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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
Structure of EVANS BLUE

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+;;;;

HIDE SMILES / InChI

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
EVANS BLUE

Approved Use

Evans blue is injected intravenously to determine plasma volume in patients of heart failure, shock or other circulatory abnormalities.

Launch Date

1981
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Assessment of blood-retinal barrier integrity.
1995 Jan
Evaluation and treatment of cancer-related fluid deficits: volume depletion and dehydration.
2001 Sep
Evans Blue Dye as an in vivo marker of myofibre damage: optimising parameters for detecting initial myofibre membrane permeability.
2002 Jan
Evans Blue-diethylenetriamine-N,N,N”,N”-pentaacetic acid-gadolinium.
2004
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

Patents

Sample Use Guides

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
Evans blue (300 uM) partially inhibited H(2)O(2) and ATP-induced contractions of rat aortic rings.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:06:29 GMT 2023
Edited
by admin
on Fri Dec 15 15:06:29 GMT 2023
Record UNII
45PG892GO1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EVANS BLUE
ORANGE BOOK   VANDF   WHO-DD  
Common Name English
NSC-8680
Code English
EVANS BLUE [ORANGE BOOK]
Common Name English
EVANS BLUE [VANDF]
Common Name English
AZOVAN BLUE [MART.]
Common Name English
EVANS BLUE [IARC]
Common Name English
DYE EVANS BLUE [VANDF]
Common Name English
1,3-NAPHTHALENEDISULFONIC ACID, 6,6'-((3,3'-DIMETHYL(1,1'-BIPHENYL)-4,4'-DIYL)BIS(AZO))BIS(4-AMINO-5-HYDROXY)-, TETRASODIUM SALT
Common Name English
Evans blue [WHO-DD]
Common Name English
EVAN'S BLUE [MI]
Common Name English
DIRECT BLUE 53 TETRASODIUM SALT
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C461
Created by admin on Fri Dec 15 15:06:29 GMT 2023 , Edited by admin on Fri Dec 15 15:06:29 GMT 2023
Code System Code Type Description
CAS
314-13-6
Created by admin on Fri Dec 15 15:06:29 GMT 2023 , Edited by admin on Fri Dec 15 15:06:29 GMT 2023
PRIMARY
EPA CompTox
DTXSID9022815
Created by admin on Fri Dec 15 15:06:29 GMT 2023 , Edited by admin on Fri Dec 15 15:06:29 GMT 2023
PRIMARY
FDA UNII
45PG892GO1
Created by admin on Fri Dec 15 15:06:29 GMT 2023 , Edited by admin on Fri Dec 15 15:06:29 GMT 2023
PRIMARY
MESH
D005070
Created by admin on Fri Dec 15 15:06:29 GMT 2023 , Edited by admin on Fri Dec 15 15:06:29 GMT 2023
PRIMARY
NSC
8680
Created by admin on Fri Dec 15 15:06:29 GMT 2023 , Edited by admin on Fri Dec 15 15:06:29 GMT 2023
PRIMARY
MERCK INDEX
m5218
Created by admin on Fri Dec 15 15:06:29 GMT 2023 , Edited by admin on Fri Dec 15 15:06:29 GMT 2023
PRIMARY Merck Index
RXCUI
4191
Created by admin on Fri Dec 15 15:06:29 GMT 2023 , Edited by admin on Fri Dec 15 15:06:29 GMT 2023
PRIMARY RxNorm
ECHA (EC/EINECS)
206-242-5
Created by admin on Fri Dec 15 15:06:29 GMT 2023 , Edited by admin on Fri Dec 15 15:06:29 GMT 2023
PRIMARY
ChEMBL
CHEMBL1015
Created by admin on Fri Dec 15 15:06:29 GMT 2023 , Edited by admin on Fri Dec 15 15:06:29 GMT 2023
PRIMARY
WIKIPEDIA
EVANS BLUE
Created by admin on Fri Dec 15 15:06:29 GMT 2023 , Edited by admin on Fri Dec 15 15:06:29 GMT 2023
PRIMARY
NCI_THESAURUS
C65605
Created by admin on Fri Dec 15 15:06:29 GMT 2023 , Edited by admin on Fri Dec 15 15:06:29 GMT 2023
PRIMARY
DRUG CENTRAL
3217
Created by admin on Fri Dec 15 15:06:29 GMT 2023 , Edited by admin on Fri Dec 15 15:06:29 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY