Details of the Drug Inactive Ingredient (DIG)

General Information of DIG (ID: E0I9JZ)
DIG Name
Methylene blue
Synonyms    Click to Show/Hide the Synonyms of This DIG
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 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 BB; 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
DIG Function
Colorant
PubChem CID
6099
Formula
C16H18ClN3S
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
   Click to Show/Hide the Molecular Data (Structure/Property) of This DIG
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=6099"></iframe>
3D MOL is not available 2D MOL
Physicochemical Properties Molecular Weight 319.9 Topological Polar Surface Area 43.9
XlogP N.A. Complexity 483
Heavy Atom Count 21 Rotatable Bond Count 1
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 4
Full List of Biological Targets of DIG (DBTs) Regulated by This DIG
      G-protein coupled receptor (GPCR)
            DBT Name: Muscarinic receptor M1 (ACM1) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 = 6.3 uM (tested by experiment) [1]
                    Tested Species Homo sapiens (Human)
                    UniProt ID ACM1_HUMAN
            DBT Name: Muscarinic receptor M2 (ACM2) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 = 0.19 uM (tested by experiment) [1]
                    Tested Species Homo sapiens (Human)
                    UniProt ID ACM2_HUMAN
            DBT Name: Opioid receptor mu (OPRM1) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 = 6.2 uM (tested by experiment) [1]
                    Tested Species Homo sapiens (Human)
                    UniProt ID OPRM_HUMAN
            DBT Name: Alpha-2A adrenoceptor (ADA2A) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 = 5.5 uM (tested by experiment) [1]
                    Tested Species Homo sapiens (Human)
                    UniProt ID ADA2A_HUMAN
            DBT Name: Histamine H3 receptor (HRH3) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 = 0.88 uM (tested by experiment) [1]
                    Tested Species Homo sapiens (Human)
                    UniProt ID HRH3_HUMAN
      Oxidoreductase (ORase)
            DBT Name: Thioredoxin reductase TR1 (TXNRD1) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 = 30000 nM (tested by experiment) [2]
                    Tested Species Homo sapiens (Human)
                    UniProt ID TRXR1_HUMAN
            DBT Name: Glutathione reductase (GSR) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 = 16000 nM (tested by experiment) [3]
                    Tested Species Homo sapiens (Human)
                    UniProt ID GSHR_HUMAN
            DBT Name: Monoamine oxidase A (MAO-A) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 = 70 nM (tested by experiment) [4]
                    Tested Species Homo sapiens (Human)
                    UniProt ID AOFA_HUMAN
            DBT Name: Prostaglandin G/H synthase 1 (COX-1) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 = 24 uM (tested by experiment) [1]
                    Tested Species Homo sapiens (Human)
                    UniProt ID PGH1_HUMAN
            DBT Name: Prostaglandin G/H synthase 2 (COX-2) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 = 1.8 uM (tested by experiment) [1]
                    Tested Species Homo sapiens (Human)
                    UniProt ID PGH2_HUMAN
      Transferase (TFase)
            DBT Name: VEGF-2 receptor (KDR) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 > 3 uM (tested by experiment) [1]
                    Tested Species Homo sapiens (Human)
                    UniProt ID VGFR2_HUMAN
      Hydrolase (HDase)
            DBT Name: Acetylcholinesterase (ACHE) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 = 0.09 uM (tested by experiment) [1]
                    Tested Species Homo sapiens (Human)
                    UniProt ID ACES_HUMAN
            DBT Name: Coagulation factor IIa (F2) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 = 24 uM (tested by experiment) [1]
                    Tested Species Homo sapiens (Human)
                    UniProt ID THRB_HUMAN
      Potential-driven transporter (PDT)
            DBT Name: Dopamine transporter (DAT) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 = 4.6 uM (tested by experiment) [1]
                    Tested Species Homo sapiens (Human)
                    UniProt ID SC6A3_HUMAN
            DBT Name: Norepinephrine transporter (NET) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 = 2.9 uM (tested by experiment) [1]
                    Tested Species Homo sapiens (Human)
                    UniProt ID SC6A2_HUMAN
            DBT Name: Serotonin transporter (SERT) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 = 8.3 uM (tested by experiment) [1]
                    Tested Species Homo sapiens (Human)
                    UniProt ID SC6A4_HUMAN
      Transmembrane channel/porin (TC/P)
            DBT Name: Amyloid-beta A4 protein (APP) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 = 500 nM (tested by experiment) [5]
                    Tested Species Homo sapiens (Human)
                    UniProt ID A4_HUMAN
            DBT Name: Potassium channel Kv11.1 (KCNH2) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 = 27.5 uM (tested by experiment) [1]
                    Tested Species Homo sapiens (Human)
                    UniProt ID KCNH2_HUMAN
      Other protein families (OPF)
            DBT Name: Neurofibrillary tangle protein (MAPT) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity EC50 = 130 nM (tested by experiment) [6]
                    Tested Species Homo sapiens (Human)
                    UniProt ID TAU_HUMAN
References
1 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
2 Interactions of methylene blue with human disulfide reductases and their orthologues from Plasmodium falciparum. Antimicrob Agents Chemother. 2008 Jan; 52(1):183-91.
3 5-substituted tetrazoles as bioisosteres of carboxylic acids. Bioisosterism and mechanistic studies on glutathione reductase inhibitors as antimalarials. J Med Chem. 2004 Nov 18; 47(24):5972-83.
4 The evaluation of 1,4-benzoquinones as inhibitors of human monoamine oxidase. Eur J Med Chem. 2017 Jul 28; 135:196-203.
5 Design and synthesis of curcumin derivatives as tau and amyloid dual aggregation inhibitors. Bioorg Med Chem Lett. 2016 Oct 15; 26(20):5024-5028.
6 Advancement of multi-target drug discoveries and promising applications in the field of Alzheimer's disease. Eur J Med Chem. 2019 May 1; 169:200-223.

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