Beclomethasone dipropionate
From DrugPedia: A Wikipedia for Drug discovery
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| Beclomethasone dipropionate
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| Systematic (IUPAC) name | |
| [(8S,9R,10S,11S,13S,14S,16S,17R)-9-chloro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-(2-propanoyloxyacetyl)-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate | |
| Identifiers | |
| CAS number | |
| ATC code | ? |
| PubChem | |
| DrugBank | |
| Chemical data | |
| Formula | C28H37ClO7 |
| Mol. mass | 521.04 |
| SMILES | & |
| Synonyms | Beclovent |
| Pharmacokinetic data | |
| Bioavailability | Converted to beclometasone-17-monopropionate (17-BMP) during absorption |
| Protein binding | 87% of 17-BMP to albumin and transcortin |
| Metabolism | By esterase enzymes found in most tissues |
| Half life | 2.8 hours |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
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| Legal status | |
| Routes | Oral & nasal inhalation, topical |
Contents |
[edit] Description
An anti-inflammatory, synthetic glucocorticoid. It is used topically as an anti-inflammatory agent and in aerosol form for the treatment of ASTHMA. Beclometasone dipropionate (INN modified) or beclomethasone dipropionate (USAN, former BAN), also referred to as beclometasone (INN), is a potent glucocorticoid steroid. In the form of an inhaler (e.g. Becotide, 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, Vancenase), it is used for the treatment of rhinitis (e.g. hayfever) and sinusitis. In some instances it is used by oral pathologists in the treatment of unusually severe canker sores.
As a cream or ointment (trade name Propaderm) it is used to treat severe inflammatory skin disorders (e.g. eczema) unresponsive to less potent steroids, but is generally avoided in the treatment of psoriasis due to the risk of rebound on withdrawal.
[edit] General Properties
*Molecular Weight
521.04
*Molecular Formula
C28H37ClO7
*IUPAC NAME
[(8S,9R,10S,11S,13S,14S,16S,17R)-9-chloro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-(2-propanoyloxyacetyl)-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate
*Canonical Smiles
CCC(=O)OCC(=O)C1(C(CC2C1(CC(C3(C2CCC4=CC(=O)C=CC43C)Cl)O)C)C)OC(=O)CC
*Isomeric Smiles
CCC(=O)OCC(=O)[C@]1([C@H](C[C@@H]2[C@@]1(C[C@@H]([C@]3([C@H]2CCC4=CC(=O)C=C[C@@]43C)Cl)O)C)C)OC(=O)CC
[edit] Chemistry
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 in ethanol.
[edit] Side effects
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.<ref>Willey R, Milne L, Crompton G, Grant I (1976). "Beclomethasone dipropionate aerosol and oropharyngeal candidiasis". Br J Dis Chest 70 (1): 32–8. doi:. PMID 1259918.</ref><ref>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:. PMID 3339197.</ref><ref>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. PMID 12839324.</ref> This may usually be prevented by rinsing the mouth with water after using the inhaler. Other side effects may rarely include: a smell not dissimilar to burning plastic, unpleasant taste, hoarseness or nasal congestion, pain or headache and visual changes. Allergic reactions rarely may occur.
Nasal corticosteroids may be associated with central serous retinopathy.<ref>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. PMID 9331207.</ref>
