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Identification
NameFluorescein
Accession NumberDB00693  (APRD00979, EXPT01447, DB07777)
TypeSmall Molecule
GroupsApproved
DescriptionA phthalic indicator dye that appears yellow-green in normal tear film and bright green in a more alkaline medium, such as the aqueous humor, and is used therapeutically as a diagnostic aid in corneal injuries and corneal trauma. It has been approved by FDA for use in externally applied drugs and cosmetics. (From Merck Index, 12th ed; American Medical Association Drug Evaluations; 1995, p2275)
Structure
Thumb
Synonyms
3,6-fluorandiol
3',6'-dihydroxyfluoran
9-(o-carboxyphenyl)-6-hydroxy-3-isoxanthenone
9-(o-carboxyphenyl)-6-hydroxy-3H-xanthen-3-one
C.I. Solvent Yellow 94
D and C Yellow No. 7
D&C Yellow No. 7
Fluoresceine
Fluoreszein
Japan Yellow 201
Resorcinolphthalein
Solvent Yellow 94
Yellow fluorescein
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ak-fluorInjection250 mg/mLIntravenousAkorn2008-10-01Not applicableUs
Ak-fluorInjection100 mg/mLIntravenousAkorn2008-10-01Not applicableUs
Bio GloStrip1 mgOphthalmicWhite Ophthalmic Services & Supply Co Ltd2009-01-28Not applicableCanada
Diofluor 10% InjectionSolution10 %IntravenousDioptic Pharmaceuticals Inc1994-12-31Not applicableCanada
Diofluor 25% InjectionSolution25 %IntravenousDioptic Pharmaceuticals Inc1994-12-31Not applicableCanada
Diofluor StripsStrip1 mgTopicalDioptic Pharmaceuticals Inc1995-12-31Not applicableCanada
FluoresciteInjection, solution100 mg/mLOphthalmicAlcon, Inc.1972-09-15Not applicableUs
Fluorescite Inj 10%Solution10 %IntravenousAlcon Canada Inc1980-12-31Not applicableCanada
Fluorescite Inj 25%Liquid25 %ParenteralAlcon Canada Inc1980-12-312009-04-24Canada
Fluorets - Stp Oph 1mgStrip1 mgOphthalmicChauvin Pharmaceuticals Limited1996-11-012013-01-07Canada
Fluorets (fluorescein Ophthalmic Strips)Strip1 mgOphthalmicDioptic Pharmaceuticals Inc1994-12-31Not applicableCanada
Funduscein 25% InjLiquid25 %IntravenousIolab Pharmaceuticals1989-12-311997-07-23Canada
Minims Fluorescein Sodium 2%Solution2 %OphthalmicValeant Canada Lp/valeant Canada s.e.c.1995-12-31Not applicableCanada
Odan-fluoresceinSolution100 mgIntravenousOdan Laboratories Ltd1984-12-31Not applicableCanada
Odan-fluoresceinLiquid250 mgIntravenousOdan Laboratories Ltd1985-12-31Not applicableCanada
Odan-fluoretsStrip1 mgOphthalmicOdan Laboratories Ltd1986-12-31Not applicableCanada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
BiogloStrip1 mg/mgOphthalmicHub Pharmaceuticals, Inc.2012-04-01Not applicableUs
BiogloStrip1 mg/1OphthalmicREMEDYREPACK INC.2014-08-04Not applicableUs
Dry Eye TestStrip.12 mg/1OphthalmicNomax Inc.2013-12-05Not applicableUs
Ful-gloStrip1 mg/1OphthalmicA S Medication Solutions2004-06-01Not applicableUs
GlostripsStrip.6 mg/1OphthalmicNomax Inc.2013-07-30Not applicableUs
GlostripsStrip1 mg/1OphthalmicNomax Inc.2013-07-30Not applicableUs
International BrandsNot Available
Brand mixtures
NameLabellerIngredients
AltafluorAltaire Pharmaceuticals Inc.
FlucaineO Cu Soft, Inc.
Fluorescein Sodium & Benoxinate Hydrochloride Ophtalmic Solution, USPBausch & Lomb Inc
Fluorescein Sodium and Benoxinate HydrochlorideBausch & Lomb Incorporated
Fluorescein Sodium and Proparacaine HydrochlorideAltaire Pharmaceuticals Inc.
FluoroxWhite Ophthalmic Services & Supply Co Ltd
FluressAkorn, Inc.
Fluress Liq OphPilkington Barnes Hind
FluroxO Cu Soft, Inc.
Minims Lidocaine and FluoresceinChauvin Pharmaceuticals Limited
Odan-fluoracaineOdan Laboratories Ltd
Salts
Name/CASStructureProperties
Fluorescein disodium
Thumb
  • InChI Key: RGPLGPBQJOQFJS-UHFFFAOYSA-L
  • Monoisotopic Mass: 376.03236278
  • Average Mass: 376.2699
DBSALT000660
Fluorescein sodium
518-47-8
Thumb
  • InChI Key: NJDNXYGOVLYJHP-UHFFFAOYSA-L
  • Monoisotopic Mass: 376.03236198
  • Average Mass: 376.275
DBSALT001432
Categories
UNIITPY09G7XIR
CAS number2321-07-5
WeightAverage: 332.3063
Monoisotopic: 332.068473494
Chemical FormulaC20H12O5
InChI KeyGNBHRKFJIUUOQI-UHFFFAOYSA-N
InChI
InChI=1S/C20H12O5/c21-11-5-7-15-17(9-11)24-18-10-12(22)6-8-16(18)20(15)14-4-2-1-3-13(14)19(23)25-20/h1-10,21-22H
IUPAC Name
3',6'-dihydroxy-3H-spiro[2-benzofuran-1,9'-xanthene]-3-one
SMILES
OC1=CC2=C(C=C1)C1(OC(=O)C3=CC=CC=C13)C1=C(O2)C=C(O)C=C1
Pharmacology
IndicationFor diagnostic imaging. Primarily indicated in diagnostic fluorescein angiography or angioscopy of the fundus and of the iris vasculature.
Structured Indications
PharmacodynamicsNot Available
Mechanism of actionFluorescein sodium is used extensively as a diagnostic tool in the field of ophthalmology. Fluorescein is a fluorescent compound or fluorophore having a maximum absorbance of 494 m and an emission maximum of 521 nm. The yellowish-green fluorescence of the compound can be used to demarcate the vascular area under observation, distinguishing it from adjacent areas. It is applied topically in the form of a drop or it can be injected intravenously to produce a fluorescein angiogram. Topical fluorescein is a useful tool in the diagnosis of corneal abrasions, corneal ulcers, herpetic corneal infections, and dry eye. Fluorescein angiography is used to diagnose and categorize macular degeneration, diabetic retinopathy, inflammatory intraocular conditions, and intraocular tumors.
TargetKindPharmacological actionActionsOrganismUniProt ID
Ig kappa chain V-II region RPMI 6410Proteinno
other
HumanP06310 details
DNANucleotideno
other
Humannot applicabledetails
Related Articles
AbsorptionRapidly distributed
Volume of distribution
  • 0.5 L/kg
Protein binding85%
MetabolismNot Available
Route of eliminationFluorescein and its metabolites are mainly eliminated via renal excretion.
Half lifeNot Available
Clearance
  • renal cl=1.75 mL/min/kg [After IV administration]
  • hepatic cl=1.50 mL/min/kg [After IV administration]
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug InteractionsNo interactions found.
Food InteractionsNot Available
References
Synthesis Reference

Richard T. Dean, Conrad P. Dorn, Jr., Tsung-Ying Shen, “Fluorescein esters and ethers and the preparation thereof.” U.S. Patent US4304720, issued January, 1972.

US4304720
General References
  1. Noga EJ, Udomkusonsri P: Fluorescein: a rapid, sensitive, nonlethal method for detecting skin ulceration in fish. Vet Pathol. 2002 Nov;39(6):726-31. [PubMed:12450204 ]
External Links
ATC CodesS01JA51S01JA01
AHFS Codes
  • 36:89.00*
PDB Entries
FDA labelNot Available
MSDSDownload (73 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9542
Blood Brain Barrier+0.8803
Caco-2 permeable-0.8076
P-glycoprotein substrateSubstrate0.5063
P-glycoprotein inhibitor INon-inhibitor0.9612
P-glycoprotein inhibitor IINon-inhibitor0.9393
Renal organic cation transporterNon-inhibitor0.8702
CYP450 2C9 substrateNon-substrate0.8032
CYP450 2D6 substrateNon-substrate0.8972
CYP450 3A4 substrateNon-substrate0.6669
CYP450 1A2 substrateNon-inhibitor0.6827
CYP450 2C9 inhibitorInhibitor0.7325
CYP450 2D6 inhibitorNon-inhibitor0.8381
CYP450 2C19 inhibitorNon-inhibitor0.7311
CYP450 3A4 inhibitorInhibitor0.5166
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7479
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9437
BiodegradationNot ready biodegradable0.9431
Rat acute toxicity2.7602 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9805
hERG inhibition (predictor II)Non-inhibitor0.9481
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Novartis pharmaceuticals corp
  • Alcon inc
Packagers
Dosage forms
FormRouteStrength
InjectionIntravenous100 mg/mL
InjectionIntravenous250 mg/mL
StripOphthalmic1 mg/mg
SolutionIntravenous10 %
SolutionIntravenous25 %
StripTopical1 mg
StripOphthalmic.12 mg/1
Injection, solutionOphthalmic100 mg/mL
LiquidParenteral25 %
StripOphthalmic1 mg
Solution / dropsOphthalmic
LiquidOphthalmic
SolutionOphthalmic
LiquidIntravenous25 %
StripOphthalmic.6 mg/1
StripOphthalmic1 mg/1
SolutionOphthalmic2 %
Solution / dropsOphthalmic; Topical
LiquidIntravenous250 mg
SolutionIntravenous100 mg
Prices
Unit descriptionCostUnit
Fluorescein 2% droptainer12.0USD ml
Fluorescite 10% ampul5.99USD ml
Fluorescein lite 25% vial4.29USD ml
Ak-fluor 25% vial3.9USD ml
Fluorescein sodium 25% vial2.4USD ml
Fluorescein lite 10% vial1.72USD ml
Ak-fluor 10% vial1.56USD ml
Fluorescein sodium 10% vial0.96USD ml
Fluorescein powder0.08USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point315 dec °CPhysProp
water solubility600 mg/mL (sodium salt)Not Available
logP3.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0255 mg/mLALOGPS
logP2.64ALOGPS
logP3.88ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)8.72ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity91.22 m3·mol-1ChemAxon
Polarizability33.14 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-1353900000-611445d6ab5246bd851eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene rings joined to each other by a pyran ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct ParentXanthenes
Alternative Parents
Substituents
  • Xanthene
  • Diaryl ether
  • Phthalide
  • Benzofuranone
  • Benzenoid
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
no
Actions
other
General Function:
Antigen binding
Specific Function:
Not Available
Gene Name:
Not Available
Uniprot ID:
P06310
Molecular Weight:
14706.62 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
2. DNA
Kind
Nucleotide
Organism
Human
Pharmacological action
no
Actions
other
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Estevez-Torres A, Gosse C, Le Saux T, Allemand JF, Croquette V, Berthoumieux H, Lemarchand A, Jullien L: Fourier analysis to measure diffusion coefficients and resolve mixtures on a continuous electrophoresis chip. Anal Chem. 2007 Nov 1;79(21):8222-31. Epub 2007 Sep 25. [PubMed:17892271 ]
  4. Huang YM, Qi YJ, Zhu YL, Tong DY, Wu XY: [Polymorphism of 7 Y-STR loci in Chinese populations by multiplex PCR genotyping using fluorescein-labeled primers]. Yi Chuan. 2007 Oct;29(10):1214-22. [PubMed:17905711 ]
  5. Pennathur S, Baldessari F, Santiago JG, Kattah MG, Steinman JB, Utz PJ: Free-solution oligonucleotide separation in nanoscale channels. Anal Chem. 2007 Nov 1;79(21):8316-22. Epub 2007 Sep 21. [PubMed:17883279 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inducer
General Function:
Vitamin d 24-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP1A1
Uniprot ID:
P04798
Molecular Weight:
58164.815 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS) (By similarity). Mediates the sodium-in...
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular Weight:
61815.78 Da
References
  1. Lu R, Chan BS, Schuster VL: Cloning of the human kidney PAH transporter: narrow substrate specificity and regulation by protein kinase C. Am J Physiol. 1999 Feb;276(2 Pt 2):F295-303. [PubMed:9950961 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Transporter activity
Specific Function:
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name:
ABCB11
Uniprot ID:
O95342
Molecular Weight:
146405.83 Da
References
  1. Wang EJ, Casciano CN, Clement RP, Johnson WW: Fluorescent substrates of sister-P-glycoprotein (BSEP) evaluated as markers of active transport and inhibition: evidence for contingent unequal binding sites. Pharm Res. 2003 Apr;20(4):537-44. [PubMed:12739759 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Transporter activity
Specific Function:
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotrexate, antiviral drugs and other xenobiotics. Confers resistance to anticancer drugs. Hydrolyzes ATP with low efficiency.
Gene Name:
ABCC1
Uniprot ID:
P33527
Molecular Weight:
171589.5 Da
References
  1. Sun H, Johnson DR, Finch RA, Sartorelli AC, Miller DW, Elmquist WF: Transport of fluorescein in MDCKII-MRP1 transfected cells and mrp1-knockout mice. Biochem Biophys Res Commun. 2001 Jun 22;284(4):863-9. [PubMed:11409873 ]
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Drug created on June 13, 2005 07:24 / Updated on December 08, 2016 11:47