NAV

Trypan blue

Identification

Summary

Trypan blue is a dye used as a visualizing aid to stain the epiretinal membranes during ophthalmic surgical vitrectomy procedures, thereby facilitating removal of the tissue.

Brand Names
MembraneBlue, VisionBlue
Generic Name
Trypan blue free acid
Commonly known or available as Trypan blue
DrugBank Accession Number
DB09158
Background

Trypan blue is a diazo dye used in ophthalmic cataract surgery to stain the anterior capsule in the presence of a mature cataract. This is done to aid in visualization before creating the continuous curvilinear capsulorhexis.

Type
Small Molecule
Groups
Approved
Structure
Similar Structures
Weight
Average: 872.87
Monoisotopic: 872.054634302
Chemical Formula
C34H28N6O14S4
Synonyms
Not Available
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Pharmacology

Indication

Trypan blue is indicated for use as an aid in ophthalmic surgery by staining the epiretinal membranes during ophthalmic surgical vitrectomy procedures, facilitating removal of the tissue.

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Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

Trypan blue ophthalmic drops selectively stains membranes in the human eye during posterior surgery, such as epiretinal membranes (ERM) and Internal Limiting Membranes (ILM).

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

6200 mg/kg (oral, rat)

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Trypan blueI2ZWO3LS3M72-57-1GLNADSQYFUSGOU-GPTZEZBUSA-J
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
MembraneblueInjection, solution0.75 mg/0.5mLIntraocular; OphthalmicDutch Ophthalmic Research Center (International) B.V.2009-02-20Not applicableUS flag
VisionblueInjection, solution0.3 mg/0.5mLIntraocular; OphthalmicD.O.R.C. Dutch Ophthalmic Research Center (International) B.V.2004-12-16Not applicableUS flag
VisionblueSolution0.06 %IntraocularDutch Ophthalmic Research Center International Bv2006-09-06Not applicableCanada flag

Categories

ATC Codes
S01KX02 — Trypan blue
Drug Categories
Classification
Not classified
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
768N7QO4KH
CAS number
2538-83-2
InChI Key
ZBNARPCCDMHDDV-HVMBLDELSA-N
InChI
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+
IUPAC Name
5-amino-3-[(E)-2-{4'-[(E)-2-(8-amino-1-hydroxy-3,6-disulfonaphthalen-2-yl)diazen-1-yl]-3,3'-dimethyl-[1,1'-biphenyl]-4-yl}diazen-1-yl]-4-hydroxynaphthalene-2,7-disulfonic acid
SMILES
CC1=CC(=CC=C1\N=N\C1=C(C=C2C=C(C=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C=C(C=C2C=C1S(O)(=O)=O)S(O)(=O)=O

References

General References
  1. Strober W: Trypan blue exclusion test of cell viability. Curr Protoc Immunol. 2001 May;Appendix 3:Appendix 3B. doi: 10.1002/0471142735.ima03bs21. [Article]
  2. FDA label [Link]
KEGG Compound
C19307
PubChem Compound
9562061
PubChem Substance
310265071
ChemSpider
14833963
RxNav
1726081
ChEBI
78900
ChEMBL
CHEMBL1089641
ZINC
ZINC000169289767
Wikipedia
Trypan_blue

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, solutionIntraocular; Ophthalmic0.75 mg/0.5mL
Injection, solutionIntraocular; Ophthalmic0.3 mg/0.5mL
SolutionIntraocular0.06 %
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US6367480No2002-04-092019-10-26US flag
US6720314No2004-04-132019-05-07US flag
US6696430No2004-02-242019-05-07US flag
US6372449No2002-04-162019-11-12US flag

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0121 mg/mLALOGPS
logP-0.04ALOGPS
logP1.13Chemaxon
logS-4.9ALOGPS
pKa (Strongest Acidic)-4.2Chemaxon
pKa (Strongest Basic)2.38Chemaxon
Physiological Charge-4Chemaxon
Hydrogen Acceptor Count20Chemaxon
Hydrogen Donor Count8Chemaxon
Polar Surface Area359.42 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity218.67 m3·mol-1Chemaxon
Polarizability86.53 Å3Chemaxon
Number of Rings6Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0000030090-4325e40dea5b4ed238b4
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00e9-6000000190-286b7136606a4a635162
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0096-0001070790-be52a904e25ca622fd92
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9002000280-44b764ea1da74e5378a7
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01vn-0020341930-de5817b2aa3cf2c12873
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0rrr-2040340900-d61a367d3ab00ef423c2
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Drug created at October 02, 2015 19:59 / Updated at January 03, 2023 04:10