Chemistry:Betamethasone

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Short description: Steroid medication
Betamethasone
Betamethasone.svg
Betamethasone2.png
Clinical data
Trade namesCelestone, Eleuphrat, others
AHFS/Drugs.comMonograph
MedlinePlusa682799
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
MetabolismLiver CYP3A4
Elimination half-life36-54 hours
ExcretionKidney (in urine)
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC22H29FO5
Molar mass392.467 g·mol−1
3D model (JSmol)
  (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]

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

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 lung maturation in order to prevent infant respiratory distress syndrome (IRDS) and to decrease the incidence and mortality from intracranial hemorrhage in premature infants.[original research?]

A cream with 0.05% betamethasone appears effective in treating phimosis in boys,[12] and often averts the need for circumcision.[13][14][15] It has replaced circumcision as the preferred treatment method for some physicians in the United Kingdom National Health Service.[16][17]

Side effects

Prolonged use of this medicine on extensive areas of skin, broken or raw skin, skin folds, or underneath airtight dressings may on rare occasions result in enough corticosteroid being absorbed to have side effects on other parts of the body; for example, by causing a decrease in the production of natural hormones by the adrenal glands.[original research?]

Betamethasone is also used prior to delivery of a preterm baby to help prepare the lungs for breathing. However, because betamethasone crosses the placenta, which is required for its beneficial effects, it may also be associated with complications, such as hypoglycemia and leukocytosis in newborns exposed in utero.[original research?]

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

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

  • Betamethasone/dexchlorpheniramine

References

  1. ↑ "Betamethasone Use During Pregnancy". 30 December 2019. https://www.drugs.com/pregnancy/betamethasone.html. 
  2. ↑ "Betamethasone 500 microgram Soluble Tablets - Summary of Product Characteristics (SmPC)". 5 April 2018. https://www.medicines.org.uk/emc/product/9098/smpc. 
  3. ↑ 3.0 3.1 3.2 3.3 3.4 3.5 3.6 3.7 3.8 3.9 "Betamethasone". The American Society of Health-System Pharmacists. https://www.drugs.com/monograph/betamethasone.html. 
  4. ↑ 4.0 4.1 "Betamethasone topical". The American Society of Health-System Pharmacists. https://www.drugs.com/monograph/betamethasone-topical.html. 
  5. ↑ "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. January 2002. doi:10.1002/jms.260. PMID 11813313. Bibcode: 2002JMSp...37...69A. 
  6. ↑ Analogue-based Drug Discovery. John Wiley & Sons. 2006. p. 485. ISBN 9783527607495. https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA485. 
  7. ↑ World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. 2019. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO. 
  8. ↑ "The Top 300 of 2021". https://clincalc.com/DrugStats/Top300Drugs.aspx. 
  9. ↑ "Betamethasone - Drug Usage Statistics". https://clincalc.com/DrugStats/Drugs/Betamethasone. 
  10. ↑ "Betamethasone Topical". 19 March 2020. https://medlineplus.gov/druginfo/meds/a682799.html. 
  11. ↑ "A randomized trial of oral betamethasone to reduce ataxia symptoms in ataxia telangiectasia". Movement Disorders 27 (10): 1312–1316. September 2012. doi:10.1002/mds.25126. PMID 22927201. 
  12. ↑ "Topical corticosteroids for treating phimosis in boys". The Cochrane Database of Systematic Reviews 9 (9): CD008973. September 2014. doi:10.1002/14651858.CD008973.pub2. PMID 25180668. 
  13. ↑ "Cost-effective treatment of phimosis". Pediatrics 102 (4): E43. October 1998. doi:10.1542/peds.102.4.e43. PMID 9755280. http://pediatrics.aappublications.org/cgi/content/full/102/4/e43.  A review of estimated costs and complications of 3 phimosis treatments.
  14. ↑ "Topical steroid application versus circumcision in pediatric patients with phimosis: a prospective randomized placebo controlled clinical trial". World Journal of Urology (Springer Science and Business Media LLC) 26 (2): 187–190. April 2008. doi:10.1007/s00345-007-0231-2. PMID 18157674. 
  15. ↑ "Phimosis and topical steroids: new clinical findings". Pediatric Surgery International 23 (4): 331–335. April 2007. doi:10.1007/s00383-007-1878-x. PMID 17308904. 
  16. ↑ "Cost-effectiveness analysis of treatments for phimosis: a comparison of surgical and medicinal approaches and their economic effect". BJU International 87 (3): 239–244. February 2001. doi:10.1046/j.1464-410x.2001.02033.x. PMID 11167650. 
  17. ↑ "Topical steroid treatment of phimosis in boys". The Journal of Urology 162 (3 Pt 1): 861–863. September 1999. doi:10.1097/00005392-199909010-00078. PMID 10458396. 
  18. ↑ 18.0 18.1 18.2 18.3 18.4 18.5 18.6 "betamethasone". F.A. Davis. 2017. http://davisplus.fadavis.com/3976/MedDeck/pdf/betamethasonesystemic.pdf. 
  19. ↑ "FDA Drug Safety Communication: FDA requires label changes to warn of rare but serious neurologic problems after epidural corticosteroid injections for pain". 23 April 2014. https://www.fda.gov/Drugs/DrugSafety/ucm394280.htm. 
  20. ↑ "Celestone Soluspan- betamethasone acetate and betamethasone sodium phosphate injection, suspension". 18 November 2019. https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=7b5489a1-e30f-450f-bd2b-00d05fd52915. 



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