Details of the Drug

General Information of Drug (ID: DMJAPE7)

Drug Name

Methylene blue

Synonyms

methylene blue; 61-73-4; Methylthioninium chloride; Swiss Blue; Chromosmon; Methylene Blue N; Methylenium ceruleum; Urolene blue; Methylene Blue chloride; Solvent blue 8; Bleu de methylene; Methylene Blue G; Methylene Blue A; External Blue 1; Methylene Blue D; Methylene Blue B; Methylene Blue anhydrous; CI Basic Blue 9; Methylene Blue ZF; Methylene Blue SP; Methylene Blue NZ; Methylene Blue BX; Methylene Blue BD; Methylene Blue SG; Tetramethylene Blue; Methylene Blue ZX; Methylene Blue FZ; Methylene Blue BP; Calcozine; 3,7-Bis-dimethylamino-phenothiazin-5-ylium

Indication

Disease Entry	ICD 11	Status	REF
Acquired methemoglobinemia	3A93	Approved	[1]

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski):
0

Molecular Weight

319.9

Topological Polar Surface Area

Not Available

Rotatable Bond Count

1

Hydrogen Bond Donor Count

0

Hydrogen Bond Acceptor Count

4

ADMET Property

Clearance: The clearance of drug is 3.0? +/- ?0.7 L/min [2]
Half-life: The concentration or amount of drug in body reduced by one-half in 5 C 6.5 hours [3]

Chemical Identifiers

Formula: C16H18ClN3S
IUPAC Name: [7-(dimethylamino)phenothiazin-3-ylidene]-dimethylazanium;chloride
Canonical SMILES: CN(C)C1=CC2=C(C=C1)N=C3C=CC(=[N+](C)C)C=C3S2.[Cl-]
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
InChIKey: CXKWCBBOMKCUKX-UHFFFAOYSA-M

Cross-matching ID

PubChem CID: 6099
ChEBI ID: CHEBI:6872
CAS Number: 61-73-4
DrugBank ID: DB09241
TTD ID: D09NYS

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Guanylate cyclase (GC)	TT6HPVC	NOUNIPROTAC	Inhibitor	[4]
Monoamine oxidase (MAO)	TT32XQJ	NOUNIPROTAC	Not Available	[5]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Methylene blue (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Levalbuterol	DM5YBO1	Moderate	Additive hypertensive effects by the combination of Methylene blue and Levalbuterol.	Asthma [CA23]	[12]
Esketamine	DMVU687	Major	Additive hypertensive effects by the combination of Methylene blue and Esketamine.	Depression [6A70-6A7Z]	[13]
Deutetrabenazine	DMUPFLI	Major	Additive hypertensive effects by the combination of Methylene blue and Deutetrabenazine.	Dystonic disorder [8A02]	[14]
Lasmiditan	DMXLVDT	Major	Additive serotonergic effects by the combination of Methylene blue and Lasmiditan.	Migraine [8A80]	[15]
Ozanimod	DMT6AM2	Major	Decreased metabolism of Methylene blue caused by Ozanimod mediated inhibition of non-CYP450 enzyme.	Multiple sclerosis [8A40]	[16]
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References

1	Recombinant Plasmodium falciparum glutathione reductase is inhibited by the antimalarial dye methylene blue. FEBS Lett. 1998 Feb 6;422(3):311-4.
2	An FDA phase I clinical trial of quinacrine sterilization (QS). Int J Gynaecol Obstet. 2003 Oct;83 Suppl 2:S45-9.
3	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4	Curcumin ameliorates high glucose-induced acute vascular endothelial dysfunction in rat thoracic aorta. Clin Exp Pharmacol Physiol. 2009 Dec;36(12):1177-82.
5	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.
6	Novel monoamine oxidase inhibitors: a patent review (2012 - 2014).Expert Opin Ther Pat. 2015 Jan;25(1):91-110.
7	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
8	LSD1 inhibitors: a patent review (2010-2015).Expert Opin Ther Pat. 2016 May;26(5):565-80.
9	Nitric oxide and nitric oxide synthase isoforms in the normal, hypertrophic, and failing heart. Mol Cell Biochem. 2010 Jan;333(1-2):191-201.
10	Activation of soluble guanylyl cyclase by the nitrovasodilator 3-morpholinosydnonimine involves formation of S-nitrosoglutathione. Mol Pharmacol. 1998 Jul;54(1):207-12.
11	Clinical pipeline report, company report or official report of Cyclerion Therapeutics.
12	Boakes AJ, Laurence DR, Teoh PC, Barar FS, Benedikter LT, Prichard BN "Interactions between sympathomimetic amines and antidepressant agents in man." Br Med J 1 (1973): 311-5. [PMID: 4685619]
13	Cerner Multum, Inc. "Australian Product Information.".
14	Product Information. Austedo (deutetrabenazine). Teva Pharmaceuticals USA, North Wales, PA.
15	Boyer EW, Shannon M "The serotonin syndrome." N Engl J Med 352 (2005): 1112-20. [PMID: 15784664]
16	Product Information. Zeposia (ozanimod). Celgene Corporation, Summit, NJ.