Chemical Component Summary

Name2-(6-HYDROXY-3-OXO-3H-XANTHEN-9-YL)-BENZOIC ACID
SynonymsFLUORESCEIN
Identifiers2-(3-hydroxy-6-oxo-xanthen-9-yl)benzoic acid
FormulaC20 H12 O5
Molecular Weight332.306
TypeNON-POLYMER
Isomeric SMILESc1ccc(c(c1)C2=C3C=CC(=O)C=C3Oc4c2ccc(c4)O)C(=O)O
InChIInChI=1S/C20H12O5/c21-11-5-7-15-17(9-11)25-18-10-12(22)6-8-16(18)19(15)13-3-1-2-4-14(13)20(23)24/h1-10,21H,(H,23,24)
InChIKeyYKGGGCXBWXHKIZ-UHFFFAOYSA-N

Chemical Details

Formal Charge0
Atom Count37
Chiral Atom Count0
Bond Count40
Aromatic Bond Count23

Drug Info: DrugBank

DrugBank IDDB00693 
NameFluorescein
Groups approved
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)
Synonyms
  • D and C Yellow No. 7
  • 9-(o-carboxyphenyl)-6-hydroxy-3-isoxanthenone
  • Fluoresceine
  • D&C Yellow No. 7
  • 9-(o-carboxyphenyl)-6-hydroxy-3H-xanthen-3-one
Brand Names
  • Altafluor
  • Fluorescein Sodium & Benoxinate Hydrochloride Ophthalmic Solution, USP
  • Ful-glo
  • Odan-fluoracaine
  • Bio Glo
IndicationFor diagnostic imaging. Primarily indicated in diagnostic fluorescein angiography or angioscopy of the fundus and of the iris vasculature.
Categories
  • BSEP/ABCB11 Substrates
  • Coloring Agents
  • Colouring Agents
  • Compounds used in a research, industrial, or household setting
  • Contrast Media
ATC-Code
  • S01JA01
  • S01JA51
CAS number2321-07-5

Drug Targets

NameTarget SequencePharmacological ActionActions
Ig kappa chain V-II region RPMI 6410MRLPAQLLGLLMLWVPGSSGDVVMTQSPLSLPVTLGQPASISCRSSQSLV...unknownother
DNA-unknownother
Solute carrier family 22 member 6MAFNDLLQQVGGVGRFQQIQVTLVVLPLLLMASHNTLQNFTAAIPTHHCR...unknownsubstrate,inhibitor
Bile salt export pumpMSDSVILRSIKKFGEENDGFESDKSYNNDKKSRLQDEKKGDGVRVGFFQL...unknownsubstrate
Multidrug resistance-associated protein 1MALRGFCSADGSDPLWDWNVTWNTSNPDFTKCFQNTVLVWVPCFYLWACF...unknownsubstrate
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL177756
PubChem 129856003, 3383
ChEMBL CHEMBL177756
CCDC/CSD NUKCOL, CAGROV, CAGRAH, CAGRIP