Flumetasone

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Flumetasone
Flumetasone.svg
Clinical data
Trade names Flucort
Other namesFlumethasone (USAN)
AHFS/Drugs.com Micromedex Detailed Consumer Information
Routes of
administration
Topical
ATC code
Legal status
Legal status
Pharmacokinetic data
Metabolism Liver, CYP3A4-mediated
Identifiers
  • (1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.016.701 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C22H28F2O5
Molar mass 410.458 g·mol−1
3D model (JSmol)
  • C[C@@H]1C[C@H]2[C@@H]3C[C@@H](C4=CC(=O)C=C[C@@]4([C@]3([C@H](C[C@@]2([C@]1(C(=O)CO)O)C)O)F)C)F
  • InChI=1S/C22H28F2O5/c1-11-6-13-14-8-16(23)15-7-12(26)4-5-19(15,2)21(14,24)17(27)9-20(13,3)22(11,29)18(28)10-25/h4-5,7,11,13-14,16-17,25,27,29H,6,8-10H2,1-3H3/t11-,13+,14+,16+,17+,19+,20+,21+,22+/m1/s1 X mark.svgN
  • Key:WXURHACBFYSXBI-GQKYHHCASA-N X mark.svgN
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Flumetasone, also known as flumethasone, [1] is a corticosteroid for topical use. It has anti-inflammatory, antipruritic, and vasoconstrictive properties, and it is approved for human and animal use for a variety of medical conditions. [2] [3]

Contents

It was patented in 1951 and approved for medical use in 1964. [4]

Chemistry and mechanism of action

Flumetasone is classified as a moderately potent corticosteroid and a glucocorticoid receptor agonist. Like other corticosteroids, it functions as an immunosuppressant by decreasing function of the lymphatic system, reducing immunoglobulin and complement concentrations, lowering lymphocyte concentrations, and preventing antigen-antibody binding. [2] Flumethasone is 420 times as potent as cortisone in an animal model for anti-inflammatory activity.[ citation needed ]

Society and culture

Names

Trade names include Locacorten, Locorten, and Orsalin. [5] It is available in combination with clioquinol, under the brand name Locacorten-Vioform (in some countries Locorten-Vioform [6] ), for the treatment of otitis externa and otomycosis. [7] It is usually formulated as the pivalic acid ester prodrug called flumetasone pivalate. [2]

Veterinary uses

In April 2023, the US Food and Drug Administration approved the first generic version of flumethasone (Bimasone), for certain diseases that cause inflammation in horses, dogs, and cats. [3] Flumetasone is recommended for the various rheumatic, allergic, dermatologic and other disease states that are known to be responsive to anti-inflammatory drugs (i.e., corticoids) in these species. [3]

In horses, flumetasone is approved for use for musculoskeletal conditions due to inflammation, such as bursitis (a painful condition that affects the fluid-filled sacs that cushion the bones, tendons and muscles near a horse's joints, often in the hip or shoulder), carpitis (inflammation of the connective tissues near the horse's carpus, which is comparable to the human wrist), osselets (arthritis in the fetlock joint of a horse, often in the front legs), and myositis (rapid muscle wasting, often in the horse's hindquarters). [3]

In dogs, Bimasone is approved for use for musculoskeletal conditions due to inflammation of muscles or joints, such as arthritis, osteoarthritis, intervertebral disc disease, and myositis. [3] The drug has proven useful in treating canine ear infections (otitis externa) when used with topical medication for similar reasons. [3] It is also approved for certain acute and chronic skin conditions (dermatoses) from various causes to help control the itchy skin (pruritus), irritation, and inflammation associated with these conditions, and for use in treating allergic reactions, such as hives, urticaria (raised itchy rash on skin), and insect bites. [3] Flumetasone is also approved for treating shock in dogs, when administered intravenously. [3]

In cats, flumetasone is approved for certain acute and chronic skin conditions (dermatoses) from various causes to help control the itchy skin (pruritus), irritation, and inflammation associated with these conditions. [3]

Related Research Articles

<span class="mw-page-title-main">Irritation</span> State of inflammation

Irritation, in biology and physiology, is a state of inflammation or painful reaction to allergy or cell-lining damage. A stimulus or agent which induces the state of irritation is an irritant. Irritants are typically thought of as chemical agents but mechanical, thermal (heat), and radiative stimuli can also be irritants. Irritation also has non-clinical usages referring to bothersome physical or psychological pain or discomfort.

The National Institute of Arthritis and Musculoskeletal and Skin Diseases (NIAMS) is one of the institutes and centers that make up the National Institutes of Health, an agency of the United States Department of Health and Human Services (HHS).

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

Prednisolone is a corticosteroid, a steroid hormone used to treat certain types of allergies, inflammatory conditions, autoimmune disorders, and cancers. Some of these conditions include adrenocortical insufficiency, high blood calcium, rheumatoid arthritis, dermatitis, eye inflammation, asthma, and multiple sclerosis. It can be taken by mouth, injected into a vein, used topically as a skin cream, or as eye drops. It differs from the similarly named prednisone in having a hydroxyl at the 11th carbon instead of a ketone.

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

Dermatomyositis (DM) is a long-term inflammatory disorder which affects the skin and the muscles. Its symptoms are generally a skin rash and worsening muscle weakness over time. These may occur suddenly or develop over months. Other symptoms may include weight loss, fever, lung inflammation, or light sensitivity. Complications may include calcium deposits in muscles or skin.

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

Betamethasone is a steroid medication. It is used for a number of diseases including rheumatic disorders such as rheumatoid arthritis and systemic lupus erythematosus, skin diseases such as dermatitis and psoriasis, allergic conditions such as asthma and angioedema, preterm labor to speed the development of the baby's lungs, Crohn's disease, cancers such as leukemia, and along with fludrocortisone for adrenocortical insufficiency, among others. It can be taken by mouth, injected into a muscle, or applied to the skin, typically in cream, lotion, or liquid forms.

In medicine, myopathy is a disease of the muscle in which the muscle fibers do not function properly. Myopathy means muscle disease. This meaning implies that the primary defect is within the muscle, as opposed to the nerves or elsewhere.

Skin disorders are among the most common health problems in dogs, and have many causes. The condition of a dog's skin and coat is also an important indicator of its general health. Skin disorders of dogs vary from acute, self-limiting problems to chronic or long-lasting problems requiring life-time treatment. Skin disorders may be primary or secondary in nature, making diagnosis complicated.

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

Desonide (INN) is a low-potency topical corticosteroid anti-inflammatory that has been available since the 1970s. It is primarily used to treat atopic dermatitis (eczema), seborrheic dermatitis, contact dermatitis and psoriasis in both adults and children. It has a fairly good safety profile and is available as a cream, ointment, lotion, and as a foam under the tradename Verdeso Foam. Other trade names for creams, lotions, and ointments include Tridesilon, DesOwen, Desonate. It is a group VI corticosteroid under US classification, the second least potent group.

<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">Myositis</span> Medical condition

Myositis is a rarely-encountered medical condition characterized by inflammation affecting the muscles. The manifestations of this condition may include skin issues, muscle weakness, and the potential involvement of other organs. Additionally, systemic symptoms like weight loss, fatigue, and low-grade fever can manifest in individuals with myositis.

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

Alclometasone is a synthetic corticosteroid for topical dermatologic use, possessing anti-inflammatory, antipruritic, and vasoconstrictive properties.

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

Mometasone, also known as mometasone y 3 s, is a steroid medication used to treat certain skin conditions, hay fever, and asthma. Specifically it is used to prevent rather than treat asthma attacks. It can be applied to the skin, inhaled, or used in the nose. Mometasone furoate, not mometasone, is used in medical products.

<span class="mw-page-title-main">Otitis externa in animals</span>

Otitis externa is an inflammation of the outer ear and ear canal. Animals are commonly prone to ear infection, and this is one of the most common manifestations of allergy in dogs. In dogs, those breeds with floppy ears are more prone, since air flow is limited and a warm, moist environment built up, which is conducive to infection. The external ear in animals is longer and deeper than in humans, which makes it easier for infection or wax to build up or be hard to remove. Complete ear canal inspection requires the use of an otoscope by a veterinarian.

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

Amcinonide is a topical glucocorticoid used to treat itching, redness and swelling associated with several dermatologic conditions such as atopic dermatitis and allergic contact dermatitis. Amcinonide can also be classified as a multi-functional small molecule corticosteroid, which has been approved by the FDA and is currently marketed as an ointment, lotion, or cream. It acts as both a transcription factor for responses to glucocorticoids and modulator for other transcription factors while also regulating phospholipase A2 activity.

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

Hydrocortisone aceponate is a veterinary corticosteroid that is used in form of creams for the treatment of various dermatoses. It is an ester of hydrocortisone (cortisol) with acetic acid and propionic acid.

<span class="mw-page-title-main">Fluticasone furoate</span> History, Structure, Drug Mechanisms of Fluticasone Furoate.

Fluticasone furoate, sold under the brand name Flonase Sensimist among others, is a corticosteroid for the treatment of non-allergic and allergic rhinitis administered by a nasal spray. It is also available as an inhaled corticosteroid to help prevent and control symptoms of asthma. It is derived from cortisol. Unlike fluticasone propionate, which is only approved for children four years and older, fluticasone furoate is approved in children as young as two years of age when used for allergies.

<span class="mw-page-title-main">Oclacitinib</span> Medication

Oclacitinib, sold under the brand name Apoquel among others, is a veterinary medication used in the control of atopic dermatitis and pruritus from allergic dermatitis in dogs at least 12 months of age. Chemically, it is a synthetic cyclohexylamino pyrrolopyrimidine janus kinase inhibitor that is relatively selective for JAK1. It inhibits signal transduction when the JAK is activated and thus helps downregulate expression of inflammatory cytokines.

<span class="mw-page-title-main">Antiarthritics</span> Drug class

An antiarthritic is any drug used to relieve or prevent arthritic symptoms, such as joint pain or joint stiffness. Depending on the antiarthritic drug class, it is used for managing pain, reducing inflammation or acting as an immunosuppressant. These drugs are typically given orally, topically or through administration by injection. The choice of antiarthritic medication is often determined by the nature of arthritis, the severity of symptoms as well as other factors, such as the tolerability of side effects.

<span class="mw-page-title-main">Topical hydrocortisone</span> Pharmaceutical drug

Topical hydrocortisone is a drug under the class of corticosteroids, which is used for the treatment of skin inflammation, itchiness and allergies. Some examples include insect bites, dermatitis and rash.

References

  1. Morton IK, Hall JM (1999). Concise Dictionary of Pharmacological Agents Properties and Synonyms. Dordrecht: Springer Netherlands. p. 122. ISBN   9789401144391.
  2. 1 2 3 "Flumethasone". National Center for Advancing Translational Sciences.
  3. 1 2 3 4 5 6 7 8 9 "FDA Approves Generic Flumethasone for Diseases in Cats, Dogs and Horse". U.S. Food and Drug Administration (FDA). 5 April 2023. Archived from the original on 7 April 2023. Retrieved 7 April 2023.PD-icon.svg This article incorporates text from this source, which is in the public domain .
  4. Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 484. ISBN   9783527607495. Archived from the original on 10 January 2023. Retrieved 7 April 2023.
  5. "Flumetasone Overview - Active Ingredient - RxReasoner". www.rxreasoner.com. Retrieved 7 February 2024.
  6. "Flumetasone/Clioquinol 0.02% w/v / 1% w/v Ear Drops solution - Summary of Product Characteristics (SmPC) - (emc)". www.medicines.org.uk. Retrieved 7 February 2024.
  7. "Locacorten Vioform Eardrops - Uses, Side Effects, Interactions - MedBroadcast.com". www.medbroadcast.com. Retrieved 7 February 2024.