Beclometasone dipropionate
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| Beclometasone dipropionate
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| Systematic (IUPAC) name | |
| [2-[(8S,9S,10S,11S,13S,14S,16S,17R)-9-chloro- 11-hydroxy-10,13,16-trimethyl-3-oxo- 17-propanoyloxy-6,7,8,11,12,14,15,16- octahydrocyclopenta[a]phenanthren-17-yl]- 2-oxo-ethyl] propanoate | |
| Identifiers | |
| CAS number | |
| ATC code | A07 D07AC15R01AD01R03BA01 |
| PubChem | |
| DrugBank | |
| Chemical data | |
| Formula | C28H37ClO7 |
| Mol. mass | 521.042 g/mol |
| 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. |
B3(AU) |
| Legal status | |
| Routes | Oral & nasal inhalation, topical |
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Beclometasone dipropionate (INN modified) or beclomethasone dipropionate (USAN, former BAN), also referred to as beclometasone (INN), is a potent Class A glucocorticoid steroid drug. In the form of an inhaler (e.g. Becotide), 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.
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.
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.[1][2][3] This may usually be prevented by rinsing the mouth with water after using the inhaler. Other side effects may rarely include unpleasant taste, hoarseness or nasal congestion, pain or headache and visual changes. Allergic reactions rarely may occur.
As a steroid, it can also cause occurrences of retina detachments, by triggering Central Serous Retinopathy.
Footnotes
- ↑ Willey R, Milne L, Crompton G, Grant I (1976). "Beclomethasone dipropionate aerosol and oropharyngeal candidiasis.". Br J Dis Chest 70 (1): 32-8. PMID 1259918.
- ↑ 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. PMID 3339197.
- ↑ 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.
Antidiarrheals, intestinal anti-inflammatory/anti-infective agents (A07) | |
|---|---|
| Intestinal anti-infectives | Antibiotics (Neomycin, Nystatin, Natamycin, Streptomycin, Polymyxin B, Paromomycin, Amphotericin B, Kanamycin, Vancomycin, Colistin, Rifaximin)
Sulfonamides (Phthalylsulfathiazole, Sulfaguanidine, Succinylsulfathiazole) other (Miconazole, Broxyquinoline, Acetarsol, Nifuroxazide, Nifurzide) |
| Intestinal adsorbents | Charcoal - Bismuth - Pectin - Kaolin - Crospovidone - Attapulgite - Diosmectite |
| Antipropulsives | Diphenoxylate - Opium - Loperamide - Difenoxin |
| Intestinal anti-inflammatory agents | corticosteroids acting locally (Prednisolone, Hydrocortisone, Prednisone, Betamethasone, Tixocortol, Budesonide, Beclometasone)
antiallergic agents, excluding corticosteroids (Cromoglicic acid) aminosalicylic acid and similar agents (Sulfasalazine, Mesalazine, Olsalazine, Balsalazide) |
| Antidiarrheal micro-organisms | Saccharomyces boulardii |
| Other antidiarrheals | Albumin tannate - Ceratonia - Racecadotril |
Decongestants and other nasal preparations (R01) | |
|---|---|
| Topical: sympathomimetics, plain | Cyclopentamine - Ephedrine - Phenylephrine - Oxymetazoline - Tetryzoline - Xylometazoline - Naphazoline - Tramazoline - Metizoline - Tuaminoheptane - Fenoxazoline - Tymazoline - Epinephrine |
| Topical: antiallergic agents, excluding corticosteroids | Cromoglicic acid - Levocabastine - Azelastine - Antazoline - Spaglumic acid - Thonzylamine - Nedocromil - Olopatadine |
| Topical: corticosteroids | Beclometasone - Prednisolone - Dexamethasone - Flunisolide - Budesonide - Betamethasone - Tixocortol - Fluticasone - Mometasone furoate - Triamcinolone - Ciclesonide |
| Topical: other nasal preparations | Calcium hexamine thiocyanate - Retinol - Ipratropium bromide - Ritiometan - Mupirocin - Hexamidine - Framycetin |
| Systemic use: Sympathomimetics | Phenylpropanolamine - Pseudoephedrine - Phenylephrine |
Drugs for obstructive airway diseases: asthma/COPD (R03) | |
|---|---|
| Adrenergics, inhalants | Short acting β2-agonists: Salbutamol/Levosalbutamol • Fenoterol • Terbutaline Long acting β2-agonists (LABA): Bambuterol • Clenbuterol • Formoterol • Salmeterol other: Epinephrine • Isoproterenol • Orciprenaline |
| Glucocorticoids | Beclometasone • Budesonide • Ciclesonide • Fluticasone • Mometasone |
| Anticholinergics | Ipratropium • Tiotropium |
| Mast cell stabilizers | Cromoglicate • Nedocromil |
| Xanthines | Aminophylline • Theobromine • Theophylline |
| Leukotriene antagonists | Montelukast • Pranlukast • Zafirlukast |
| Combination products | Budesonide/formoterol • Fluticasone/salmeterol • Ipratropium/salbutamol |
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
