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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=CC=CC=C1C2=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

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

Originator

Approval Year

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
FLUORESCITE
Diagnostic
FLUORESCITE

Cmax

ValueDoseCo-administeredAnalytePopulation
10.9 μg/mL
188 mg single, intravenous
FLUORESCEIN blood
Homo sapiens
10.9 μg/mL
188 mg single, intravenous
FLUORESCEIN blood
Homo sapiens
3.5 μg/mL
188 mg single, oral
FLUORESCEIN blood
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
1350 μg × min/mL
188 mg single, intravenous
FLUORESCEIN blood
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
286 min
188 mg single, intravenous
FLUORESCEIN blood
Homo sapiens
267 min
188 mg single, oral
FLUORESCEIN blood
Homo sapiens

Doses

PubMed

Sample Use Guides

In Vivo Use Guide
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