Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C16H18N3S.Cl.H2O |
| Molecular Weight | 337.867 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.[Cl-].CN(C)C1=CC2=[S+]C3=CC(=CC=C3N=C2C=C1)N(C)C
InChI
InChIKey=WQVSELLRAGBDLX-UHFFFAOYSA-M
InChI=1S/C16H18N3S.ClH.H2O/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;1H2/q+1;;/p-1
| Molecular Formula | C16H18N3S |
| Molecular Weight | 284.399 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | HO |
| Molecular Weight | 17.0073 |
| Charge | -1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: http://www.mdpoison.com/media/SOP/mdpoisoncom/healthcareprofessionals/antidote-facts/Methylene%20Blue%20Antidote%20Facts.pdf |
https://clinicaltrials.gov/ct2/show/NCT01797978 | https://www.pharmgkb.org/pathway/PA165980834
Curator's Comment: http://www.mdpoison.com/media/SOP/mdpoisoncom/healthcareprofessionals/antidote-facts/Methylene%20Blue%20Antidote%20Facts.pdf |
https://clinicaltrials.gov/ct2/show/NCT01797978 | https://www.pharmgkb.org/pathway/PA165980834
Methylene blue, also known as methylthioninium chloride, is a medication from WHO's list of essential medicines. Upon administration, methylene blue is converted to leukomethylene blue by erythrocyte methemoblobin reductase in the presence of NADPH. Leukomethylene blue than reduces methemoglobin to oxyhemoglobin, thus restoring oxygen carrying capacity of the blood. Methylene blue is also used as a dye for various diagnostic procedures, for treatment of ifosfamide toxicity and for in vitro staining. Historically, it was used as a photosensitizer for photodynamic therapy for topical treatment of dermatologic or mucocutaneous infections, as an antidote for cyanide poisoning, but these applications are no longer approved. Methylene blue is investigated in clinical trials for treatment of septic shock and Alzheimer's disease.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P00387|||Q9UL55 Gene ID: 1727.0 Gene Symbol: CYB5R3 Target Organism: Homo sapiens (Human) |
|||
Target ID: CHEMBL2111350 |
5.3 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | METHYLENE BLUE Approved UseUsed for methemoglobinemia associated with certain drugs (e.g., dapsone, benzocaine, lidocaine), occupational or other exposures to toxic chemicals (e.g., hydrazine, amine-substituted benzenes, nitro-substituted benzenes, nitrates, nitrites), or substance abuse (e.g., inhalation or ingestion of volatile nitrites). |
|||
| Primary | METHYLENE BLUE Approved UseManagement of ifosfamide-induced encephalopathy |
|||
| Diagnostic | METHYLENE BLUE Approved UseHas been used as diagnostic (visualizing) dye in a variety of procedures, including sentinel lymph node biopsy in cancer patients (e.g., breast cancer patients), endoscopic evaluation of lesions in patients with GERD or Barrett's esophagus, urologic evaluation in patients with ureteral or renal pelvis injury, and thoroscopic procedures in patients with pulmonary nodules. |
|||
| Primary | METHYLENE BLUE Approved UseHas been used as a photosensitizer for photodynamic therapy for topical treatment of dermatologic or mucocutaneous infections (e.g., herpes labialis, eczema herpeticum, oral candidiasis, cutaneous leishmaniasis, chromoblastomycosis) or chronic dermatologic or mucocutaneous conditions (e.g., plaque psoriasis, oral lichen planus). |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Preventing | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
8 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10952480/ |
100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
METHYLENE BLUE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
2917 ng/mL |
2 mg/kg single, intravenous dose: 2 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
METHYLENE BLUE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
134 μM × min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10952480/ |
100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
METHYLENE BLUE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
13977 ng × h/mL |
2 mg/kg single, intravenous dose: 2 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
METHYLENE BLUE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
6.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10952480/ |
100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
METHYLENE BLUE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
24 h |
2 mg/kg single, intravenous dose: 2 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
METHYLENE BLUE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
6% |
2 mg/kg single, intravenous dose: 2 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
METHYLENE BLUE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
72 mg/kg 4 times / day multiple, intravenous Highest studied dose Dose: 72 mg/kg, 4 times / day Route: intravenous Route: multiple Dose: 72 mg/kg, 4 times / day Sources: |
unhealthy, 0.5-4.9 |
Other AEs: Anemia... |
1 g single, intravenous Overdose |
healthy, 3 |
Disc. AE: Tachycardia, Cyanosis... AEs leading to discontinuation/dose reduction: Tachycardia Sources: Cyanosis |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Anemia | 0.8% | 72 mg/kg 4 times / day multiple, intravenous Highest studied dose Dose: 72 mg/kg, 4 times / day Route: intravenous Route: multiple Dose: 72 mg/kg, 4 times / day Sources: |
unhealthy, 0.5-4.9 |
| Cyanosis | Disc. AE | 1 g single, intravenous Overdose |
healthy, 3 |
| Tachycardia | Disc. AE | 1 g single, intravenous Overdose |
healthy, 3 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1. | 2013-09-05 |
|
| The specific interaction of the photosensitizer methylene blue with acetylcholinesterase provides a model system for studying the molecular consequences of photodynamic therapy. | 2013-03-25 |
|
| Inhibition of the bioactivation of the neurotoxin MPTP by antioxidants, redox agents and monoamine oxidase inhibitors. | 2011-08 |
|
| Dual action of phenylarsine oxide on the glucose transport activity of GLUT1. | 2009-12-10 |
|
| Superoxide signaling in pain is independent of nitric oxide signaling. | 2009-10-28 |
|
| Methylene blue provides behavioral and metabolic neuroprotection against optic neuropathy. | 2009-04 |
|
| Methylthioninium chloride reverses cognitive deficits induced by scopolamine: comparison with rivastigmine. | 2009-01 |
|
| Effect of manganese on luteinizing hormone-releasing hormone secretion in adult male rats. | 2007-05 |
|
| Ifosfamide-related encephalopathy in elderly patients : report of five cases and review of the literature. | 2007 |
|
| Methemoglobinemia-induced cardio-respiratory failure secondary to topical anesthesia. | 2006-11-24 |
|
| Pharmacologic reductions of total tau levels; implications for the role of microtubule dynamics in regulating tau expression. | 2006-07-26 |
|
| [Ifosfamide induced encephalopathy: 15 observations]. | 2006-02 |
|
| Ifosfamide-induced encephalopathy with or without using methylene blue. | 2005-09-22 |
|
| Ifosfamide encephalopathy: a case report. | 2005-06-14 |
|
| Evaluating risk factors for the development of ifosfamide encephalopathy. | 2005-06 |
|
| Methylene blue for lithium-induced refractory hypotension in off-pump coronary artery bypass graft: report of two cases. | 2004-02 |
|
| Methylene blue: the drug of choice for catecholamine-refractory vasoplegia after cardiopulmonary bypass? | 2003-06 |
|
| Delayed cardioprotection induced by nitroglycerin is mediated by alpha-calcitonin gene-related peptide. | 2002-04 |
|
| Ifosfamide induced encephalopathy following chemotherapy of Non-Hodgkin's Lymphoma. | 2001-12 |
|
| Improvement of preservation with cardioplegic solution by nitroglycerin-induced delayed preconditioning is mediated by calcitonin gene-related peptide. | 2001-12 |
|
| Severe methemoglobinemia from topical anesthetic spray: case report, discussion and qualitative systematic review. | 2001-01 |
|
| Methylene blue in the treatment and prevention of ifosfamide-induced encephalopathy: report of 12 cases and a review of the literature. | 2000-01 |
|
| [The enhancement of formalin induced agitation behavior by intrathecal administration of prostaglandin E1]. | 1999-08 |
|
| Spinal antinociceptive effect of epidural nonsteroidal antiinflammatory drugs on nitric oxide-induced hyperalgesia in rats. | 1999-07 |
|
| Alternative approaches to the management of priapism. | 1998-03 |
|
| Ifosfamide encephalopathy and methylene-blue: a case report. | 1996-08 |
|
| [Successful treatment with methylene blue of ifosfamide-induced central nervous system effects]. | 1996-04-26 |
|
| Methylene blue and the neurotoxic mechanisms of ifosfamide encephalopathy. | 1996 |
|
| [Treatment of ifosfamide induced encephalopathy with methylene-blue]. | 1995-07 |
|
| Methylene blue for ifosfamide-associated encephalopathy. | 1995-05-04 |
|
| Nitric oxide is a central mediator of penile erection. | 1994-11 |
|
| Neurotoxicity in conscious rats following intraventricular SNAP, a nitric oxide donor. | 1994-07 |
|
| Prevention by NG-nitro-L-arginine methyl ester of apomorphine- and oxytocin-induced penile erection and yawning: site of action in the brain. | 1994-07 |
|
| Multifactorial mediation of post norepinephrine induced intestinal hyperemia. | 1994-06 |
|
| Toxic oil stimulates collagen synthesis acting at a pretranslational level in cultured fat-storing cells. | 1994-03 |
|
| Defenses against oxidation in human erythrocytes: role of glutathione reductase in the activation of glucose decarboxylation by hemolytic drugs. | 1991-04 |
|
| Cardiovascular depressant effects of N-methyl- and N-isobutyl-1,2-diphenyl ethanolamines: elucidation of the mechanisms of action. | 1991-01-01 |
|
| Acquired methemoglobinemia and hemolytic anemia after usual doses of phenazopyridine. | 1982-02 |
Patents
Sample Use Guides
Main route of adminitration is intravenous, 1-2 mg/kg by slow IV injection. Inject slowly over several minutes (usually 3–10 minutes). Historically was also administered orally, but oral preparations are no longer commercially available in US. As a photosensitizer is administered topically. For a diagnostic purposes is administered by local instillation or injection.
Route of Administration:
Other
Suspension of erytrocytes from acid/citrate/dextrose-treated blood were incubabed on air with 0.5M M-sodium nitrite solution in isoosmotic saline. The erytrocytes were separated by centrifugation, washed, and incubated at pH 7.4 and 37°C with 10 mM glucose and 10 uM Methylene Blue. Samples were taken at defined intervals and hemolysed with 10 vol of ice-cold water, after that the content of mehtemoglobin, hemoglobins intermediate and oxyhemoglobin was estimated.
| Substance Class |
Chemical
Created
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admin
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Edited
Tue Apr 01 21:17:47 GMT 2025
by
admin
on
Tue Apr 01 21:17:47 GMT 2025
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| Record UNII |
O3YJW1TB3C
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| Record Status |
Validated (UNII)
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| Record Version |
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67183-68-0
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16211647
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O3YJW1TB3C
Created by
admin on Tue Apr 01 21:17:47 GMT 2025 , Edited by admin on Tue Apr 01 21:17:47 GMT 2025
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ANHYDROUS->SOLVATE | |||
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PARENT -> SALT/SOLVATE |
