Betamethasone
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Systematic (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
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Clinical data |
Trade names |
Celestone |
AHFS/Drugs.com |
monograph |
Pregnancy
category |
- US: C (Risk not ruled out)
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Routes of
administration |
Oral,Topical,IM |
Legal status |
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Pharmacokinetic data |
Bioavailability |
? |
Metabolism |
hepatic CYP3A4 |
Biological half-life |
36-54 hours |
Excretion |
Renal (in urine) |
Identifiers |
CAS Number |
378-44-9 Y |
ATC code |
A07EA04 C05AA05 D07AC01 H02AB01 R01AD06 R03BA04 S01BA06 S02BA07 S03BA03 |
PubChem |
CID 9782 |
IUPHAR/BPS |
7061 |
DrugBank |
DB00443 Y |
ChemSpider |
9399 Y |
UNII |
9842X06Q6M Y |
KEGG |
D00244 Y |
ChEBI |
CHEBI:3077 Y |
ChEMBL |
CHEMBL632 Y |
Chemical data |
Formula |
C22H29FO5 |
Molar mass |
392.461 |
SMILES
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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
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InChI
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InChI=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 Y
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Key:UREBDLICKHMUKA-DVTGEIKXSA-N Y
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(verify) |
Betamethasone is a steroid medication.[1] 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, Crohn disease, cancers such as leukemia, and along with fludrocortisone for adrenocortical insufficiency, among others.[1] It can be taken by mouth, injected into a muscle, or applied as a cream.[1][2] When given by injection, anti-inflammatory effects begin in around two hours and last for seven days.[1]
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.[1] The cream commonly results in increased hair growth and skin irritation.[2] Betamethasone belongs to the glucocorticoid class of medication.[1]
Betamethasone was approved for medical use in the United States in 1961.[1] The cream is on the World Health Organization's List of Essential Medicines, the most important medication needed in a basic health system.[3] It is available as a generic medication.[1] In the United States the pills and injectable solution are expensive while the cream is not.[4]
Contents
- 1 Medical uses
- 2 Side effects
- 3 Forms
- 4 See also
- 5 References
- 6 External links
Medical uses
Betamethasone is a corticosteroid that is available as pill, by injection, and as a cream.
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 betamethasone/calcipotriol. 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.
In a randomized controlled trial Betamethasone was shown to reduce some of the ataxia symptoms associated with Ataxia Telangiectasia (A-T) by 28-31%.[5]
Alternative medical approach for large microcystic CCAMs – Betamethasone therapy[citation needed]
Betamethasone is also used prior to delivery of a preterm baby to help prepare the lung for breathing.
Steroids such as betamethasone are also used to treat phimosis (tight foreskin) in males.[6]
Side effects
- Skin irritation, e.g. itching, burning, stinging.
- Thinning of the skin.
- Changes in skin pigmentation and coloration.
- Stretch marks (striae).
- Groupings of fine blood vessels becoming prominent under the skin (telangiectasia).
- Excessive hair growth (hypertrichosis).
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.
A cream with 0.05% betamethasone appears effective in treating phimosis in boys, and often averts the need for circumcision.[7][8][9] It has replaced circumcision as the preferred treatment method for some physicians in the British National Health Service.[10][11]
Betamethasone is also used to stimulate fetal lung maturation (prevention of IRDS), and to decrease the incidence and mortality from intracranial hemorrhage in premature infants. 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.[citation needed]
Forms
Betamethasone is available in a number of compound forms: betamethasone dipropionate (branded as Diprosone, Diprolene, Celestamine, Procort in Pakistan and others), sodium phosphate (branded as Bentelan in Italy[12]) and valerate (branded as Audavate, Betnovate, Celestone, Fucibet, and others). 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 for using in psoriatic skin conditions. In Mexico it is also sold mixed with both clotrimazole and gentamicin to add an antibacterial agent to the mix.
See also
- Betamethasone/dexchlorpheniramine
References
- ^ a b c d e f g h "Betamethasone". The American Society of Health-System Pharmacists. Retrieved Dec 2, 2015.
- ^ a b "Betamethasone topical". The American Society of Health-System Pharmacists. Retrieved Dec 2, 2015.
- ^ "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.
- ^ Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 186,201. ISBN 9781284057560.
- ^ 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 (Sep 1, 2012). "A randomized trial of oral betamethasone to reduce ataxia symptoms in ataxia telangiectasia.". Movement disorders : official journal of the Movement Disorder Society 27 (10): 1312–6. doi:10.1002/mds.25126. PMID 22927201.
- ^ Moreno, G; Corbalán, J; Peñaloza, B; Pantoja, T (2 September 2014). "Topical corticosteroids for treating phimosis in boys.". The Cochrane database of systematic reviews 9: CD008973. PMID 25180668.
- ^ Van Howe RS (1998). "Cost-effective treatment of phimosis". Pediatrics 102 (4): E43. doi:10.1542/peds.102.4.e43. PMID 9755280. A review of estimated costs and complications of 3 phimosis treatments.
- ^ Topical steroid application versus circumcision in pediatric patients with phimosis: a prospective randomized placebo controlled clinical trial, World Journal of Urology, 2008, 26, pp.187-190
- ^ Phimosis and topical steroids: new clinical findings, Pediatric Surgery International, 2007, 23, pp.331-335
- ^ Berdeu D, Sauze L, Ha-Vinh P, Blum-Boisgard C (2001). "Cost-effectiveness analysis of treatments for phimosis: a comparison of surgical and medicinal approaches and their economic effect". BJU Int. 87 (3): 239–44. doi:10.1046/j.1464-410x.2001.02033.x. PMID 11167650.
- ^ Chu CC, Chen KC, Diau GY (1999). "Topical steroid treatment of phimosis in boys". J. Urol. 162 (3 Pt 1): 861–3. doi:10.1097/00005392-199909010-00078. PMID 10458396.
- ^ http://farmaco.agenziafarmaco.it/index.php?SEARCH=yes&DESCR_SPECIALITA2=BENTELAN
External links
- "Betamethasone". safefetus.com.
Glucocorticoids and antiglucocorticoids (H02)
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Glucocorticoids |
Pregnene |
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Pregnenedione |
- Hydrocortisone (cortisol)# (Hydrocortisone aceponate
- Hydrocortisone buteprate
- Hydrocortisone butyrate)
- Budesonide
- Ciclesonide
- Deflazacort
- Medrysone
- Tixocortol
- Halogenated at 6: Cloprednol
- Halogenated, with FG at 16: Halcinonide
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Pregnadiene |
- Rimexolone
- Halogenated, with FG at 16: Flunisolide
- Triamcinolone
- Amcinonide
- Fluocinolone acetonide (Fluocinonide)
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Pregnadienediol |
- Prednisone (Meprednisone)
- Halogenated at 9: Fluorometholone
- Halogenated, with FG at 16: Fluocortolone (Clocortolone
- Diflucortolone
- Fluocortin)
- Desoximetasone
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Pregnadienetriol |
- Prednisolone# (Methylprednisolone
- Methylprednisolone aceponate
- Prednicarbate
- Prednylidene)
- Desonide
- Halogenated: Fluprednisolone (Difluprednate
- Fluperolone)
- Halogenated, with FG at 16: Dexamethasone#
- Betamethasone (Clobetasol
- Clobetasone
- Diflorasone
- Halometasone
- Ulobetasol)
- Beclometasone
- Paramethasone
- Alclometasone
- Fluclorolone acetonide
- Flumetasone
- Fluprednidene
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Pregnatriene |
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Androstene |
- Halogenated, with FG at 16: Fluticasone (Fluticasone propionate
- Fluticasone furoate)
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Others/unsorted |
- Halogenated: Loteprednol
- Halogenated, with FG at 16: Fludroxycortide
- Formocortal
- Mometasone furoate
- Promestriene
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Antiglucocorticoids |
- SGRMs: Dagrocorat§
- Fosdagrocorat§
- Mapracorat†
- Antagonists: Ketoconazole
- Mifepristone
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Synthesis modifiers |
- Acetoxolone
- Aminoglutethimide
- Carbenoxolone
- Enoxolone
- Ketoconazole
- Metyrapone
- Mitotane
- Trilostane
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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Antidiarrheals, intestinal anti-inflammatory and anti-infective agents (A07)
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Rehydration |
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Intestinal anti-infectives |
- Antibiotics
- Amphotericin B
- Colistin
- Fidaxomicin
- Kanamycin
- Natamycin
- Neomycin
- Nystatin
- Paromomycin
- Polymyxin B
- Rifaximin
- Streptomycin
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- Phthalylsulfathiazole
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Intestinal adsorbents |
- Charcoal
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- Pectin
- Kaolin
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Antipropulsives (opioids) |
- Opium tincture (laudanum)
- Codeine
- Morphine
- Camphorated opium tincture (paregoric)
- crosses BBB: Diphenoxylate (Diphenoxylate/atropine)
- Difenoxin
- does not cross BBB: Eluxadoline
- Loperamide
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Intestinal anti-inflammatory agents |
- corticosteroids acting locally
- Prednisolone
- Hydrocortisone
- Prednisone
- Betamethasone
- Tixocortol
- Budesonide
- Beclometasone
- antiallergic agents, excluding corticosteroids
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Antidiarrheal micro-organisms |
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Other antidiarrheals |
- Albumin tannate
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Vasoprotectives (C05)
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Antihemorrhoidals for topical use |
corticosteroids |
- Hydrocortisone
- Prednisolone
- Betamethasone
- Fluorometholone
- Fluocortolone
- Dexamethasone
- Fluocinolone acetonide
- Fluocinonide
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local anesthetics |
- Lidocaine
- Tetracaine
- Benzocaine
- Dibucaine
- Procaine
- Oxetacaine
- Pramocaine
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other |
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Antivaricose therapy |
heparins or heparinoids for topical use |
- Organo-heparinoid
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sclerosing agents for local injection |
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other |
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Capillary stabilising agents |
bioflavonoids |
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other |
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Decongestants and other nasal preparations (R01)
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Topical |
Sympathomimetics, plain
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Antiallergic agents,
excluding corticosteroids
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- mast cell stabilizer (some are also antihistamines) (Cromoglicic acid
- Nedocromil
- Azelastine
- Olopatadine
- Lodoxamide)
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Corticosteroids
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- Beclometasone dipropionate
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Other nasal preparations
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Systemic use:
Sympathomimetics |
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Drugs for obstructive airway diseases: asthma/COPD (R03)
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Long-acting β2 agonists (LABA) |
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Ultra-long-acting β2 agonists |
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Other |
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Glucocorticoids |
- Beclometasone#
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Anticholinergics/
muscarinic antagonist |
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Mast cell stabilizers |
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Xanthines |
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Thromboxane receptor antagonists |
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Non-xanthine PDE4 inhibitors |
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Others/unknown |
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Combination products |
- Aclidinium/formoterol
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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Drugs used for diseases of the ear (S02)
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Infection |
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Corticosteroids |
- Betamethasone
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- Prednisolone
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Analgesics and anesthetics |
- Lidocaine
- Cocaine
- Phenazone
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Glucocorticoid signaling
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Receptor
(ligands) |
GR
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Agonists
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Mixed (SEGRAs)
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- Dagrocorat
- Fosdagrocorat
- Mapracorat
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Antagonists
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- 3α-Hydroxytibolone
- 3β-Hydroxytibolone
- Aglepristone
- Asoprisnil
- C108297
- C113176
- CORT-108297
- Cyproterone acetate
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- Ketoconazole
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- LLY-2707
- Miconazole
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- ORG-34116
- ORG-34517 (SCH-900636)
- ORG-34850
- Pregnenolone 16α-carbonitrile
- Spironolactone
- Telapristone
- Tibolone
- Toripristone
- Ulipristal acetate
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Enzyme |
Modulators
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- See here instead (modulators of 20,22-desmolase, 17α-hydroxylase/17,20-lyase, 3β-HSD, 11β-HSD, 21-hydroxylase, 11β-hydroxylase, and 18-hydroxylase).
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Others |
Precursors
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- Cholesterol
- 22R-Hydroxycholesterol
- 20α,22R-Dihydroxycholesterol
- Pregnenolone
- Pregnenolone sulfate
- 17-Hydroxypregnenolone
- Progesterone
- 17-Hydroxyprogesterone
- 11-Deoxycorticosterone
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Indirect
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- ACTH (corticotropin)
- CRH
- DHEA
- DHEA sulfate
- Plasma proteins (albumin, transcortin)
- Vasopressin
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See also: Androgenics • Estrogenics • Mineralocorticoids • Progestogenics
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