Betamethasone

Last updated

Betamethasone
Betamethasone.svg
Betamethasone2.png
Clinical data
Trade names Celestone, Eleuphrat, others
AHFS/Drugs.com Monograph
MedlinePlus a682799
License data
Pregnancy
category
Routes of
administration 		By mouth, topical, intramuscular
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only) [2]
  • US: ℞-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Metabolism Liver CYP3A4
Elimination half-life 36-54 hours
Excretion Kidney (in urine)
Identifiers
  • (8S,9R,10S,11S,13S,14S,16S,17R)-9-Fluoro- 11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl- 6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro- 3H-cyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.006.206 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C22H29FO5
Molar mass 392.467 g·mol−1
3D model (JSmol)
  • O=C(CO)[C@]3(O)[C@]2(C[C@H](O)[C@]4(F)[C@@]/1(\C(=C/C(=O)\C=C\1)CC[C@H]4[C@@H]2C[C@@H]3C)C)C
  • InChI=1S/C22H29FO5/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,23)17(26)10-20(16,3)22(12,28)18(27)11-24/h6-7,9,12,15-17,24,26,28H,4-5,8,10-11H2,1-3H3/t12-,15-,16-,17-,19-,20-,21-,22-/m0/s1 Yes check.svgY
  • Key:UREBDLICKHMUKA-DVTGEIKXSA-N Yes check.svgY
   (verify)

Betamethasone is a steroid medication. [3] 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. [3] It can be taken by mouth, injected into a muscle, or applied to the skin, typically in cream, lotion, or liquid forms. [3] [4]

Contents

Serious side effects include an increased risk of infection, muscle weakness, severe allergic reactions, and psychosis. [3] Long-term use may cause adrenal insufficiency. [3] Stopping the medication suddenly following long-term use may be dangerous. [3] The cream commonly results in increased hair growth and skin irritation. [4] Betamethasone belongs to the glucocorticoid class of medication. [3] It is a stereoisomer of dexamethasone, the two compounds differing only in the spatial configuration of the methyl group at position 16 (see steroid nomenclature). [5]

Betamethasone was patented in 1958, and approved for medical use in the United States in 1961. [3] [6] The cream and ointment are on the World Health Organization's List of Essential Medicines. [7] It is available as a generic medication. [3] In 2021, it was the 251st most commonly prescribed medication in the United States, with more than 1 million prescriptions. [8] [9]

Medical uses

Betnovate ointment Betnovateonitemntcream.JPG
Betnovate ointment

Betamethasone is a corticosteroid that is available as a pill, by injection, and as an ointment, cream, lotion, gel, or aerosol (spray) for the skin, and a foam for the scalp. [10] When given by injection, anti-inflammatory effects begin in around two hours and last for seven days. [3]

It is used as a topical cream to relieve skin irritation, such as itching and flaking from eczema. It is used as a treatment for local psoriasis, as betamethasone dipropionate and salicylic acid, or as the combination calcipotriol/betamethasone dipropionate.[ citation needed ] Betamethasone sodium phosphate is used orally and via injection with the same indications as other steroids. Many betamethasone-based pharmaceuticals include the steroid as the valerate ester.[ citation needed ]

In a randomized controlled trial betamethasone was shown to reduce some of the ataxia (poor coordination) symptoms associated with ataxia telangiectasia (A-T) by 28-31%. [11]

Betamethasone is also used to stimulate fetal maturation of the lungs and cerebral blood vessels. [3]

A cream with 0.05% betamethasone appears effective in treating phimosis in boys, [12] and often averts the need for circumcision. [13] [14] [15] Longer-term research is needed on this treatment method. [12] This approach has replaced circumcision as the preferred treatment method for some physicians in the British National Health Service. [16] [17]

Side effects

Betamethasone crosses the placenta. [3]

When injected into the epidural space or the spine, it may cause serious side effects like loss of vision, stroke, and paralysis. [19]

Pharmacology

Forms

Betamethasone is available in a number of compound forms: betamethasone dipropionate (branded as Diprosone, Diprolene, Celestamine, Procort (in Pakistan), and others), betamethasone sodium phosphate (branded as Bentelan in Italy) and betamethasone valerate (branded as Audavate, Betnovate, Celestone, Fucibet, and others).[ citation needed ] In the United States and Canada, betamethasone is mixed with clotrimazole and sold as Lotrisone and Lotriderm. It is also available in combination with salicylic acid (branded as Diprosalic) for using in psoriatic skin conditions. In some countries, it is also sold mixed with both clotrimazole and gentamicin to add an antibacterial agent to the mix.[ citation needed ]

Betamethasone sodium phosphate mixed with betamethasone acetate is available in the United States as Celestone Soluspan. [20]

See also

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">Paraphimosis</span> Medical condition

Paraphimosis is an uncommon medical condition in which the foreskin of a penis becomes trapped behind the glans penis, and cannot be reduced. If this condition persists for several hours or there is any sign of a lack of blood flow, paraphimosis should be treated as a medical emergency, as it can result in gangrene.

Phimosis is a condition in which the foreskin of the penis cannot stretch to allow it to be pulled back past the glans. A balloon-like swelling under the foreskin may occur with urination. In teenagers and adults, it may result in pain during an erection, but is otherwise not painful. Those affected are at greater risk of inflammation of the glans, known as balanitis, and other complications.

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

Clobetasol propionate is a corticosteroid used to treat skin conditions such as eczema, contact dermatitis, seborrheic dermatitis, steroid responsive dermatosis, and psoriasis.

<span class="mw-page-title-main">Betamethasone dipropionate</span> Glucocorticoid steroid (chemical compound)

Betamethasone dipropionate is a glucocorticoid steroid with anti-inflammatory and immunosuppressive properties. It is applied as a topical cream, ointment, lotion or gel (Diprolene) to treat itching and other skin conditions such as eczema. Minor side effects include dry skin and mild, temporary stinging when applied. Betamethasone dipropionate is a "super high potency" corticosteroid used to treat inflammatory skin conditions such as dermatitis, eczema and psoriasis. It is a synthetic analog of the adrenal corticosteroids. Although its exact mechanism of action is not known, it is effective when applied topically to cortico-responsive inflammatory dermatoses. It is available as a generic medication.

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

Betamethasone valerate is a synthetic glucocorticoid ester. It is the 17-valerate ester of betamethasone. Betamethasone valerate is often used to treat mild eczema with good efficacy and lower incidence of steroid induced adverse effects due to its lower potency compared to other glucocorticoids. Betamethasone-17-valerate is available in cream, ointment, lotion, and foam preparations for topical use.

<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">Calcipotriol</span> Chemical compound

Calcipotriol, also known as calcipotriene, is a synthetic derivative of calcitriol, a form of vitamin D. It is used in the treatment of psoriasis. It is safe for long-term application in psoriatic skin conditions.

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

Mometasone, also known as mometasone furoate, 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">Diflorasone diacetate</span> Chemical compound and topical steroid

Diflorasone diacetate is a topical steroid that comes in the form of a cream. It is manufactured by E. Fougera & Co. and is used as an anti-inflammatory and anti-itching agent, like other topical corticosteroids. It is prescribed for psoriasis and atopic dermatitis, among other conditions. With respect to potency, it is regarded as a Class I corticosteroid [of classes I – VII] in the United States.

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

Clotrimazole, sold under the brand name Lotrimin, among others, is an antifungal medication. It is used to treat vaginal yeast infections, oral thrush, diaper rash, tinea versicolor, and types of ringworm including athlete's foot and jock itch. It can be taken by mouth or applied as a cream to the skin or in the vagina.

<span class="mw-page-title-main">Steroid-induced skin atrophy</span> Medical condition

Steroid-induced skin atrophy is thinning of the skin as a result of prolonged exposure to topical steroids. In people with psoriasis using topical steroids it occurs in up to 5% of people after a year of use. Intermittent use of topical steroids for atopic dermatitis is safe and does not cause skin thinning.

<span class="mw-page-title-main">Tinea incognita</span> Fungal skin infection caused by the presence of a topical immunosuppressive agent

Tinea incognita, also spelled tinea incognito, is a fungal infection of the skin that generally looks odd for a typical tinea infection. The border of the skin lesion is usually blurred and it appears to have florid growth.

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">Calcipotriol/betamethasone dipropionate</span> Combination drug

Calcipotriol/betamethasone dipropionate, sold under the brand name Taclonex among others, is a fixed-dose combination medication of the synthetic vitamin D3 analog calcipotriol (also known as calcipotriene) and the synthetic corticosteroid betamethasone dipropionate for the treatment of plaque psoriasis. It is used in the form of ointment, topical suspension, gel, aerosol, and foam.

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

Clascoterone, sold under the brand name Winlevi, is an antiandrogen medication which is used topically in the treatment of acne. It is also under development in a higher concentration for the treatment of androgen-dependent scalp hair loss, under the brand name Breezula. The medication is used as a cream by application to the skin, for instance the face and scalp.

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

Domoprednate is a synthetic glucocorticoid corticosteroid which was developed in the late 1970s and 1980s.

Clotrimazole/betamethasone dipropionate, sold under the brand name Lotrisone among others, is a topical medication used for the treatment of fungal infections of the feet, groin, and body in people 17 years of age and older. It is a combination of clotrimazole and betamethasone dipropionate. It is applied to the skin.

<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.

References

  1. ↑ "Betamethasone Use During Pregnancy". Drugs.com. 30 December 2019. Retrieved 29 March 2020.
  2. ↑ "Betamethasone 500 microgram Soluble Tablets - Summary of Product Characteristics (SmPC)". (emc). 5 April 2018. Retrieved 29 March 2020.
  3. 1 2 3 4 5 6 7 8 9 10 11 12 "Betamethasone". The American Society of Health-System Pharmacists. Archived from the original on 8 December 2015. Retrieved 2 December 2015.
  4. 1 2 "Betamethasone topical". The American Society of Health-System Pharmacists. Archived from the original on 8 December 2015. Retrieved 2 December 2015.
  5. ↑ Antignac JP, Le Bizec B, Monteau F, Andre F (January 2002). "Differentiation of betamethasone and dexamethasone using liquid chromatography/positive electrospray tandem mass spectrometry and multivariate statistical analysis". Journal of Mass Spectrometry. 37 (1): 69–75. Bibcode:2002JMSp...37...69A. doi:10.1002/jms.260. PMID   11813313.
  6. ↑ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 485. ISBN   9783527607495.
  7. ↑ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl: 10665/325771 . WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  8. ↑ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  9. ↑ "Betamethasone - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.
  10. ↑ "Betamethasone Topical". MedlinePlus. 19 March 2020. Retrieved 29 March 2020.
  11. ↑ Zannolli R, Buoni S, Betti G, Salvucci S, Plebani A, Soresina A, et al. (September 2012). "A randomized trial of oral betamethasone to reduce ataxia symptoms in ataxia telangiectasia". Movement Disorders. 27 (10): 1312–1316. doi:10.1002/mds.25126. PMID   22927201. S2CID   23696748.
  12. 1 2 Moreno G, Ramirez C, Corbalán J, Peñaloza B, Morel Marambio M, Pantoja T (January 2024). "Topical corticosteroids for treating phimosis in boys". The Cochrane Database of Systematic Reviews. 1 (1): CD008973. doi:10.1002/14651858.CD008973.pub3. PMC   10809033 . PMID   38269441.
  13. ↑ Van Howe RS (October 1998). "Cost-effective treatment of phimosis". Pediatrics. 102 (4): E43. doi: 10.1542/peds.102.4.e43 . PMID   9755280. Archived from the original on 19 August 2009. A review of estimated costs and complications of 3 phimosis treatments.
  14. ↑ Esposito C, Centonze A, Alicchio F, Savanelli A, Settimi A (April 2008). "Topical steroid application versus circumcision in pediatric patients with phimosis: a prospective randomized placebo controlled clinical trial". World Journal of Urology. 26 (2). Springer Science and Business Media LLC: 187–190. doi:10.1007/s00345-007-0231-2. PMID   18157674. S2CID   8922151.
  15. ↑ Zampieri N, Corroppolo M, Zuin V, Bianchi S, Camoglio FS (April 2007). "Phimosis and topical steroids: new clinical findings". Pediatric Surgery International. 23 (4): 331–335. doi:10.1007/s00383-007-1878-x. PMID   17308904. S2CID   22849471.
  16. ↑ Berdeu D, Sauze L, Ha-Vinh P, Blum-Boisgard C (February 2001). "Cost-effectiveness analysis of treatments for phimosis: a comparison of surgical and medicinal approaches and their economic effect". BJU International. 87 (3): 239–244. doi: 10.1046/j.1464-410x.2001.02033.x . PMID   11167650. S2CID   2161551.
  17. ↑ Chu CC, Chen KC, Diau GY (September 1999). "Topical steroid treatment of phimosis in boys". The Journal of Urology. 162 (3 Pt 1): 861–863. doi:10.1097/00005392-199909010-00078. PMID   10458396.
  18. 1 2 3 4 5 6 7 "betamethasone" (PDF). F.A. Davis. 2017. Archived (PDF) from the original on 8 September 2017. Retrieved 7 March 2017.
  19. ↑ "FDA Drug Safety Communication: FDA requires label changes to warn of rare but serious neurologic problems after epidural corticosteroid injections for pain". FDA. 23 April 2014. Archived from the original on 11 August 2016. Retrieved 15 August 2016.
  20. ↑ "Celestone Soluspan- betamethasone acetate and betamethasone sodium phosphate injection, suspension". DailyMed. 18 November 2019. Retrieved 29 March 2020.
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