Rose bengal
Identification
- Name
- 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, 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
Structure for Rose bengal (DB11182)
- Synonyms
- Not Available
- Product Ingredients
Ingredient UNII CAS InChI Key Rose bengal potassium 1ZPG1ELY14 632-68-8 AZJPTIGZZTZIDR-UHFFFAOYSA-L Rose bengal sodium 956575SN5L 632-69-9 UWBXIFCTIZXXLS-UHFFFAOYSA-L - Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Unlock Additional DataGloStrips Strip 1.3 mg/1 Ophthalmic Nomax Inc. 2013-08-20 Not applicable US 
RoseGlo Strip 1.5 mg/1.5mg Ophthalmic Hub Pharmaceuticals 2012-04-01 2012-04-01 US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
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A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Unlock Additional DataOdan-rose Solution Ophthalmic Odan Laboratories Ltd 1989-12-31 Not applicable Canada 
Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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- Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End GloStrips Rose bengal sodium (1.3 mg/1) Strip Ophthalmic Nomax Inc. 2013-08-20 Not applicable US RoseGlo Rose bengal sodium (1.5 mg/1.5mg) Strip Ophthalmic Hub Pharmaceuticals 2012-04-01 2012-04-01 US - Categories
- Coloring Agents
- Colouring Agents
- Compounds used in a research, industrial, or household setting
- Diagnostic Agents
- Fluoresceins
- Fluorescent Dyes
- Heterocyclic Compounds, Fused-Ring
- Indicators and Reagents
- Laboratory Chemicals
- Luminescent Agents
- Ophthalmologicals
- Other Diagnostics
- Sensory Organs
- Spiro Compounds
- Xanthenes
- 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.
- 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
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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Learn moreInteractions
- 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
- Not Available
References
- General References
- 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]
- 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]
- Feenstra RP, Tseng SC: What is actually stained by rose bengal? Arch Ophthalmol. 1992 Jul;110(7):984-93. [PubMed:1637285]
- 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]
- 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]
- 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
Phase Status Purpose Conditions Count 1 Completed Treatment Breast Cancer 1 1 Completed Treatment Melanoma 2 1 Recruiting Treatment Cancer Metastatic to the Liver / Hepatocellular Carcinoma That is Not Amenable to Resection, Transplant or Other Potentially Curative / Hepatocellular,Carcinoma / Metastatic Breast Cancer / Metastatic Colon Cancer / Metastatic Colorectal Cancer (MCRC) / Metastatic Lung Cancer / Metastatic Melanoma / Metastatic Ocular Melanoma / Metastatic Uveal Melanoma / Pancreatic Cancer Metastatic / Therapies 1 1 Recruiting Treatment Neuroendocrine Tumors Metastatic to the Liver 1 1, 2 Recruiting Treatment Melanoma 1 2 Completed Treatment Melanoma 1 2 Completed Treatment Psoriasis 3 2 Terminated Treatment Psoriasis Vulgaris (Plaque Psoriasis) 1 3 Terminated Treatment Cutaneous Melanoma / Recurrent Melanoma 1 Not Available No Longer Available Not Available Approved Alternative Therapy / Cutaneous or Subcutaneous Tumors Where There is no Comparable or Satisfactory 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage forms
Form Route Strength Strip Ophthalmic 1.3 mg/1 Solution Ophthalmic Strip Ophthalmic 1.5 mg/1.5mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) Decomposes MSDS - Predicted Properties
Property Value Source Water Solubility 0.000681 mg/mL ALOGPS logP 6.02 ALOGPS logP 8.78 ChemAxon logS -6.2 ALOGPS pKa (Strongest Acidic) 2.55 ChemAxon pKa (Strongest Basic) 1.89 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 83.83 Å2 ChemAxon Rotatable Bond Count 1 ChemAxon Refractivity 176.05 m3·mol-1 ChemAxon Polarizability 63.8 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 0 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Taxonomy
- Classification
- Not classified
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
- 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]
- Tseng SC, Zhang SH: Interaction between rose bengal and different protein components. Cornea. 1995 Jul;14(4):427-35. [PubMed:7545566]
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
- 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
- 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
- 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 December 12, 2019 07:27