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=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
| 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 | 22.98976928 |
| 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 Date2006 |
|||
| Diagnostic | FLUORESCITE Approved UseInjection 10% is indicated in diagnostic fluorescein angiography or angioscopy of the retina and iris vasculature Launch Date2006 |
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 |
|---|---|---|
| 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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:53:19 GMT 2025
by
admin
on
Mon Mar 31 17:53:19 GMT 2025
|
| Record UNII |
93X55PE38X
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Related Record | Type |
|---|
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Preferred Name | English | ||
|
Preferred Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
EPA PESTICIDE CODE |
128839
Created by
admin on Mon Mar 31 17:53:19 GMT 2025 , Edited by admin on Mon Mar 31 17:53:19 GMT 2025
|
||
|
Food Contact Sustance Notif, (FCN No.) |
FCN NO. 31
Created by
admin on Mon Mar 31 17:53:19 GMT 2025 , Edited by admin on Mon Mar 31 17:53:19 GMT 2025
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
10608
Created by
admin on Mon Mar 31 17:53:19 GMT 2025 , Edited by admin on Mon Mar 31 17:53:19 GMT 2025
|
PRIMARY | |||
|
DTXSID9025328
Created by
admin on Mon Mar 31 17:53:19 GMT 2025 , Edited by admin on Mon Mar 31 17:53:19 GMT 2025
|
PRIMARY | |||
|
SUB13905MIG
Created by
admin on Mon Mar 31 17:53:19 GMT 2025 , Edited by admin on Mon Mar 31 17:53:19 GMT 2025
|
PRIMARY | |||
|
100000089870
Created by
admin on Mon Mar 31 17:53:19 GMT 2025 , Edited by admin on Mon Mar 31 17:53:19 GMT 2025
|
PRIMARY | |||
|
518-47-8
Created by
admin on Mon Mar 31 17:53:19 GMT 2025 , Edited by admin on Mon Mar 31 17:53:19 GMT 2025
|
PRIMARY | |||
|
208-253-0
Created by
admin on Mon Mar 31 17:53:19 GMT 2025 , Edited by admin on Mon Mar 31 17:53:19 GMT 2025
|
PRIMARY | |||
|
57789
Created by
admin on Mon Mar 31 17:53:19 GMT 2025 , Edited by admin on Mon Mar 31 17:53:19 GMT 2025
|
PRIMARY | RxNorm | ||
|
93X55PE38X
Created by
admin on Mon Mar 31 17:53:19 GMT 2025 , Edited by admin on Mon Mar 31 17:53:19 GMT 2025
|
PRIMARY | |||
|
FLUORESCEIN SODIUM
Created by
admin on Mon Mar 31 17:53:19 GMT 2025 , Edited by admin on Mon Mar 31 17:53:19 GMT 2025
|
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. | ||
|
C65723
Created by
admin on Mon Mar 31 17:53:19 GMT 2025 , Edited by admin on Mon Mar 31 17:53:19 GMT 2025
|
PRIMARY | |||
|
m5462
Created by
admin on Mon Mar 31 17:53:19 GMT 2025 , Edited by admin on Mon Mar 31 17:53:19 GMT 2025
|
PRIMARY | Merck Index | ||
|
CHEMBL177756
Created by
admin on Mon Mar 31 17:53:19 GMT 2025 , Edited by admin on Mon Mar 31 17:53:19 GMT 2025
|
PRIMARY | |||
|
93X55PE38X
Created by
admin on Mon Mar 31 17:53:19 GMT 2025 , Edited by admin on Mon Mar 31 17:53:19 GMT 2025
|
PRIMARY | |||
|
DBSALT001432
Created by
admin on Mon Mar 31 17:53:19 GMT 2025 , Edited by admin on Mon Mar 31 17:53:19 GMT 2025
|
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 |