Identification

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Name
Rose bengal free acid
Commonly known or available as Rose bengal
Accession Number
DB11182
Type
Small Molecule
Groups
Approved, Investigational
Description

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 1, 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.

Structure
Thumb
Synonyms
Not Available
Product Ingredients
IngredientUNIICASInChI Key
Rose bengal potassium1ZPG1ELY14632-68-8AZJPTIGZZTZIDR-UHFFFAOYSA-L
Rose bengal sodium956575SN5L632-69-9UWBXIFCTIZXXLS-UHFFFAOYSA-L
Active Moieties
NameKindUNIICASInChI Key
Rose Bengal ATunknown1IID5XA5GB18265-55-9JMWHLOJMXZVRMC-UHFFFAOYSA-L
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
GloStripsStrip1.3 mg/1OphthalmicNomax Inc.2013-08-20Not applicableUs
RoseGloStrip1.5 mg/1.5mgOphthalmicHub Pharmaceuticals2012-04-012012-04-01Us
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
GloStripsRose bengal sodium (1.3 mg/1)StripOphthalmicNomax Inc.2013-08-20Not applicableUs
RoseGloRose bengal sodium (1.5 mg/1.5mg)StripOphthalmicHub Pharmaceuticals2012-04-012012-04-01Us
Categories
UNII
Not Available
CAS number
Not Available
Weight
Average: 973.673
Monoisotopic: 971.499157746
Chemical Formula
C20H4Cl4I4O5
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

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.

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.

Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

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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.

Toxicity

Rose Bengal induces cytotoxic effects in different cell lines 4.

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

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. [PubMed:27177220]
  2. Tabery HM: Toxic effect of rose bengal dye on the living human corneal epithelium. Acta Ophthalmol Scand. 1998 Apr;76(2):142-5. [PubMed:9591941]
  3. Feenstra RP, Tseng SC: What is actually stained by rose bengal? Arch Ophthalmol. 1992 Jul;110(7):984-93. [PubMed:1637285]
  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. [PubMed:8776564]
  5. Klaassen CD: Pharmacokinetics of rose bengal in the rat, rabbit, dog and guinea pig. Toxicol Appl Pharmacol. 1976 Oct;38(1):85-100. [PubMed:982474]
  6. Tseng SC, Zhang SH: Interaction between rose bengal and different protein components. Cornea. 1995 Jul;14(4):427-35. [PubMed:7545566]
External Links
Human Metabolome Database
HMDB0036613
PubChem Substance
347911147
ChemSpider
23774
ChEBI
87202
ChEMBL
CHEMBL1208422
Wikipedia
Rose_bengal
ATC Codes
S01JA02 — Rose bengal sodium
AHFS Codes
  • 36:89.00* — Other Diagnostics
MSDS
Download (47.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentPsoriasis3

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
StripOphthalmic1.3 mg/1
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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Classification
Not classified

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Other
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. [PubMed:8776564]

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. [PubMed:8776564]
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. [PubMed:8776564]
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. [PubMed:8776564]

Drug created on December 03, 2015 09:51 / Updated on June 16, 2019 07:01