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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

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

PubMed

TitleDatePubMed
A case of Alport's syndrome and retinal degeneration.
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
Isolation and characterization of rheumatoid arthritis synovial fibroblasts from primary culture--primary culture cells markedly differ from fourth-passage cells.
2001
Adenoma of the retinal pigment epithelium simulating a juxtapapillary choroidal neovascular membrane.
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
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
Diode laser photocoagulation of choroidal neovascularization associated with retinal pigment epithelial detachment.
2001 Feb
Real-time detection of Brucella abortus, Brucella melitensis and Brucella suis.
2001 Feb
Fluorescein angiography in laser treatment of diabetic macular edema.
2001 Feb
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
[Exudative idiopathic juxtafoveolar retinal telangiectasis].
2001 Jan
Solitary nonreactive choroidal tuberculoma in a patient with acquired immune deficiency syndrome.
2001 Jan
Translocation of the macula for management of subfoveal choroidal neovascularization: comparison of results in age-related macular degeneration and degenerative myopia.
2001 Jan
Macular traction detachment and diabetic macular edema associated with posterior hyaloidal traction.
2001 Jan
Central retinal vascular obstruction secondary to melanocytoma of the optic disc.
2001 Jan
Autosomal dominant cone and cone-rod dystrophy with mutations in the guanylate cyclase activator 1A gene-encoding guanylate cyclase activating protein-1.
2001 Jan
Acute idiopathic blind spot enlargement syndrome: a review of 27 new cases.
2001 Jan
A new drug-screening procedure for photosensitizing agents used in photodynamic therapy for CNV.
2001 Jan
Computer algorithms for the automated measurement of retinal arteriolar diameters.
2001 Jan
Simultaneous measurements of intracellular cAMP and L-type Ca2+ current in single frog ventricular myocytes.
2001 Jan 1
Effects of methyl-beta-cyclodextrin on cryosurvival of boar spermatozoa.
2001 Jan-Feb
Surgical management of exudative retinal detachment associated with central serous chorioretinopathy.
2001 Jan-Feb
Effect of particle size of polymeric nanospheres on intravitreal kinetics.
2001 Jan-Feb
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
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 GMT 2023 , Edited by admin on Fri Dec 15 15:18:04 GMT 2023
Food Contact Sustance Notif, (FCN No.) FCN NO. 31
Created by admin on Fri Dec 15 15:18:04 GMT 2023 , Edited by admin on Fri Dec 15 15:18:04 GMT 2023
Code System Code Type Description
PUBCHEM
10608
Created by admin on Fri Dec 15 15:18:04 GMT 2023 , Edited by admin on Fri Dec 15 15:18:04 GMT 2023
PRIMARY
EVMPD
SUB13905MIG
Created by admin on Fri Dec 15 15:18:04 GMT 2023 , Edited by admin on Fri Dec 15 15:18:04 GMT 2023
PRIMARY
SMS_ID
100000089870
Created by admin on Fri Dec 15 15:18:04 GMT 2023 , Edited by admin on Fri Dec 15 15:18:04 GMT 2023
PRIMARY
CAS
518-47-8
Created by admin on Fri Dec 15 15:18:04 GMT 2023 , Edited by admin on Fri Dec 15 15:18:04 GMT 2023
PRIMARY
ECHA (EC/EINECS)
208-253-0
Created by admin on Fri Dec 15 15:18:04 GMT 2023 , Edited by admin on Fri Dec 15 15:18:04 GMT 2023
PRIMARY
RXCUI
57789
Created by admin on Fri Dec 15 15:18:04 GMT 2023 , Edited by admin on Fri Dec 15 15:18:04 GMT 2023
PRIMARY RxNorm
FDA UNII
93X55PE38X
Created by admin on Fri Dec 15 15:18:04 GMT 2023 , Edited by admin on Fri Dec 15 15:18:04 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
FLUORESCEIN SODIUM
Created by admin on Fri Dec 15 15:18:04 GMT 2023 , Edited by admin on Fri Dec 15 15:18:04 GMT 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 GMT 2023 , Edited by admin on Fri Dec 15 15:18:04 GMT 2023
PRIMARY
MERCK INDEX
m5462
Created by admin on Fri Dec 15 15:18:04 GMT 2023 , Edited by admin on Fri Dec 15 15:18:04 GMT 2023
PRIMARY Merck Index
ChEMBL
CHEMBL177756
Created by admin on Fri Dec 15 15:18:04 GMT 2023 , Edited by admin on Fri Dec 15 15:18:04 GMT 2023
PRIMARY
DAILYMED
93X55PE38X
Created by admin on Fri Dec 15 15:18:04 GMT 2023 , Edited by admin on Fri Dec 15 15:18:04 GMT 2023
PRIMARY
DRUG BANK
DBSALT001432
Created by admin on Fri Dec 15 15:18:04 GMT 2023 , Edited by admin on Fri Dec 15 15:18:04 GMT 2023
PRIMARY