Betamethasone
{{Short description|Steroid medication}}
{{Use dmy dates|date=June 2022}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Infobox drug
| Watchedfields = changed
| verifiedrevid = 459977512
| image = Betamethasone.svg
| image_class = skin-invert-image
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| image2 = Betamethasone2.png
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| pronounce =
| tradename = Celestone, Eleuphrat, others
| Drugs.com = {{drugs.com|monograph|betamethasone}}
| MedlinePlus = a682799
| DailyMedID = Betamethasone
| pregnancy_AU = C
| pregnancy_AU_comment = {{cite web | title=Betamethasone Use During Pregnancy | website=Drugs.com | date=30 December 2019 | url=https://www.drugs.com/pregnancy/betamethasone.html | access-date=29 March 2020}}
| pregnancy_category=
| routes_of_administration = By mouth, topical, intramuscular
| class =
| ATCvet =
| ATC_prefix = A07
| ATC_suffix = EA04
| ATC_supplemental = {{ATC|C05|AA05}} {{ATC|D07|AC01}} {{ATC|D07|BC01}} {{ATC|D07|CC01}} {{ATC|D07|XC01}} {{ATC|H02|AB01}} {{ATC|R01|AD06}} {{ATC|R03|BA04}} {{ATC|S01|BA06}} {{ATC|S01|BB04}} {{ATC|S01|CA05}} {{ATC|S01|CB04}} {{ATC|S02|BA07}} {{ATC|S03|BA03}} {{ATC|S03|CA06}}
| legal_AU = S4
| legal_AU_comment =
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| legal_UK = POM
| legal_US = Rx-only
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| legal_UN_comment =
| legal_status = Rx-only
| bioavailability =
| protein_bound =
| metabolites =
| onset =
| elimination_half-life = 36-54 hours
| duration_of_action =
| excretion = Kidney (in urine)
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 378-44-9
| CAS_supplemental =
| PubChem = 9782
| IUPHAR_ligand = 7061
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00443
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 9399
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 9842X06Q6M
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00244
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 3077
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 632
| NIAID_ChemDB =
| PDB_ligand =
| synonyms =
| IUPAC_name = (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
| C=22 | H=29 | F=1 | O=5
| SMILES = 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
| Jmol =
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChI_comment =
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = UREBDLICKHMUKA-DVTGEIKXSA-N
| density =
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Betamethasone is a steroid medication.{{cite web|title=Betamethasone|url=https://www.drugs.com/monograph/betamethasone.html|publisher=The American Society of Health-System Pharmacists|access-date=2 December 2015|url-status=live|archive-url=https://web.archive.org/web/20151208152909/http://www.drugs.com/monograph/betamethasone.html|archive-date=8 December 2015}} 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.{{cite web|title=Betamethasone topical|url=https://www.drugs.com/monograph/betamethasone-topical.html|publisher=The American Society of Health-System Pharmacists|access-date=2 December 2015|url-status=live|archive-url=https://web.archive.org/web/20151208025858/https://www.drugs.com/monograph/betamethasone-topical.html|archive-date=8 December 2015}}
Serious side effects include an increased risk of infection, muscle weakness, severe allergic reactions, and psychosis. Long-term use may cause adrenal insufficiency. Stopping the medication suddenly following long-term use may be dangerous. The cream commonly results in increased hair growth and skin irritation. Betamethasone belongs to the glucocorticoid class of medication. 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).{{cite journal | vauthors = Antignac JP, Le Bizec B, Monteau F, Andre F | title = Differentiation of betamethasone and dexamethasone using liquid chromatography/positive electrospray tandem mass spectrometry and multivariate statistical analysis | journal = Journal of Mass Spectrometry | volume = 37 | issue = 1 | pages = 69–75 | date = January 2002 | pmid = 11813313 | doi = 10.1002/jms.260 | bibcode = 2002JMSp...37...69A }}
Betamethasone was patented in 1958, and approved for medical use in the United States in 1961.{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=485 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA485 }} The cream and ointment are on the World Health Organization's List of Essential Medicines.{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO | hdl-access=free }} It is available as a generic medication. In 2022, it was the 263rd most commonly prescribed medication in the United States, with more than 1{{nbsp}}million prescriptions.{{cite web | title=The Top 300 of 2022 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=30 August 2024 | archive-date=30 August 2024 | archive-url=https://web.archive.org/web/20240830202410/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}{{cite web | title = Betamethasone Drug Usage Statistics, United States, 2013 - 2022 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Betamethasone | access-date = 30 August 2024 }}
Medical uses
File:Betnovateonitemntcream.JPG
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.{{cite web | title=Betamethasone Topical | website=MedlinePlus | date=19 March 2020 | url=https://medlineplus.gov/druginfo/meds/a682799.html | access-date=29 March 2020 }} When given by injection, anti-inflammatory effects begin in around two hours and last for seven days.
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.{{fact|date=November 2023}} 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.{{fact|date=November 2023}}
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%.{{cite journal | vauthors = Zannolli R, Buoni S, Betti G, Salvucci S, Plebani A, Soresina A, Pietrogrande MC, Martino S, Leuzzi V, Finocchi A, Micheli R, Rossi LN, Brusco A, Misiani F, Fois A, Hayek J, Kelly C, Chessa L | title = A randomized trial of oral betamethasone to reduce ataxia symptoms in ataxia telangiectasia | journal = Movement Disorders | volume = 27 | issue = 10 | pages = 1312–1316 | date = September 2012 | pmid = 22927201 | doi = 10.1002/mds.25126 | s2cid = 23696748 }}
Betamethasone is also used to stimulate fetal maturation of the lungs and cerebral blood vessels.
A cream with 0.05% betamethasone appears effective in treating phimosis in boys,{{cite journal | vauthors = Moreno G, Ramirez C, Corbalán J, Peñaloza B, Morel Marambio M, Pantoja T | title = Topical corticosteroids for treating phimosis in boys | journal = The Cochrane Database of Systematic Reviews | volume = 1 | issue = 1 | pages = CD008973 | date = January 2024 | pmid = 38269441 | pmc = 10809033 | doi = 10.1002/14651858.CD008973.pub3 }} and often averts the need for circumcision.{{cite journal | vauthors = Van Howe RS | title = Cost-effective treatment of phimosis | journal = Pediatrics | volume = 102 | issue = 4 | pages = E43 | date = October 1998 | pmid = 9755280 | doi = 10.1542/peds.102.4.e43 | doi-access = free }} A review of estimated costs and complications of 3 phimosis treatments.{{cite journal | vauthors = Esposito C, Centonze A, Alicchio F, Savanelli A, Settimi A | title = Topical steroid application versus circumcision in pediatric patients with phimosis: a prospective randomized placebo controlled clinical trial | journal = World Journal of Urology | volume = 26 | issue = 2 | pages = 187–190 | date = April 2008 | pmid = 18157674 | doi = 10.1007/s00345-007-0231-2 | publisher = Springer Science and Business Media LLC | s2cid = 8922151 }}{{cite journal | vauthors = Zampieri N, Corroppolo M, Zuin V, Bianchi S, Camoglio FS | title = Phimosis and topical steroids: new clinical findings | journal = Pediatric Surgery International | volume = 23 | issue = 4 | pages = 331–335 | date = April 2007 | pmid = 17308904 | doi = 10.1007/s00383-007-1878-x | s2cid = 22849471 }} Longer-term research is needed on this treatment method. This approach has replaced circumcision as the preferred treatment method for some physicians in the British National Health Service.{{cite journal | vauthors = Berdeu D, Sauze L, Ha-Vinh P, Blum-Boisgard C | title = Cost-effectiveness analysis of treatments for phimosis: a comparison of surgical and medicinal approaches and their economic effect | journal = BJU International | volume = 87 | issue = 3 | pages = 239–244 | date = February 2001 | pmid = 11167650 | doi = 10.1046/j.1464-410x.2001.02033.x | s2cid = 2161551 | doi-access = free }}{{cite journal | vauthors = Chu CC, Chen KC, Diau GY | title = Topical steroid treatment of phimosis in boys | journal = The Journal of Urology | volume = 162 | issue = 3 Pt 1 | pages = 861–863 | date = September 1999 | pmid = 10458396 | doi = 10.1097/00005392-199909010-00078 }}
Side effects
- Euphoria
- Depression
- Adrenal suppression
- Hypertension
- Groupings of fine blood vessels becoming prominent under the skin, petechiae
- Excessive hair growth (hypertrichosis)
- Ecchymoses{{cite web | url = http://davisplus.fadavis.com/3976/MedDeck/pdf/betamethasonesystemic.pdf | publisher = F.A. Davis | title = betamethasone | date = 2017 | access-date = 7 March 2017 | url-status = live | archive-url = https://web.archive.org/web/20170908175627/https://davisplus.fadavis.com/3976/MedDeck/pdf/betamethasonesystemic.pdf | archive-date = 8 September 2017 }}
Betamethasone crosses the placenta.
When injected into the epidural space or the spine, it may cause serious side effects like loss of vision, stroke, and paralysis.{{cite web|title=FDA Drug Safety Communication: FDA requires label changes to warn of rare but serious neurologic problems after epidural corticosteroid injections for pain|url=https://www.fda.gov/drugs/drug-safety-and-availability/fda-drug-safety-communication-fda-requires-label-changes-warn-rare-serious-neurologic-problems-after|website=FDA|access-date=15 August 2016|date=23 April 2014|url-status=live|archive-url=https://web.archive.org/web/20160811081058/https://www.fda.gov/Drugs/DrugSafety/ucm394280.htm|archive-date=11 August 2016}}
Pharmacology
{{main|Glucocorticoid#Pharmacology}}
Forms
{{singlesource|section|date=November 2023}}
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).{{fact|date=November 2023}} 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.{{fact|date=November 2023}}
Betamethasone sodium phosphate mixed with betamethasone acetate is available in the United States as Celestone Soluspan.{{cite web |title=Celestone Soluspan- betamethasone acetate and betamethasone sodium phosphate injection, suspension |website=DailyMed |date=18 November 2019 |url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=7b5489a1-e30f-450f-bd2b-00d05fd52915 |access-date=29 March 2020}}
See also
References
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{{Glucocorticoids}}
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Category:Fluorinated corticosteroids
Category:Drugs developed by Merck & Co.