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Details

Stereochemistry ACHIRAL
Molecular Formula C34H28N6O14S4
Molecular Weight 872.878
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of TRYPAN BLUE FREE ACID

SMILES

CC1=CC(=CC=C1\N=N\C2=C(C=C3C=C(C=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=C(C=C6C=C5S(O)(=O)=O)S(O)(=O)=O

InChI

InChIKey=ZBNARPCCDMHDDV-HVMBLDELSA-N
InChI=1S/C34H28N6O14S4/c1-15-7-17(3-5-25(15)37-39-31-27(57(49,50)51)11-19-9-21(55(43,44)45)13-23(35)29(19)33(31)41)18-4-6-26(16(2)8-18)38-40-32-28(58(52,53)54)12-20-10-22(56(46,47)48)14-24(36)30(20)34(32)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)/b39-37+,40-38+

HIDE SMILES / InChI

Molecular Formula C34H28N6O14S4
Molecular Weight 872.878
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 2
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.drugs.com/cons/trypan-blue-intraocular.html | https://www.ncbi.nlm.nih.gov/pubmed/5995371 | https://www.drugs.com/dosage/membraneblue.html | https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/021670lbl.pdf

Trypan blue (trade name MembraneBlue, VisionBlue) is a vital stain used to selectively color dead tissues or cells blue. Live cells or tissues with intact cell membranes are not colored. Since cells are very selective in the compounds that pass through the membrane, in a viable cell trypan blue is not absorbed; however, it traverses the membrane in a dead cell. Hence, dead cells are shown as a distinctive blue color under a microscope. Since live cells are excluded from staining, this staining method is also described as a dye exclusion method. This dye may be a cause of certain birth defects such as encephalocele. Trypan blue is commonly used in microscopy (for cell counting) and in laboratory mice for assessment of tissue viability. The method cannot distinguish between necrotic and apoptotic cells. Trypan blue is also used in ophthalmic cataract surgery to stain the anterior capsule in the presence of a mature cataract, to aid in visualization, before creating the continuous curvilinear capsulorhexis.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
MembraneBlue

Approved Use

Indications and Usage. For use as an aid in ophthalmic posterior surgery; Facilitating removal of epiretinal tissue.
Diagnostic
VisionBlue

Approved Use

Indications and Usage. VisionBlue® is indicated for use as an aid in ophthalmic surgery by staining the anterior capsule of the lens.

Launch Date

2004
Diagnostic
MembraneBlue

Approved Use

Indications and Usage. For use as an aid in ophthalmic posterior surgery; Facilitating removal of epiretinal tissue.
PubMed

PubMed

TitleDatePubMed
Acrolein and chloroacetaldehyde: an examination of the cell and cell-free biomarkers of toxicity.
2013 Feb 25
Patents

Patents

Sample Use Guides

Before injection of MembraneBlue™ 0.15% perform a ‘fluid-air exchange’, i.e. filling the entire vitreous cavity with air, to prevent aqueous dilution of MembraneBlue™ 0.15%. MembraneBlue™ 0.15% is carefully applied to the retinal membrane using a blunt cannula attached to the MembraneBlue™ 0.15% syringe, without allowing the cannula to contact or damage the retina. Sufficient staining is expected on contact with the membrane. All excess dye should be removed from the vitreous cavity before performing an air-fluid exchange, to prevent unnecessary spreading of the dye. MembraneBlue™ 0.15% can also be injected directly in a BSS filled vitreous cavity (instead of injecting under air). Clinical use demonstrated that, after complete vitreous and posterior hyaloid removal, sufficient staining is achieved after 30 seconds of application under BSS.
Route of Administration: Other
Cultured human retinal pigment epithelium cells were exposed for 5 minutes to various concentrations of trypan blue (0.06%, 0.15%, 0.30%), and cell viability was confocally measured.
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:26:00 GMT 2023
Edited
by admin
on Fri Dec 15 18:26:00 GMT 2023
Record UNII
768N7QO4KH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRYPAN BLUE FREE ACID
Common Name English
2,7-NAPHTHALENEDISULFONIC ACID, 3,3'-((3,3'-DIMETHYL(1,1'-BIPHENYL)-4,4'-DIYL)BIS(AZO))BIS(5-AMINO-4-HYDROXY-
Common Name English
Classification Tree Code System Code
NDF-RT N0000175533
Created by admin on Fri Dec 15 18:26:00 GMT 2023 , Edited by admin on Fri Dec 15 18:26:00 GMT 2023
NDF-RT N0000175536
Created by admin on Fri Dec 15 18:26:00 GMT 2023 , Edited by admin on Fri Dec 15 18:26:00 GMT 2023
Code System Code Type Description
DAILYMED
768N7QO4KH
Created by admin on Fri Dec 15 18:26:00 GMT 2023 , Edited by admin on Fri Dec 15 18:26:00 GMT 2023
PRIMARY
FDA UNII
768N7QO4KH
Created by admin on Fri Dec 15 18:26:00 GMT 2023 , Edited by admin on Fri Dec 15 18:26:00 GMT 2023
PRIMARY
RXCUI
1726081
Created by admin on Fri Dec 15 18:26:00 GMT 2023 , Edited by admin on Fri Dec 15 18:26:00 GMT 2023
PRIMARY RxNorm
CAS
2538-83-2
Created by admin on Fri Dec 15 18:26:00 GMT 2023 , Edited by admin on Fri Dec 15 18:26:00 GMT 2023
PRIMARY
DRUG BANK
DB09158
Created by admin on Fri Dec 15 18:26:00 GMT 2023 , Edited by admin on Fri Dec 15 18:26:00 GMT 2023
PRIMARY
CHEBI
78900
Created by admin on Fri Dec 15 18:26:00 GMT 2023 , Edited by admin on Fri Dec 15 18:26:00 GMT 2023
PRIMARY
EPA CompTox
DTXSID8048313
Created by admin on Fri Dec 15 18:26:00 GMT 2023 , Edited by admin on Fri Dec 15 18:26:00 GMT 2023
PRIMARY
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