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| {{Short description|Glucocorticoid steroid (chemical compound)}} | |||
| {{Drugbox | |||
| {{Infobox drug | |||
| | IUPAC_name = phenanthren-17-yl] propanoate | |||
| | Verifiedfields = changed | |||
| | image = Betamethasone_dipropionate.png | |||
| | verifiedrevid = 486407176 | |||
| | drug_name = | |||
| | INN = | |||
| | type = <!-- empty --> | |||
| | image = Betamethasone_dipropionate.svg | |||
| | image2 = Betamethasone-dipropionate-from-xtal-Mercury-3D-balls-thin.png | |||
| | width = | |||
| | alt = | |||
| | caption = | |||
| <!--Clinical data--> | <!-- Clinical data --> | ||
| | |
| pronounce = | ||
| | tradename = Diprolene, Sernivo, Diprosone, others | |||
| | Drugs.com = {{drugs.com|monograph|betamethasone}} | | Drugs.com = {{drugs.com|monograph|betamethasone}} | ||
| | MedlinePlus = a682799 | |||
| | pregnancy_category = | |||
| | licence_CA = <!-- Health Canada may use generic or brand name (generic name preferred) --> | |||
| | legal_status = | |||
| | licence_EU = <!-- EMA uses INN (or special INN_EMA) --> | |||
| | routes_of_administration = topical | |||
| | DailyMedID = Betamethasone_dipropionate | |||
| | licence_US = <!-- FDA may use generic or brand name (generic name preferred) --> | |||
| | pregnancy_AU = B3 | |||
| | pregnancy_AU_comment = | |||
| | pregnancy_US = <!-- A / B / C / D / X / N --> | |||
| | pregnancy_US_comment = | |||
| | pregnancy_category= | |||
| | dependency_liability = | |||
| | addiction_liability = | |||
| | routes_of_administration = ] | |||
| | class = | |||
| | ATCvet = | |||
| | ATC_prefix = A07 | |||
| | ATC_suffix = EA04 | |||
| | ATC_supplemental = {{ATC|C05|AA05}} {{ATC|D07|AC01}} {{ATC|D07|XC01}} {{ATC|H02|AB01}} {{ATC|R01|AD06}} {{ATC|R03|BA04}} {{ATC|S01|BA06}} {{ATC|S01|CB04}} {{ATC|S02|BA07}} {{ATC|S03|BA03}} {{ATC|D07|CC01}} {{ATC|S01|CA05}} {{ATC|S03|CA06}} {{ATC|D07|BC01}} {{ATC|S01|BB04}} | |||
| <!-- |
<!-- Legal status --> | ||
| | |
| legal_AU = S4 | ||
| | |
| legal_AU_comment = | ||
| | legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F--> | |||
| | metabolism = | |||
| | legal_BR_comment = | |||
| | elimination_half-life = | |||
| | legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII --> | |||
| | legal_CA_comment = | |||
| | legal_DE = <!-- Anlage I, II, III or Unscheduled--> | |||
| | legal_DE_comment = | |||
| | legal_NZ = <!-- Class A, B, C --> | |||
| | legal_NZ_comment = | |||
| | legal_UK = POM | |||
| | legal_UK_comment = <ref>{{cite web | title=Diprosone Cream - Summary of Product Characteristics (SmPC) | work = Electronic Medicines Compendium (EMC) | publisher = Datapharm Ltd. | date=19 September 2019 | url=https://www.medicines.org.uk/emc/product/6405/smpc | access-date=14 April 2020}}</ref> | |||
| | legal_US = Rx-only | |||
| | legal_US_comment = | |||
| | legal_UN = <!-- N I, II, III, IV / P I, II, III, IV--> | |||
| | legal_UN_comment = | |||
| | legal_status = <!-- For countries not listed above --> | |||
| <!-- |
<!-- Pharmacokinetic data --> | ||
| | bioavailability = | |||
| | protein_bound = | |||
| | metabolism = | |||
| | metabolites = | |||
| | onset = | |||
| | elimination_half-life = | |||
| | duration_of_action = | |||
| | excretion = | |||
| <!-- Identifiers --> | |||
| | CAS_number_Ref = {{cascite|changed|??}} | |||
| | CAS_number = 5593-20-4 | | CAS_number = 5593-20-4 | ||
| | |
| CAS_supplemental = | ||
| | ATC_suffix = | |||
| | ATC_supplemental = | |||
| | PubChem = 21800 | | PubChem = 21800 | ||
| | |
| IUPHAR_ligand = | ||
| | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | |||
| | DrugBank = DBSALT000851 | |||
| | DrugBank2_Ref = {{drugbankcite|correct|drugbank}} | |||
| | DrugBank2 = DB00443 | |||
| | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | |||
| | ChemSpiderID = 20490 | | ChemSpiderID = 20490 | ||
| | UNII_Ref = {{fdacite|correct|FDA}} | |||
| | UNII = 826Y60901U | |||
| | KEGG_Ref = | |||
| | KEGG = D01637 | |||
| | ChEBI_Ref = {{ebicite|correct|EBI}} | |||
| | ChEBI = 31276 | |||
| | ChEMBL_Ref = {{ebicite|changed|EBI}} | |||
| | ChEMBL = 1200384 | | ChEMBL = 1200384 | ||
| | NIAID_ChemDB = | |||
| | PDB_ligand = | |||
| | synonyms = Betamethasone-17,21-dipropionate | |||
| <!--Chemical data--> | <!-- Chemical and physical data --> | ||
| | IUPAC_name = phenanthren-17-yl] propanoate | |||
| | C=28 | H=37 | F=1 | O=7 | | C=28 | H=37 | F=1 | O=7 | ||
| | SMILES = O=C(OCC(=O)3(OC(=O)CC)2(C(O)4(F)/1(\C(=C/C(=O)\C=C\1)CC42C3C)C)C)CC | |||
| | molecular_weight = 504.59 g/mol | |||
| | Jmol = | |||
| | smiles = O=C(OCC(=O)3(OC(=O)CC)2(C(O)4(F)/1(\C(=C/C(=O)\C=C\1)CC42C3C)C)C)CC | |||
| | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | |||
| | InChI = 1/C28H37FO7/c1-6-23(33)35-15-22(32)28(36-24(34)7-2)16(3)12-20-19-9-8-17-13-18(30)10-11-25(17,4)27(19,29)21(31)14-26(20,28)5/h10-11,13,16,19-21,31H,6-9,12,14-15H2,1-5H3/t16-,19-,20-,21-,25-,26-,27-,28-/m0/s1 | |||
| | StdInChI = 1S/C28H37FO7/c1-6-23(33)35-15-22(32)28(36-24(34)7-2)16(3)12-20-19-9-8-17-13-18(30)10-11-25(17,4)27(19,29)21(31)14-26(20,28)5/h10-11,13,16,19-21,31H,6-9,12,14-15H2,1-5H3/t16-,19-,20-,21-,25-,26-,27-,28-/m0/s1 | |||
| | InChIKey = CIWBQSYVNNPZIQ-XYWKZLDCBG | |||
| | StdInChI_comment = | |||
| | synonyms = Betamethasone-17,21-dipropionate | |||
| | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | |||
| | StdInChIKey = CIWBQSYVNNPZIQ-XYWKZLDCSA-N | |||
| | density = | |||
| | density_notes = | |||
| | melting_point = | |||
| | melting_high = | |||
| | melting_notes = | |||
| | boiling_point = | |||
| | boiling_notes = | |||
| | solubility = | |||
| | sol_units = | |||
| | specific_rotation = | |||
| }} | }} | ||
| '''Betamethasone dipropionate''' is a ] ] with ] and ] |
'''Betamethasone dipropionate''' is a ] ] with ] and ] properties. It is applied as a ] cream, ointment, lotion or gel ('''Diprolene''') to treat ] and other skin conditions such as ]. Minor side effects include dry skin and mild, temporary stinging when applied.<ref name="brand">{{cite web |url=https://www.drugs.com/sfx/betamethasone-dipropionate-side-effects.html |title=Betamethasone Dipropionate Side Effects |work=] }}</ref> Betamethasone dipropionate is a "super high potency" corticosteroid used to treat inflammatory skin conditions such as ], ] and ]. 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.<ref name="drugs.com"/> It is available as a ].<ref>{{cite web |title=Betamethasone Monograph for Professionals |website=Drugs.com |date=26 December 2019 |url=https://www.drugs.com/monograph/betamethasone.html |access-date=15 August 2020}}</ref> | ||
| ==Adverse effects== | |||
| Brand names include Alphatrex, Beta-Val, Diprolene, Diprolene AF, Diprosone, and Luxiq. | |||
| Although the absorption of betamethasone dipropionate is small, when used for prolonged periods of time (periods exceeding two weeks), or across a large surface area (total use greater than 50 grams per week), it can have adverse effects. One such effect is the ability of the corticosteroid to suppress the ].<ref name="drugs.com"/><ref name="RxList">{{cite web |title=Diprolene Ointment |url=http://www.rxlist.com/diprolene-ointment-drug/indications-dosage.htm#D |work=RxList |date=29 June 2021 }}</ref> This can lead to a depression in the release of adrenal hormones such as ] and ], or ACTH. Symptoms of HPA axis suppression are often subtle and variable, but can often be detected using simple blood or urine tests such at ACTH stimulation test or urinary free cortisol.<ref name="RxList" /> Those at increased risk for HPA axis suppression are those who are more likely to absorb more of the steroid through the skin. These groups include: | |||
| * Those who have used topical corticosteroids over a prolonged period of time | |||
| Minor side effects include dry skin and mild, temporary stinging when applied.<ref name="brand">, '']''</ref> | |||
| * Those who have used corticosteroids to cover a large surface area | |||
| * Those with broken skin barrier or extensive abrasions | |||
| * Those who have recently undergone stress (such as illness, trauma, surgery) | |||
| * Children under the age of 12 | |||
| HPA axis suppression is preventable by supplementation with glucocorticosteroids. If HPA axis suppression occurs, it is often reversed shortly after discontinuation of treatment.<ref>{{cite web |vauthors=Ault A |date=25 March 2005 |title=Adrenal Suppression From Topical Corticosteroids Surprisingly High|url=http://www.medpagetoday.com/Dermatology/Steroids/777 |archive-url=https://web.archive.org/web/20160301074517/http://www.medpagetoday.com/Dermatology/Steroids/777 |archive-date=1 March 2016 |work=MedPage Today }}</ref> | |||
| ==Pharmacology== | |||
| ===Mechanism of action=== | |||
| {{further|Glucocorticoid#Mechanism of action}} | |||
| ===Pharmacokinetics=== | |||
| Absorption of topical corticosteroids depends on several factors such as the vehicle, or delivery system used by the drug, the integrity of the epidermal barrier, and whether or not an occlusive bandage is used in combination with the drug.<ref name="drugs.com">{{cite web |title=Diprolene |url=https://www.drugs.com/pro/diprolene.html#dosage |work=Drugs.com |date=1 June 2021 }}</ref> | |||
| The absorption of topical betamethasone dipropionate is theoretically minuscule; however, if absorbed it follows the same pharmacokinetic profile as is typical of systemic corticosteroids. It is metabolized primarily by the liver by hydrolysis to its metabolites B17P (primary) and ] and the 6β-hydroxy derivatives of those metabolites, and it is excreted primarily by the kidneys.<ref name="drugs.com"/><ref name=Enstilar>{{cite web |title=Enstilar (calcipotriene and betamethasone dipropionate) Foam, 0.005%/0.064% for topical use. Full Prescribing Information |url=http://enstilar.com/pdf/enstilar-pi.pdf |location=Parsippany, NJ |publisher=LEO Pharma Inc |date=2015 |access-date=2015-11-21 |archive-date=2018-09-20 |archive-url=https://web.archive.org/web/20180920190124/http://enstilar.com/pdf/enstilar-pi.pdf |url-status=dead }}</ref> | |||
| ==Chemistry== | |||
| Betamethasone dipropionate is a white to almost white crystalline powder.{{medcn|date=April 2020}} | |||
| ==Regulation== | |||
| Betamethasone dipropionate was patented by ] in 1987, as an augmented cream/lotion, Diprolene in the U.S., and Disprosone in Europe.<ref>, "Profile for Tradename: Diprolene AF", ''DrugPatentWatch.com</ref> These patents expired in 2003 and 2007 respectively leading to generic production of betamethasone dipropionate. During this time other topical corticosteroids such as ] and ] also became available as generic creams. Merck filed for "pediatric exclusivity" in 2001 launching a clinical trial to prove betamethasone dipropionate's safety and efficacy for use in pediatrics.<ref>{{cite web |title=Diprolene Pediatric Exclusivity |url=http://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/19-555S008_Diprosone_admindocs.pdf |work=Centerfor Drug Evaluation and Research |publisher=U.S. Food and Drug Administration |date=}}</ref> | |||
| ] has also been used in the formulation of ] such as ], ] and ]. | |||
| * Prestium Pharma: Luxiq (betamethasone valerate) Foam, 0.12% <ref>{{cite web |title=Luxíq |work= Connetics Corporation |url=http://www.luxiq.com |archive-url=https://web.archive.org/web/20070303114823/http://www.luxiq.com/ |archive-date=3 March 2007 }}</ref> is a mid-strength corticosteroid foam used primarily to treat psoriasis or other inflammatory conditions of the scalp. | |||
| * Merck: Lotrisone (containing betamethasone dipropionate, ])<ref name="Lotrisone label">{{cite web |title=Lotrisone- clotrimazole and betamethasone dipropionate cream |work=DailyMed |publisher=U.S. National Library of Medicine |date=14 June 2019 |url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=40ec029d-8af0-4f8f-bea1-1d38779ec232 |access-date=13 April 2020}}</ref> contains both a corticosteroid (betamethasone) and anti-fungal agent (clotrimazole) and is used to treat fungal infections that are also inflamed | |||
| * Leo Pharma: Taclonex (containing betamethasone dipropionate, ])<ref>{{cite web |title=TACLONEX Highlights of Prescribing Information |work=LEO Laboratories Ltd. |url=http://www.taclonex.com/ }}</ref> is a combination of corticosteroid (betamethasone) and a vitamin D analogue (calcipotriene) and is used to treat frequent and persistent dermatatoses by reducing inflammation and promoting healing of the skin barrier. | |||
| == Names == | |||
| Brand names include Alphatrex, Beta-Val, Diprolene, Diprolene AF, Diprosalic (with ])<ref>{{cite book |vauthors=Weller RB, Hunter HJ, Mann MW |chapter=Formulary 1: Topical Treatments |title=Clinical Dermatology |date=27 January 2015 |publisher=John Wiley & Sons |isbn=978-0-470-65952-6 |page=402 |chapter-url=https://books.google.com/books?id=W69YBQAAQBAJ&dq=diprosalic+ointment&pg=PA402 |access-date=2 December 2022 |language=en}}</ref> Diprosone, Dovobet (LEO Pharma A/S),<ref>{{cite web |url=https://www.medicines.org.uk/emc/product/1609/smpc#gref |title=Dovobet Ointment - Summary of Product Characteristics (SMPC) |work=Electronic Medicines Compendium (EMC) |publisher=Datapharm Ltd. }}</ref> Eleuphrat and Luxiq.{{citation needed|date=April 2020}} | |||
| ] | |||
| == See also == | |||
| * {{Portal-inline|Medicine}} | |||
| == References == | == References == | ||
| {{Reflist}} | |||
| <references/> | |||
| == |
== External links == | ||
| * {{cite web |title=Betamethasone dipropiona |url=https://druginfo.nlm.nih.gov/drugportal/name/betamethasone%20dipropionate |publisher=U.S. National Library of Medicine |department=Drug Information Portalte }} | |||
| * ] | |||
| {{Glucocorticoids}} | |||
| {{Glucocorticoidics}} | |||
| {{DEFAULTSORT:Betamethasone Dipropionate}} | {{DEFAULTSORT:Betamethasone Dipropionate}} | ||
| ] | |||
| ] | ] | ||
| ] | ] | ||
| {{Pharma-stub}} | |||
Latest revision as of 21:10, 22 January 2025
Glucocorticoid steroid (chemical compound) Pharmaceutical compound | |
 | |
| Clinical data | |
|---|---|
| Trade names | Diprolene, Sernivo, Diprosone, others |
| Other names | Betamethasone-17,21-dipropionate |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a682799 |
| License data | |
| Pregnancy category |
|
| Routes of administration | Topical |
| ATC code | |
| Legal status | |
| Legal status | |
| Identifiers | |
IUPAC name
| |
| CAS Number | |
| PubChem CID | |
| DrugBank | |
| ChemSpider | |
| UNII | |
| KEGG | |
| ChEBI | |
| ChEMBL | |
| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.024.551  |
| Chemical and physical data | |
| Formula | C28H37FO7 |
| Molar mass | 504.595 g·mol |
| 3D model (JSmol) | |
SMILES
| |
InChI
| |
| (what is this?) (verify) | |
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.
Adverse effects
Although the absorption of betamethasone dipropionate is small, when used for prolonged periods of time (periods exceeding two weeks), or across a large surface area (total use greater than 50 grams per week), it can have adverse effects. One such effect is the ability of the corticosteroid to suppress the hypothalamic–pituitary–adrenal axis. This can lead to a depression in the release of adrenal hormones such as cortisol and adrenocorticotropic hormone, or ACTH. Symptoms of HPA axis suppression are often subtle and variable, but can often be detected using simple blood or urine tests such at ACTH stimulation test or urinary free cortisol. Those at increased risk for HPA axis suppression are those who are more likely to absorb more of the steroid through the skin. These groups include:
- Those who have used topical corticosteroids over a prolonged period of time
- Those who have used corticosteroids to cover a large surface area
- Those with broken skin barrier or extensive abrasions
- Those who have recently undergone stress (such as illness, trauma, surgery)
- Children under the age of 12
HPA axis suppression is preventable by supplementation with glucocorticosteroids. If HPA axis suppression occurs, it is often reversed shortly after discontinuation of treatment.
Pharmacology
Mechanism of action
Further information: Glucocorticoid § Mechanism of actionPharmacokinetics
Absorption of topical corticosteroids depends on several factors such as the vehicle, or delivery system used by the drug, the integrity of the epidermal barrier, and whether or not an occlusive bandage is used in combination with the drug.
The absorption of topical betamethasone dipropionate is theoretically minuscule; however, if absorbed it follows the same pharmacokinetic profile as is typical of systemic corticosteroids. It is metabolized primarily by the liver by hydrolysis to its metabolites B17P (primary) and betamethasone and the 6β-hydroxy derivatives of those metabolites, and it is excreted primarily by the kidneys.
Chemistry
Betamethasone dipropionate is a white to almost white crystalline powder.
Regulation
Betamethasone dipropionate was patented by Merck in 1987, as an augmented cream/lotion, Diprolene in the U.S., and Disprosone in Europe. These patents expired in 2003 and 2007 respectively leading to generic production of betamethasone dipropionate. During this time other topical corticosteroids such as triamcinolone acetonide and clobetasol propionate also became available as generic creams. Merck filed for "pediatric exclusivity" in 2001 launching a clinical trial to prove betamethasone dipropionate's safety and efficacy for use in pediatrics.
Betamethasone has also been used in the formulation of combination products such as Luxiq, Lotrisone and Taclonex.
- Prestium Pharma: Luxiq (betamethasone valerate) Foam, 0.12% is a mid-strength corticosteroid foam used primarily to treat psoriasis or other inflammatory conditions of the scalp.
- Merck: Lotrisone (containing betamethasone dipropionate, clotrimazole) contains both a corticosteroid (betamethasone) and anti-fungal agent (clotrimazole) and is used to treat fungal infections that are also inflamed
- Leo Pharma: Taclonex (containing betamethasone dipropionate, calcipotriol) is a combination of corticosteroid (betamethasone) and a vitamin D analogue (calcipotriene) and is used to treat frequent and persistent dermatatoses by reducing inflammation and promoting healing of the skin barrier.
Names
Brand names include Alphatrex, Beta-Val, Diprolene, Diprolene AF, Diprosalic (with salicylic acid) Diprosone, Dovobet (LEO Pharma A/S), Eleuphrat and Luxiq.
See also
References
- "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
- "Diprosone Cream - Summary of Product Characteristics (SmPC)". Electronic Medicines Compendium (EMC). Datapharm Ltd. 19 September 2019. Retrieved 14 April 2020.
- "Betamethasone Dipropionate Side Effects". drugs.com.
- ^ "Diprolene". Drugs.com. 1 June 2021.
- "Betamethasone Monograph for Professionals". Drugs.com. 26 December 2019. Retrieved 15 August 2020.
- ^ "Diprolene Ointment". RxList. 29 June 2021.
- Ault A (25 March 2005). "Adrenal Suppression From Topical Corticosteroids Surprisingly High". MedPage Today. Archived from the original on 1 March 2016.
- "Enstilar (calcipotriene and betamethasone dipropionate) Foam, 0.005%/0.064% for topical use. Full Prescribing Information" (PDF). Parsippany, NJ: LEO Pharma Inc. 2015. Archived from the original (PDF) on 2018-09-20. Retrieved 2015-11-21.
- DIPROLENE AF Drug Profile, "Profile for Tradename: Diprolene AF", DrugPatentWatch.com
- "Diprolene Pediatric Exclusivity" (PDF). Centerfor Drug Evaluation and Research. U.S. Food and Drug Administration.
- "Luxíq". Connetics Corporation. Archived from the original on 3 March 2007.
- "Lotrisone- clotrimazole and betamethasone dipropionate cream". DailyMed. U.S. National Library of Medicine. 14 June 2019. Retrieved 13 April 2020.
- "TACLONEX Highlights of Prescribing Information". LEO Laboratories Ltd.
- Weller RB, Hunter HJ, Mann MW (27 January 2015). "Formulary 1: Topical Treatments". Clinical Dermatology. John Wiley & Sons. p. 402. ISBN 978-0-470-65952-6. Retrieved 2 December 2022.
- "Dovobet Ointment - Summary of Product Characteristics (SMPC)". Electronic Medicines Compendium (EMC). Datapharm Ltd.
External links
- "Betamethasone dipropiona". Drug Information Portalte. U.S. National Library of Medicine.
| Glucocorticoids and antiglucocorticoids (D07, H02) | |
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| Glucocorticoids | |
| Antiglucocorticoids |
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| Synthesis modifiers | |
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