Beclometasone dipropionate

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Beclometasone dipropionate
Beclometasone dipropionate.png
Beclometasone-dipropionate-3D-balls.png
Systematic (IUPAC) name
(8S,9R,10S,11S,13S,14S,16S,17R)-9-chloro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-[2-(propionyloxy)acetyl]-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl propionate
Clinical data
AHFS/Drugs.commonograph
MedlinePlusa681047
Pregnancy cat.
Legal status
RoutesOral and nasal inhalation, topical
Pharmacokinetic data
BioavailabilityConverted to beclometasone-17-monopropionate (17-BMP) during absorption
Protein binding87% of 17-BMP to albumin and transcortin
MetabolismBy esterase enzymes found in most tissues
Half-life2.8 hours
ExcretionBiliary (60%), renal (12%)
Identifiers
CAS number5534-09-8 YesY
ATC codeA07EA07 D07AC15, R01AD01, R03BA01
PubChemCID 21700
DrugBankDB00394
ChemSpider20396 YesY
UNII5B307S63B2 YesY
ChEBICHEBI:3002 YesY
ChEMBLCHEMBL1200500 N
Chemical data
FormulaC28H37ClO7 
Mol. mass521.042 g/mol
 N (what is this?)  (verify)
 
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Beclometasone dipropionate
Beclometasone dipropionate.png
Beclometasone-dipropionate-3D-balls.png
Systematic (IUPAC) name
(8S,9R,10S,11S,13S,14S,16S,17R)-9-chloro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-[2-(propionyloxy)acetyl]-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl propionate
Clinical data
AHFS/Drugs.commonograph
MedlinePlusa681047
Pregnancy cat.
Legal status
RoutesOral and nasal inhalation, topical
Pharmacokinetic data
BioavailabilityConverted to beclometasone-17-monopropionate (17-BMP) during absorption
Protein binding87% of 17-BMP to albumin and transcortin
MetabolismBy esterase enzymes found in most tissues
Half-life2.8 hours
ExcretionBiliary (60%), renal (12%)
Identifiers
CAS number5534-09-8 YesY
ATC codeA07EA07 D07AC15, R01AD01, R03BA01
PubChemCID 21700
DrugBankDB00394
ChemSpider20396 YesY
UNII5B307S63B2 YesY
ChEBICHEBI:3002 YesY
ChEMBLCHEMBL1200500 N
Chemical data
FormulaC28H37ClO7 
Mol. mass521.042 g/mol
 N (what is this?)  (verify)

Beclometasone dipropionate (INN modified) or beclomethasone dipropionate (USAN, former BAN) is a potent glucocorticoid steroid. It is a prodrug of the free form, beclometasone (INN). In the form of an inhaler (e.g. Clenil, Qvar), a wide number of brands of which are available, it is used for the prophylaxis of asthma. As a nasal spray (e.g. Beconase, alanase, Vancenase) or nasal aerosol (e.g. Qnasl), it is used for the treatment of rhinitis (hay fever) and sinusitis). In some instances, it is used by oral pathologists in the treatment of unusually severe aphthous ulcers.

As a cream or ointment (trade name Propaderm), it is used to treat severe inflammatory skin disorders (such as eczema) unresponsive to less potent steroids, but is generally avoided in the treatment of psoriasis due to the risk of rebound on withdrawal.

It is also licensed to treat ulcerative colitis in conjunction with doses of 5-aminosalicylates in the United Kingdom in the form of a gastric acid-resistant, periodic-release tablet marketed under the brand name Clipper. 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]

Side effects[edit]

Occasionally, it may cause a cough upon inhalation. Deposition on the tongue and throat may promote oral candidiasis, which appears as a white coating, possibly with irritation.[2][3][4] This may usually be prevented by rinsing the mouth with water after using the inhaler. Other side effects may rarely include: a smell similar to burning plastic, unpleasant taste, hoarseness or nasal congestion, pain or headache, and visual changes. Allergic reactions may occur, but rarely.

Nasal corticosteroids may be associated with central serous retinopathy.[5]

Chemistry[edit]

It is a white to creamy-white, odorless powder which is very slightly soluble in water, very soluble in chloroform, and freely soluble in acetone and ethanol.

See also[edit]

References[edit]

  1. ^ "WHO Model List of EssentialMedicines". World Health Organization. October 2013. Retrieved 22 April 2014. 
  2. ^ Willey R, Milne L, Crompton G, Grant I (1976). "Beclomethasone dipropionate aerosol and oropharyngeal candidiasis". Br J Dis Chest 70 (1): 32–8. doi:10.1016/0007-0971(76)90004-8. PMID 1259918. 
  3. ^ Salzman G, Pyszczynski D (1988). "Oropharyngeal candidiasis in patients treated with beclomethasone dipropionate delivered by metered-dose inhaler alone and with Aerochamber". J Allergy Clin Immunol 81 (2): 424–8. doi:10.1016/0091-6749(88)90911-6. PMID 3339197. 
  4. ^ Fukushima C, Matsuse H, Tomari S, Obase Y, Miyazaki Y, Shimoda T, Kohno S (2003). "Oral candidiasis associated with inhaled corticosteroid use: comparison of fluticasone and beclomethasone". Ann Allergy Asthma Immunol 90 (6): 646–51. doi:10.1016/S1081-1206(10)61870-4. PMID 12839324. 
  5. ^ Haimovici R, Gragoudas ES, Duker JS, Sjaarda RN, Eliott D (October 1997). "Central serous chorioretinopathy associated with inhaled or intranasal corticosteroids". Ophthalmology 104 (10): 1653–60. doi:10.1016/s0161-6420(97)30082-7. PMID 9331207.