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Identification
NameFluorescein
Accession NumberDB00693  (APRD00979, DB07777, EXPT01447)
Typesmall molecule
Groupsapproved
Description

A 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
SynonymLanguageCode
3,6-fluorandiolNot AvailableNot Available
3',6'-dihydroxyfluoranNot AvailableNot Available
9-(o-carboxyphenyl)-6-hydroxy-3-isoxanthenoneNot AvailableNot Available
9-(o-carboxyphenyl)-6-hydroxy-3H-xanthen-3-oneNot AvailableNot Available
C.I. Solvent Yellow 94Not AvailableNot Available
D and C Yellow No. 7Not AvailableNot Available
D&C Yellow No. 7Not AvailableNot Available
FluoreszeinNot AvailableNot Available
Japan Yellow 201Not AvailableNot Available
ResorcinolphthaleinNot AvailableNot Available
Solvent Yellow 94Not AvailableNot Available
Yellow fluoresceinNot AvailableNot Available
Salts
Name/CAS Structure Properties
Fluorescein disodium
Thumb
  • InChI Key: RGPLGPBQJOQFJS-UHFFFAOYSA-L
  • Monoisotopic Mass: 376.03236278
  • Average Mass: 376.2699
DBSALT000660
Brand names
NameCompany
AK-FLUORNot Available
FluoresciteNot Available
Brand mixtures
Brand NameIngredients
Fluoracaine Oph SolutionFluorescein Sodium + Proxymetacain Hcl
Fluorescein Sodium & Benoxinate Hydrochloride Ophtalmic Solution, USPBenoxinate Hydrochloride + Fluorescein Sodium
FluressBenoxinate Hydrochloride + Fluorescein Sodium
Categories
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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassBenzopyrans
SubclassDibenzopyrans
Direct parentXanthenes
Alternative parentsDiarylethers; Phthalides; Phenols and Derivatives; Carboxylic Acid Esters; Enols; Dialkyl Ethers; Polyamines
Substituentsdiaryl ether; phthalide; benzofuranone; benzofuran; phenol derivative; benzene; carboxylic acid ester; dialkyl ether; enol; carboxylic acid derivative; polyamine; ether
Classification descriptionThis compound belongs to the xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene ring joined to each other by a pyran ring.
Pharmacology
IndicationFor diagnostic imaging. Primarily indicated in diagnostic fluorescein angiography or angioscopy of the fundus and of the iris vasculature.
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.
AbsorptionRapidly distributed
Volume of distribution
  • 0.5 L/kg
Protein binding85%
Metabolism
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
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9542
Blood Brain Barrier + 0.8803
Caco-2 permeable - 0.8076
P-glycoprotein substrate Substrate 0.5063
P-glycoprotein inhibitor I Non-inhibitor 0.9612
P-glycoprotein inhibitor II Non-inhibitor 0.9393
Renal organic cation transporter Non-inhibitor 0.8702
CYP450 2C9 substrate Non-substrate 0.8032
CYP450 2D6 substrate Non-substrate 0.8972
CYP450 3A4 substrate Non-substrate 0.6669
CYP450 1A2 substrate Non-inhibitor 0.6827
CYP450 2C9 substrate Inhibitor 0.7325
CYP450 2D6 substrate Non-inhibitor 0.8381
CYP450 2C19 substrate Non-inhibitor 0.7311
CYP450 3A4 substrate Inhibitor 0.5166
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7479
Ames test Non AMES toxic 0.9133
Carcinogenicity Non-carcinogens 0.9437
Biodegradation Not ready biodegradable 0.9431
Rat acute toxicity 2.7602 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9805
hERG inhibition (predictor II) Non-inhibitor 0.9481
Pharmacoeconomics
Manufacturers
  • Novartis pharmaceuticals corp
  • Alcon inc
Packagers
Dosage forms
FormRouteStrength
LiquidIntravenous
LiquidOphthalmic
SolutionIntravenous
StripOphthalmic
StripTopical
Prices
Unit descriptionCostUnit
Fluorescein 2% droptainer12.0USDml
Fluorescite 10% ampul5.99USDml
Fluorescein lite 25% vial4.29USDml
Ak-fluor 25% vial3.9USDml
Fluorescein sodium 25% vial2.4USDml
Fluorescein lite 10% vial1.72USDml
Ak-fluor 10% vial1.56USDml
Fluorescein sodium 10% vial0.96USDml
Fluorescein powder0.08USDg
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 solubility2.55e-02 g/lALOGPS
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 area75.99ChemAxon
rotatable bond count0ChemAxon
refractivity91.22ChemAxon
polarizability33.14ChemAxon
number of rings5ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraGC-MS
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 Reference
  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
External Links
ResourceLink
KEGG DrugD01261
PubChem Compound16850
PubChem Substance46504703
ChemSpider15968
ChEBI31624
ChEMBLCHEMBL177756
PharmGKBPA164746009
HETFLU
Drug Product Database2026252
RxListhttp://www.rxlist.com/cgi/generic2/fluorescein.htm
WikipediaFluorescein
ATC CodesS01JA01
AHFS Codes
  • 36:89.00*
PDB Entries
FDA labelNot Available
MSDSshow(73 KB)
Interactions
Drug InteractionsSearched, but no interactions found.
Food InteractionsNot Available

Targets

1. Ig kappa chain V-II region RPMI 6410

Kind: protein

Organism: Human

Pharmacological action: no

Actions: other

Components

Name UniProt ID Details
Ig kappa chain V-II region RPMI 6410 P06310 Details

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
  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
  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

2. DNA

Kind: nucleotide

Organism: Human

Pharmacological action: no

Actions: other

Components

Name UniProt ID Details

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
  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
  3. Estevez-Torres A, Gosse C, Saux TL, 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 Sep 25;. Pubmed
  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
  5. Pennathur S, Baldessari F, Santiago JG, Kattah MG, Steinman JB, Utz PJ: Free-Solution Oligonucleotide Separation in Nanoscale Channels. Anal Chem. 2007 Sep 21;. Pubmed

Enzymes

1. Cytochrome P450 1A1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Cytochrome P450 1A1 P04798 Details

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. Epub 2009 Nov 24. Pubmed

Transporters

1. Solute carrier family 22 member 6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 6 Q4U2R8 Details

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

2. Bile salt export pump

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Bile salt export pump O95342 Details

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

3. Multidrug resistance-associated protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Multidrug resistance-associated protein 1 P33527 Details

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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:11