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Showing drug card for Fluorescein (DB00693)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-06-23 18:06:00
Primary Accession Number DB00693
Secondary Accession Number
  • APRD00979
  • EXPT01447
Name Fluorescein
Drug Type
  • Approved
  • Small Molecule
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)
Synonyms Not Available
Brand Names
  1. Acid Yellow 73
  2. Eosin
  3. Fluorescein Sodium salt
  4. Fluorescein acid
  5. Fluorescein disodium salt
  6. Fluorescein disodium salt dihydrate
  7. Fluorescein sodium
  8. Fluorescein, Disodium Salt, Fluorescein, disodium salt
  9. Fluorescite
  10. Funduscein-25
  11. Uranin
  12. Uranine
Brand Mixtures
  1. Fluoracaine Oph Soln (Fluorescein Sodium + Proxymetacain Hcl)
  2. Fluorescein Sodium & Benoxinate Hydrochloride Ophtalmic Solution, Usp (Benoxinate Hydrochloride + Fluorescein Sodium)
  3. Fluress (Benoxinate Hydrochloride + Fluorescein Sodium)
  4. Fluress Liq Oph (Benoxinate Hydrochloride + Fluorescein Sodium)
Chemical IUPAC Name 3',6'-dihydroxyspiro[2-benzofuran-3,9'-xanthene]-1-one
Chemical Formula C20H12O5
Chemical Structure Structure
CAS Registry Number 2321-07-5
InChI Identifier InChI=1/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
InChI Key GNBHRKFJIUUOQI-UHFFFAOYAZ
KEGG Drug D01261 Link Image
KEGG Compound Not Available
PubChem Compound 16850 Link Image
PubChem Substance 7848324 Link Image
ChEBI ID Not Available
PharmGKB ID Not Available
HET ID FLG Link Image
GenBank ID Not Available
Drug ID Number [DIN] 02026252 Link Image
RxList Link http://www.rxlist.com/cgi/generic2/fluorescein.htm Link Image
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Fluorescein Link Image
FDA Label Not Available
Material Safety Data Sheet (MSDS)
Synthesis Reference Not Available
Average Molecular Weight 332.3063
Monoisotopic Molecular Weight 332.0685
State Solid
Melting Point 315 oC
Experimental Water Solubility 600 mg/mL (sodium salt) Source: PhysProp
Predicted Water Solubility 2.55e-02 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 3.4 Source: PhysProp
Predicted LogP 2.64 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -4.11 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID 1X9Q Link Image
Experimental PDB File Show
Experimental PDB Structure
Isomeric SMILES OC1=CC2=C(C=C1)C1(OC(=O)C3=CC=CC=C13)C1=C(O2)C=C(O)C=C1
Canonical SMILES OC1=CC2=C(C=C1)C1(OC(=O)C3=CC=CC=C13)C1=C(O2)C=C(O)C=C1
Drug Category
  • Contrast Media
  • Fluorescent Dyes
ATC Codes
AHFS Codes
  • 36:89.00*
Indication For diagnostic imaging. Primarily indicated in diagnostic fluorescein angiography or angioscopy of the fundus and of the iris vasculature.
Pharmacology 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
Toxicity Not Available
Protein Binding 85%
Biotransformation Not Available
Half Life Not Available
Dosage Forms
Form Route
Liquid Intravenous
Liquid Ophthalmic
Solution Intravenous
Strip Ophthalmic
Strip Topical
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Not Available
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
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 Link Image]
  2. Wikipedia Link Image
  3. RxList Link Image
Organisms Affected
  • Humans and other mammals
Targets
  1. DNA
  2. Ig kappa chain V-II region 26-10
  3. Bilin-binding protein
Drug Target 1 [top]
Target 1 ID 874
Target 1 Name DNA
Target 1 Synonyms
  1. Deoxyribonucleic acid
Target 1 Gene Name Not Available
Target 1 Protein Sequence Not Available
Target 1 Number of Residues 0
Target 1 Molecular Weight 7656 (double strand)
Target 1 Theoretical pI Not Available
Target 1 GO Classification
Function
information storage
information transfer
Process
DNA replication and chromosomal cycle
DNA replication
DNA-dependent DNA replication
DNA replication, synthesis of RNA primer
transcription
transcription, DNA dependent
Component
cell
intracellular
nucleus
mitochondria
Target 1 General Function Biological information storage and information transfer
Target 1 Specific Function 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.
Target 1 Pathways
Name SMPDB Link KEGG Link
DNA polymerase map03030 Link Image
RNA polymerase map03020 Link Image
Target 1 Reactions
  • DNA + DNA polymerase + nNTP = 2 DNA + nNDP; DNA + RNA polymerase + NTP = mRNA + nNDP
Target 1 Pfam Domain Function Not Available
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • None
Target 1 Essentiality Essential
Target 1 GenBank ID Protein Not Available
Target 1 UniProtKB/Swiss-Prot ID Not Available
Target 1 UniProtKB/Swiss-Prot Entry Name Not Available
Target 1 PDB ID 1BNA Link Image
Target 1 PDB File Show
Target 1 3D Structure
Target 1 Cellular Location
  • Nucleus and mitochondria
Target 1 Gene Sequence >Example: Dickerson dodecamer 
CGCGAATTCGCG
Target 1 GenBank Gene ID
Target 1 GeneCard ID Not Available
Target 1 GenAtlas ID Not Available
Target 1 HGNC ID Not Available
Target 1 Chromosome Location Not Available
Target 1 Locus All loci
Target 1 SNPs Not Available
Target 1 General References
  1. Nadeau D, Marchand C: Change in the kinetics of sulphacetamide tissue distribution in Walker tumor-bearing rats. Drug Metab Dispos. 1975 Nov-Dec;3(6):565-76. [PubMed Link Image]
Target 1 Drug References
  1. 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 Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]
  3. 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 Link Image]
  4. 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 Link Image]
  5. 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 Link Image]
Drug Target 2 [top]
Target 2 ID 2706
Target 2 Name Ig kappa chain V-II region 26-10
Target 2 Synonyms Not Available
Target 2 Gene Name Not Available
Target 2 Protein Sequence >Ig kappa chain V-II region 26-10 
DVVMTQTPLSLPVSLGDQASISCRSSQSLVHSNGNTYLNWYLQKAGQSPKLLIYKVSNRF
SGVPDRFSGSGSGTDFTLKISRVEAEDLGIYFCSQTTHVPPTFGGGTKLEIKR
Target 2 Number of Residues 114
Target 2 Molecular Weight 12273
Target 2 Theoretical pI 9.17
Target 2 GO Classification Not Available
Target 2 General Function Not Available
Target 2 Specific Function Not Available
Target 2 Pathways Not Available
Target 2 Reactions Not Available
Target 2 Pfam Domain Function
Target 2 Signals
  • None
Target 2 Transmembrane Regions
  • None
Target 2 Essentiality Essential
Target 2 GenBank ID Protein Not Available
Target 2 UniProtKB/Swiss-Prot ID P01631 Link Image
Target 2 UniProtKB/Swiss-Prot Entry Name KV2A7_MOUSE Link Image
Target 2 PDB ID 1MAK Link Image
Target 2 PDB File Show
Target 2 3D Structure
Target 2 Cellular Location Not Available
Target 2 Gene Sequence Not Available
Target 2 GenBank Gene ID
Target 2 GeneCard ID Not Available
Target 2 GenAtlas ID Not Available
Target 2 HGNC ID Not Available
Target 2 Chromosome Location Not Available
Target 2 Locus Not Available
Target 2 SNPs Not Available
Target 2 General References
  1. Novotny J, Margolies MN: Amino acid sequence of the light chain variable region from a mouse anti-digoxin hybridoma antibody. Biochemistry. 1983 Mar 1;22(5):1153-8. [PubMed Link Image]
Target 2 Drug References
  1. 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 Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]
Drug Target 3 [top]
Target 3 ID 2850
Target 3 Name Bilin-binding protein
Target 3 Synonyms
  1. BBP
  2. Bilin-binding protein precursor
Target 3 Gene Name Not Available
Target 3 Protein Sequence >Bilin-binding protein precursor 
MQYLIVLALVAAASANVYHDGACPEVKPVDNFDWSNYHGKWWEVAKYPNSVEKYGKCGWA
EYTPEGKSVKVSNYHVIHGKEYFIEGTAYPVGDSKIGKIYHKLTYGGVTKENVFNVLSTD
NKNYIIGYYCKYDEDKKGHQDFVWVLSRSKVLTGEAKTAVENYLIGSPVVDSQKLVYSDF
SEAACKVNN
Target 3 Number of Residues 192
Target 3 Molecular Weight 21306
Target 3 Theoretical pI 7.11
Target 3 GO Classification
Function
transporter activity
binding
Process
physiological process
cellular physiological process
transport
Component
Not Available
Target 3 General Function Cell wall/membrane/envelope biogenesis
Target 3 Specific Function This protein binds the blue pigments bilins
Target 3 Pathways Not Available
Target 3 Reactions Not Available
Target 3 Pfam Domain Function
Target 3 Signals
  • 1-15
Target 3 Transmembrane Regions
  • None
Target 3 Essentiality Essential
Target 3 GenBank ID Protein 434995 Link Image
Target 3 UniProtKB/Swiss-Prot ID P09464 Link Image
Target 3 UniProtKB/Swiss-Prot Entry Name BBP_PIEBR Link Image
Target 3 PDB ID 1BBP Link Image
Target 3 PDB File Show
Target 3 3D Structure
Target 3 Cellular Location Not Available
Target 3 Gene Sequence >570 bp 
ATGCAGTACTTGATTGTTCTTGCTCTAGTAGCGGCCGCGTCCGCCAACGTGTACCACGAC
GGTGCCTGTCCCGAAGTCAAGCCAGTCGACAACTTCGACTGGTCAAACTACCACGGAAAA
TGGTGGGAAGTCGCCAAATACCCCAACTCAGTTGAGAAGTACGGAAAGTGCGGATGGGCT
GAGTACACTCCTGAAGGCAAGAGTGTCAAAGTTTCGAACTACCACGTAATCCACGGCAAG
GAATACTTTATTGAAGGAACTGCCTACCCAGTTGGTGACTCCAAGATTGGAAAGATCTAC
CACAAGCTGACTTACGGAGGTGTCACCAAGGAGAACGTATTCAACGTACTCTCCACTGAC
AACAAGAACTACATCATCGGATACTACTGCAAATACGACGAGGACAAGAAGGGACACCAA
GACTTCGTCTGGGTGCTCTCTAGATCCAAGGTCCTTACTGGTGAAGCCAAGACCGCTGTC
GAGAACTACCTTATCGGCTCCCCAGTAGTCGACTCCCAGAAACTGGTATACAGTGACTTC
TCTGAAGCCGCCTGCAAGGTCAACAATTAA
Target 3 GenBank Gene ID
Target 3 GeneCard ID Not Available
Target 3 GenAtlas ID Not Available
Target 3 HGNC ID Not Available
Target 3 Chromosome Location Not Available
Target 3 Locus Not Available
Target 3 SNPs Not Available
Target 3 General References
  1. Suter F, Kayser H, Zuber H: The complete amino-acid sequence of the bilin-binding protein from Pieris brassicae and its similarity to a family of serum transport proteins like the retinol-binding proteins. Biol Chem Hoppe Seyler. 1988 Jun;369(6):497-505. [PubMed Link Image]
  2. Huber R, Schneider M, Mayr I, Muller R, Deutzmann R, Suter F, Zuber H, Falk H, Kayser H: Molecular structure of the bilin binding protein (BBP) from Pieris brassicae after refinement at 2.0 A resolution. J Mol Biol. 1987 Dec 5;198(3):499-513. [PubMed Link Image]
  3. Schmidt FS, Skerra A: The bilin-binding protein of Pieris brassicae. cDNA sequence and regulation of expression reveal distinct features of this insect pigment protein. Eur J Biochem. 1994 Feb 1;219(3):855-63. [PubMed Link Image]
Target 3 Drug References
  1. Beste G, Schmidt FS, Stibora T, Skerra A: Small antibody-like proteins with prescribed ligand specificities derived from the lipocalin fold. Proc Natl Acad Sci U S A. 1999 Mar 2;96(5):1898-903. [PubMed Link Image]
  2. Korndorfer IP, Beste G, Skerra A: Crystallographic analysis of an "anticalin" with tailored specificity for fluorescein reveals high structural plasticity of the lipocalin loop region. Proteins. 2003 Oct 1;53(1):121-9. [PubMed Link Image]
  3. Vopel S, Muhlbach H, Skerra A: Rational engineering of a fluorescein-binding anticalin for improved ligand affinity. Biol Chem. 2005 Nov;386(11):1097-104. [PubMed Link Image]
  4. 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 Link Image]
  5. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]

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.