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Details

Stereochemistry ACHIRAL
Molecular Formula C20H10O5.2Na
Molecular Weight 376.2699
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLUORESCEIN SODIUM

SMILES

[Na+].[Na+].[O-]C(=O)C1=C(C=CC=C1)C2=C3C=CC(=O)C=C3OC4=C2C=CC([O-])=C4

InChI

InChIKey=NJDNXYGOVLYJHP-UHFFFAOYSA-L
InChI=1S/C20H12O5.2Na/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);;/q;2*+1/p-2

HIDE SMILES / InChI

Molecular Formula C20H10O5
Molecular Weight 330.2904
Charge -2
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
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

1.14350398E12
Diagnostic
FLUORESCITE

Approved Use

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

Launch Date

1.14350398E12
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
n = 1
Health Status: unhealthy
Population Size: 1
Sources:
PubMed

PubMed

TitleDatePubMed
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
Retrograde infusion of fluorescein to confirm location and patency of a glaucoma drainage device.
2001 Feb
Long-term study of endonasal duraplasty and review of the literature.
2001 Feb
Inhibition of vascular smooth muscle cell proliferation by DNA-RNA chimeric hammerhead ribozyme targeting to rat platelet-derived growth factor A-chain mRNA.
2001 Feb
Adenoma of the retinal pigment epithelium simulating a juxtapapillary choroidal neovascular membrane.
2001 Feb
Ocular phenotype of bothnia dystrophy, an autosomal recessive retinitis pigmentosa associated with an R234W mutation in the RLBP1 gene.
2001 Feb
Perifoveal vitreous detachment is the primary pathogenic event in idiopathic macular hole formation.
2001 Feb
Differentiation between presumed ocular histoplasmosis syndrome and multifocal choroiditis with panuveitis based on morphology of photographed fundus lesions and fluorescein angiography.
2001 Feb
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 Feb
External beam irradiation of subfoveal choroidal neovascularization complicating age-related macular degeneration: one-year results of a prospective, double-masked, randomized clinical trial.
2001 Feb
Nitric oxide production is increased in the spermatic veins of adolescents with left idiophatic varicocele.
2001 Feb
All angiogenesis is not the same: Distinct patterns of response to antiangiogenic therapy in experimental neuroblastoma and Wilms tumor.
2001 Feb
[Ophthalmoscopic findings in 3 patients with panarteritis nodosa and review of the literature].
2001 Jan
Clinical grading of corneal staining of non-contact lens wearers.
2001 Jan
[Age-related macular degeneration (AMD)--therapeutic possibilities and new approaches].
2001 Jan
Use of teleoptometry to evaluate acceptability of rigid gas-permeable contact lens fits.
2001 Jan
Conjunctival histologic findings of dry eye and non-dry eye contact lens wearing subjects.
2001 Jan
Visualization of the transport of primary and secondary bile acids across liver tissue in rats: in vivo study with fluorescent bile acids.
2001 Jan
[A case of central retinal vein occlusion followed by branch retinal artery occlusion].
2001 Jan
Clinicopathological findings consistent with primary Sjögren's syndrome in a subset of patients diagnosed with chronic fatigue syndrome: preliminary observations.
2001 Jan
[Exudative idiopathic juxtafoveolar retinal telangiectasis].
2001 Jan
Retinopathy due to juvenile polymyositis.
2001 Jan-Feb
Subretinal hemorrhage from a retinal arterial macroaneurysm simulating a choroidal melanoma.
2001 Jan-Feb
Progressive outer retinal necrosis in a patient with nephrotic syndrome.
2001 Jan-Feb
Effects of methyl-beta-cyclodextrin on cryosurvival of boar spermatozoa.
2001 Jan-Feb
Study of temporal and perfusion physiology of skin capillaries in the dorsum of the foot.
2001 Jan-Feb
Effect of ions and nucleotides on the interactions of yeast Rad51 protein with single-stranded oligonucleotides.
2001 Mar
Nitric oxide distribution and production in the guinea pig cochlea.
2001 Mar
Preservation of ganglion cell layer neurons in age-related macular degeneration.
2001 Mar
Comparison of retinal transit times and retinal blood flow: a study in monkeys.
2001 Mar
Vascular patterns in pterygium and conjunctival autografting: a pilot study using indocyanine green anterior segment angiography.
2001 Mar
Value of nasal endoscopy and probing in the diagnosis and management of children with congenital epiphora.
2001 Mar
Reduced amplitude and delayed latency in foveal response of multifocal electroretinogram in early age related macular degeneration.
2001 Mar
Ocular pharmacokinetics in rabbits using a novel dual probe microdialysis technique.
2001 Mar
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 Fri Dec 15 15:18:04 UTC 2023
Edited
by admin
on Fri Dec 15 15:18:04 UTC 2023
Record UNII
93X55PE38X
Record Status Validated (UNII)
Record Version
  • Download
Related Record Type
Name Type Language
FLUORESCEIN SODIUM
EP   MART.   ORANGE BOOK   USP   VANDF   WHO-DD   WHO-IP  
Common Name English
SOLUBLE FLUORESCEIN
Common Name English
SPIRO(ISOBENZOFURAN-1(3H),9'-(9H)XANTHENE)-3-ONE, 3'6'-DIHYDROXY, DISODIUM SALT
Common Name English
FLUORESCEIN SODIUM [VANDF]
Common Name English
3',6'-DIHYDROXYSPIRO(ISOBENZOFURAN-1(3H),9'-(9H)XANTHEN)-3-ONE
Systematic Name English
FLUORESCEIN SODIUM [EP MONOGRAPH]
Common Name English
RESORCINOL PHTHALEIN SODIUM
Common Name English
Fluorescein sodium [WHO-DD]
Common Name English
FLUORESCEIN DISODIUM SALT [MI]
Common Name English
KI202(1) [INCI]
Common Name English
KI202(2) [INCI]
Common Name English
FLUORESCEIN SODIUM [MART.]
Common Name English
KI202
Common Name English
Fluorescein disodium salt
MI  
Common Name English
SPIRO(ISOBENZOFURAN-1(3H),9'-(9H)XANTHEN)-3-ONE, 3',6'-DIHYDROXY-, SODIUM SALT (1:2)
Common Name English
FLUORESCEIN SODIUM COMPONENT OF ALTAFLUOR BENOX
Brand Name English
FLUORESCEIN SODIUM [EP IMPURITY]
Common Name English
FLUORESCEIN SODIUM [USP MONOGRAPH]
Common Name English
FLUORESCEIN SODIUM [WHO-IP]
Common Name English
FLUORESCEIN SODIUM [JAN]
Common Name English
FLUORESCEIN, DISODIUM SALT
Common Name English
FLUORESCEIN SODIUM [ORANGE BOOK]
Common Name English
KI202(2)
INCI  
INCI  
Official Name English
KI202(1)
INCI  
INCI  
Official Name English
FLUORESCEINUM NATRICUM [WHO-IP LATIN]
Common Name English
DISODIUM 2-(6-OXIDO-3-OXO-3H-XANTHEN-9-YL)BENZOATE
Systematic Name English
BENZOIC ACID, 2-(6-HYDROXY-3-OXO-3H-XANTHEN-9-YL)-, DISODIUM SALT
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 128839
Created by admin on Fri Dec 15 15:18:04 UTC 2023 , Edited by admin on Fri Dec 15 15:18:04 UTC 2023
Food Contact Sustance Notif, (FCN No.) FCN NO. 31
Created by admin on Fri Dec 15 15:18:04 UTC 2023 , Edited by admin on Fri Dec 15 15:18:04 UTC 2023
Code System Code Type Description
PUBCHEM
10608
Created by admin on Fri Dec 15 15:18:04 UTC 2023 , Edited by admin on Fri Dec 15 15:18:04 UTC 2023
PRIMARY
EVMPD
SUB13905MIG
Created by admin on Fri Dec 15 15:18:04 UTC 2023 , Edited by admin on Fri Dec 15 15:18:04 UTC 2023
PRIMARY
SMS_ID
100000089870
Created by admin on Fri Dec 15 15:18:04 UTC 2023 , Edited by admin on Fri Dec 15 15:18:04 UTC 2023
PRIMARY
CAS
518-47-8
Created by admin on Fri Dec 15 15:18:04 UTC 2023 , Edited by admin on Fri Dec 15 15:18:04 UTC 2023
PRIMARY
ECHA (EC/EINECS)
208-253-0
Created by admin on Fri Dec 15 15:18:04 UTC 2023 , Edited by admin on Fri Dec 15 15:18:04 UTC 2023
PRIMARY
RXCUI
57789
Created by admin on Fri Dec 15 15:18:04 UTC 2023 , Edited by admin on Fri Dec 15 15:18:04 UTC 2023
PRIMARY RxNorm
FDA UNII
93X55PE38X
Created by admin on Fri Dec 15 15:18:04 UTC 2023 , Edited by admin on Fri Dec 15 15:18:04 UTC 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
FLUORESCEIN SODIUM
Created by admin on Fri Dec 15 15:18:04 UTC 2023 , Edited by admin on Fri Dec 15 15:18:04 UTC 2023
PRIMARY Description: An orange-red powder; odourless. Solubility: Soluble in 1.5 parts of water; soluble in ethanol (~750 g/l) TS. Category: Diagnostic agent in ophthalmology.Storage: Fluorescein sodium should be kept in a well-closed container, protected from light. Additional information: Fluorescein sodium is hygroscopic. Definition: Fluorescein sodium contains not less than 98.0% and not more than 100.5% of C20H10Na2O5, calculated with reference to the dried substance.
NCI_THESAURUS
C65723
Created by admin on Fri Dec 15 15:18:04 UTC 2023 , Edited by admin on Fri Dec 15 15:18:04 UTC 2023
PRIMARY
MERCK INDEX
m5462
Created by admin on Fri Dec 15 15:18:04 UTC 2023 , Edited by admin on Fri Dec 15 15:18:04 UTC 2023
PRIMARY Merck Index
ChEMBL
CHEMBL177756
Created by admin on Fri Dec 15 15:18:04 UTC 2023 , Edited by admin on Fri Dec 15 15:18:04 UTC 2023
PRIMARY
DAILYMED
93X55PE38X
Created by admin on Fri Dec 15 15:18:04 UTC 2023 , Edited by admin on Fri Dec 15 15:18:04 UTC 2023
PRIMARY
DRUG BANK
DBSALT001432
Created by admin on Fri Dec 15 15:18:04 UTC 2023 , Edited by admin on Fri Dec 15 15:18:04 UTC 2023
PRIMARY
Related Record Type Details
SUB_CONCEPT->SUBSTANCE
PARENT -> SALT/SOLVATE
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