Fluocinolone acetonide

Last updated

Fluocinolone acetonide
Fluocinolone acetonide.svg
Fluocinolone acetonide (Ball-n-Stick).png
Clinical data
Trade names Synalar, others
AHFS/Drugs.com Monograph
Monograph
Pregnancy
category
  • AU:A
Routes of
administration
Topical, ophthalmic intravitreal injection
ATC code
Legal status
Legal status
Pharmacokinetic data
Metabolism Liver, CYP3A4-mediated
Elimination half-life 1.3 to 1.7 hours
Identifiers
  • (1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.000.607 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C24H30F2O6
Molar mass 452.495 g·mol−1
3D model (JSmol)
  • O=C\1\C=C5/[C@@](/C=C/1)(C)[C@]2(F)[C@H]([C@H]3[C@](C[C@@H]2O)([C@@]4(OC(O[C@@H]4C3)(C)C)C(=O)CO)C)C[C@@H]5F
  • InChI=1S/C24H30F2O6/c1-20(2)31-19-9-13-14-8-16(25)15-7-12(28)5-6-21(15,3)23(14,26)17(29)10-22(13,4)24(19,32-20)18(30)11-27/h5-7,13-14,16-17,19,27,29H,8-11H2,1-4H3/t13-,14-,16-,17-,19+,21-,22-,23-,24+/m0/s1 Yes check.svgY
  • Key:FEBLZLNTKCEFIT-VSXGLTOVSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Fluocinolone acetonide is a fluorinated corticosteroid primarily used in dermatology to reduce skin inflammation and relieve itching. [2] It is a synthetic hydrocortisone derivative. The fluorine substitution at position 9 in the steroid nucleus greatly enhances its activity. It was first synthesized in 1959 in the Research Department of Syntex Laboratories S.A. Mexico City. [3] Preparations containing it were first marketed under the brand name Synalar.

Contents

Fluocinolone acetonide was also found to strongly potentiate TGF-β-associated chondrogenesis of bone marrow mesenchymal stem/progenitor cells, by increasing the levels of collagen type II by more than 100 fold compared to the widely used dexamethasone. [4]

Fluocinolone acetonide intravitreal implants have been used to treat non-infectious uveitis. A systematic review could not determine with any confidence whether fluocinolone acetonide implants are superior to standard of care treatment for uveitis. [5] A fluocinolone acetonide intravitreal implant with the brand name Iluvien is sold by biopharmaceutical company Alimera Sciences to treat diabetic macular edema. [6]

It was approved for medical use in 1961. [7]

Classification

Fluocinolone is a group V (0.025%) or group VI (0.01%) corticosteroid under US classification.

Brand names

Fluocinolone acetonide is available under the brand names Flucort-N, Iluvien, Synalar, Yutiq, [8] and others. [2] [9]

Related Research Articles

<span class="mw-page-title-main">Corticosteroid</span> Class of steroid hormones

Corticosteroids are a class of steroid hormones that are produced in the adrenal cortex of vertebrates, as well as the synthetic analogues of these hormones. Two main classes of corticosteroids, glucocorticoids and mineralocorticoids, are involved in a wide range of physiological processes, including stress response, immune response, and regulation of inflammation, carbohydrate metabolism, protein catabolism, blood electrolyte levels, and behavior.

<span class="mw-page-title-main">Dexamethasone</span> Corticosteroid medication

Dexamethasone is a fluorinated glucocorticoid medication used to treat rheumatic problems, a number of skin diseases, severe allergies, asthma, chronic obstructive lung disease, croup, brain swelling, eye pain following eye surgery, superior vena cava syndrome, and along with antibiotics in tuberculosis. In adrenocortical insufficiency, it may be used in combination with a mineralocorticoid medication such as fludrocortisone. In preterm labor, it may be used to improve outcomes in the baby. It may be given by mouth, as an injection into a muscle, as an injection into a vein, as a topical cream or ointment for the skin or as a topical ophthalmic solution to the eye. The effects of dexamethasone are frequently seen within a day and last for about three days.

The National Eye Institute (NEI) is part of the U.S. National Institutes of Health (NIH), an agency of the U.S. Department of Health and Human Services. The mission of NEI is "to eliminate vision loss and improve quality of life through vision research." NEI consists of two major branches for research: an extramural branch that funds studies outside NIH and an intramural branch that funds research on the NIH campus in Bethesda, Maryland. Most of the NEI budget funds extramural research.

<span class="mw-page-title-main">Prednisone</span> Steroid medication

Prednisone is a glucocorticoid medication mostly used to suppress the immune system and decrease inflammation in conditions such as asthma, COPD, and rheumatologic diseases. It is also used to treat high blood calcium due to cancer and adrenal insufficiency along with other steroids. It is taken by mouth.

<span class="mw-page-title-main">Macular edema</span> Medical condition

Macular edema occurs when fluid and protein deposits collect on or under the macula of the eye and causes it to thicken and swell (edema). The swelling may distort a person's central vision, because the macula holds tightly packed cones that provide sharp, clear, central vision to enable a person to see detail, form, and color that is directly in the centre of the field of view.

<span class="mw-page-title-main">Uveitis</span> Inflammation of the uvea of the eye

Uveitis is inflammation of the uvea, the pigmented layer of the eye between the inner retina and the outer fibrous layer composed of the sclera and cornea. The uvea consists of the middle layer of pigmented vascular structures of the eye and includes the iris, ciliary body, and choroid. Uveitis is described anatomically, by the part of the eye affected, as anterior, intermediate or posterior, or panuveitic if all parts are involved. Anterior uveitis (iridocyclitis) is the most common, with the incidence of uveitis overall affecting approximately 1:4500, most commonly those between the ages of 20–60. Symptoms include eye pain, eye redness, floaters and blurred vision, and ophthalmic examination may show dilated ciliary blood vessels and the presence of cells in the anterior chamber. Uveitis may arise spontaneously, have a genetic component, or be associated with an autoimmune disease or infection. While the eye is a relatively protected environment, its immune mechanisms may be overcome resulting in inflammation and tissue destruction associated with T-cell activation.

<span class="mw-page-title-main">Triamcinolone acetonide</span> Medicinal chemical compound, steroid

Triamcinolone acetonide, sold under the brand name Kenalog among others, is a synthetic corticosteroid medication used topically to treat various skin conditions, to relieve the discomfort of mouth sores, and by injection into joints to treat various joint conditions. It is also injected into lesions to treat inflammation in some parts of the body, particularly the skin. In nasal spray form, it is used to treat allergic rhinitis. It is used for the treatment of macular edema associated with uveitis. It is a more potent derivative of triamcinolone, and is about eight times as potent as prednisone.

<span class="mw-page-title-main">Ganciclovir</span> Chemical compound

Ganciclovir, sold under the brand name Cytovene among others, is an antiviral medication used to treat cytomegalovirus (CMV) infections.

Stem-cell therapy uses stem cells to treat or prevent a disease or condition. As of 2024, the only FDA-approved therapy using stem cells is hematopoietic stem cell transplantation. This usually takes the form of a bone marrow or peripheral blood stem cell transplantation, but the cells can also be derived from umbilical cord blood. Research is underway to develop various sources for stem cells as well as to apply stem-cell treatments for neurodegenerative diseases and conditions such as diabetes and heart disease.

<span class="mw-page-title-main">Intermediate uveitis</span> Medical condition

Intermediate uveitis is a form of uveitis localized to the vitreous and peripheral retina. Primary sites of inflammation include the vitreous of which other such entities as pars planitis, posterior cyclitis, and hyalitis are encompassed. Intermediate uveitis may either be an isolated eye disease or associated with the development of a systemic disease such as multiple sclerosis or sarcoidosis. As such, intermediate uveitis may be the first expression of a systemic condition. Infectious causes of intermediate uveitis include Epstein–Barr virus infection, Lyme disease, HTLV-1 virus infection, cat scratch disease, and hepatitis C.

Mesenchymal stem cells (MSCs) are multipotent cells found in multiple human adult tissues, including bone marrow, synovial tissues, and adipose tissues. Since they are derived from the mesoderm, they have been shown to differentiate into bone, cartilage, muscle, and adipose tissue. MSCs from embryonic sources have shown promise scientifically while creating significant controversy. As a result, many researchers have focused on adult stem cells, or stem cells isolated from adult humans that can be transplanted into damaged tissue.

Topical steroids are the topical forms of corticosteroids. Topical steroids are the most commonly prescribed topical medications for the treatment of rash and eczema. Topical steroids have anti-inflammatory properties and are classified based on their skin vasoconstrictive abilities. There are numerous topical steroid products. All the preparations in each class have the same anti-inflammatory properties but essentially differ in base and price.

<span class="mw-page-title-main">Osteochondroprogenitor cell</span>

Osteochondroprogenitor cells are progenitor cells that arise from mesenchymal stem cells (MSC) in the bone marrow. They have the ability to differentiate into osteoblasts or chondrocytes depending on the signalling molecules they are exposed to, giving rise to either bone or cartilage respectively. Osteochondroprogenitor cells are important for bone formation and maintenance.

Prochymal is a stem cell therapy made by Osiris Therapeutics. It is the first stem cell therapy approved by Canada. It is also the first therapy approved by Canada for acute graft-vs-host disease (GvHD). Also known as remestemcel-L, Prochymal was sold to Australia-based Mesoblast in 2013 at which time its brand name was changed to Ryoncil.

<span class="mw-page-title-main">Intravitreal injection</span> Method of administration of drugs into the eye by injection with a fine needle

Intravitreal injection is the method of administration of drugs into the eye by injection with a fine needle. The medication will be directly applied into the vitreous humor. It is used to treat various eye diseases, such as age-related macular degeneration (AMD), diabetic retinopathy, and infections inside the eye such as endophthalmitis. As compared to topical administration, this method is beneficial for a more localized delivery of medications to the targeted site, as the needle can directly pass through the anatomical eye barrier and dynamic barrier. It could also minimize adverse drug effects on other body tissues via the systemic circulation, which could be a possible risk for intravenous injection of medications. Although there are risks of infections or other complications, with suitable precautions throughout the injection process, chances for these complications could be lowered.

<span class="mw-page-title-main">Topical glucocorticoids</span>

Topical glucocorticoids are the topical forms of glucocorticoids. Topical glucocorticoids are used in the treatment of many skin conditions. They provide anti-inflammatory, antimitotic, and immune-system suppressing actions through various mechanisms.

<span class="mw-page-title-main">Secondary glaucoma</span>

Secondary glaucoma is a collection of progressive optic nerve disorders associated with a rise in intraocular pressure (IOP) which results in the loss of vision. In clinical settings, it is defined as the occurrence of IOP above 21 mmHg requiring the prescription of IOP-managing drugs. It can be broadly divided into two subtypes: secondary open-angle glaucoma and secondary angle-closure glaucoma, depending on the closure of the angle between the cornea and the iris. Principal causes of secondary glaucoma include optic nerve trauma or damage, eye disease, surgery, neovascularization, tumours and use of steroid and sulfa drugs. Risk factors for secondary glaucoma include uveitis, cataract surgery and also intraocular tumours. Common treatments are designed according to the type and the underlying causative condition, in addition to the consequent rise in IOP. These include drug therapy, the use of miotics, surgery or laser therapy.

<span class="mw-page-title-main">Uveitic glaucoma</span> Glaucoma caused by uveitis or its treatments

Uveitic glaucoma is most commonly a progression stage of noninfectious anterior uveitis or iritis.

<span class="mw-page-title-main">Intravitreal implants</span>

Intravitreal implants are micro device-like inserts injected into the posterior segment of the eye to treat retinal diseases releasing therapeutic drugs at a set rate over a desired period of time. The posterior segment of the eye consists of the sclera, choroid, fovea, vitreous humor, optic nerve, and retina.

References

  1. "Regulatory Decision Summary for Iluvien". Drug and Health Product Portal. Health Canada. 23 October 2014.
  2. 1 2 "Fluocinolone (Topical) Monograph for Professionals". Drugs.com. 19 January 2024. Retrieved 7 July 2024.
  3. Mills JS, Bowers A, Djerassi C, Ringold HJ (1960). "Steroids CXXXVII. Synthesis of a New Class of Potent Cortical Hormones. 6α,9α-Difluoro-16α-Hydroxyprednisolone and its Acetonide". Journal of the American Chemical Society. 80 (13): 3399–3404. doi:10.1021/ja01498a041.
  4. Hara ES, Ono M, Pham HT, Sonoyama W, Kubota S, Takigawa M, et al. (September 2015). "Fluocinolone Acetonide Is a Potent Synergistic Factor of TGF-β3-Associated Chondrogenesis of Bone Marrow-Derived Mesenchymal Stem Cells for Articular Surface Regeneration". Journal of Bone and Mineral Research. 30 (9): 1585–1596. doi:10.1002/jbmr.2502. PMC   5569386 . PMID   25753754.{{cite journal}}: CS1 maint: overridden setting (link)
  5. Reddy A, Liu SH, Brady CJ, Sieving PC, Palestine AG (August 2023). "Corticosteroid implants for chronic non-infectious uveitis". The Cochrane Database of Systematic Reviews. 2023 (8): CD010469. doi:10.1002/14651858.CD010469.pub4. PMC   10464657 . PMID   37642198.
  6. "Real-world study shows long-term safety, efficacy of Iluvien in DME". Healio. 2 July 2020. Retrieved 28 October 2020.
  7. Fischer J, Ganellin CR, eds. (2006). "Tables of Structural and Functional Analogues: Systemic Hormonal Preparations". Analogue-based Drug Discovery. John Wiley & Sons. p. 485. ISBN   9783527607495.
  8. "Yutiq- fluocinolone acetonide implant". DailyMed. 16 October 2023. Retrieved 25 December 2023.
  9. "Fluocinolone ophthalmic implant Uses, Side Effects & Warnings". Drugs.com. 6 October 2023. Retrieved 7 July 2024.