METHYLENE BLUE

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Search structure


Trade Names	PROVAYBLUE
Synonyms	Basic blue 9 trihydrate C.I. 52015 C.i. basic blue 9 trihydrate CI 52015 CI-52015 DNDI1417128 Methylene blue Methylene blue trihydrate Methylthionine chloride Methylthionine hydrochloride Methylthioninium chloride NSC-215213 NSC-617593 NSC-759135 Provayblue Trx0014 Urolene blue
Status
Molecule Category	Mixture
UNII	ZMZ79891ZH
EPA CompTox	DTXSID3047009


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	RBTBFTRPCNLSDE-UHFFFAOYSA-N
Smiles	CN(C)c1ccc2nc3ccc(=[N+](C)C)cc-3sc2c1
InChI	InChI=1S/C16H18N3S/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/q+1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C16H24ClN3O3S
Molecular Weight	373.91
AlogP	2.5
Hydrogen Bond Acceptor	3.0
Hydrogen Bond Donor	0.0
Number of Rotational Bond	1.0
Polar Surface Area	19.14
Molecular species	NEUTRAL
Aromatic Rings	1.0
Heavy Atoms	20.0

Bioactivity

Mechanism of Action	Action	Reference
Reducing agent	None	FDA

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Oxidoreductase	-	4370	-	-	24
Enzyme Transferase	-	6100	-	-	-
Membrane receptor	-	550	-	-	5
Other cytosolic protein	-	2200	-	-	-
Unclassified protein	-	3300	-	-	54-67

Assay Description	Organism	Bioactivity	Reference
DNDI: Inhibition of Human African Trypanosomiasis (HAT), STIB 795, in vitro	Trypanosoma brucei brucei	20.0 nM
Antimalarial activity against Plasmodium falciparum gametocytes by GFP-luciferase reporter gene assay	Plasmodium falciparum	12.0 nM
Inhibition of Setaria cervi glutathione reductase at 2 to 200 uM	Setaria cervi	24.0 %
Antitrypanosomal activity against infective form of Trypanosoma brucei brucei strain 427 assessed as growth inhibition	Trypanosoma brucei brucei	400.0 nM
Antimalarial activity against Plasmodium falciparum K1 assessed as inhibition of [3H]hypoxanthine incorporation preincubated for 48 hrs measured 24 hrs post [3H]hypoxanthine addition by liquid scintillation counting	Plasmodium falciparum K1	5.2 nM
Antimalarial activity against Plasmodium falciparum NFS4 assessed as inhibition of [3H]hypoxanthine incorporation preincubated for 48 hrs measured 24 hrs post [3H]hypoxanthine addition by liquid scintillation counting	Plasmodium falciparum	4.2 nM
Inhibition of amyloid beta (1-42) aggregation (unknown origin) after 24 hrs by thioflavin T fluorescence method	Homo sapiens	550.0 nM
Inhibition of human recombinant MAOA using kynuramine substrate assessed as reduction in MAO-generated 4-hydroxyquinoline level by fluorescence spectrophotometry	Homo sapiens	70.0 nM
Inhibition of Amyloid beta (1 to 40) (unknown origin) aggregation assessed as amount of fibrils formation after 2 hrs by thioflavin T based spectrofluorimetric method	Homo sapiens	4.5 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	99.16 %
Inhibition of Escherichia coli GroEL expressed in Escherichia coliDH5alpha/Escherichia coli GroES expressed in Escherichia coli BL21 (DE3) assessed as reduction in GroEL/GroES-mediated denatured soluble pig heart MDH refolding by measuring MDH enzyme activity using sodium mesoxalate as substrate after 20 to 40 mins by malachite green dye based spectrometric analysis relative to untreated control	Escherichia coli	54.0 %
Inhibition of Escherichia coli GroEL expressed in Escherichia coli DH5alpha/Escherichia coli GroES expressed in Escherichia coli BL21 (DE3) assessed as reduction in GroEL/GroES-mediated denatured rhodanese refolding by measuring rhodanese enzyme activity after 45 mins by Fe(SCN)3 dye based spectrometric analysis relative to untreated control	Escherichia coli	67.0 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	-9.1 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	-9.023 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.02 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.07 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.07 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.02 %

Cross References

Resources	Reference
ChEBI	43830
ChEMBL	CHEMBL191083
DrugBank	DB08167
DrugCentral	1763
FDA SRS	ZMZ79891ZH
PDB	MBT
PubChem	104827
SureChEMBL	SCHEMBL109755
ZINC	ZINC000012414057
ChEMBL	CHEMBL550495
FDA SRS	T42P99266K
PubChem	104827
SureChEMBL	SCHEMBL1207311

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).