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
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
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 |
DescriptionSources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=ebb3883c-71f6-4fd0-a7e6-0ba8e1136dd9Curator's Comment: description was created based on several sources, including:
http://www.drugbank.ca/drugs/DB00693
https://en.wikipedia.org/wiki/Fluorescein
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=ebb3883c-71f6-4fd0-a7e6-0ba8e1136dd9
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
Sources: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4176484/
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.
Originator
Approval Year
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Diagnostic | FLUORESCITE Approved UseInjection 10% is indicated in diagnostic fluorescein angiography or angioscopy of the retina and iris vasculature Launch Date1.14350398E12 |
|||
Diagnostic | FLUORESCITE Approved UseInjection 10% is indicated in diagnostic fluorescein angiography or angioscopy of the retina and iris vasculature Launch Date1.14350398E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4039592/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4039592/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
286 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4039592/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4039592/ |
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 |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
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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 |
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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
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:18:04 UTC 2023
by
admin
on
Fri Dec 15 15:18:04 UTC 2023
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Record UNII |
93X55PE38X
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Record Status |
Validated (UNII)
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Record Version |
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-
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Classification Tree | Code System | Code | ||
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EPA PESTICIDE CODE |
128839
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Food Contact Sustance Notif, (FCN No.) |
FCN NO. 31
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10608
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SUB13905MIG
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100000089870
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518-47-8
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208-253-0
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57789
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93X55PE38X
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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
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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. | ||
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C65723
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m5462
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PRIMARY | Merck Index | ||
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CHEMBL177756
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93X55PE38X
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DBSALT001432
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PARENT -> SALT/SOLVATE |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |