Methylene blue
Highest phase reached
Approved
Drug type
Small molecule
First approval year
2016
- First approval year
- 2016
- Listing at source
- Listed
- Highest phase reached
- Approved
- Drug type
- Small molecule
- Drug name
- Methylene blue
- Molecular weight
- 373.91
- Structure (SMILES)
- CN(C)c1ccc2nc3ccc(=[N+](C)C)cc-3sc2c1.O.O.O.[Cl-]
- provayblue
- Provayblue
- basic blue 9
- Basic blue 9
- basic blue 9 trihydrate
- Basic blue 9 trihydrate
- c i 52015
- c i basic blue 9
- c i basic blue 9 trihydrate
- C.I. 52015
- C.i. basic blue 9
- C.i. basic blue 9 trihydrate
- ci 52015
- CI 52015
- CI-52015
- intravenous methylene blue
- Intravenous Methylene blue
- lowacryl blue 9
- Lowacryl blue 9
- methylene blue
- Methylene blue
- Methylene Blue
- METHYLENE BLUE [HPUS]
- METHYLENE BLUE [IARC]
- METHYLENE BLUE [II]
- METHYLENE BLUE [ORANGE BOOK]
- METHYLENE BLUE [USP MONOGRAPH]
And 23 more, listed on the interactive page.
- CAS registry numbers
- 7220-79-3
- ChEMBL ID
- CHEMBL550495
- InChIKey
- XQAXGZLFSSPBMK-UHFFFAOYSA-M
- PubChem compound IDs
- 104827
- RxNorm IDs (RxCUI)
- 6878
- FDA ingredient codes (UNII)
- T42P99266K
- V03AB17
- V04CG05
Sources for recorded values
- Applicant
- PROVEPHARM SAS
- Approval date
- 8 Apr 2016
- Application number
- NDA204630
- Patents
- 0
- Designations
- 2
- Earliest recorded loss of exclusivity
- 8 Jan 2027
- First in class
- No
- Fast track
- No
- Breakthrough designation
- No
- Orphan designation
- No
- Priority review
- No
- Orphan exclusivity
- No
- Accelerated approval
- No
- Availability
- Prescription only
- Boxed warning
- Yes
Administration routes
- Parenteral
Open Targets mechanisms
- Mechanism
- Soluble guanylate cyclase inhibitor
- Action type
- Inhibitor
- Target
- Soluble guanylate cyclase
- Condition
- Wounds and Injuries
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000546
- Subject identifier
- D014947
- Condition
- Severe Acute Respiratory Syndrome
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000694
- Subject identifier
- D045169
- Condition
- Malaria
- Highest recorded phase
- 2
- Condition identifier
- EFO:0001068
- Subject identifier
- D008288
- Condition
- Stress Disorders, Post-Traumatic
- Highest recorded phase
- 2
- Condition identifier
- EFO:0001358
- Subject identifier
- D013313
- Condition
- Abscess
- Highest recorded phase
- 2
- Condition identifier
- EFO:0003030
- Subject identifier
- D000038
- Condition
- Urinary Tract Infections
- Highest recorded phase
- 4
- Condition identifier
- EFO:0003103
- Subject identifier
- D014552
- Condition
- Dysuria
- Highest recorded phase
- 3
- Condition identifier
- EFO:0003901
- Subject identifier
- D053159
- Condition
- Shock, Septic
- Highest recorded phase
- 3
- Condition identifier
- EFO:0006834
- Subject identifier
- D012772
- Condition
- Glucosephosphate Dehydrogenase Deficiency
- Highest recorded phase
- 1
- Condition identifier
- EFO:0007287
- Subject identifier
- D005955
- Condition
- Malaria, Falciparum
- Highest recorded phase
- 2
- Condition identifier
- EFO:0007444
- Subject identifier
- D016778
- Condition
- Tooth Diseases
- Highest recorded phase
- 2
- Condition identifier
- EFO:1001216
- Subject identifier
- D014076
- Condition
- Jaundice
- Highest recorded phase
- 1
- Condition identifier
- HP:0000952
- Subject identifier
- D007565
- Condition
- Sepsis
- Highest recorded phase
- 1
- Condition identifier
- HP:0100806
- Subject identifier
- D018805
- Condition
- Bipolar Disorder
- Highest recorded phase
- 3
- Condition identifier
- MONDO:0004985
- Subject identifier
- D001714
- Condition
- Severe Acute Respiratory Syndrome
- Highest recorded phase
- 2
- Condition identifier
- MONDO:0100096
- Subject identifier
- D045169
- Condition identifier
- EFO_0000546
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000694
- Highest recorded phase
- 1
- Condition identifier
- EFO_0001068
- Highest recorded phase
- 2
- Condition identifier
- EFO_0001358
- Highest recorded phase
- 2
- Condition identifier
- EFO_0003030
- Highest recorded phase
- 2
- Condition identifier
- EFO_0003103
- Condition identifier
- EFO_0003901
- Highest recorded phase
- 3
- Condition identifier
- EFO_0005762
- Condition identifier
- EFO_0006834
- Highest recorded phase
- 3
- Condition identifier
- EFO_0007287
- Highest recorded phase
- 1
- Condition identifier
- EFO_0007444
- Highest recorded phase
- 2
- Condition identifier
- EFO_0008506
- Condition identifier
- EFO_0009954
- Condition identifier
- EFO_1001068
- Condition identifier
- EFO_1001216
- Highest recorded phase
- 2
- Condition identifier
- EFO_1001459
- Highest recorded phase
- 1
- Condition identifier
- EFO_1001839
- Condition identifier
- HP_0000739
- Highest recorded phase
- 3
- Condition identifier
- HP_0000789
- Condition identifier
- HP_0001945
- Highest recorded phase
- 2
- Condition identifier
- HP_0002018
- Highest recorded phase
- 2
- Condition identifier
- HP_0002027
- Highest recorded phase
- 2
- Condition identifier
- HP_0100543
- Highest recorded phase
- 1
- Condition identifier
- HP_0100806
- Highest recorded phase
- 3
- Condition identifier
- MONDO_0001117
And 28 more, listed on the interactive page.
Warnings
- Warning
- Black Box Warning
Open Targets warnings
- Warning
- Black Box Warning
- Country
- United States
- Event
- agitation
- Reports
- 21
- Reporting signal score
- 33.2931
- Event
- alkalosis
- Reports
- 2
- Reporting signal score
- 8.52146
- Event
- amniotic cavity infection
- Reports
- 2
- Reporting signal score
- 6.96562
- Event
- amylase increased
- Reports
- 7
- Reporting signal score
- 22.0506
- Event
- anaphylactic reaction
- Reports
- 10
- Reporting signal score
- 9.73468
- Event
- anaphylactic shock
- Reports
- 8
- Reporting signal score
- 12.6089
- Event
- aphasia
- Reports
- 7
- Reporting signal score
- 9.97171
- Event
- blindness cortical
- Reports
- 2
- Reporting signal score
- 7.63205
- Event
- blood creatine phosphokinase increased
- Reports
- 11
- Reporting signal score
- 15.2091
- Event
- blood lactate dehydrogenase increased
- Reports
- 7
- Reporting signal score
- 12.2934
- Event
- blood phosphorus increased
- Reports
- 3
- Reporting signal score
- 8.86699
- Event
- blood potassium increased
- Reports
- 8
- Reporting signal score
- 17.4968
- Event
- bradycardia
- Reports
- 12
- Reporting signal score
- 11.7685
- Event
- brain injury
- Reports
- 3
- Reporting signal score
- 7.13051
- Event
- bundle branch block right
- Reports
- 4
- Reporting signal score
- 9.39267
- Event
- cardiac arrest
- Reports
- 10
- Reporting signal score
- 15.7183
- Event
- cardiogenic shock
- Reports
- 12
- Reporting signal score
- 33.2425
- Event
- chromaturia
- Reports
- 15
- Reporting signal score
- 38.8943
- Event
- clonus
- Reports
- 11
- Reporting signal score
- 42.4813
- Event
- coma
- Reports
- 8
- Reporting signal score
- 8.76078
- Event
- coma scale abnormal
- Reports
- 7
- Reporting signal score
- 21.9261
- Event
- compartment syndrome
- Reports
- 5
- Reporting signal score
- 15.5031
- Event
- confusion postoperative
- Reports
- 2
- Reporting signal score
- 10.5551
- Event
- confusional state
- Reports
- 27
- Reporting signal score
- 33.1171
- Event
- cyanosis central
- Reports
- 4
- Reporting signal score
- 20.7614
And 67 more, listed on the interactive page.
- NCT00159510
- NCT00214877
- NCT00354380
- NCT00545935
- NCT00917202
- NCT02831023
- NCT01188694
- NCT01407887
- NCT02851108
- NCT01657448
- NCT01668433
- NCT02240498
- NCT06052956
- NCT02555488
- NCT03177070
- NCT03379389
- NCT04089072
- NCT04295993
- NCT04446871
- NCT04109859
- NCT04370288
- NCT04635605
- NCT04933864
- NCT05004805
- NCT04619290
- Dose
- 1 mg/kg
- Route
- Intravenous
- How often
- Every 1 hour as needed, up to 2 doses
- Dilute in 50 mL 5% Dextrose Injection before use
- Do not administer subcutaneously
- Inspect for particulate matter and discoloration
- Use immediately after preparation
- Hydrogen bond acceptors
- 3
- Hydrogen bond donors
- 0
- Polar surface area
- 19.14
- Calculated partition coefficient (ALogP)
- 2.5
- Prodrug
- Yes
- Chirality
- Achiral
- Inorganic
- No
- Rule-of-five violations
- 0
- Rotatable bonds
- 1
- Heavy atoms
- 24
- Molecular formula
- C16H24ClN3O3S
- Monoisotopic mass
- 373.1226905
- Natural product
- No
- 0037-6321
- 0143-9094
- 0178-0745
- 0485-0151
- 0517-0125
- 0517-0371
- 0517-0374
- 0517-0381
- 12539-144
- 14789-119
- 15243-344
- 28595-224
- 28595-299
- 54288-147
- 54288-159
- 58657-456
- 68462-698
- 70700-328
- 71288-811
- 82432-104
- 82449-002
- 82449-003
- 70121-2715
- 70121-2716
- 70710-1837
And 5 more, listed on the interactive page.
- Recorded assays
- 667
- Active assays
- 277
- Confirmatory
- Other
- Summary
Solubility
- Median
- 53,400,000
- Mean
- 53,400,000
- Minimum
- 53,400,000
- Maximum
- 53,400,000
- Unit
- nM
- Assays
- 1
- Standard deviation
- 0
- Summary method
- median
- Censored results excluded
- 0
- Other units excluded
- 0
- Unknown units excluded
- 0
Measurement types
- Solubility
Related records
Trials (82)
- 3D Printing for Nodule Localization
- A French Observational Study of Indocyanine Green for Patients With Breast Cancer Having a Sentinel Lymph Node Biopsy.
- A Phase 2 Study of Methylene Blue Photodynamic Therapy for Treatment of Breast Abscesses
- Acquired Methemoglobinemia Observational Registry
- Adjunctive Methylene Blue for Immunotherapy-related CRS and ICANS: Phase I Study
- Adjunctive Methylene Blue in Septic Shock
- Antimicrobial Photodynamic Therapy as an Adjunct Treatment for Periodontal Disease in Down's Syndrome Patients
- Application of Surgical Navigation System in Sentinel Lymph Node of Breast Cancer Research
- Clinical and Microbiologic Outcomes of aPDT in the Non-surgical Treatment of Implant Inflammation
- Clinical Application of Methylene Blue for Treatment of Covid-19 Patients
- Clinical Study of Methylene Blue - Mediated Photodynamic Therapy for Diabetic Lower Limb Ulcer
- Comparing the Antibacterial Effect of 810 nm Diode Laser and Photodynamic Therapy
- Comparison Between Two Techniques During Thyroidectomy (Conventional Dissection Technique and Injection of Methylene Blue Dye Into Inferior Thyroid Artery Technique) Regarding Recurrent Laryngeal Nerve Identification and Preservation
- COVID-19 Methylene Blue Antiviral Treatment
- COVID-19 Treatment Using Methylene Blue and Photodynamic Therapy
- Dose Parameters for Photodynamic Therapy on Periodontal Disease
- Early Methylene Blue in the Microhemodynamics of Septic Patients
- Effect of Methylene Blue on Perioperative Organ Function in Patients With Obstructive Jaundice
- Effects of Methylene Blue in Healthy Aging, Mild Cognitive Impairment and Alzheimer's Disease
- Effects of USP Methylene Blue on Cognitive and fMRI Brain Activity
Approved for (1)
In development for (12)
- Abscess Phase 2
- Bipolar disorder Phase 3
- Colorectal cancer Phase 3
- COVID-19 Phase 2
- G6PD deficiency Phase 1
- Injury Phase 2
- Malaria Phase 2
- Plasmodium falciparum malaria Phase 2
- Post-traumatic stress disorder Phase 2
- Severe acute respiratory syndrome Phase 2
- Tooth disorder Phase 2
- Toxic shock syndrome Phase 3
Other linked conditions (5)
- Breast cancer
- Drug-induced methemoglobinemia
- Hyperparathyroidism
- Obstructive jaundice
- Periodontal disorder