Details
Stereochemistry | ACHIRAL |
Molecular Formula | C34H24N6O14S4.4Na |
Molecular Weight | 960.805 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 2 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].[Na+].[Na+].[Na+].CC1=CC(=CC=C1\N=N\C2=CC=C3C(=CC(=C(N)C3=C2O)S([O-])(=O)=O)S([O-])(=O)=O)C4=CC(C)=C(C=C4)\N=N\C5=C(O)C6=C(N)C(=CC(=C6C=C5)S([O-])(=O)=O)S([O-])(=O)=O
InChI
InChIKey=ATNOAWAQFYGAOY-GPTZEZBUSA-J
InChI=1S/C34H28N6O14S4.4Na/c1-15-11-17(3-7-21(15)37-39-23-9-5-19-25(55(43,44)45)13-27(57(49,50)51)31(35)29(19)33(23)41)18-4-8-22(16(2)12-18)38-40-24-10-6-20-26(56(46,47)48)14-28(58(52,53)54)32(36)30(20)34(24)42;;;;/h3-14,41-42H,35-36H2,1-2H3,(H,43,44,45)(H,46,47,48)(H,49,50,51)(H,52,53,54);;;;/q;4*+1/p-4/b39-37+,40-38+;;;;
Molecular Formula | Na |
Molecular Weight | 22.9898 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C34H24N6O14S4 |
Molecular Weight | 868.846 |
Charge | -4 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 2 |
Optical Activity | NONE |
Evans Blue (EBD) is an azo dye which has a very high affinity for serum albumin. It can be useful in physiology in estimating the proportion of body water contained in blood plasma. Evans Blue Dye is widely used to study blood vessel and cellular membrane permeability as it is non-toxic, it can be administered as an intravital dye and it binds to serum albumin – using this as its transporter molecule. The EBD–albumin conjugate (EBA) can be: (i) identified macroscopically by the striking blue colour within tissue; (ii) observed by red auto-fluorescence in tissue sections examined by fluorescence microscopy; and (iii) assessed and quantified by spectrophotometry for serum samples, or homogenised tissue. has recently been utilised in mdx mice to identify permeable skeletal myofibres that have become damaged as a result of muscular dystrophy. EBD has the potential to be a useful vital stain of myofibre permeability in other models of skeletal muscle injury and membrane-associated fragility. Evans Blue is a potent inhibitor of L-glutamate uptake into synaptic vesicles. It also inhibits AMPA and kainate receptor-mediated currents (IC50 values are 220 and 150 nM respectively). P2X-selective purinoceptor antagonist.
CNS Activity
Curator's Comment: Evans blue dye binds tightly but reversibly to albumin in vivo, resulting in an Mr 68,500 marker that does not cross an intact BBB, but that will stain brain parenchyma following disruption. Evans blue’s low propensity to cross the intact BBB provides the advantage that it
will not carry attached toxins into the brain and the disadvantage that it cannot be used as a
carrier to deliver drugs to the brain.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3253 |
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Target ID: CHEMBL2009 |
220.0 nM [IC50] | ||
Target ID: CHEMBL3683 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8967991 |
150.0 nM [IC50] | ||
Target ID: P51172 Gene ID: 6339.0 Gene Symbol: SCNN1D Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16107516 |
143.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Diagnostic | EVANS BLUE Approved UseEvans blue is injected intravenously to determine plasma volume in patients of heart failure, shock or other circulatory abnormalities. Launch Date1981 |
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Diagnostic | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Assessment of blood-retinal barrier integrity. | 1995 Jan |
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Evaluation and treatment of cancer-related fluid deficits: volume depletion and dehydration. | 2001 Sep |
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Evans Blue Dye as an in vivo marker of myofibre damage: optimising parameters for detecting initial myofibre membrane permeability. | 2002 Jan |
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Evans Blue-diethylenetriamine-N,N,N”,N”-pentaacetic acid-gadolinium. | 2004 |
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Markers for blood-brain barrier integrity: how appropriate is Evans blue in the twenty-first century and what are the alternatives? | 2015 |
|
Albumin-Binding Evans Blue Derivatives for Diagnostic Imaging and Production of Long-Acting Therapeutics. | 2016 Oct 19 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21168441
Mice: A 2% solution of Evans Blue in normal saline (4 mL/kg of body weight) was injected either
into the jugular vein or intraperitoneally.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10963730
Evans blue (300 uM) partially inhibited H(2)O(2) and ATP-induced contractions of rat aortic rings.
Substance Class |
Chemical
Created
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admin
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Edited
Fri Dec 15 15:06:29 GMT 2023
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admin
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Fri Dec 15 15:06:29 GMT 2023
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Record UNII |
45PG892GO1
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Record Status |
Validated (UNII)
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NCI_THESAURUS |
C461
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314-13-6
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DTXSID9022815
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45PG892GO1
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D005070
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8680
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m5218
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4191
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206-242-5
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CHEMBL1015
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EVANS BLUE
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C65605
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3217
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Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE |
Related Record | Type | Details | ||
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ACTIVE MOIETY |