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)
|
Legal status |
|
Routes of
administration |
Oral,Topical,IM |
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 |
Molecular mass |
392.461 |
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
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InChI
-
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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Y (what is this?) (verify) |
Betamethasone is a potent glucocorticoid steroid with anti-inflammatory and immunosuppressive properties. Unlike other drugs with these effects, betamethasone does not cause water retention. It is applied as a topical cream, ointment, foam, lotion or gel to treat itching. Betamethasone sodium phosphate is sometimes prescribed as an intramuscular injection (I.M) for itching from various ailments, including allergic reactions to poison ivy and similar plants.
It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.[1]
Contents
- 1 Medical uses
- 2 Side effects
- 3 Forms
- 4 See also
- 5 References
- 6 External links
Medical uses
Betamethasone is a corticosteroid 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%.[2]
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.
Betamethasone is also used to treat phimosis (tight foreskin) in uncircumcised boys. [3]
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.[4][5][6] It has replaced circumcision as the preferred treatment method for some physicians in the British National Health Service.[7][8]
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[9]) 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
- ^ "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.
- ^ 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.
- ^ http://www.ncbi.nlm.nih.gov/pubmed/8976781
- ^ 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)
|
|
Agonists |
Pregnene |
|
|
Pregnenedione |
- Hydrocortisone (cortisol)# (Hydrocortisone aceponate
- Hydrocortisone buteprate
- Hydrocortisone butyrate)
- Budesonide
- Ciclesonide
- Deflazacort
- Medrysone
- Tixocortol
- Halogenated at 6: Cloprednol
- Halogenated, with FG at 16: Halcinonide
|
|
Pregnadiene |
- Rimexolone
- Halogenated, with FG at 16: Flunisolide
- Triamcinolone
- Amcinonide
- Fluocinolone acetonide (Fluocinonide)
|
|
Pregnadienediol |
- Prednisone (Meprednisone)
- Halogenated at 9: Fluorometholone
- Halogenated, with FG at 16: Fluocortolone (Clocortolone
- Diflucortolone
- Fluocortin)
- Desoximetasone
|
|
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
|
|
Pregnatriene |
|
|
Androstene |
- Halogenated, with FG at 16: Fluticasone (Fluticasone propionate
- Fluticasone furoate)
|
|
Others/unsorted |
- Halogenated: Loteprednol
- Halogenated, with FG at 16: Fludroxycortide
- Formocortal
- Mometasone furoate
- Promestriene
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|
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Antagonists /
SGRMs |
- Antagonists: Ketoconazole
- Mifepristone
|
|
Synthesis modifiers |
- Acetoxolone
- Aminoglutethimide
- Carbenoxolone
- Enoxolone
- Ketoconazole
- Metyrapone
- Mitotane
- Trilostane
|
|
-
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
|
|
Index of hormones
|
|
Description |
- Glands
- Hormones
- thyroid
- mineralocorticoids
- Physiology
- Development
|
|
Disease |
- Diabetes
- Congenital
- Neoplasms and cancer
- Other
- Symptoms and signs
|
|
Treatment |
- Procedures
- Drugs
- calcium balance
- corticosteroids
- oral hypoglycemics
- pituitary and hypothalamic
- thyroid
|
|
|
Antidiarrheals, intestinal anti-inflammatory and anti-infective agents (A07)
|
|
Rehydration |
|
|
Intestinal anti-infectives |
- Antibiotics
- Amphotericin B
- Colistin
- Fidaxomicin
- Kanamycin
- Natamycin
- Neomycin
- Nystatin
- Paromomycin
- Polymyxin B
- Rifaximin
- Streptomycin
- Vancomycin
- Sulfonamides
- Phthalylsulfathiazole
- Succinylsulfathiazole
- Sulfaguanidine
|
|
Intestinal adsorbents |
- Charcoal
- Bismuth
- Pectin
- Kaolin
- Crospovidone
- Attapulgite
- Diosmectite
|
|
Antipropulsives (opioids) |
- Opium tincture (laudanum)
- Codeine
- Morphine
- Camphorated opium tincture (paregoric)
- crosses BBB: Diphenoxylate (Diphenoxylate/atropine)
- Difenoxin
- does not cross BBB: Eluxadoline
- Loperamide
|
|
Intestinal anti-inflammatory agents |
- corticosteroids acting locally
- Prednisolone
- Hydrocortisone
- Prednisone
- Betamethasone
- Tixocortol
- Budesonide
- Beclometasone
- antiallergic agents, excluding corticosteroids
- aminosalicylic acid and similar agents
- Sulfasalazine
- Mesalazine
- Olsalazine
- Balsalazide
|
|
Antidiarrheal micro-organisms |
|
|
Other antidiarrheals |
- Albumin tannate
- Ceratonia
- Crofelemer
- Octreotide
- Racecadotril
|
|
Index of digestion
|
|
Description |
- Anatomy
- Physiology
- Development
|
|
Disease |
- Congenital
- Neoplasms and cancer
- Inflammatory bowel disease
- Gluten sensitivity
- Other
- Symptoms and signs
- Blood tests
|
|
Treatment |
- Procedures
- Drugs
- anabolic steroids
- antacids
- diarrhoea and infection
- bile and liver
- functional gastrointestinal disorders
- laxatives
- peptic ulcer and reflux
- nausea and vomiting
- other
- Surgery
|
|
|
Vasoprotectives (C05)
|
|
Antihemorrhoidals for topical use |
corticosteroids |
- Hydrocortisone
- Prednisolone
- Betamethasone
- Fluorometholone
- Fluocortolone
- Dexamethasone
- Fluocinolone acetonide
- Fluocinonide
|
|
local anesthetics |
- Lidocaine
- Tetracaine
- Benzocaine
- Dibucaine
- Procaine
- Oxetacaine
- Pramocaine
|
|
other |
|
|
|
Antivaricose therapy |
heparins or heparinoids for topical use |
- Organo-heparinoid
- Sodium apolate
- Heparin
- Pentosan polysulfate
|
|
sclerosing agents for local injection |
- Monoethanolamine oleate
- Polidocanol
- Inverted sugar syrup
- Sodium tetradecyl sulfate
- Phenol
|
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other |
|
|
|
Capillary stabilising agents |
bioflavonoids |
- Rutoside
- Monoxerutin
- Diosmin
- Troxerutin
- Hidrosmin
|
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other |
|
|
|
Index of the circulatory system
|
|
Description |
- Anatomy
- Arteries
- head and neck
- arms
- chest
- abdomen
- legs
- Veins
- head and neck
- arms
- chest
- abdomen and pelvis
- legs
- Development
- Cells
- Physiology
|
|
Disease |
- Congenital
- Neoplasms and cancer
- Lymphatic vessels
- Injury
- Vasculitis
- Other
- Symptoms and signs
|
|
Treatment |
- Procedures
- Drugs
- beta blockers
- channel blockers
- diuretics
- nonsympatholytic vasodilatory antihypertensives
- peripheral vasodilators
- renin–angiotensin system
- sympatholytic antihypertensives
- vasoprotectives
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Decongestants and other nasal preparations (R01)
|
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Topical |
Sympathomimetics, plain
|
- Cyclopentamine
- Ephedrine
- Epinephrine
- Fenoxazoline
- Levomethamphetamine
- Metizoline
- Naphazoline
- Oxymetazoline
- Phenylephrine
- Propylhexedrine
- Tetryzoline
- Tramazoline
- Tuaminoheptane
- Tymazoline
- Xylometazoline
|
|
Antiallergic agents,
excluding corticosteroids
|
- histamine antagonists (Levocabastine
- Antazoline
- Thonzylamine)
- mast cell stabilizer (some are also antihistamines) (Cromoglicic acid
- Nedocromil
- Azelastine
- Olopatadine
- Lodoxamide)
|
|
Corticosteroids
|
- Beclometasone dipropionate
- Betamethasone
- Budesonide
- Ciclesonide
- Dexamethasone
- Flunisolide
- Fluticasone
- Mometasone furoate
- Prednisolone
- Tixocortol
- Triamcinolone
|
|
Other nasal preparations
|
- Cafaminol
- Calcium hexamine thiocyanate
- Eucalyptus oil
- Framycetin
- Hexamidine
- Hyaluronan
- Ipratropium bromide
- Mupirocin
- Retinol
- Ritiometan
- Saline water
|
|
|
Systemic use:
Sympathomimetics |
- Phenylephrine
- Phenylpropanolamine
- Phenylpropylamine
- Pseudoephedrine (+loratadine)
|
|
Index of the respiratory system
|
|
Description |
- Anatomy
- Physiology
- Development
|
|
Disease |
- Congenital
- Neoplasms and cancer
- Chest trauma
- Infection
- common cold
- pneumonia
- tuberculosis
- Other
- Symptoms and signs
|
|
Treatment |
- Procedures
- Drugs
- nasal
- throat
- obstructive airway diseases
- cough and cold
- histaminergics
- pulmonary arterial hypertension
- other
- Surgery
|
|
|
Drugs for obstructive airway diseases: asthma/COPD (R03)
|
|
Adrenergics, inhalants |
Short acting β2-agonists |
- Bitolterol
- Carbuterol
- Fenoterol
- Pirbuterol
- Procaterol
- Reproterol
- Rimiterol
- Salbutamol#/Levosalbutamol
- Terbutaline
- Tulobuterol
|
|
Long acting β2-agonists (LABA) |
- Arformoterol
- Bambuterol
- Clenbuterol
- Formoterol
- Salmeterol
- Salmefamol
- Ultra LABA: Indacaterol, Olodaterol, Vilanterol
|
|
other |
- Epinephrine#
- Hexoprenaline
- Isoprenaline (Isoproterenol)
- Orciprenaline (Metaproterenol)
|
|
|
Glucocorticoids |
- Beclometasone#
- Betamethasone
- Budesonide
- Ciclesonide
- Flunisolide
- Fluticasone
- Mometasone
- Triamcinolone
|
|
Anticholinergics/
muscarinic antagonist |
- Aclidinium bromide
- Glycopyrronium bromide
- Ipratropium bromide#
- Oxitropium bromide
- Tiotropium bromide
- Umeclidinium bromide
|
|
Mast cell stabilizers |
|
|
Xanthines |
- Acefylline
- Ambuphylline
- Bamifylline
- Doxofylline
- Enprofylline
- Etamiphylline
- Proxyphylline
- Theobromine
- Theophylline/Aminophylline/Choline theophyllinate
|
|
Eicosanoid inhibition |
Leukotriene antagonists |
- Montelukast
- Pranlukast
- Zafirlukast
|
|
Arachidonate 5-lipoxygenase inhibitors |
- Baicalein§
- Caffeic acid§
- Curcumin§
- Hyperforin§
- Meclofenamate sodium§
- St John's wort§
- Zileuton
|
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Thromboxane receptor antagonists |
|
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Non-xanthine PDE4 inhibitors |
|
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Others/unknown |
- Amlexanox
- Eprozinol
- Fenspiride
- Omalizumab
|
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Combination products |
- Aclidinium/formoterol
- Beclometasone/formoterol
- Budesonide/formoterol
- Fluticasone furoate/vilanterol
- Fluticasone/salmeterol
- Indacaterol/glycopyrrolate
- Ipratropium bromide/salbutamol
- Mometasone/formoterol
- Umeclidinium bromide/vilanterol
|
|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
Index of the respiratory system
|
|
Description |
- Anatomy
- Physiology
- Development
|
|
Disease |
- Congenital
- Neoplasms and cancer
- Chest trauma
- Infection
- common cold
- pneumonia
- tuberculosis
- Other
- Symptoms and signs
|
|
Treatment |
- Procedures
- Drugs
- nasal
- throat
- obstructive airway diseases
- cough and cold
- histaminergics
- pulmonary arterial hypertension
- other
- Surgery
|
|
|
Drugs used for diseases of the ear (S02)
|
|
Infection |
- Acetic acid
- Aluminium acetotartrate
- Boric acid
- Chloramphenicol
- Chlorhexidine
- Ciprofloxacin
- Clioquinol
- Gentamicin
- Hydrogen peroxide
- Miconazole
- Neomycin
- Nitrofurazone
- Ofloxacin
- Polymyxin B
- Rifamycin
- Tetracycline
|
|
Corticosteroids |
- Betamethasone
- Dexamethasone
- Fluocinolone acetonide
- Hydrocortisone
- Prednisolone
|
|
Analgesics and anesthetics |
- Lidocaine
- Cocaine
- Phenazone
|
|
Index of the ear
|
|
Description |
- Anatomy
- Physiology
- Development
|
|
Disease |
- Congenital
- Other
- Symptoms and signs
- Tests
|
|
Treatment |
|
|
|
Glucocorticoid signaling
|
|
Receptor
(ligands) |
GR
|
Agonists
|
|
|
Mixed (SEGRAs)
|
- Dagrocorat
- Fosdagrocorat
- Mapracorat
|
|
Antagonists
|
- 3α-Hydroxytibolone
- 3β-Hydroxytibolone
- Aglepristone
- Asoprisnil
- C108297
- C113176
- CORT-108297
- Cyproterone acetate
- Guggulsterone
- Ketoconazole
- Lilopristone
- LLY-2707
- Miconazole
- Mifepristone
- Onapristone
- Org 34850
- Pregnenolone 16α-carbonitrile
- Spironolactone
- Telapristone
- Tibolone
- Toripristone
- Ulipristal acetate
|
|
|
|
Enzyme |
Modulators
|
- See here instead (modulators of 20,22-desmolase, 17α-hydroxylase/17,20-lyase, 3β-HSD, 11β-HSD, 21-hydroxylase, 11β-hydroxylase, and 18-hydroxylase).
|
|
|
Others |
Precursors/prohormones
|
- Cholesterol
- 22R-Hydroxycholesterol
- 20α,22R-Dihydroxycholesterol
- Pregnenolone
- Pregnenolone sulfate
- 17-Hydroxypregnenolone
- Progesterone
- 17-Hydroxyprogesterone
- 11-Deoxycorticosterone
|
|
Indirect
|
- ACTH (corticotropin)
- CRH
- DHEA
- DHEA sulfate
- Plasma proteins (albumin, transcortin)
- Vasopressin
|
|
|
See also: Androgenics • Estrogenics • Mineralocorticoids • Progestogenics
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