U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C20H12O5
Molecular Weight 332.307
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Fluorescein

SMILES

OC1=CC2=C(C=C1)C3(OC(=O)C4=C3C=CC=C4)C5=C(O2)C=C(O)C=C5

InChI

InChIKey=GNBHRKFJIUUOQI-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C20H12O5
Molecular Weight 332.307
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including: http://www.drugbank.ca/drugs/DB00693 https://en.wikipedia.org/wiki/Fluorescein

Fluorescein is a synthetic organic compound available as a dark orange/red powder slightly soluble in water and alcohol. It is widely used as a fluorescent tracer for many applications. Fluorescein was first synthesized by Adolf von Baeyer in 1871. It can be prepared from phthalic anhydride and resorcinol in the presence of zinc chloride via the Friedel-Crafts reaction. Fuorescein sodium is used intravenously in diagnostic fluorescein angiography or angioscopy of the retina and iris vasculature. Fluorescein sodium responds to electromagnetic radiation and light between the wavelengths of 465-490 nm and fluoresces, i.e., emits light at wavelengths of 520-530 nm. Thus, the hydrocarbon is excited by blue light and emits light that appears yellowish-green. Following intravenous injection of fluorescein sodium in an aqueous solution, the unbound fraction of the fluorescein can be excited with a blue light flash from a fundus camera as it circulates through the ocular vasculature, and the yellowish green fluorescence of the dye is captured by the camera. In the fundus, the fluorescence of the dye demarcates the retinal and/or choroidal vasculature under observation, distinguishing it from adjacent areas/structures. Topical, oral, and intravenous use of fluorescein can cause adverse reactions, including nausea, vomiting, hives, acute hypotension, anaphylaxis and related anaphylactoid reaction, causing cardiac arrest and sudden death due to anaphylactic shock. The most common adverse reaction is nausea, due to a difference in the pH from the body and the pH of the sodium fluorescein dye; a number of other factors however, are considered contributors as well. The nausea usually is transient and subsides quickly. Intravenous use has the most reported adverse reactions, including sudden death, but this may reflect greater use rather than greater risk. Both oral and topical uses have been reported to cause anaphylaxis, including one case of anaphylaxis with cardiac arrest (resuscitated) following topical use in an eye drop. Reported rates of adverse reactions vary from 1% to 6%. The higher rates may reflect study populations that include a higher percentage of persons with prior adverse reactions. The risk of an adverse reaction is 25 times higher if the person has had a prior adverse reaction. The risk can be reduced with prior (prophylactic) use of antihistamines and prompt emergency management of any ensuing anaphylaxis. A simple prick test may help to identify persons at greatest risk of adverse reaction

CNS Activity

Curator's Comment: Known to be CNS non-penetrant in human. (In addition to Transendothelial electrical resistance measurements, paracellular permeability of two fluorescent tracer molecules that do not cross the BBB in a significant amount (sodium fluorescein (Na-F)) However, also known to be CNS penetrant in rat: Normalized sodium fluorescein uptake into brain tissue was calculated and is expressed as a fold increase in fluorescence by comparison with the uptake in uninfected mice. To visualize sodium fluorescein accumulation in different regions of the CNS, the brain was exposed to a UV light source and photographed using a Nikon digital camera on a Leitz Microlab microscope.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
FLUORESCITE

Approved Use

Injection 10% is indicated in diagnostic fluorescein angiography or angioscopy of the retina and iris vasculature

Launch Date

2006
Diagnostic
FLUORESCITE

Approved Use

Injection 10% is indicated in diagnostic fluorescein angiography or angioscopy of the retina and iris vasculature

Launch Date

2006
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
10.9 μg/mL
188 mg single, intravenous
dose: 188 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
FLUORESCEIN blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
10.9 μg/mL
188 mg single, intravenous
dose: 188 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
FLUORESCEIN blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
3.5 μg/mL
188 mg single, oral
dose: 188 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUORESCEIN blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1350 μg × min/mL
188 mg single, intravenous
dose: 188 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
FLUORESCEIN blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
286 min
188 mg single, intravenous
dose: 188 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
FLUORESCEIN blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
267 min
188 mg single, oral
dose: 188 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUORESCEIN blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
364 mg/kg single, intravenous
Highest studied dose
Dose: 364 mg/kg
Route: intravenous
Route: single
Dose: 364 mg/kg
Sources:
unhealthy
Health Status: unhealthy
Sources:
PubMed

PubMed

TitleDatePubMed
Effect of ions and nucleotides on the interactions of yeast Rad51 protein with single-stranded oligonucleotides.
2001-03
Nitric oxide distribution and production in the guinea pig cochlea.
2001-03
Preservation of ganglion cell layer neurons in age-related macular degeneration.
2001-03
Comparison of retinal transit times and retinal blood flow: a study in monkeys.
2001-03
Vascular patterns in pterygium and conjunctival autografting: a pilot study using indocyanine green anterior segment angiography.
2001-03
Value of nasal endoscopy and probing in the diagnosis and management of children with congenital epiphora.
2001-03
Reduced amplitude and delayed latency in foveal response of multifocal electroretinogram in early age related macular degeneration.
2001-03
Ocular pharmacokinetics in rabbits using a novel dual probe microdialysis technique.
2001-03
Retinopathy due to juvenile polymyositis.
2001-02-24
Subretinal hemorrhage from a retinal arterial macroaneurysm simulating a choroidal melanoma.
2001-02-24
Progressive outer retinal necrosis in a patient with nephrotic syndrome.
2001-02-24
Effects of methyl-beta-cyclodextrin on cryosurvival of boar spermatozoa.
2001-02-24
Study of temporal and perfusion physiology of skin capillaries in the dorsum of the foot.
2001-02-15
Retrograde infusion of fluorescein to confirm location and patency of a glaucoma drainage device.
2001-02
Long-term study of endonasal duraplasty and review of the literature.
2001-02
Inhibition of vascular smooth muscle cell proliferation by DNA-RNA chimeric hammerhead ribozyme targeting to rat platelet-derived growth factor A-chain mRNA.
2001-02
Adenoma of the retinal pigment epithelium simulating a juxtapapillary choroidal neovascular membrane.
2001-02
Ocular phenotype of bothnia dystrophy, an autosomal recessive retinitis pigmentosa associated with an R234W mutation in the RLBP1 gene.
2001-02
Perifoveal vitreous detachment is the primary pathogenic event in idiopathic macular hole formation.
2001-02
Differentiation between presumed ocular histoplasmosis syndrome and multifocal choroiditis with panuveitis based on morphology of photographed fundus lesions and fluorescein angiography.
2001-02
Photodynamic therapy of subfoveal choroidal neovascularization in age-related macular degeneration with verteporfin: two-year results of 2 randomized clinical trials-tap report 2.
2001-02
External beam irradiation of subfoveal choroidal neovascularization complicating age-related macular degeneration: one-year results of a prospective, double-masked, randomized clinical trial.
2001-02
Nitric oxide production is increased in the spermatic veins of adolescents with left idiophatic varicocele.
2001-02
All angiogenesis is not the same: Distinct patterns of response to antiangiogenic therapy in experimental neuroblastoma and Wilms tumor.
2001-02
[Ophthalmoscopic findings in 3 patients with panarteritis nodosa and review of the literature].
2001-01
Clinical grading of corneal staining of non-contact lens wearers.
2001-01
[Age-related macular degeneration (AMD)--therapeutic possibilities and new approaches].
2001-01
Use of teleoptometry to evaluate acceptability of rigid gas-permeable contact lens fits.
2001-01
Conjunctival histologic findings of dry eye and non-dry eye contact lens wearing subjects.
2001-01
Visualization of the transport of primary and secondary bile acids across liver tissue in rats: in vivo study with fluorescent bile acids.
2001-01
[A case of central retinal vein occlusion followed by branch retinal artery occlusion].
2001-01
Clinicopathological findings consistent with primary Sjögren's syndrome in a subset of patients diagnosed with chronic fatigue syndrome: preliminary observations.
2001-01
[Exudative idiopathic juxtafoveolar retinal telangiectasis].
2001-01
A case of Alport's syndrome and retinal degeneration.
2001
Retinal and choroidal vascular changes in heterozygous Fabry disease.
2001
Neovascularization associated with cytomegalovirus retinitis.
2001
Central retinal vein occlusion associated with primary pulmonary hypertension.
2001
Diabetic papillopathy with macular star mimicking clinically significant diabetic macular edema.
2001
Epipapillary adenoma of retinal pigment epithelium.
2001
Bilateral ocular ischemic syndrome in Takayasu disease.
2001
Sector retinitis pigmentosa with bitemporal visual field defects and macular hole.
2001
Visual recovery from macular phototoxic injury following cataract surgery.
2001
Surgical removal of a laser-induced choroidal neovascular membrane.
2001
Purtscher's retinopathy secondary to airbag injury.
2001
Bilateral prepapillary loops with unilateral branch retinal artery occlusion following thrombus at the loop apex.
2001
Diagnostic and therapeutic challenges.
2001
Choroidal granulomas in systemic sarcoidosis.
2001
Familial primary pulmonary hypertension and associated ocular findings.
2001
Immune recovery vitritis and uveitis in AIDS: clinical predictors, sequelae, and treatment outcomes.
2001
Isolation and characterization of rheumatoid arthritis synovial fibroblasts from primary culture--primary culture cells markedly differ from fourth-passage cells.
2001
Patents

Sample Use Guides

Adult Dose: Injection 10% (100 mg/mL) is 500 mg; For children, the dose should be calculated on the basis of 7.7 mg for each kg of actual body weight (or 35 mg for each 10 pounds of body weight) up to a maximum of 500 mg
Route of Administration: Intravenous
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:55:10 GMT 2025
Edited
by admin
on Mon Mar 31 17:55:10 GMT 2025
Record UNII
TPY09G7XIR
Record Status FAILED
Record Version
  • Download
Name Type Language
YELLOW 7
INCI  
INCI  
Preferred Name English
ACID YELLOW 73
INCI  
INCI  
Preferred Name English
Fluorescein
EP   HSDB   II   JAN   MART.   MI   USP   USP-RS   VANDF   WHO-DD  
Common Name English
KI201
INCI  
INCI  
Preferred Name English
D & C YELLOW NO. 7 K7133
Brand Name English
FLUORESCEIN [HSDB]
Common Name English
NSC-667256
Code English
NSC-759114
Code English
FLUORESCEIN [MI]
Common Name English
FLUORESCEIN [VANDF]
Common Name English
FLUORESCEIN [USP MONOGRAPH]
Common Name English
FLUORESCEIN [EP MONOGRAPH]
Common Name English
FLUORESCEIN [MART.]
Common Name English
CI 45350:1
Code English
D&C YELLOW NO. 7
Common Name English
SPIRO(ISOBENZOFURAN-1(3H),9'-(9H)XANTHEN)-3-ONE, 3',6'-DIHYDROXY-
Systematic Name English
Fluorescein [WHO-DD]
Common Name English
FLUORESCEIN [JAN]
Common Name English
FLUORESCEIN [USP-RS]
Common Name English
FLUORESCEIN [II]
Common Name English
Classification Tree Code System Code
WHO-ATC S01JA51
Created by admin on Mon Mar 31 17:55:10 GMT 2025 , Edited by admin on Mon Mar 31 17:55:10 GMT 2025
WHO-VATC QS01JA51
Created by admin on Mon Mar 31 17:55:10 GMT 2025 , Edited by admin on Mon Mar 31 17:55:10 GMT 2025
NDF-RT N0000175536
Created by admin on Mon Mar 31 17:55:10 GMT 2025 , Edited by admin on Mon Mar 31 17:55:10 GMT 2025
WHO-ESSENTIAL MEDICINES LIST 14.1
Created by admin on Mon Mar 31 17:55:10 GMT 2025 , Edited by admin on Mon Mar 31 17:55:10 GMT 2025
NCI_THESAURUS C390
Created by admin on Mon Mar 31 17:55:10 GMT 2025 , Edited by admin on Mon Mar 31 17:55:10 GMT 2025
WHO-ATC S01JA01
Created by admin on Mon Mar 31 17:55:10 GMT 2025 , Edited by admin on Mon Mar 31 17:55:10 GMT 2025
WHO-VATC QS01JA01
Created by admin on Mon Mar 31 17:55:10 GMT 2025 , Edited by admin on Mon Mar 31 17:55:10 GMT 2025
NDF-RT N0000175533
Created by admin on Mon Mar 31 17:55:10 GMT 2025 , Edited by admin on Mon Mar 31 17:55:10 GMT 2025
Code System Code Type Description
MESH
D019793
Created by admin on Mon Mar 31 17:55:10 GMT 2025 , Edited by admin on Mon Mar 31 17:55:10 GMT 2025
PRIMARY
ChEMBL
CHEMBL177756
Created by admin on Mon Mar 31 17:55:10 GMT 2025 , Edited by admin on Mon Mar 31 17:55:10 GMT 2025
PRIMARY
CAS
2321-07-5
Created by admin on Mon Mar 31 17:55:10 GMT 2025 , Edited by admin on Mon Mar 31 17:55:10 GMT 2025
PRIMARY
DRUG CENTRAL
1207
Created by admin on Mon Mar 31 17:55:10 GMT 2025 , Edited by admin on Mon Mar 31 17:55:10 GMT 2025
PRIMARY
EVMPD
SUB13902MIG
Created by admin on Mon Mar 31 17:55:10 GMT 2025 , Edited by admin on Mon Mar 31 17:55:10 GMT 2025
PRIMARY
RXCUI
25138
Created by admin on Mon Mar 31 17:55:10 GMT 2025 , Edited by admin on Mon Mar 31 17:55:10 GMT 2025
PRIMARY RxNorm
DRUG BANK
DB00693
Created by admin on Mon Mar 31 17:55:10 GMT 2025 , Edited by admin on Mon Mar 31 17:55:10 GMT 2025
PRIMARY
EPA CompTox
DTXSID0038887
Created by admin on Mon Mar 31 17:55:10 GMT 2025 , Edited by admin on Mon Mar 31 17:55:10 GMT 2025
PRIMARY
MERCK INDEX
m5462
Created by admin on Mon Mar 31 17:55:10 GMT 2025 , Edited by admin on Mon Mar 31 17:55:10 GMT 2025
PRIMARY Merck Index
SMS_ID
100000092805
Created by admin on Mon Mar 31 17:55:10 GMT 2025 , Edited by admin on Mon Mar 31 17:55:10 GMT 2025
PRIMARY
WIKIPEDIA
FLUORESCEIN
Created by admin on Mon Mar 31 17:55:10 GMT 2025 , Edited by admin on Mon Mar 31 17:55:10 GMT 2025
PRIMARY
NSC
667256
Created by admin on Mon Mar 31 17:55:10 GMT 2025 , Edited by admin on Mon Mar 31 17:55:10 GMT 2025
PRIMARY
CHEBI
31624
Created by admin on Mon Mar 31 17:55:10 GMT 2025 , Edited by admin on Mon Mar 31 17:55:10 GMT 2025
PRIMARY
NCI_THESAURUS
C61766
Created by admin on Mon Mar 31 17:55:10 GMT 2025 , Edited by admin on Mon Mar 31 17:55:10 GMT 2025
PRIMARY
LACTMED
Fluorescein
Created by admin on Mon Mar 31 17:55:10 GMT 2025 , Edited by admin on Mon Mar 31 17:55:10 GMT 2025
PRIMARY
NSC
759114
Created by admin on Mon Mar 31 17:55:10 GMT 2025 , Edited by admin on Mon Mar 31 17:55:10 GMT 2025
PRIMARY
ECHA (EC/EINECS)
219-031-8
Created by admin on Mon Mar 31 17:55:10 GMT 2025 , Edited by admin on Mon Mar 31 17:55:10 GMT 2025
PRIMARY
PUBCHEM
16850
Created by admin on Mon Mar 31 17:55:10 GMT 2025 , Edited by admin on Mon Mar 31 17:55:10 GMT 2025
PRIMARY
DAILYMED
TPY09G7XIR
Created by admin on Mon Mar 31 17:55:10 GMT 2025 , Edited by admin on Mon Mar 31 17:55:10 GMT 2025
PRIMARY
FDA UNII
TPY09G7XIR
Created by admin on Mon Mar 31 17:55:10 GMT 2025 , Edited by admin on Mon Mar 31 17:55:10 GMT 2025
PRIMARY
HSDB
2128
Created by admin on Mon Mar 31 17:55:10 GMT 2025 , Edited by admin on Mon Mar 31 17:55:10 GMT 2025
PRIMARY
RS_ITEM_NUM
1277004
Created by admin on Mon Mar 31 17:55:10 GMT 2025 , Edited by admin on Mon Mar 31 17:55:10 GMT 2025
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY