DrugBank: Fluorescein (DB00693)

targets (2) enzymes (1) transporters (3)

Identification

Name

Fluorescein

Accession Number

DB00693 (APRD00979, DB07777, EXPT01447)

Type

small molecule

Groups

approved

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

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

2-(6-Hydroxy-3-oxo-3H-xanthen-9-yl)-benzoic acid

Brand names

Acid Yellow 73
Eosin
Fluorescein acid
Fluorescein disodium salt
Fluorescein disodium salt dihydrate
Fluorescein sodium
Fluorescein Sodium salt
Fluorescein, Disodium Salt, Fluorescein, disodium salt
Fluorescite
Funduscein-25
Uranin
Uranine

Brand name mixtures

Fluoracaine Oph Soln (Fluorescein Sodium + Proxymetacain Hcl)
Fluorescein Sodium & Benoxinate Hydrochloride Ophtalmic Solution, Usp (Benoxinate Hydrochloride + Fluorescein Sodium)
Fluress (Benoxinate Hydrochloride + Fluorescein Sodium)
Fluress Liq Oph (Benoxinate Hydrochloride + Fluorescein Sodium)

Categories

Contrast Media
Fluorescent Dyes

CAS number

2321-07-5

Weight

Average: 332.3063
Monoisotopic: 332.068473494

Chemical Formula

C₂₀H₁₂O₅

InChI Key

InChIKey=GNBHRKFJIUUOQI-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

Plain Text

IUPAC Name

3',6'-dihydroxy-3H-spiro[2-benzofuran-1,9'-xanthene]-3-one

SMILES

OC1=CC2=C(C=C1)C1(OC(=O)C3=C1C=CC=C3)C1=C(O2)C=C(O)C=C1

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Organic

Classes

Xanthenes

Substructures

Xanthenes
Carboxylic Acids and Derivatives
Benzofurans
Hydroxy Compounds
Pyrans
Benzyl Alcohols and Derivatives
Acetates
Benzoates
Phenols and Derivatives
Lactones
Ethers
Benzene and Derivatives
Benzyl Esters
Benzylacetates
Methoxyphenols
Benzopyrans
Heterocyclic compounds
Aromatic compounds
Anisoles
Benzoyl Derivatives
Phenyl Esters

Pharmacology

Indication

For diagnostic imaging. Primarily indicated in diagnostic fluorescein angiography or angioscopy of the fundus and of the iris vasculature.

Pharmacodynamics

Not Available

Mechanism of action

Fluorescein 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.

Absorption

Rapidly distributed

Volume of distribution

0.5 L/kg

Protein binding

85%

Metabolism

Route of elimination

Fluorescein and its metabolites are mainly eliminated via renal excretion.

Half life

Not Available

Clearance

renal cl=1.75 mL/min/kg [After IV administration]
hepatic cl=1.50 mL/min/kg [After IV administration]

Toxicity

Not Available

Affected organisms

Humans and other mammals

Pathways

Not Available

Pharmacoeconomics

Manufacturers

Novartis pharmaceuticals corp
Alcon inc

Packagers

Dosage forms

Form	Route	Strength
Liquid	Intravenous
Liquid	Ophthalmic
Solution	Intravenous
Strip	Ophthalmic
Strip	Topical

Prices

Unit description	Cost	Unit
Fluorescein 2% droptainer	12.0 USD	ml
Fluorescite 10% ampul	5.99 USD	ml
Fluorescein lite 25% vial	4.29 USD	ml
Ak-fluor 25% vial	3.9 USD	ml
Fluorescein sodium 25% vial	2.4 USD	ml
Fluorescein lite 10% vial	1.72 USD	ml
Ak-fluor 10% vial	1.56 USD	ml
Fluorescein sodium 10% vial	0.96 USD	ml
Fluorescein powder	0.08 USD	g

Patents

Not Available

Properties

State

solid

Melting point

315 oC

Experimental Properties

Property	Value	Source
water solubility	600 mg/mL (sodium salt)	PhysProp
logP	3.4	PhysProp

Predicted Properties

Property	Value	Source
water solubility	2.55e-02 g/l	ALOGPS
logP	2.64	ALOGPS
logP	3.88	ChemAxon Molconvert
logS	-4.11	ALOGPS
pKa	9.32	ChemAxon Molconvert
hydrogen acceptor count	3	ChemAxon Molconvert
hydrogen donor count	2	ChemAxon Molconvert
polar surface area	75.99	ChemAxon Molconvert
rotatable bond count	0	ChemAxon Molconvert
refractivity	91.22	ChemAxon Molconvert
polarizability	33.14	ChemAxon Molconvert

References

Synthesis Reference

Not Available

General Reference

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

Resource	Link
KEGG Drug	D01261
PubChem Compound	16850
PubChem Substance	46504703
ChemSpider	15968
ChEBI	31624
ChEMBL	31624
HET	FLU
Drug Product Database	2026252
RxList	http://www.rxlist.com/cgi/generic2/fluorescein.htm
Wikipedia	http://en.wikipedia.org/wiki/Fluorescein

ATC Codes

S01JA01

AHFS Codes

36:89.00*

PDB Entries

1X9Q

FDA label

Not Available

MSDS

show (73 KB)

Interactions

Drug Interactions

Drug	Interaction

Food Interactions

Not Available

Targets
1. Ig kappa chain V-II region RPMI 6410 Pharmacological action: no Actions: other Organism class: human UniProt ID: P06310 Protein Sequence: FASTA References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed 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 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 Pharmacological action: no Actions: other DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes. Gene Sequence: FASTA References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed 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 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 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 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

Targets

1. Ig kappa chain V-II region RPMI 6410

Pharmacological action: no
Actions: other
Organism class: human
UniProt ID: P06310 Link_out

Protein Sequence: FASTA

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
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
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

Pharmacological action: no
Actions: other

DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes.

Gene Sequence: FASTA

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
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
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
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
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 Actions: inducer 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 UniProt ID: P04798 Gene: CYP1A1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: 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

Enzymes

1. Cytochrome P450 1A1

Actions: inducer

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

UniProt ID: P04798 Link_out

Gene: CYP1A1 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

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 Actions: inhibitor UniProt ID: Q4U2R8 Gene: hROAT1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: 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 Actions: substrate Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes UniProt ID: O95342 Gene: ABCB11 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: 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 Actions: substrate May participate directly in the active transport of drugs into subcellular organelles or influence drug distribution indirectly. Confers resistance to anticancer drugs. Transports LTC4. May protect milk against xenobiotics UniProt ID: P33527 Gene: ABCC1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: 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

Transporters

1. Solute carrier family 22 member 6

Actions: inhibitor
UniProt ID: Q4U2R8 Link_out

Gene: hROAT1 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

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

Actions: substrate

Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes

UniProt ID: O95342 Link_out

Gene: ABCB11 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

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

Actions: substrate

May participate directly in the active transport of drugs into subcellular organelles or influence drug distribution indirectly. Confers resistance to anticancer drugs. Transports LTC4. May protect milk against xenobiotics

UniProt ID: P33527 Link_out

Gene: ABCC1 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

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

Comments

Drug created on June 13, 2005 07:24 / Updated on October 11, 2011 12:17

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.