Rose bengal

Identification

Generic Name
Rose bengal
DrugBank Accession Number
DB11182
Background

Rose bengal is a pink stain derived as an analogue of fluorescein. Its disodium salt in ophthalmic solutions has been used as a diagnostic agent in suspected damage to conjunctival and corneal cells. It is also used in laboratory settings, including the preparation of Foraminifera for microscopic analysis and suppression of bacterial growth in several microbiological media. A direct cytotoxic effect of Rose bengal on microorganisms and cancer cells has been observed, questioning its potential antitumor actions via intralesional injections. The clinical applications of rose bengal as injectable formulation under the name PV-10 in melanoma, breast cancer and skin conditions such as eczema and psoriasis are being investigated in clinical trials.1

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 973.673
Monoisotopic: 971.499157746
Chemical Formula
C20H4Cl4I4O5
Synonyms
Not Available

Pharmacology

Indication

Indicated as a diagnostic agent in routine ocular examinations or when superficial conjunctiva or corneal tissue change is suspected, and as an aid in the diagnosis of keratoconjunctivitis sicca, keratitis, abrasions or corrosions as well as the detection of foreign bodies.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Rose bengal is a staining agent that visualized ocular surfaces of both diseased and dead cells in vivo 2. It has also shown to stain healthy cultured cells, including rabbit corneal epithelial cells, in a rapid, dose-dependent manner 3. Various studies demonstrate the cytotoxic effects of rose bengal in different cell cultures, including smooth-muscle cells from human intestine, endothelial cells from bovinepulmonary artery, rabbit Tenon fibro-blasts, and rabbit and human corneal epithelial cells 2. Cellular morphological changes such as detachment, separation, loss of motility and disruption, in addition to swelling, intracytoplasmic vacuole formation and lysis have been manifested with the treatment of rose bengal 2, indicating that rose Bengal is not a vital dye.

Mechanism of action

Rose Bengal stains both the nuclei and cell walls of dead or degenerated epithelial cells of the cornea and conjunctiva, and stain the mucus of the precorneal tear film. It is proposed that the staining ability of rose bengal is dependent on the status of tear film protection rather than cell viability, as tear components such as albumin and mucin can block the rose bengal uptake 6. It induces intrinsic cytotoxic effects by causing cellular morphologic changes, subsequent loss of cellular motility, cell detachment, and cell death 3. It mediates inhibitory actions on bovine corneal endothelial cells and attenuates cell proliferation 4.

Absorption

No information available.

Volume of distribution

No information available.

Protein binding

Tear component comprising of different proteins, such as albumin (although not very common as tear component), lactoferrin, and transferrin, can bind to rose bengal dye and act as diffusion barrier to prevent dye uptake by cells and subsequent cell staining. Lysosymes in tear film can also bind to rose bengal to form precipitates to attenuate cell uptake 6.

Metabolism

No information available.

Route of elimination

Rose bengal undergoes biliary excretion 5.

Half-life

Doses between 0.01 and 10 mg/kg in rat resulted in an initial biological half-life of 2 min and a terminal half-life of 100 min. The biological half-life for excretion is around 30 minutes in rats and rabbits 5.

Clearance

No information available.

Adverse Effects
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Toxicity

Rose Bengal induces cytotoxic effects in different cell lines 4.

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
Rose bengal potassium1ZPG1ELY14632-68-8AZJPTIGZZTZIDR-UHFFFAOYSA-L
Rose bengal sodium956575SN5L632-69-9UWBXIFCTIZXXLS-UHFFFAOYSA-L
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
GloStripsStrip1.3 mg/1OphthalmicNomax Inc.2013-08-20Not applicableUS flag
RoseGloStrip1.5 mg/1.5mgOphthalmicHub Pharmaceuticals2012-04-012012-04-01US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Odan-roseSolution10 mg / mLOphthalmicOdan Laboratories Ltd1989-12-31Not applicableCanada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
GloStripsRose bengal sodium (1.3 mg/1)StripOphthalmicNomax Inc.2013-08-20Not applicableUS flag
RoseGloRose bengal sodium (1.5 mg/1.5mg)StripOphthalmicHub Pharmaceuticals2012-04-012012-04-01US flag

Categories

ATC Codes
S01JA02 — Rose bengal sodium
Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
VDNLFJGJEQUWRB-UHFFFAOYSA-N
InChI
InChI=1S/C20H4Cl4I4O5/c21-10-8(9(20(31)32)11(22)13(24)12(10)23)7-3-1-5(25)16(29)14(27)18(3)33-19-4(7)2-6(26)17(30)15(19)28/h1-2,29H,(H,31,32)
IUPAC Name
2,3,4,5-tetrachloro-6-(6-hydroxy-2,4,5,7-tetraiodo-3-oxo-3H-xanthen-9-yl)benzoic acid
SMILES
OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C(O)=C(I)C=C12

References

General References
  1. Liu H, Innamarato PP, Kodumudi K, Weber A, Nemoto S, Robinson JL, Crago G, McCardle T, Royster E, Sarnaik AA, Pilon-Thomas S: Intralesional rose bengal in melanoma elicits tumor immunity via activation of dendritic cells by the release of high mobility group box 1. Oncotarget. 2016 Jun 21;7(25):37893-37905. doi: 10.18632/oncotarget.9247. [Article]
  2. Tabery HM: Toxic effect of rose bengal dye on the living human corneal epithelium. Acta Ophthalmol Scand. 1998 Apr;76(2):142-5. [Article]
  3. Feenstra RP, Tseng SC: What is actually stained by rose bengal? Arch Ophthalmol. 1992 Jul;110(7):984-93. [Article]
  4. Lee YC, Park CK, Kim MS, Kim JH: In vitro study for staining and toxicity of rose bengal on cultured bovine corneal endothelial cells. Cornea. 1996 Jul;15(4):376-85. [Article]
  5. Klaassen CD: Pharmacokinetics of rose bengal in the rat, rabbit, dog and guinea pig. Toxicol Appl Pharmacol. 1976 Oct;38(1):85-100. [Article]
  6. Tseng SC, Zhang SH: Interaction between rose bengal and different protein components. Cornea. 1995 Jul;14(4):427-35. [Article]
Human Metabolome Database
HMDB0036613
PubChem Substance
347911147
ChemSpider
23774
RxNav
9471
ChEBI
87202
ChEMBL
CHEMBL1208422
ZINC
ZINC000150338646
Wikipedia
Rose_bengal
MSDS
Download (47.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3Active Not RecruitingTreatmentCandida albicans infection / Smoking, Cigarette1
3Not Yet RecruitingTreatmentBacterial Keratitis1
3RecruitingTreatmentAcanthamoeba Keratitis / Fungal infections of the cornea1
3TerminatedTreatmentCutaneous Melanoma1
2CompletedTreatmentMelanoma1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
StripOphthalmic1.3 mg/1
SolutionOphthalmic10 mg / mL
StripOphthalmic1.5 mg/1.5mg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)DecomposesMSDS
Predicted Properties
PropertyValueSource
Water Solubility0.000681 mg/mLALOGPS
logP6.02ALOGPS
logP8.78Chemaxon
logS-6.2ALOGPS
pKa (Strongest Acidic)2.55Chemaxon
pKa (Strongest Basic)1.89Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area83.83 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity176.05 m3·mol-1Chemaxon
Polarizability63.8 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0g6r-0400000009-eba6fce35e4b87f44857
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0000000009-5cba21fc1320e8e6020e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0000000009-57f5a0319a157d33dc7c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0000000009-c8cb9ed0d008555fb220
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0000000009-a601bee631cb1bb9eb84
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0g4l-0000000019-6f2b47b2e07ac0470af9
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004j-0000000449-63a80251b1d3a865ea38
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-194.793611
predicted
DarkChem Lite v0.1.0
[M-H]-239.43535
predicted
DeepCCS 1.0 (2019)
[M+H]+198.804411
predicted
DarkChem Lite v0.1.0
[M+H]+241.83092
predicted
DeepCCS 1.0 (2019)
[M+Na]+194.758711
predicted
DarkChem Lite v0.1.0
[M+Na]+247.74342
predicted
DeepCCS 1.0 (2019)

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Ligand
General Function
Lysozyme activity
Specific Function
Lysozymes have primarily a bacteriolytic function; those in tissues and body fluids are associated with the monocyte-macrophage system and enhance the activity of immunoagents.
Gene Name
LYZ
Uniprot ID
P61626
Uniprot Name
Lysozyme C
Molecular Weight
16536.885 Da
References
  1. Lee YC, Park CK, Kim MS, Kim JH: In vitro study for staining and toxicity of rose bengal on cultured bovine corneal endothelial cells. Cornea. 1996 Jul;15(4):376-85. [Article]
  2. Tseng SC, Zhang SH: Interaction between rose bengal and different protein components. Cornea. 1995 Jul;14(4):427-35. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Lee YC, Park CK, Kim MS, Kim JH: In vitro study for staining and toxicity of rose bengal on cultured bovine corneal endothelial cells. Cornea. 1996 Jul;15(4):376-85. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Serine-type endopeptidase activity
Specific Function
Transferrins are iron binding transport proteins which can bind two Fe(3+) ions in association with the binding of an anion, usually bicarbonate.Lactotransferrin is a major iron-binding and multifu...
Gene Name
LTF
Uniprot ID
P02788
Uniprot Name
Lactotransferrin
Molecular Weight
78181.225 Da
References
  1. Lee YC, Park CK, Kim MS, Kim JH: In vitro study for staining and toxicity of rose bengal on cultured bovine corneal endothelial cells. Cornea. 1996 Jul;15(4):376-85. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Transferrin receptor binding
Specific Function
Transferrins are iron binding transport proteins which can bind two Fe(3+) ions in association with the binding of an anion, usually bicarbonate. It is responsible for the transport of iron from si...
Gene Name
TF
Uniprot ID
P02787
Uniprot Name
Serotransferrin
Molecular Weight
77063.195 Da
References
  1. Lee YC, Park CK, Kim MS, Kim JH: In vitro study for staining and toxicity of rose bengal on cultured bovine corneal endothelial cells. Cornea. 1996 Jul;15(4):376-85. [Article]

Drug created at December 03, 2015 16:51 / Updated at March 18, 2024 16:48