Betamethasone
|  | 
|  | 
| 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 | 
| 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 | 
| 
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
Key:UREBDLICKHMUKA-DVTGEIKXSA-N Y | 
| 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. 
| 
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|  |  
| Agonists | 
| Pregnene |  |  
|  |  
| Pregnenedione | 
Hydrocortisone (cortisol)# (Hydrocortisone aceponateHydrocortisone buteprateHydrocortisone butyrate)BudesonideCiclesonideDeflazacortMedrysoneTixocortolHalogenated at 6: CloprednolHalogenated, with FG at 16: Halcinonide |  
|  |  
| Pregnadiene | 
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|  |  
| Pregnadienediol | 
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|  |  
| Pregnadienetriol | 
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|  |  
| Pregnatriene |  |  
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| Androstene | 
Halogenated, with FG at 16: Fluticasone (Fluticasone propionateFluticasone furoate) |  
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#WHO-EM‡Withdrawn from marketClinical trials:
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| local anesthetics | 
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| 
#WHO-EM‡Withdrawn from marketClinical trials:
†Phase III§Never to phase III 
| Index of the respiratory system |  
|  |  
| Description | 
Anatomy
PhysiologyDevelopment |  
|  |  
| Disease | 
CongenitalNeoplasms and cancerChest traumaInfection
common coldpneumoniatuberculosisOtherSymptoms and signs |  
|  |  
| Treatment | 
Procedures
Drugs
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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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