Betamethasone

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	℞ (Prescription only)
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 (WHO) 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
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Betamethasone is a steroid medication. 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. It can be taken by mouth, injected into a muscle, or applied as a cream. When given by injection, anti-inflammatory effects begin in around two hours and last for seven days.

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. The cream commonly results in increased hair growth and skin irritation. Betamethasone belongs to the glucocorticoid class of medication.

Betamethasone was approved for medical use in the United States in 1961. The cream is on the World Health Organization's List of Essential Medicines, the most important medication needed in a basic health system. It is available as a generic medication. In the United States the pills and injectable solution are expensive while the cream is not.

Medical uses

Betamethasone is a corticosteroid that is available as pill, by injection, and as a cream.

It 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%.

Alternative medical approach for large microcystic CCAMs – Betamethasone therapy

Betamethasone is also used prior to delivery of a preterm baby to help prepare the lung for breathing.

Steroids such as betamethasone is also used to treat phimosis (tight foreskin) in uncircumcised boys.

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. It has replaced circumcision as the preferred treatment method for some physicians in the British National Health Service.

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.

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) 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