Methylene Blue Cation

Summary

Methylene Blue Cation (CHEMBL191083) is an approved small molecule.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• Clinical trials: 77
• Chemistry: 284.4 Da · C16H18N3S+

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL191083
Name	Methylene Blue Cation
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	4139
ChEBI	CHEBI:43830
Molecular formula	C16H18N3S+
Molecular weight	284.4
InChIKey	RBTBFTRPCNLSDE-UHFFFAOYSA-N

SMILES: CN(C)C1=CC2=C(C=C1)N=C3C=CC(=[N+](C)C)C=C3S2

IUPAC name: [7-(dimethylamino)phenothiazin-3-ylidene]-dimethylazanium

ChEBI definition: An organic cation that is phenothiazin-5-ium substituted by dimethylamino groups at positions 3 and 7. The chloride salt is the histological dye ‘methylene blue’.

Also known as: Dndi1417128, SID29215388, SID50112749, SID124893332, DNDI1417128, methylene blue, Methylene blue, Methylene Blue, METHYLENE BLUE

Parent form; salt/anhydrous children: CHEMBL405110, CHEMBL550495

Patent coverage: 4,000 distinct patent families (7,622 SureChEMBL compound mentions), from 4 matched compound structure(s). One matched structure accounts for 7,034 (92%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 15 (assay-derived). Sample: Tyrosyl-DNA phosphodiesterase 1, Microtubule-associated protein tau, Fructose-bisphosphate aldolase, ATP-dependent DNA helicase Q1, RecQ-like DNA helicase BLM, Inositol monophosphatase 1, 4’-phosphopantetheinyl transferase ffp, Ferritin light chain, Histone-lysine N-methyltransferase 2A, Thyroid hormone receptor beta.

Bioactivity

ChEMBL activities: 6 potent at pChembl ≥ 5 of 22 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
MAOA	7.16	IC50	70	nM	CHEMBL_ACT_15183054
APP	6.26	IC50	550	nM	CHEMBL_ACT_14999890
MAPT	5.7	Potency	1995	nM	CHEMBL_ACT_4064805
MAPT	5.66	IC50	2200	nM	CHEMBL_ACT_14999924
MAPT	5.55	Potency	2818	nM	CHEMBL_ACT_3965819
MAOB	5.36	IC50	4370	nM	CHEMBL_ACT_15183033

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

0 indications (0 at ChEMBL trial phase 4).

Clinical trials

Total trials: 77.

Phase distribution

Phase	Trials
Not specified	28
PHASE2	21
PHASE3	8
PHASE4	7
PHASE1	7
EARLY_PHASE1	3
PHASE2/PHASE3	2
PHASE1/PHASE2	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT07164807	PHASE4	NOT_YET_RECRUITING	Efficacy of Methylene Blue Plus Ropivacaine for Post-Hemorrhoidectomy Pain.
NCT01386879	PHASE4	TERMINATED	Evaluation of Above the Cuff Suctioning During General Anesthesia
NCT02910765	PHASE4	UNKNOWN	Methylene Blue and Ozone in Early Sepsis
NCT03120637	PHASE4	COMPLETED	Evaluating in Cirrhotics With Refractory Vasoplegia the Effect of Methylene Blue
NCT03395223	PHASE4	COMPLETED	MEthylene Blue In Patients With Acquired Methemoglobinemia
NCT04054999	PHASE4	COMPLETED	Methylene Blue vs Cyanokit for Intraoperative Vasoplegic Syndrome in Liver Transplant Patients
NCT04187053	PHASE4	COMPLETED	Clinical and Microbiologic Outcomes of aPDT in the Non-surgical Treatment of Implant Inflammation
NCT06306001	PHASE2/PHASE3	NOT_YET_RECRUITING	Intravenous Methylene Blue for Treating Refractory Neonatal Septic Shock
NCT06660680	PHASE3	ENROLLING_BY_INVITATION	The Effect of Methylene Blue Infiltrating Injection on Anal Pain After Milligan-Morgan Surgery: A Randomized Controlled Clinical Study
NCT00214877	PHASE3	COMPLETED	Methylene Blue for Cognitive Dysfunction in Bipolar Disorder
NCT01847612	PHASE3	COMPLETED	Use of Indocyanine Green Cholangiography and Methylene Blue to Detect Postoperative Biliary Fistula After Hepatectomy
NCT03038503	PHASE3	UNKNOWN	What Should be the Next Vasopressor for Severe Septic Shock? Methylene Blue or Terlipressin
NCT03178747	PHASE3	UNKNOWN	Tzanck Smear With Methylene Blue Stain for Herpes
NCT04295993	PHASE3	UNKNOWN	Methylene Blue and Microcirculation in Septic Shock
NCT04446871	PHASE2/PHASE3	COMPLETED	Methylene Blue in Early Septic Shock
NCT06532240	PHASE3	COMPLETED	Methylene Blue for the Treatment of Septic Shock
NCT06900140	PHASE3	COMPLETED	Adjunctive Methylene Blue in Septic Shock
NCT06052956	PHASE2	NOT_YET_RECRUITING	Efficacy of Methylene Blue Photodynamic Therapy for Treatment of Deep Tissue Abscesses
NCT06887036	PHASE2	RECRUITING	Methylene Blue Treatment of Chronic Hepatitis B Virus Infection
NCT07179003	PHASE2	NOT_YET_RECRUITING	A Phase 2 Study of Methylene Blue Photodynamic Therapy for Treatment of Breast Abscesses
NCT00354380	PHASE2	COMPLETED	Safety and Efficacy of Methylene Blue Combined With Artesunate or Amodiaquine for Malaria Treatment in Children of Burkina Faso: a Pilot Study
NCT00784849	PHASE2	COMPLETED	Feasibility of One-Step Sentinel Lymph Node (SLN) Biopsy With Radiolabeled Methylene Blue (IND 70,627)
NCT01276054	PHASE2	TERMINATED	Sentinel and/or Axillary Lymph Node Biopsy With or Without Axillary Reverse Mapping in Reducing Incidence and Severity of Arm Lymphedema in Stage 0-2 Patients.
NCT02380573	PHASE2	COMPLETED	Effects of Methylene Blue in Healthy Aging, Mild Cognitive Impairment and Alzheimer’s Disease
NCT02555488	PHASE2	UNKNOWN	Comparing the Antibacterial Effect of 810 nm Diode Laser and Photodynamic Therapy
NCT02831023	PHASE2	COMPLETED	Phase 2 Efficacy Study of Primaquine and Methylene Blue
NCT02851108	PHASE2	COMPLETED	Methylene Blue Against Falciparum Malaria in Burkina Faso
NCT03177070	PHASE2	COMPLETED	Fluorescent Imaging & Methylene Blue: Ureter Study
NCT03446599	PHASE2	WITHDRAWN	Hemodynamic Effects of Methylene Blue vs Hydroxocobalamin in Patients at Risk of Vasoplegia During Cardiac Surgery
NCT03469284	PHASE2	COMPLETED	MOM’s PAIN (Methylene Blue for Oral Mucositis’ PAIN)
NCT04089072	PHASE2	UNKNOWN	Methylene Blue as a Third-line Vasopressor in Septic Shock
NCT04110418	PHASE2	UNKNOWN	Methylene Blue Versus Vasopressin Analogue for Treatment of Septic Shock in Preterm Neonate
NCT04376788	PHASE2	UNKNOWN	Exchange Transfusion Versus Plasma From Convalescent Patients With Methylene Blue in Patients With COVID-19
NCT04635605	PHASE2	COMPLETED	Methylene Blue Treatment of COVID-19
NCT05004805	PHASE2	COMPLETED	COVID-19 Methylene Blue Antiviral Treatment
NCT05090657	PHASE2	COMPLETED	Nasal Photodisinfection in All Patients Presenting for Surgery for a Wide Range of Surgical Procedures
NCT05092165	PHASE2	COMPLETED	Methylene Blue for the Prevention of Hypotension During Hemodialysis
NCT05797818	PHASE1/PHASE2	COMPLETED	Red Light Photobiomodulation and Topical Disinfectants
NCT07212842	PHASE2	COMPLETED	Methylene Blue-Enhanced Ultrafiltration Improves Outcomes After Cardiopulmonary Bypass
NCT07169487	PHASE1	RECRUITING	Adjunctive Methylene Blue for Immunotherapy-related CRS and ICANS: Phase I Study

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).