Trypan blue

Identification

Name
Trypan blue free acid
Commonly known or available as Trypan blue
Accession Number
DB09158
Type
Small Molecule
Groups
Approved
Description

Trypan blue is a diazo dye 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.

Structure
Thumb
Synonyms
Not Available
Product Ingredients
IngredientUNIICASInChI Key
Trypan blueI2ZWO3LS3M72-57-1GLNADSQYFUSGOU-GPTZEZBUSA-J
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
MembraneblueInjection, solution0.75 mg/0.5mLIntraocular; OphthalmicDutch Ophthalmic Research Center (International) B.V.2009-02-20Not applicableUs
VisionblueInjection, solution0.3 mg/0.5mLIntraocular; OphthalmicD.O.R.C. Dutch Ophthalmic Research Center (International) B.V.2004-12-16Not applicableUs
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
D.O.R.C. Vision BlueSolution / drops0.06 %IntraocularDutch Ophthalmic Research Center International Bv2006-09-06Not applicableCanada
Categories
UNII
768N7QO4KH
CAS number
2538-83-2
Weight
Average: 872.87
Monoisotopic: 872.054634302
Chemical Formula
C34H28N6O14S4
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

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.

Associated Therapies
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
Toxicity

6200 mg/kg (oral, rat)

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

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. [PubMed:18432654]
  2. FDA label [Link]
External Links
KEGG Compound
C19307
PubChem Compound
9562061
PubChem Substance
310265071
ChemSpider
14833963
ChEBI
78900
ChEMBL
CHEMBL1089641
Wikipedia
Trypan_blue
AHFS Codes
  • 36:58.00 — Ocular Disorders

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Solution / dropsIntraocular0.06 %
Injection, solutionIntraocular; Ophthalmic0.75 mg/0.5mL
Injection, solutionIntraocular; Ophthalmic0.3 mg/0.5mL
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6367480No1999-10-262019-10-26Us
US6720314No1999-05-072019-05-07Us

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
Not Available

Taxonomy

Classification
Not classified

Drug created on October 02, 2015 13:59 / Updated on November 14, 2018 12:57