Drug Details

General Information of the Drug (ID: DR5094)
Name
Methylene blue
Synonyms
methylene blue; 61-73-4; Basic blue 9; Methylthioninium chloride; Swiss Blue; Solvent blue 8; Chromosmon; 3,7-Bis(dimethylamino)phenothiazin-5-ium chloride; Methylene Blue N; Methylene Blue BB; Methylene Blue anhydrous; Bleu de methylene; Methylene Blue chloride; External Blue 1; Methylene Blue A; Methylene Blue B; Methylene Blue D; Methylene Blue G; C.I. Basic Blue 9; Calcozine Blue ZF; Methylene Blue BD; Methylene Blue BP; Methylene Blue BX; Methylene Blue BZ; Methylene Blue FZ; Methylene Blue GZ; Methylene Blue NZ; Methylene Blue SG; Methylene Blue SP; Methylene Blue ZF; Methylene Blue ZX; Tetramethylene Blue; Methylene Blue 2B; Methylenium ceruleum; Methylene Blue BBA; Methylene Blue BPC; Methylene Blue HGG; Methylene Blue IAD; Methylene Blue JFA; Sandocryl Blue BRL; Methylenblau; Methylene Blue 2BF; Methylene Blue 2BN; Methylene Blue 2BP; M-B Tabs; Rember; Mitsui Methylene Blue; Methylthionium chloride; Leather Pure Blue HB; Methylthionine chloride; Modr methylenova; Schultz No. 1038; Aizen Methylene Blue BH; Aizen Methylene Blue FZ; Methylene Blue polychrome; Methylene Blue Zinc Free; Yamamoto Methylene Blue B; D And C Blue Number 1; Tetramethylthionine chloride; Methylene Blue (Medicinal); Yamamoto Methylene Blue ZF; Ext D and C Blue No. 1; Methylene Blue I (Medicinal); Cloruro de metiltioninio; Methylene Blue NF (Medicinal); Methylthioninii chloridum; Hidaco Methylene Blue Salt Free; Methylene Blue BB (Zinc Free); Methylene Blue USP (Medicinal); Phenothiazin-5-ium, 3,7-bis(dimethylamino)-, chloride; Chlorure de methylthioninium; Methylene Blue USP XII (Medicinal); UNII-8NAP7826UB; Methylene Blue Chloride (Biological stain); C.I. 52015; X 138; 3,7-Bis(dimethylamino)phenazathionium chloride; MFCD00012111; 8NAP7826UB; CHEBI:6872; Urolene blue; Methylene Blue (C.I. 52015); CI 52015; azul de metileno; Phenothiazin-5-ium, 3,7-bis(dimethylamino)-, chloride (1:1); DSSTox_CID_3296; N-[7-(dimethylamino)-3H-phenothiazin-3-ylidene]-N-methylmethanaminium chloride; Ceruleum methylenum; DSSTox_RID_76963; DSSTox_GSID_23296; 12262-49-6; Methylenum coeruleum; CI-52015; CI Basic Blue 9; Caswell No. 567; Methylenblau [German]; Methylthionini chloridum; 3H-Phenothiazine, 3-methochloride; Modr Methylenova [Czech]; CHEMBL405110; Modr zasadita 9; Modr Zasadita 9 [Czech]; CAS-61-73-4; N-(7-(dimethylamino)-3H-phenothiazin-3-ylidene)-N-methylmethanaminium chloride; NSC3089; CCRIS 833; Metiltioninio cloruro [DCIT]; Metiltioninio cloruro; Modr Rozpoustedlova 8 [Czech]; 3H-Phenothiazine, 7-(dimethylamino)-3-(methylimino)-, 3-methochloride; Modr rozpoustedlova 8; NSC215213; NSC617593; C.I. 52 015; HSDB 1405; Methylene Blue, pure, certified, residual water; NSC-215213; NSC-617593; NCGC00167496-01; NCGC00167496-03; Phenothiazin-5-ium,7-bis(dimethylamino)-, chloride; EINECS 200-515-2; Methylthioninii chloridum [INN-Latin]; EPA Pesticide Chemical Code 039505; NSC 215213; Cloruro de metiltioninio [INN-Spanish]; WLN: T C666 BS EY INJ EUK1&1 MN1&1 &G &421; Provayblue; Chlorure de methylthioninium [INN-French]; [7-(dimethylamino)phenothiazin-3-ylidene]dimethylamine, chloride; Lowacryl blue 9; Methylene Azure II; Prestwick_326; Ehrlichs reagent III; Loefflers Methylene Blue; Methylene Blue (Inhibitor); SCHEMBL1351; MLS000719838; DOG (COUCH) GRASS Powder; DTXSID0023296; Methylthioninium chloride [INN]; C.I. Basic Blue 9 (8CI); HMS2598O03; Pharmakon1600-01505444; CI NO 52015; NSC-3089; Tox21_112497; Tox21_302087; NSC759135; s4535; SBB060907; STK018918; AKOS000486124; AKOS015916406; Tox21_112497_1; CCG-267696; DB09241; MCULE-7744087830; NSC-759135; 4-(1-HYDROXY-ETHYL)-BENZOICACID; NCGC00255351-01; 105504-42-5; AC-15225; AK326199; AS-35256; Basic Blue 9;Tetramethylthionine chloride; HY-14536; Methylene Blue, 1% w/v aqueous solution; SMR000304367; ST093058; SY076497; Methylthioninium Chloride (Methylene Blue); Methylene Blue (C.I. 52015) BioChemica; A0574; FT-0622580; M0501; ST50406802; C00220; 3,7-Bis(dimethylamino)-5-phenothiazinium Chloride; Q422134; 3,7-bis(dimethylamino)-phenothiazin-5-ium chloride salt; [7-(dimethylamino)phenothiazin-3-ylidene]-dimethylazanium;chloride; [7-(dimethylamino)dibenzo[b,e]1,4-thiazin-3-yl]dimethylamine, chloride; 3-N,3-N,7-N,7-N-tetramethylphenothiazin-5-ium-3,7-diamine;chloride; 1341-90-8; 152071-32-4; 6476-03-5; 97130-83-1
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Molecular Type
Small molecule
Disease Acquired methaemoglobinaemia [ICD-11: 3A93] Approved [1]
Structure
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2D MOL

3D MOL

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Formula
C16H18ClN3S
PubChem CID
6099
Canonical SMILES
CN(C)C1=CC2=C(C=C1)N=C3C=CC(=[N+](C)C)C=C3S2.[Cl-]
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
InChIKey
CXKWCBBOMKCUKX-UHFFFAOYSA-M
CAS Number
CAS 61-73-4
ChEBI ID
CHEBI:6872
TTD Drug ID
D09NYS
DrugBank ID
DB09241
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Salicylic acid      Salix abscondita     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model MDA-MB-231 CVCL_0062 Breast adenocarcinoma Homo sapiens
                    Experimental
                    Result(s)		 Cancer cell killing efficiency of MB increases in the combination with SA due to reduction prevention and stabilization of monomeric form of MB.
Target and Pathway
Target(s) Guanylate cyclase (GC)  Molecule Info  [3]
Monoamine oxidase (MAO)  Molecule Info  [4]
References
Reference 1 Recombinant Plasmodium falciparum glutathione reductase is inhibited by the antimalarial dye methylene blue. FEBS Lett. 1998 Feb 6;422(3):311-4.
Reference 2 Combination photodynamic therapy of human breast cancer using salicylic acid and methylene blue. Spectrochim Acta A Mol Biomol Spectrosc. 2017 Sep 5;184:198-203.
Reference 3 Curcumin ameliorates high glucose-induced acute vascular endothelial dysfunction in rat thoracic aorta. Clin Exp Pharmacol Physiol. 2009 Dec;36(12):1177-82.
Reference 4 Photoluminescence of CdTe nanocrystals modulated by methylene blue and DNA. A label-free luminescent signaling nanohybrid platform. Phys Chem Chem Phys. 2009 Jul 7;11(25):5062-9.
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