of elimination
Excreted in urine and bile. About 75% of an oral dose excreted in urine, primarily as stabilized colorless leukomethylene blue.
- Half-life
5–6.5 hours (after IV dose).
- Clearance
3.0 ± 0.7 L/min.
- Adverse Effects
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LD50 = 1180 mg/kg ( Rat ).
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
Interacting Gene/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details Glucose-6-phosphate 1-dehydrogenase Villeurbanne Not Available 1000_1002delACC ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Torun Not Available 1006A->G ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Sunderland Not Available 105_107delCAT ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Iwatsuki Not Available 1081G->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Serres Not Available 1082C->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Tondela Not Available 1084_1101delCTGAACGAGCGCAAGGCC ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Loma Linda Not Available 1089C->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Aachen Not Available 1089C->G ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Tenri Not Available 1096A->G ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Montpellier Not Available 1132G>A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Calvo Mackenna Not Available 1138A->G ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Riley Not Available 1139T->C ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Olomouc Not Available 1141T->C ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Tomah Not Available 1153T->C ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Lynwood Not Available 1154G->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Madrid Not Available 1155C->G ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Iowa, Walter Reed, Springfield Not Available 1156A->G ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Beverly Hills, Genova, Iwate, Niigata, Yamaguchi Not Available 1160G->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Hartford Not Available 1162A->G ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Praha Not Available 1166A->G ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Krakow Not Available 1175T>C ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Wisconsin Not Available 1177C->G ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Nashville, Anaheim, Portici Not Available 1178G->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Alhambra Not Available 1180G->C ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Bari Not Available 1187C->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Puerto Limon Not Available 1192G->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Covao do Lobo Not Available 1205C>A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Clinic Not Available 1215G->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Utrecht Not Available 1225C->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Suwalki Not Available 1226C->G ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Riverside Not Available 1228G->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Japan, Shinagawa Not Available 1229G->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Kawasaki Not Available 1229G->C ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Munich Not Available 1231A->G ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Georgia Not Available 1284C->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Sumare Not Available 1292T->G ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Telti/Kobe Not Available 1318C->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Santiago de Cuba, Morioka Not Available 1339G->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Harima Not Available 1358T->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Figuera da Foz Not Available 1366G->C ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Amiens Not Available 1367A>T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Bangkok Noi Not Available 1376G->T, 1502T->G ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Fukaya Not Available 1462G->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Campinas Not Available 1463G->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Buenos Aires Not Available 1465C>T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Arakawa Not Available 1466C->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Brighton Not Available 1488_1490delGAA ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Kozukata Not Available 159G->C ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Amsterdam Not Available 180_182delTCT ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase No name Not Available 202G->A, 376A->G, 1264C>G ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Swansea Not Available 224T->C ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Urayasu Not Available 281_283delAGA ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Vancouver Not Available 317C->G544C->T592C->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Mt Sinai Not Available 376A->G, 1159C->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Plymouth Not Available 488G->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Volendam Not Available 514C->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Shinshu Not Available 527A->G ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Chikugo Not Available 535A->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Tsukui Not Available 561_563delCTC ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Pedoplis-Ckaro Not Available 573C>G ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Santiago Not Available 593G->C ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Minnesota, Marion, Gastonia, LeJeune Not Available 637G->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Cincinnati Not Available 637G->T, 1037A->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Harilaou Not Available 648T->G ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase North Dallas Not Available 683_685delACA ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Asahikawa Not Available 695G->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Durham Not Available 713A->G ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Stonybrook Not Available 724_729delGGCACT ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Wayne Not Available 769C->G ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Aveiro Not Available 806G->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Cleveland Corum Not Available 820G->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Lille Not Available 821A>T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Bangkok Not Available 825G>C ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Sugao Not Available 826C->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase La Jolla Not Available 832T->C ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Wexham Not Available 833C->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Piotrkow Not Available 851T>C ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase West Virginia Not Available 910G->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Omiya Not Available 921G->C ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Nara Not Available 953_976delCCACCAAAGGGTACCTGGAC GACC ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Manhattan Not Available 962G->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Rehevot Not Available 964T->C ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Honiara Not Available 99A->G / 1360C->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Tokyo, Fukushima Not Available 1246G->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Chatham Not Available 1003G->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Fushan Not Available 1004C->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Partenope Not Available 1052G->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Ierapetra Not Available 1057C->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Anadia Not Available 1193A->G ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Abeno Not Available 1220A->C ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Surabaya Not Available 1291G->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Pawnee Not Available 1316G->C ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase S. Antioco Not Available 1342A->G ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Cassano Not Available 1347G->C ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Hermoupolis Not Available 1347G->C / 1360C->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Union,Maewo, Chinese-2, Kalo Not Available 1360C->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Andalus Not Available 1361G->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Cosenza Not Available 1376G->C ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Canton, Taiwan- Hakka, Gifu-like, Agrigento-like Not Available 1376G->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Flores Not Available 1387C->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Kaiping, Anant, Dhon, Sapporo-like, Wosera Not Available 1388G->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Kamogawa Not Available 169C->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Costanzo Not Available 179T>C ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Amazonia Not Available 185C->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Songklanagarind Not Available 196T->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Hechi Not Available 202G->A / 871G->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Namouru Not Available 208T->C ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Bao Loc Not Available 352T>C ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Crispim Not Available 375G->T, 379G->T383T->C384C>T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Acrokorinthos Not Available 376A->G / 463C->G ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Santa Maria Not Available 376A->G / 542A->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Ananindeua Not Available 376A->G / 871G->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Vanua Lava Not Available 383T->C ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Valladolid Not Available 406C->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Belem Not Available 409C->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Liuzhou Not Available 442G->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Shenzen Not Available 473G>A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Taipei ‚ÄúChinese- 3‚Äù Not Available 493A->G ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Toledo Not Available 496C>T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Naone Not Available 497G->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Nankang Not Available 517T->C ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Miaoli Not Available 519C->G ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Mediterranean, Dallas, Panama‚ Sassari, Cagliari, Birmingham Not Available 563C->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Coimbra Shunde Not Available 592C->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Nilgiri Not Available 593G>A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Radlowo Not Available 679C->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Roubaix Not Available 811G>C ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Haikou Not Available 835A->G ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Chinese-1 Not Available 835A->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Mizushima Not Available 848A>G ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Osaka Not Available 853C->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Viangchan, Jammu Not Available 871G->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Seoul Not Available 916G->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Ludhiana Not Available 929G->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Farroupilha Not Available 977C->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Chinese-5 Not Available 1024C->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Rignano Not Available 130G>A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Orissa Not Available 131C->G ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase G6PDNice Not Available 1380G>C ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Kamiube, Keelung Not Available 1387C->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Neapolis Not Available 1400C->G ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Aures Not Available 143T->C ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Split Not Available 1442C->G ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Kambos Not Available 148C->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Palestrina Not Available 170G>A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Metaponto Not Available 172G->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Musashino Not Available 185C->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Asahi Not Available 202G->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase A- (202), Ferrara I Not Available 202G->A / 376A->G ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Murcia Oristano Not Available 209A->G ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Ube Konan Not Available 241C->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Lagosanto Not Available 242G->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Guangzhou Not Available 274C->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Hammersmith Not Available 323T->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Sinnai Not Available 34G->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase A- (680) Not Available 376A->G / 680G->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase A- (968), Betica,Selma, Guantanamo Not Available 376A->G / 968T->C ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Salerno Pyrgos Not Available 383T>G ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Quing Yan Not Available 392G->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Lages Not Available 40G->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Ilesha Not Available 466G->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Mahidol Not Available 487G->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Malaga Not Available 542A->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Sibari Not Available 634A->G ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Mexico City Not Available 680G->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Nanning Not Available 703C->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Seattle, Lodi, Modena, Ferrara II, Athens-like Not Available 844G->C ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Bajo Maumere Not Available 844G->T ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Montalbano Not Available 854G->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Kalyan-Kerala, Jamnaga, Rohini Not Available 949G->A ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Gaohe Not Available 95A->G ADR Inferred Risk of severe hemolytic anemia or paradoxical methemoglobinemia. Details
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 software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Methylene blue is combined with 1,2-Benzodiazepine. Abacavir Abacavir may decrease the excretion rate of Methylene blue which could result in a higher serum level. Abaloparatide Methylene blue may increase the orthostatic hypotensive activities of Abaloparatide. Abametapir The serum concentration of Methylene blue can be increased when it is combined with Abametapir. Abatacept The metabolism of Methylene blue can be increased when combined with Abatacept. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Methylene blue trihydrate T42P99266K 7220-79-3 XQAXGZLFSSPBMK-UHFFFAOYSA-M - Active Moieties
Name Kind UNII CAS InChI Key Methylthioninium ionic ZMZ79891ZH 7060-82-4 RBTBFTRPCNLSDE-UHFFFAOYSA-N - Product Images
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Methylene Blue Injection 10 mg/1mL Intravenous Bpi Labs Llc 2023-05-15 Not applicable US 
Methylene Blue Injection, solution 10 mg/1mL Intravenous AMERICAN REGENT, INC. 1990-09-30 2014-04-01 US Methylene Blue Injection 10 mg/1mL Intravenous Akorn 2009-04-01 Not applicable US Methylene Blue Injection, solution 10 mg/1mL Intravenous AMERICAN REGENT, INC. 1990-09-30 2013-11-01 US Methylene Blue Injection, solution 10 mg/1mL Intravenous AMERICAN REGENT, INC. 1990-09-30 2014-04-01 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Methylene blue Injection 5 mg/1mL Intravenous Zydus Lifesciences Limited 2023-12-05 Not applicable US Methylene blue Injection 5 mg/1mL Intravenous Zydus Pharmaceuticals USA Inc. 2023-12-05 Not applicable US Methylene blue Injection 5 mg/1mL Intravenous Zydus Lifesciences Limited 2023-12-05 Not applicable US Methylene blue Injection 5 mg/1mL Intravenous Zydus Pharmaceuticals USA Inc. 2023-12-05 Not applicable US - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Methylene Bleu Liq 1% Liquid 1 % Oral Laboratoire Atlas Inc 1951-12-31 Not applicable Canada 
Methylene Bleu Liq 2% Liquid 2 % Oral Laboratoire Atlas Inc 1951-12-31 Not applicable Canada Methylene Blue Solution 1% Liquid 1 % Oral; Topical Rougier Pharma Division Of Ratiopharm Inc 1981-12-31 2015-10-01 Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Blue Collyrium Methylene blue (0.2 mg / mL) + Naphazoline hydrochloride (0.5 mg / mL) Liquid Ophthalmic Sandoz S.P.A. 1997-05-13 2019-08-01 Canada BUCO-BLEU KOLLUTUVAR, 15 ML Methylene blue (0.15 g/15ml) + Resorcinol (0.075 g/15ml) Solution Topical TAB ILAC VE SAGLIK URUNLERI SAN TIC LTD STI 2011-12-22 Not applicable Turkey 
Collyre Bleu Methylene blue (0.2 mg / mL) + Naphazoline hydrochloride (0.5 mg / mL) Solution / drops Ophthalmic Sabex Inc 1991-12-31 1997-11-26 Canada Collyre Bleu Laiter Methylene blue (0.2 mg / mL) + Naphazoline nitrate (0.5 mg / mL) Solution / drops Ophthalmic Frilab Sa 1986-12-31 Not applicable Canada Eau Resolutive Soker Methylene blue (.1365 mg / 30 g) + Camphor (.715 mg / 30 g) + Cupric sulfate (28.925 mg / 30 g) + Resorcinol (58.565 mg / 30 g) + Zinc sulfate (88.4 mg / 30 g) Liquid Topical Produits Francais Labs Inc. 1930-12-31 1997-05-30 Canada - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Azuphen Mb Methylene blue trihydrate (10 mg/1) + Hyoscyamine sulfate dihydrate (0.12 mg/1) + Methenamine (120 mg/1) + Phenyl salicylate (36 mg/1) + Sodium phosphate, monobasic, monohydrate (40.8 mg/1) Capsule Oral Burel Pharmaceuticals, Llc 2015-09-28 2016-11-01 US Darcalma Methylene blue trihydrate (10.8 mg/1) + Hyoscyamine sulfate dihydrate (0.12 mg/1) + Methenamine (81.6 mg/1) + Phenyl salicylate (36.2 mg/1) + Sodium phosphate, monobasic, unspecified form (40.8 mg/1) Tablet Oral River's Edge Pharmaceuticals, LLC 2008-12-22 2011-07-31 US Darcalma Methylene blue trihydrate (10.8 mg/1) + Hyoscyamine sulfate dihydrate (.12 mg/1) + Methenamine (81.6 mg/1) + Phenyl salicylate (36.2 mg/1) + Sodium phosphate, monobasic, unspecified form (40.8 mg/1) Tablet Oral Kylemore Pharmaceuticals, LLC 2009-12-01 2009-12-02 US Darpaz Methylene blue trihydrate (10.8 mg/1) + Hyoscyamine sulfate dihydrate (.12 mg/1) + Methenamine (81 mg/1) + Phenyl salicylate (32.4 mg/1) + Sodium phosphate, monobasic (40.8 mg/1) Tablet Oral River's Edge Pharmaceuticals, LLC 2008-12-01 2011-05-31 US Hyolev Mb Methylene blue trihydrate (10.8 mg/1) + Hyoscyamine sulfate dihydrate (0.12 mg/1) + Methenamine (81 mg/1) + Phenyl salicylate (32.4 mg/1) + Sodium phosphate, monobasic, monohydrate (40.8 mg/1) Tablet Oral Burel Pharmaceuticals, Llc 2015-06-26 2016-11-01 US
Categories
- ATC Codes
- V03AB17 — Methylthioninium chloride
- V03AB — Antidotes
- V03A — ALL OTHER THERAPEUTIC PRODUCTS
- V03 — ALL OTHER THERAPEUTIC PRODUCTS
- V — VARIOUS
- Drug Categories
- Agents that produce hypertension
- Agents that reduce seizure threshold
- Antidepressive Agents
- Antidotes
- Antipsychotic Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP1A2 Inducers
- Cytochrome P-450 CYP1A2 Inducers (strength unknown)
- Cytochrome P-450 CYP1A2 Inhibitors
- Cytochrome P-450 CYP1A2 Inhibitors (strength unknown)
- Cytochrome P-450 CYP1A2 Substrates
- Cytochrome P-450 CYP2B6 Inhibitors
- Cytochrome P-450 CYP2B6 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2C19 Inhibitors
- Cytochrome P-450 CYP2C19 inhibitors (strength unknown)
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP2C8 Inhibitors
- Cytochrome P-450 CYP2C8 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2C9 Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A5 Inhibitors
- Cytochrome P-450 CYP3A5 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Diagnostic Agents
- Drugs causing inadvertant photosensitivity
- Drugs that are Mainly Renally Excreted
- Enzyme Inhibitors
- Gastric Function
- Heterocyclic Compounds, Fused-Ring
- MATE 1 Inhibitors
- MATE 2 Inhibitors
- MATE inhibitors
- Miscellaneous Therapeutic Agents
- Monoamine Oxidase Inhibitors
- Neurotoxic agents
- OCT2 Inhibitors
- Oxidation-Reduction Agent
- P-glycoprotein inhibitors
- P-glycoprotein substrates
- Phenothiazines
- Photosensitizing Agents
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Sulfur Compounds
- Tests for Gastric Secretion
- UGT1A4 Inhibitors
- UGT1A9 Inhibitors
- 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 / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organic chloride salts / Hydrocarbon derivatives
- Substituents
- Amine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Benzothiazine / Dialkylarylamine / Heteroaromatic compound / Hydrocarbon derivative / Organic chloride salt / Organic nitrogen compound
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- organic chloride salt (CHEBI:6872)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 8NAP7826UB
- CAS number
- 61-73-4
- InChI Key
- CXKWCBBOMKCUKX-UHFFFAOYSA-M
- InChI
- InChI=1S/C16H18N3S.ClH/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;1H/q+1;/p-1
- IUPAC Name
- 3,7-bis(dimethylamino)-5λ⁴-phenothiazin-5-ylium chloride
- SMILES
- [Cl-].CN(C)C1=CC2=[S+]C3=C(C=CC(=C3)N(C)C)N=C2C=C1
References
- General References
- Ozal E, Kuralay E, Yildirim V, Kilic S, Bolcal C, Kucukarslan N, Gunay C, Demirkilic U, Tatar H: Preoperative methylene blue administration in patients at high risk for vasoplegic syndrome during cardiac surgery. Ann Thorac Surg. 2005 May;79(5):1615-9. [Article]
- Tuman KJ, McCarthy RJ, O'Connor CJ, Holm WE, Ivankovich AD: Angiotensin-converting enzyme inhibitors increase vasoconstrictor requirements after cardiopulmonary bypass. Anesth Analg. 1995 Mar;80(3):473-9. [Article]
- Meissner PE, Mandi G, Coulibaly B, Witte S, Tapsoba T, Mansmann U, Rengelshausen J, Schiek W, Jahn A, Walter-Sack I, Mikus G, Burhenne J, Riedel KD, Schirmer RH, Kouyate B, Muller O: Methylene blue for malaria in Africa: results from a dose-finding study in combination with chloroquine. Malar J. 2006 Oct 8;5:84. [Article]
- Boylston M, Beer D: Methemoglobinemia: a case study. Crit Care Nurse. 2002 Aug;22(4):50-5. [Article]
- Pelgrims J, De Vos F, Van den Brande J, Schrijvers D, Prove A, Vermorken JB: Methylene blue in the treatment and prevention of ifosfamide-induced encephalopathy: report of 12 cases and a review of the literature. Br J Cancer. 2000 Jan;82(2):291-4. [Article]
- product info [Link]
- Article [Link]
- article [Link]
- Drug info [Link]
- Monograph [Link]
- msds [Link]
- FDA Approved Drug Products: PROVAYBLUE (methylene blue) injection, for intravenous use [Link]
- External Links
- KEGG Compound
- C00220
- PubChem Compound
- 6099
- PubChem Substance
- 310265144
- ChemSpider
- 5874
- 6878
- ChEBI
- 6872
- ChEMBL
- CHEMBL405110
- Wikipedia
- Methylene_blue
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 dataNot Available Completed Not Available Breast Cancer 1 somestatus stop reason just information to hide Not Available Completed Not Available Hyperparathyroidism 1 somestatus stop reason just information to hide Not Available Completed Not Available Methemoglobinemia / Methemoglobinemia, Acquired 1 somestatus stop reason just information to hide Not Available Completed Basic Science Chronic Periodontitis (Disorder) 1 somestatus stop reason just information to hide Not Available Completed Diagnostic Melanoma / Sentinel Node 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Liquid Ophthalmic Solution Topical Solution / drops Ophthalmic Tablet Oral Liquid Topical Tablet, extended release Oral 25 MG Liquid Oral 1 % Liquid Oral 2 % Injection Intravenous 10 mg/1mL Injection, solution Intravenous 10 mg/1mL Liquid Intramuscular; Intravenous 10 mg / mL Liquid Intravenous 1 % Injection, solution Intravenous 50 mg/5ml Liquid Intravenous 10 mg / mL Solution Intravenous 10 mg / mL Solution Parenteral 10 mg / mL Liquid Oral; Topical 1 % Injection, solution Intravenous 5 mg/ml Injection, solution Intravenous 100 MG/10ML Capsule Oral Injection Intravenous 5 mg/1mL Injection, solution Oral; Parenteral 5 mg/ml Tablet, coated Oral Tablet, sugar coated Oral Injection, solution Intravenous 8.81 mg/1ml - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 100 to 110 °C (with decomposition) Not Available - Predicted Properties
Property Value Source Water Solubility 0.0296 mg/mL ALOGPS logP 3.61 ALOGPS logP 2.61 Chemaxon logS -4 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 33.1 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
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 182.4517334 predictedDarkChem Lite v0.1.0 [M-H]- 182.7828334 predictedDarkChem Lite v0.1.0 [M-H]- 168.1967 predictedDeepCCS 1.0 (2019) [M+H]+ 183.2603334 predictedDarkChem Lite v0.1.0 [M+H]+ 183.3319334 predictedDarkChem Lite v0.1.0 [M+H]+ 170.55467 predictedDeepCCS 1.0 (2019) [M+Na]+ 183.3206334 predictedDarkChem Lite v0.1.0 [M+Na]+ 183.1680334 predictedDarkChem Lite v0.1.0 [M+Na]+ 176.93633 predictedDeepCCS 1.0 (2019)
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Has guanylyl cyclase on binding to the beta-1 subunit
- Specific Function
- GTP binding
- Gene Name
- GUCY1A2
- Uniprot ID
- P33402
- Uniprot Name
- Guanylate cyclase soluble subunit alpha-2
- Molecular Weight
- 81749.185 Da
References
- Ginimuge PR, Jyothi SD: Methylene blue: revisited. J Anaesthesiol Clin Pharmacol. 2010 Oct;26(4):517-20. [Article]
- Evora PR: Methylene Blue Is a Guanylate Cyclase Inhibitor That Does Not Interfere with Nitric Oxide Synthesis. Tex Heart Inst J. 2016 Feb 1;43(1):103. doi: 10.14503/THIJ-15-5629. eCollection 2016 Feb. [Article]
- Masaki E, Kondo I: Methylene blue, a soluble guanylyl cyclase inhibitor, reduces the sevoflurane minimum alveolar anesthetic concentration and decreases the brain cyclic guanosine monophosphate content in rats. Anesth Analg. 1999 Aug;89(2):484-9. doi: 10.1097/00000539-199908000-00045. [Article]
- Oz M, Lorke DE, Hasan M, Petroianu GA: Cellular and molecular actions of Methylene Blue in the nervous system. Med Res Rev. 2011 Jan;31(1):93-117. doi: 10.1002/med.20177. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In the brain and peripheral nervous system, NO displays many properties of a neurotransmitter. Probably has nitrosylase activity and mediates cysteine S-nitrosylation of cytoplasmic target proteins such SRR
- Specific Function
- arginine binding
- Gene Name
- NOS1
- Uniprot ID
- P29475
- Uniprot Name
- Nitric oxide synthase 1
- Molecular Weight
- 160969.095 Da
References
- Mayer B, Brunner F, Schmidt K: Inhibition of nitric oxide synthesis by methylene blue. Biochem Pharmacol. 1993 Jan 26;45(2):367-74. doi: 10.1016/0006-2952(93)90072-5. [Article]
- Ginimuge PR, Jyothi SD: Methylene blue: revisited. J Anaesthesiol Clin Pharmacol. 2010 Oct;26(4):517-20. [Article]
- Volke V, Wegener G, Vasar E, Rosenberg R: Methylene blue inhibits hippocampal nitric oxide synthase activity in vivo. Brain Res. 1999 May 1;826(2):303-5. doi: 10.1016/s0006-8993(99)01253-6. [Article]
- Oz M, Lorke DE, Hasan M, Petroianu GA: Cellular and molecular actions of Methylene Blue in the nervous system. Med Res Rev. 2011 Jan;31(1):93-117. doi: 10.1002/med.20177. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- In vitro inhibitor. Relevance to humans is unknown.
- General Function
- UDP-glucuronosyltransferase (UGT) that catalyzes phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase the metabolite's water solubility, thereby facilitating excretion into either the urine or bile (PubMed:18177842, PubMed:24641623). Essential for the elimination and detoxification of drugs, xenobiotics and endogenous compounds (PubMed:18177842). Involved in the glucuronidation of calcidiol, which is the major circulating form of vitamin D3 essential for the regulation of calcium and phosphate homeostasis (PubMed:24641623). Also glucuronidates the biologically active form of vitamin D3, calcitriol, probably leading to its biliary transport and intestinal reabsorption (PubMed:18177842)
- Specific Function
- enzyme binding
- Gene Name
- UGT1A4
- Uniprot ID
- P22310
- Uniprot Name
- UDP-glucuronosyltransferase 1A4
- Molecular Weight
- 60024.535 Da
References
- FDA Approved Drug Products: PROVAYBLUE (methylene blue) injection, for intravenous use [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- In vitro inhibitor. Relevance to humans is unknown.
- General Function
- UDP-glucuronosyltransferase (UGT) that catalyzes phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase the metabolite's water solubility, thereby facilitating excretion into either the urine or bile (PubMed:12181437, PubMed:15470161, PubMed:15472229, PubMed:18004212, PubMed:18052087, PubMed:18674515, PubMed:19545173). Essential for the elimination and detoxification of drugs, xenobiotics and endogenous compounds (PubMed:12181437, PubMed:18004212). Catalyzes the glucuronidation of endogenous estrogen hormones such as estradiol and estrone (PubMed:15472229). Also catalyzes the glucuronidation of the isoflavones genistein, daidzein, glycitein, formononetin, biochanin A and prunetin, which are phytoestrogens with anticancer and cardiovascular properties (PubMed:18052087, PubMed:19545173). Involved in the glucuronidation of the AGTR1 angiotensin receptor antagonist caderastan, a drug which can inhibit the effect of angiotensin II (PubMed:18674515). Involved in the biotransformation of 7-ethyl-10-hydroxycamptothecin (SN-38), the pharmacologically active metabolite of the anticancer drug irinotecan (PubMed:12181437, PubMed:20610558). Also metabolizes mycophenolate, an immunosuppressive agent (PubMed:15470161, PubMed:18004212)
- Specific Function
- enzyme binding
- Gene Name
- UGT1A9
- Uniprot ID
- O60656
- Uniprot Name
- UDP-glucuronosyltransferase 1A9
- Molecular Weight
- 59940.495 Da
References
- FDA Approved Drug Products: PROVAYBLUE (methylene blue) injection, for intravenous use [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitorInducer
- Curator comments
- In vitro inhibitor. Relevance to humans is unknown.
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:11555828, PubMed:12865317). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2 (PubMed:11555828, PubMed:12865317). Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). May act as a major enzyme for all-trans retinoic acid biosynthesis in the liver. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376). Primarily catalyzes stereoselective epoxidation of the last double bond of polyunsaturated fatty acids (PUFA), displaying a strong preference for the (R,S) stereoisomer (PubMed:19965576). Catalyzes bisallylic hydroxylation and omega-1 hydroxylation of PUFA (PubMed:9435160). May also participate in eicosanoids metabolism by converting hydroperoxide species into oxo metabolites (lipoxygenase-like reaction, NADPH-independent) (PubMed:21068195). Plays a role in the oxidative metabolism of xenobiotics. Catalyzes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin (PubMed:14725854). Metabolizes caffeine via N3-demethylation (Probable)
- Specific Function
- aromatase activity
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58406.915 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- In vitro inhibitor. Relevance to humans is unknown.
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of endocannabinoids and steroids (PubMed:12865317, PubMed:21289075). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the epoxidation of double bonds of arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:21289075). Hydroxylates steroid hormones, including testosterone at C-16 and estrogens at C-2 (PubMed:12865317, PubMed:21289075). Plays a role in the oxidative metabolism of xenobiotics, including plant lipids and drugs (PubMed:11695850, PubMed:22909231). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850)
- Specific Function
- anandamide 11,12 epoxidase activity
- Gene Name
- CYP2B6
- Uniprot ID
- P20813
- Uniprot Name
- Cytochrome P450 2B6
- Molecular Weight
- 56277.81 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- In vitro inhibitor. Relevance to humans is unknown.
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Primarily catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) with a preference for the last double bond (PubMed:15766564, PubMed:19965576, PubMed:7574697). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes all trans-retinoic acid toward its 4-hydroxylated form (PubMed:11093772). Displays 16-alpha hydroxylase activity toward estrogen steroid hormones, 17beta-estradiol (E2) and estrone (E1) (PubMed:14559847). Plays a role in the oxidative metabolism of xenobiotics. It is the principal enzyme responsible for the metabolism of the anti-cancer drug paclitaxel (taxol) (PubMed:26427316)
- Specific Function
- arachidonic acid epoxygenase activity
- Gene Name
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids and steroids (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:15766564, PubMed:19965576, PubMed:7574697, PubMed:9866708). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Exhibits low catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes bisallylic hydroxylation and hydroxylation with double-bond migration of polyunsaturated fatty acids (PUFA) (PubMed:9435160, PubMed:9866708). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan (PubMed:25994031)
- Specific Function
- (R)-limonene 6-monooxygenase activity
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- Curator comments
- In vitro inhibitor. Relevance to humans is unknown.
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of polyunsaturated fatty acids (PUFA) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates PUFA specifically at the omega-1 position (PubMed:18577768). Catalyzes the epoxidation of double bonds of PUFA (PubMed:19965576, PubMed:20972997). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine. Hydroxylates fenbendazole at the 4' position (PubMed:23959307)
- Specific Function
- (R)-limonene 6-monooxygenase activity
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55944.565 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- In vitro inhibitor. Relevance to humans is unknown.
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
- Specific Function
- 1,8-cineole 2-exo-monooxygenase activity
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- In vitro inhibitor. Relevance to humans is unknown.
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of steroid hormones and vitamins (PubMed:10681376, PubMed:11093772, PubMed:12865317, PubMed:2732228). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:10681376, PubMed:11093772, PubMed:12865317, PubMed:2732228). Exhibits high catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes 6beta-hydroxylation of the steroid hormones testosterone, progesterone, and androstenedione (PubMed:2732228). Catalyzes the oxidative conversion of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes all trans-retinoic acid (atRA) to 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Also involved in the oxidative metabolism of xenobiotics, including calcium channel blocking drug nifedipine and immunosuppressive drug cyclosporine (PubMed:2732228)
- Specific Function
- aromatase activity
- Gene Name
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Enzyme that can both act as a NAD(P)H-dependent reductase and a S-nitroso-CoA-dependent nitrosyltransferase (PubMed:10620517, PubMed:18241201, PubMed:27207795, PubMed:38056462, PubMed:7929092). Promotes fetal heme degradation during development (PubMed:10858451, PubMed:18241201, PubMed:7929092). Also expressed in adult tissues, where it acts as a regulator of hematopoiesis, intermediary metabolism (glutaminolysis, glycolysis, TCA cycle and pentose phosphate pathway) and insulin signaling (PubMed:27207795, PubMed:29500232, PubMed:38056462). Has a broad specificity oxidoreductase activity by catalyzing the NAD(P)H-dependent reduction of a variety of flavins, such as riboflavin, FAD or FMN, biliverdins, methemoglobin and PQQ (pyrroloquinoline quinone) (PubMed:10620517, PubMed:18241201, PubMed:7929092). Contributes to fetal heme catabolism by catalyzing reduction of biliverdin IXbeta into bilirubin IXbeta in the liver (PubMed:10858451, PubMed:18241201, PubMed:7929092). Biliverdin IXbeta, which constitutes the major heme catabolite in the fetus is not present in adult (PubMed:10858451, PubMed:18241201, PubMed:7929092). Does not reduce bilirubin IXalpha (PubMed:10858451, PubMed:18241201, PubMed:7929092). Can also reduce the complexed Fe(3+) iron to Fe(2+) in the presence of FMN and NADPH (PubMed:10620517). Acts as a protein nitrosyltransferase by catalyzing nitrosylation of cysteine residues of target proteins, such as HMOX2, INSR and IRS1 (PubMed:38056462). S-nitroso-CoA-dependent nitrosyltransferase activity is mediated via 'ping-pong' mechanism: BLVRB first associates with both S-nitroso-CoA and protein substrate, nitric oxide group is then transferred from S-nitroso-CoA to Cys-109 and Cys-188 residues of BLVRB and from S-nitroso-BLVRB to the protein substrate (PubMed:38056462). Inhibits insulin signaling by mediating nitrosylation of INSR and IRS1, leading to their inhibition (PubMed:38056462)
- Specific Function
- biliberdin reductase NAD+ activity
- Gene Name
- BLVRB
- Uniprot ID
- P30043
- Uniprot Name
- Flavin reductase (NADPH)
- Molecular Weight
- 22119.215 Da
References
- FDA Approved Drug Products: PROVAYBLUE (methylene blue) injection, for intravenous use [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of fatty acids, steroids and retinoids (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:19965576, PubMed:20972997). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 20-hydroxyeicosatetraenoic acid ethanolamide (20-HETE-EA) and 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:18698000, PubMed:21289075). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Catalyzes the oxidative transformations of all-trans retinol to all-trans retinal, a precursor for the active form all-trans-retinoic acid (PubMed:10681376). Also involved in the oxidative metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants
- Specific Function
- anandamide 11,12 epoxidase activity
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017)
- Specific Function
- antioxidant activity
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Albumin
- Molecular Weight
- 69365.94 Da
References
- He LL, Wang YX, Wu XX, Liu XP, Wang X, Liu B, Wang X: Enhancement of the binding affinity of methylene blue to site I in human serum albumin by cupric and ferric ions. Luminescence. 2015 Dec;30(8):1380-8. doi: 10.1002/bio.2910. Epub 2015 Mar 31. [Article]
- Kozaki A, Watanabe J: Dose dependency of apparent volumes of distribution for methylene blue in rabbits. J Pharmacobiodyn. 1981 Jan;4(1):49-57. doi: 10.1248/bpb1978.4.49. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Translocates drugs and phospholipids across the membrane (PubMed:2897240, PubMed:35970996, PubMed:8898203, PubMed:9038218). Catalyzes the flop of phospholipids from the cytoplasmic to the exoplasmic leaflet of the apical membrane. Participates mainly to the flop of phosphatidylcholine, phosphatidylethanolamine, beta-D-glucosylceramides and sphingomyelins (PubMed:8898203). Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells (PubMed:2897240, PubMed:35970996, PubMed:9038218)
- Specific Function
- ABC-type xenobiotic transporter activity
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- ATP-dependent translocase ABCB1
- Molecular Weight
- 141477.255 Da
References
- Senarathna SM, Page-Sharp M, Crowe A: The Interactions of P-Glycoprotein with Antimalarial Drugs, Including Substrate Affinity, Inhibition and Regulation. PLoS One. 2016 Apr 5;11(4):e0152677. doi: 10.1371/journal.pone.0152677. eCollection 2016. [Article]
- Khdair A, Handa H, Mao G, Panyam J: Nanoparticle-mediated combination chemotherapy and photodynamic therapy overcomes tumor drug resistance in vitro. Eur J Pharm Biopharm. 2009 Feb;71(2):214-22. doi: 10.1016/j.ejpb.2008.08.017. Epub 2008 Aug 29. [Article]
- FDA Approved Drug Products: PROVAYBLUE (methylene blue) injection, for intravenous use [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- In vitro inhibition. Relevance to humans is unknown.
- General Function
- Electrogenic voltage-dependent transporter that mediates the transport of a variety of organic cations such as endogenous bioactive amines, cationic drugs and xenobiotics (PubMed:9260930, PubMed:9687576). Functions as a Na(+)-independent, bidirectional uniporter (PubMed:21128598, PubMed:9687576). Cation cellular uptake or release is driven by the electrochemical potential, i.e. membrane potential and concentration gradient (PubMed:15212162, PubMed:9260930, PubMed:9687576). However, may also engage electroneutral cation exchange when saturating concentrations of cation substrates are reached (By similarity). Predominantly expressed at the basolateral membrane of hepatocytes and proximal tubules and involved in the uptake and disposition of cationic compounds by hepatic and renal clearance from the blood flow (PubMed:15783073). Implicated in monoamine neurotransmitters uptake such as histamine, dopamine, adrenaline/epinephrine, noradrenaline/norepinephrine, serotonin and tyramine, thereby supporting a physiological role in the central nervous system by regulating interstitial concentrations of neurotransmitters (PubMed:16581093, PubMed:17460754, PubMed:9687576). Also capable of transporting dopaminergic neuromodulators cyclo(his-pro), salsolinol and N-methyl-salsolinol, thereby involved in the maintenance of dopaminergic cell integrity in the central nervous system (PubMed:17460754). Mediates the bidirectional transport of acetylcholine (ACh) at the apical membrane of ciliated cell in airway epithelium, thereby playing a role in luminal release of ACh from bronchial epithelium (PubMed:15817714). Also transports guanidine and endogenous monoamines such as vitamin B1/thiamine, creatinine and N-1-methylnicotinamide (NMN) (PubMed:12089365, PubMed:15212162, PubMed:17072098, PubMed:24961373, PubMed:9260930). Mediates the uptake and efflux of quaternary ammonium compound choline (PubMed:9260930). Mediates the bidirectional transport of polyamine agmatine and the uptake of polyamines putrescine and spermidine (PubMed:12538837, PubMed:21128598). Able to transport non-amine endogenous compounds such as prostaglandin E2 (PGE2) and prostaglandin F2-alpha (PGF2-alpha) (PubMed:11907186). Also involved in the uptake of xenobiotic 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP) (PubMed:12395288, PubMed:16394027). May contribute to regulate the transport of organic compounds in testis across the blood-testis-barrier (Probable)
- Specific Function
- acetylcholine transmembrane transporter activity
- Gene Name
- SLC22A2
- Uniprot ID
- O15244
- Uniprot Name
- Solute carrier family 22 member 2
- Molecular Weight
- 62579.99 Da
References
- FDA Approved Drug Products: PROVAYBLUE (methylene blue) injection, for intravenous use [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- In vitro inhibition. Relevance to humans is unknown.
- General Function
- Multidrug efflux pump that functions as a H(+)/organic cation antiporter. Mediates the efflux of cationic compounds, such as the model cations, tetraethylammonium (TEA) and 1-methyl-4-phenylpyridinium (MPP+), the platinum-based drug oxaliplatin or weak bases that are positively charged at physiological pH, cimetidine, the platinum-based drugs cisplatin and oxaliplatin or the antidiabetic drug metformin. Mediates the efflux of endogenous compounds such as, creatinine, thiamine and estrone-3-sulfate. Plays a physiological role in the excretion of drugs, toxins and endogenous metabolites through the kidney
- Specific Function
- antiporter activity
- Gene Name
- SLC47A2
- Uniprot ID
- Q86VL8
- Uniprot Name
- Multidrug and toxin extrusion protein 2
- Molecular Weight
- 65083.915 Da
References
- FDA Approved Drug Products: PROVAYBLUE (methylene blue) injection, for intravenous use [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- In vitro inhibition. Relevance to humans is unknown.
- General Function
- Multidrug efflux pump that functions as a H(+)/organic cation antiporter (PubMed:16330770, PubMed:17509534). Plays a physiological role in the excretion of cationic compounds including endogenous metabolites, drugs, toxins through the kidney and liver, into urine and bile respectively (PubMed:16330770, PubMed:17495125, PubMed:17509534, PubMed:17582384, PubMed:18305230, PubMed:19158817, PubMed:21128598, PubMed:24961373). Mediates the efflux of endogenous compounds such as creatinine, vitamin B1/thiamine, agmatine and estrone-3-sulfate (PubMed:16330770, PubMed:17495125, PubMed:17509534, PubMed:17582384, PubMed:18305230, PubMed:19158817, PubMed:21128598, PubMed:24961373). May also contribute to regulate the transport of cationic compounds in testis across the blood-testis-barrier (Probable)
- Specific Function
- antiporter activity
- Gene Name
- SLC47A1
- Uniprot ID
- Q96FL8
- Uniprot Name
- Multidrug and toxin extrusion protein 1
- Molecular Weight
- 61921.585 Da
References
- FDA Approved Drug Products: PROVAYBLUE (methylene blue) injection, for intravenous use [Link]
Drug created at October 23, 2015 20:18 / Updated at October 13, 2024 00:21