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Betamethasone dipropionate

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 skin conditions such as eczema. Minor side effects include dry skin and mild, temporary stinging when applied.[3] 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.[4] It is available as a generic medication.[5]

Betamethasone dipropionate
Clinical data
Trade namesDiprolene, Sernivo, Diprosone, others
Other namesBetamethasone-17,21-dipropionate
AHFS/Drugs.comMonograph
MedlinePlusa682799
License data
  • US DailyMedBetamethasone_dipropionate
Pregnancy
category
  • AU: B3
Routes of
administration
Topical
ATC code
Legal status
Legal status
Identifiers
  • [(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
  • 5593-20-4 N
PubChem CID
  • 21800
DrugBank
  • DBSALT000851 Y
  • DB00443 Y
ChemSpider
  • 20490 Y
UNII
  • 826Y60901U
KEGG
  • D01637
ChEBI
  • CHEBI:31276 Y
ChEMBL
  • ChEMBL1200384 N
CompTox Dashboard (EPA)
  • DTXSID2022672
ECHA InfoCard100.024.551
Chemical and physical data
FormulaC28H37FO7
Molar mass504.595 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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=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 Y
  • Key:CIWBQSYVNNPZIQ-XYWKZLDCSA-N Y
 NY (what is this?)  (verify)

Adverse effects edit

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.[4][6] 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 edit

Mechanism of action edit

Pharmacokinetics edit

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.[4]

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.[4][8]

Chemistry edit

Betamethasone dipropionate is a white to almost white crystalline powder.[medical citation needed]

Regulation edit

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 edit

Brand names include Alphatrex, Beta-Val, Diprolene, Diprolene AF, Diprosalic (with salicylic acid)[14] Diprosone, Dovobet (LEO Pharma A/S),[15] Eleuphrat and Luxiq.[citation needed]

 
A tube of Diprosalic ointment

References edit

  1. ^ "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.
  2. ^ "Diprosone Cream - Summary of Product Characteristics (SmPC)". Electronic Medicines Compendium (EMC). Datapharm Ltd. 19 September 2019. Retrieved 14 April 2020.
  3. ^ "Betamethasone Dipropionate Side Effects". drugs.com.
  4. ^ a b c d "Diprolene". Drugs.com. 1 June 2021.
  5. ^ "Betamethasone Monograph for Professionals". Drugs.com. 26 December 2019. Retrieved 15 August 2020.
  6. ^ a b "Diprolene Ointment". RxList. 29 June 2021.
  7. ^ Ault A (25 March 2005). . MedPage Today. Archived from the original on 1 March 2016.
  8. ^ (PDF). Parsippany, NJ: LEO Pharma Inc. 2015. Archived from the original (PDF) on 2018-09-20. Retrieved 2015-11-21.
  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. ^ . Connetics Corporation. Archived from the original on 3 March 2007.
  12. ^ "Lotrisone- clotrimazole and betamethasone dipropionate cream". DailyMed. U.S. National Library of Medicine. 14 June 2019. Retrieved 13 April 2020.
  13. ^ "TACLONEX Highlights of Prescribing Information". LEO Laboratories Ltd.
  14. ^ 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.
  15. ^ "Dovobet Ointment - Summary of Product Characteristics (SMPC)". Electronic Medicines Compendium (EMC). Datapharm Ltd.

External links edit

  • "Betamethasone dipropionate". Drug Information Portal. U.S. National Library of Medicine.

betamethasone, dipropionate, glucocorticoid, steroid, with, anti, inflammatory, immunosuppressive, abilities, applied, topical, cream, ointment, lotion, diprolene, treat, itching, other, skin, conditions, such, eczema, minor, side, effects, include, skin, mild. 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 skin conditions such as eczema Minor side effects include dry skin and mild temporary stinging when applied 3 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 4 It is available as a generic medication 5 Betamethasone dipropionateClinical dataTrade namesDiprolene Sernivo Diprosone othersOther namesBetamethasone 17 21 dipropionateAHFS Drugs comMonographMedlinePlusa682799License dataUS DailyMed Betamethasone dipropionatePregnancycategoryAU B3Routes ofadministrationTopicalATC codeA07EA04 WHO C05AA05 WHO D07AC01 WHO D07XC01 WHO H02AB01 WHO R01AD06 WHO R03BA04 WHO S01BA06 WHO S01CB04 WHO S02BA07 WHO S03BA03 WHO D07CC01 WHO S01CA05 WHO S03CA06 WHO D07BC01 WHO S01BB04 WHO Legal statusLegal statusAU S4 Prescription only UK POM Prescription only 2 US WARNING 1 Rx onlyIdentifiersIUPAC 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 propanoateCAS Number5593 20 4 NPubChem CID21800DrugBankDBSALT000851 YDB00443 YChemSpider20490 YUNII826Y60901UKEGGD01637ChEBICHEBI 31276 YChEMBLChEMBL1200384 NCompTox Dashboard EPA DTXSID2022672ECHA InfoCard100 024 551Chemical and physical dataFormulaC 28H 37F O 7Molar mass504 595 g mol 13D model JSmol Interactive imageSMILES 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 CCInChI 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 YKey CIWBQSYVNNPZIQ XYWKZLDCSA N Y N Y what is this verify Contents 1 Adverse effects 2 Pharmacology 2 1 Mechanism of action 2 2 Pharmacokinetics 3 Chemistry 4 Regulation 5 Names 6 References 7 External linksAdverse effects editAlthough 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 4 6 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 12HPA axis suppression is preventable by supplementation with glucocorticosteroids If HPA axis suppression occurs it is often reversed shortly after discontinuation of treatment 7 Pharmacology editMechanism of action edit Further information Glucocorticoid Mechanism of action Pharmacokinetics edit 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 4 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 6b hydroxy derivatives of those metabolites and it is excreted primarily by the kidneys 4 8 Chemistry editBetamethasone dipropionate is a white to almost white crystalline powder medical citation needed Regulation editBetamethasone 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 editBrand names include Alphatrex Beta Val Diprolene Diprolene AF Diprosalic with salicylic acid 14 Diprosone Dovobet LEO Pharma A S 15 Eleuphrat and Luxiq citation needed nbsp A tube of Diprosalic ointmentReferences edit 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 a b c d Diprolene Drugs com 1 June 2021 Betamethasone Monograph for Professionals Drugs com 26 December 2019 Retrieved 15 August 2020 a b 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 Luxiq 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 amp 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 edit Betamethasone dipropionate Drug Information Portal U S National Library of Medicine Portal nbsp Medicine Retrieved from https en wikipedia org w index php title Betamethasone dipropionate amp oldid 1182595617, wikipedia, wiki, book, books, library,

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