fluorescein
Approved
Nov 10, 1976
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 — NCATS
Clinical trial activity
48 trials · 47 clinical orgs · 10 marketing orgs
Earliest trial started Aug 1, 2004 (NCT00856869)
Timeline
1970s
2000s
- Jan 1, 2004
Earliest Phase 1 Sponsor(trial)
- Mar 28, 2006
Alcon — NDA Secondary Org
- Mar 28, 2006
Nestle — NDA Secondary Org
- Jan 1, 2008
Earliest Phase 2 Sponsor(trial)
- Jan 1, 2008
Earliest Phase 3 Sponsor(trial)
- Aug 8, 2008
Akorn, Inc. — NDA Secondary Org
- Aug 8, 2008
LONG GROVE PHARMS — Marketing Organization
2010s
- Dec 14, 2017
Altair Therapeutics — Marketing Organization
- Dec 14, 2017
Altair Therapeutics — NDA Secondary Org
2020s
- Mar 9, 2020
Bausch Health Companies — NDA Secondary Org
- Sep 25, 2023
Nexus Pharmaceuticals — Marketing Organization
- Apr 30, 2026
BPI — Marketing Organization
- Jun 1, 2026
Zydus Discovery DMCC — Marketing Organization
Indications
Studied for
- Accidental Falls · Phase 2
- Adenolymphoma · Phase 2
- Adenoma, Pleomorphic · Phase 2
- Adenomatous Polyps · Phase 1
- Barrett Esophagus · Early Phase 1
- Brain Neoplasms · Phase 4
- Breast Neoplasms · Phase 1/Phase 2
- Cerebrovascular Disorders · Phase 4
- Colonic Polyps · Phase 1
- Corneal Diseases · Phase 3
- Dermatology · Phase 2
- Diabetic Retinopathy · Early Phase 1
- Endometrial Neoplasms · Early Phase 1
- Fallopian Tube Neoplasms · Early Phase 1
- Fluorescein Angiography · Phase 4
- Gastroesophageal Reflux · Early Phase 1
- Glioblastoma · Phase 3
- Hamartoma · Early Phase 1
- Heart Septal Defects, Atrial · Phase 1
- Heart Septal Defects, Ventricular · Phase 2
- Hepatitis, Viral, Human · Phase 2
- Hypertrophy, Left Ventricular · Phase 2
- Intestinal Neoplasms · Phase 4
- Irritable Bowel Syndrome · Phase 1
- Liver Cirrhosis · Phase 3
- Macular Degeneration · Early Phase 1
- Neoplasms · Phase 4
- Neuroma, Acoustic · Phase 2
- Non-alcoholic Fatty Liver Disease · Phase 2
- Ovarian Neoplasms · Early Phase 1
- Paget Disease, Extramammary · Phase 2
- Pharmacokinetics · Phase 1
- Retinal Diseases · Phase 4
- Retinal Vein Occlusion · Early Phase 1
- Squamous Cell Carcinoma of Head and Neck · Phase 2
- Thyroid Diseases · Phase 2
- Thyroidectomy · Phase 2
- Ureteral Diseases · Phase 4
- Urination Disorders · Phase 1
- Vascular Diseases · Phase 4
Mechanism of action
- Unspecified targetOTHER
Disclosing agent
- UnclearUnclear
Unclear unclear
Combination products
altafluor benox
with benoxinate
Approval history
- approvedNov 10, 1976
Chemistry & pharmacology
SMILES
O=C(O)c1ccccc1-c1c2ccc(=O)cc-2oc2cc(O)ccc12- Mol. weight
- 332.31 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- No
- Chirality
- Achiral Molecule
- Inorganic
- No
- Polymer
- No
- Availability
- Prescription Only
Oral
No
Parenteral
No
Topical
No
Sources
- ChEMBLCHEMBL177756 ↗
- WikipediaFluorescein ↗
- NCATSTPY09G7XIR ↗
- ChEMBLCHEMBL4297067 ↗
- ChEMBLCHEMBL1628233 ↗
- ChEMBLCHEMBL1057 ↗
Also known as
- 3',6'-dihydroxyfluoran
- 3',6'-dihydroxyfluoran
- 3,6-fluorandiol
- 3,6-fluorandiol
- 9-(o-carboxyphenyl)-6-hydroxy-3h-xanthen-3-one
- 9-(o-carboxyphenyl)-6-hydroxy-3h-xanthen-3-one
- 9-(o-carboxyphenyl)-6-hydroxy-3-isoxanthenone
- 9-(o-carboxyphenyl)-6-hydroxy-3-isoxanthenone
- ak-fluor
- c.i. solvent yellow 94
- c.i. solvent yellow 94
- d and c yellow no. 7
- d and c yellow no. 7
- d&c yellow no. 7
- d&c yellow no. 7
- fluor-amps
- fluorescein
- fluorescein
- fluorescein
- fluorescein
- fluorescein
- fluorescein
- fluorescein
- fluorescein
- fluorescein acid
- fluoresceine
- fluoresceine
- fluorescein lisicol
- fluorescein sodium
- fluorescein sodium
- fluorescein sodium
- fluorescein sodium
- fluorescein sodium
- fluorescein sodium
- fluorescein, soluble
- fluorescein, soluble
- fluorescite
- fluorescite
- fluoreszein
- fluoreszein
- fluorets
- fluorets
- funduscein
- funduscein
- funduscein-25
- funduscein-25
- funduscein-25
- japan yellow 201
- japan yellow 201
- nrl972
- nrl972
- resorcinolphthalein
- resorcinolphthalein
- resorcinolphthalein
- retinofluor
- sodium fluorescein
- sodium fluorescein
- solvent yellow 94
- solvent yellow 94
- uranin
- vst-1001
- yellow fluorescein
- yellow fluorescein
- yellow fluorescein
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT06873815 | Phase 2 | Mar 7, 2025 | Memorial Sloan-Kettering Cancer Center |
| NCT06054178 | Phase 2 | Mar 31, 2024 | Stanford University |
| NCT05664555 | Phase 4 | Feb 1, 2023 | Seoul National University |
| NCT05556525 | N/A | Dec 15, 2022 | Mayo Clinic, National Cancer Institute (NCI) |
| NCT04597801 | Phase 2 | Oct 31, 2020 | Carl Zeiss Meditec, Inc., Technical University of Munich |
| NCT04687488 | N/A | Jul 23, 2020 | Katholieke Universiteit Leuven |
| NCT07230548 | Phase 3 | Jun 10, 2020 | Medical University of Vienna |
| NCT04351373 | Phase 2 | Jun 1, 2020 | Mayo Clinic |
| NCT04017975 | Phase 2 | Aug 31, 2019 | Harvard University, National Heart, Lung, and Blood Institute (NHLBI) |
| NCT04071080 | Phase 1 | Aug 22, 2019 | Medicor Research Inc., UpTru Inc. |
| NCT04008121 | Early Phase 1 (Phase 1) | Jul 31, 2019 | MediBeacon |
| NCT03752203 | N/A | Jul 31, 2019 | University of Colorado, University of Colorado, Denver |
| NCT03189134 | Phase 1 | Apr 2, 2018 | Harvard University, National Heart, Lung, and Blood Institute (NHLBI) |
| NCT03297489 | Early Phase 1 (Phase 1) | Nov 6, 2017 | State University of New York, Buffalo |
| NCT03291977 | Phase 3 | Oct 5, 2017 | University of Rennes |
| NCT03244982 | Phase 4 | Oct 1, 2017 | Kresge Eye Institute |
| NCT03220711 | Phase 1 | Jul 28, 2017 | University of Michigan |
| NCT02857374 | N/A | Nov 3, 2016 | National Cancer Institute (NCI), State University of New York, Buffalo |
| NCT02971800 | N/A | Aug 1, 2016 | Laval University |
| NCT02757417 | N/A | Jul 1, 2016 | Case Western Reserve University |
Organizations
Research & Development (47)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Norgine | For profit | 8 | 8 | 3 | 2004 |
| National Cancer Institute (NCI) | Government | 4 | 0 | 1 | 2009 |
| State University of New York, Buffalo | Academic/Hospital | 3 | 3 | 2 | 2013 |
| University of Utah | Academic/Hospital | 3 | 2 | 1 | 2008 |
| Carl Zeiss Meditec, Inc. | For profit | 2 | 0 | 1 | 2016 |
| Harvard University | Academic/Hospital | 2 | 2 | 2 | 2018 |
| Mayo Clinic | Academic/Hospital | 2 | 2 | 2 | 2020 |
| MHAPT Zarita Johanna University Hospital | Academic/Hospital | 2 | 0 | 1 | 2006 |
| National Heart, Lung, and Blood Institute (NHLBI) | Government | 2 | 0 | 2 | 2018 |
| Shandong University | Academic/Hospital | 2 | 2 | 2 | 2015 |
| Stanford University | Academic/Hospital | 2 | 2 | 2 | 2009 |
| St. Ivan Rilski's University Hospital | Academic/Hospital | 2 | 0 | 2 | 2004 |
| University of Colorado, Denver | Academic/Hospital | 2 | 2 | 1 | 2015 |
| Advent Health | Academic/Hospital | 1 | 1 | 1 | 2015 |
| Baylor University | Academic/Hospital | 1 | 1 | 1 | 2009 |
| Case Western Reserve University | Academic/Hospital | 1 | 1 | 1 | 2016 |
| Columbia University | Academic/Hospital | 1 | 1 | 1 | 2015 |
| Dartmouth University | Academic/Hospital | 1 | 1 | 1 | 2016 |
| Duke University | Academic/Hospital | 1 | 0 | 1 | 2008 |
| Hoosier Cancer Research Network | Academic/Hospital | 1 | 1 | 1 | 2014 |
Marketing (14)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| Akorn, Inc. | For profit | NDA2 | Aug 8, 2008 |
| Alcon | For profit | NDA2 | Mar 28, 2006 |
| Altair Therapeutics | For profit | MKTG | Dec 14, 2017 |
| Altair Therapeutics | For profit | NDA2 | Dec 14, 2017 |
| BPI | For profit | MKTG | Apr 30, 2026 |
| Bausch Health Companies | For profit | NDA2 | Mar 9, 2020 |
| Bausch Health Companies | For profit | NDA2 | Mar 9, 2020 |
| LONG GROVE PHARMS | For profit | MKTG | Aug 8, 2008 |
| Nestle | For profit | NDA2 | Mar 28, 2006 |
| Nexus Pharmaceuticals | For profit | MKTG | Sep 25, 2023 |
| Nexus Pharmaceuticals | For profit | SYN | Sep 25, 2023 |
| Novartis | For profit | NDA2 | Nov 10, 1976 |
| Novartis | For profit | NDA | Nov 10, 1976 |
| Zydus Discovery DMCC | For profit | MKTG | Jun 1, 2026 |