Betamethasone dipropionate

Betamethasone dipropionate
Clinical data
Trade namesDiprolene, Sernivo, Diprosone, others
Other namesBetamethasone-17,21-dipropionate
AHFS/Drugs.comMonograph
MedlinePlusa682799
License data
Pregnancy
category
  • AU: B3
Routes of
administration		Topical
ATC code
Legal status
Legal status
Identifiers
IUPAC name
  • [(8S,9R,10S,11S,13S,14S,16S,17R)-9-fluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-(2-propanoyloxyacetyl)-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.024.551
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Chemical and physical data
FormulaC28H37FO7
Molar mass504.595 g·mol−1
3D model (JSmol)
SMILES
  • O=C(OCC(=O)[C@]3(OC(=O)CC)[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)CC
InChI
  • InChI=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 checkY
  • Key:CIWBQSYVNNPZIQ-XYWKZLDCSA-N checkY
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Betamethasone dipropionate is a glucocorticoid steroid with anti-inflammatory and immunosuppressive abilities. It is applied as a topical cream, ointment, lotion or gel (Diprolene) to treat itching and other minor skin conditions such as eczema. Minor side effects include dry skin and mild, temporary stinging when applied.[2] 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.[3] It is available as a generic medication.[4]

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.[3][5] 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.[6] 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.[7]

Pharmacology

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.[3]

The absorption of topical betamethasone dipropionate is theoretically minuscule; however, if absorbed it follows the same pharmacokinetic profile that 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.[3][8]

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.[9] 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.[10]

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% [11] is a mid-strength corticosteroid foam used primarily to treat psoriasis or other inflammatory conditions of the scalp.
  • Merck: Lotrisone (containing betamethasone dipropionate, clotrimazole)[12] 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)[13] 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, Diprosone, Eleuphrat and Luxiq.

References

  1. ↑ "Diprosone Cream - Summary of Product Characteristics (SmPC)". (emc). 19 September 2019. Retrieved 14 April 2020.
  2. ↑ "Betamethasone Dipropionate Side Effects". drugs.com.
  3. 1 2 3 4 "Diprolene". Drugs.com. 1 June 2021.
  4. ↑ "Betamethasone Monograph for Professionals". Drugs.com. 26 December 2019. Retrieved 15 August 2020.
  5. ↑ "Diprolene Ointment". RxList. 29 June 2021.
  6. ↑ "Diprolene Ointment". RxList. 29 June 2021.
  7. ↑ Ault A (25 March 2005). "Adrenal Suppression From Topical Corticosteroids Surprisingly High". MedPage Today. Archived from the original on 1 March 2016.
  8. ↑ "Enstilar (calcipotriene and betamethasone dipropionate) Foam, 0.005%/0.064% for topical use. Full Prescribing Information" (PDF). Parsippany, NJ: LEO Pharma Inc. 2015.
  9. ↑ DIPROLENE AF Drug Profile, "Profile for Tradename: Diprolene AF", DrugPatentWatch.com
  10. ↑ "Diprolene Pediatric Exclusivity" (PDF). Centerfor Drug Evaluation and Research. U.S. Food and Drug Administration.
  11. ↑ "Luxíq". Connetics Corporation. Archived from the original on 3 March 2007.
  12. ↑ "Lotrisone- clotrimazole and betamethasone dipropionate cream". DailyMed. 14 June 2019. Retrieved 13 April 2020.
  13. ↑ "TACLONEX Highlights of Prescribing Information". LEO Laboratories Ltd.
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