Brilliant blue G

Identification

Summary

Brilliant blue G is a disclosing agent used in ophthalmological surgery to stain the internal limiting membrane (ILM).

Generic Name
Brilliant blue G
DrugBank Accession Number
DB15594
Background

Brilliant Blue G is used in an ophthalmic solution for staining the internal limiting membrane (ILM) of the eye during ophthalmic procedures.1,2 This membrane is thin and translucent, making it difficult to identify during eye surgeries that require high levels of visual accuracy. Brilliant blue G, like its name, imparts a vibrant blue color, facilitating identification of the ILM. It was approved by the FDA for ophthalmic use on December 20, 2019.8

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 854.02
Monoisotopic: 853.28313753
Chemical Formula
C47H48N3NaO7S2
Synonyms
  • Acid Blue 90
  • Brilliant blue G
  • C.I. Acid Blue 90
  • Coomassie Brilliant Blue G
External IDs
  • BBG-250

Pharmacology

Indication

This drug is indicated for selectively staining the internal limiting membrane (ILM).8

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Pharmacodynamics

Brilliant Blue G aids in ophthalmologic surgery by rendering it easier to identify the internal limiting membrane (ILM) for surgical removal.8

Mechanism of action

The internal limiting membrane (ILM) is a thin and translucent structure that demarcates the transition from the retina from the vitreous body of the eye. It acts as a scaffold on which excessive tissue can grow, which results in visual distortion when it is projected onto the neighbouring retina. This causes visual loss and/or distortion.4

An epiretinal membrane (also known as ERM) is a fibrous type of tissue that can be found on the inner surface of the retina and occurs idiopathically, and in some cases, retinal detachment and inflammation. It is often found on the surface of the internal limiting membrane (ILM), causing visual loss and distortion.4 The above condition as well as the associated macular pucker5 or traction maculopathy6 can affect the ILM, contributing to visual complications. The removal of the ILM with or without vitrectomy is often a simple solution to these conditions.

Brilliant Blue G specifically stains the internal limiting membrane (ILM) in the eye without staining the epiretinal membrane or the retina, allowing for easier surgical removal. The mechanism of its specific staining that is limited to the ILM is currently not fully understood.8

TargetActionsOrganism
AInternal limiting membrane (ILM)
binder
Humans
Absorption

Due to the fact that this drug is administered by intravitreal injection and subsequently removed after staining, it is not expected to be significantly absorbed systemically.8

Volume of distribution

This drug is administered via intravitreal injection and likely distributes only to parts of the eye.8

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

This dye is removed in a clinical setting after the surgical procedure in which it was used.8

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

The intraperitoneal TDLO in rats is 100 mg/kg.9 No overdose information is available at this time.8 When compared to other ophthalmological dyes, brilliant blue G appears to have a comparable safety profile.7 Ensure to remove the dye immediately after staining.8

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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Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
TissueblueSolution0.25 mg / mLIntravitrealDutch Ophthalmic Research Center International Bv2021-09-30Not applicableCanada flag
TissueblueInjection, solution0.0125 mg/0.5mLIntraocular; OphthalmicD.O.R.C. Dutch Ophthalmic Research Center (International) B.V.2019-12-31Not applicableUS flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylbenzamines. These are aromatic compounds consisting of a benzyl group that is N-linked to a benzamine.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylmethylamines
Direct Parent
Phenylbenzamines
Alternative Parents
Diphenylmethanes / Aromatic monoterpenoids / Benzenesulfonic acids and derivatives / Monocyclic monoterpenoids / 1-sulfo,2-unsubstituted aromatic compounds / Benzenesulfonyl compounds / Aminophenyl ethers / Phenoxy compounds / Aminotoluenes / Aniline and substituted anilines
show 15 more
Substituents
1-sulfo,2-unsubstituted aromatic compound / Alkyl aryl ether / Amine / Aminophenyl ether / Aminotoluene / Aniline or substituted anilines / Aralkylamine / Aromatic homomonocyclic compound / Aromatic monoterpenoid / Arylsulfonic acid or derivatives
show 35 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
M1ZRX790SI
CAS number
6104-58-1
InChI Key
RWVGQQGBQSJDQV-UHFFFAOYSA-M
InChI
InChI=1S/C47H49N3O7S2.Na/c1-6-49(31-35-11-9-13-43(29-35)58(51,52)53)40-21-25-45(33(4)27-40)47(37-15-17-38(18-16-37)48-39-19-23-42(24-20-39)57-8-3)46-26-22-41(28-34(46)5)50(7-2)32-36-12-10-14-44(30-36)59(54,55)56;/h9-30H,6-8,31-32H2,1-5H3,(H2,51,52,53,54,55,56);/q;+1/p-1
IUPAC Name
sodium 3-({[4-({4-[(4-ethoxyphenyl)amino]phenyl}[(1E,4E)-4-{ethyl[(3-sulfonatophenyl)methyl]iminiumyl}-2-methylcyclohexa-2,5-dien-1-ylidene]methyl)-3-methylphenyl](ethyl)amino}methyl)benzene-1-sulfonate
SMILES
[Na+].CCOC1=CC=C(NC2=CC=C(C=C2)C(=C2\C=C/C(/C=C2C)=[N+](/CC)CC2=CC(=CC=C2)S([O-])(=O)=O)\C2=C(C)C=C(C=C2)N(CC)CC2=CC(=CC=C2)S([O-])(=O)=O)C=C1

References

General References
  1. Gandorfer A, Haritoglou C, Kampik A: Staining of the ILM in macular surgery. Br J Ophthalmol. 2003 Dec;87(12):1530; author reply 1530. doi: 10.1136/bjo.87.12.1530. [Article]
  2. Semeraro F, Morescalchi F, Duse S, Gambicorti E, Russo A, Costagliola C: Current Trends about Inner Limiting Membrane Peeling in Surgery for Epiretinal Membranes. J Ophthalmol. 2015;2015:671905. doi: 10.1155/2015/671905. Epub 2015 Sep 3. [Article]
  3. Enaida H, Hisatomi T, Hata Y, Ueno A, Goto Y, Yamada T, Kubota T, Ishibashi T: Brilliant blue G selectively stains the internal limiting membrane/brilliant blue G-assisted membrane peeling. Retina. 2006 Jul-Aug;26(6):631-6. doi: 10.1097/01.iae.0000236469.71443.aa. [Article]
  4. Guber J, Pereni I, Scholl HPN, Guber I, Haynes RJ: Outcomes after Epiretinal Membrane Surgery with or Without Internal Limiting Membrane Peeling. Ophthalmol Ther. 2019 Jun;8(2):297-303. doi: 10.1007/s40123-019-0185-7. Epub 2019 Apr 19. [Article]
  5. Sheard RM, Sethi C, Gregor Z: Acute macular pucker. Ophthalmology. 2003 Jun;110(6):1178-84. doi: 10.1016/S0161-6420(03)00266-5. [Article]
  6. Konidaris V, Androudi S, Brazitikos P: Myopic traction maculopathy: study with spectral domain optical coherence tomography and review of the literature. Hippokratia. 2009 Apr;13(2):110-3. [Article]
  7. Awad D, Schrader I, Bartok M, Mohr A, Gabel D: Comparative toxicology of trypan blue, brilliant blue G, and their combination together with polyethylene glycol on human pigment epithelial cells. Invest Ophthalmol Vis Sci. 2011 Jun 9;52(7):4085-90. doi: 10.1167/iovs.10-6336. [Article]
  8. Brilliant Blue G Opthalmic solution [Link]
  9. Brilliant Blue G MSDS, Cayman Chem [Link]
ChemSpider
4884338
BindingDB
50277548
RxNav
1998867
ChEMBL
CHEMBL4173394
Wikipedia
Coomassie_Brilliant_Blue
FDA label
Download (74.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3Unknown StatusTreatmentEpiretinal Membranes / Macular Holes1
Not AvailableCompletedTreatmentMacular Holes / Surgery1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, solutionIntraocular; Ophthalmic0.0125 mg/0.5mL
SolutionIntravitreal0.25 mg / mL
Prices
Not Available
Patents
Not Available

Properties

State
Liquid
Experimental Properties
PropertyValueSource
water solubility1mg/mLhttps://www.sigmaaldrich.com/catalog/product/sial/b0770?lang=en®ion=CA
Predicted Properties
PropertyValueSource
Water Solubility3.46e-05 mg/mLALOGPS
logP4.35ALOGPS
logP5.64Chemaxon
logS-7.4ALOGPS
pKa (Strongest Acidic)-2.3Chemaxon
pKa (Strongest Basic)3.73Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count9Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area141.91 Å2Chemaxon
Rotatable Bond Count15Chemaxon
Refractivity258.32 m3·mol-1Chemaxon
Polarizability91.89 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

Targets

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1. Internal limiting membrane (ILM)
Kind
Group
Organism
Humans
Pharmacological action
Yes
Actions
Binder
Curator comments
Brilliant blue G stains the internal limiting membrane of the eye.
An important anatomical structure in the eye requiring visualization during surgery.
References
  1. Awad D, Schrader I, Bartok M, Mohr A, Gabel D: Comparative toxicology of trypan blue, brilliant blue G, and their combination together with polyethylene glycol on human pigment epithelial cells. Invest Ophthalmol Vis Sci. 2011 Jun 9;52(7):4085-90. doi: 10.1167/iovs.10-6336. [Article]
  2. Enaida H, Hisatomi T, Hata Y, Ueno A, Goto Y, Yamada T, Kubota T, Ishibashi T: Brilliant blue G selectively stains the internal limiting membrane/brilliant blue G-assisted membrane peeling. Retina. 2006 Jul-Aug;26(6):631-6. doi: 10.1097/01.iae.0000236469.71443.aa. [Article]
  3. Brilliant Blue G Opthalmic solution [Link]

Drug created at December 20, 2019 20:47 / Updated at August 05, 2021 01:52