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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2012/11/26 23:48:48」(JST)

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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), it is used for the treatment of rhinitis (e.g. 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 (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.

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.

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: 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.^[4]

References

^ 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.
^ 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.
^ 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.
^ 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.

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English Journal

Oral beclomethasone dipropionate as an initial treatment for stages 1-2 gastrointestinal tract acute graft-versus-host disease following unrelated cord blood transplantation.

Yamamoto H1, Uchida N2,3, Uchida Y4, Nishida A1, Ota H1, Kageyama K1, Nasu I4, Wada S1, Kaji D1, Ishiwata K1, Takagi S1, Tsuji M1, Asano-Mori Y1, Matsuno N1, Yamamoto G1, Masuoka K1, Izutsu K1,5, Wake A1, Yoneyama A6, Makino S7, Ito T4, Hayashi M4, Taniguchi S1,5.
Annals of hematology.Ann Hematol.2015 Dec;94(12):2073-5. doi: 10.1007/s00277-015-2483-z. Epub 2015 Sep 16.
PMID 26374433

Multivariate Analysis of Effects of Asthmatic Patient Respiratory Profiles on the In Vitro Performance of a Reservoir Multidose and a Capsule-Based Dry Powder Inhaler.

Buttini F1,2, Pasquali I3, Brambilla G3, Copelli D3, Alberi MD3, Balducci AG4, Bettini R5, Sisti V3.
Pharmaceutical research.Pharm Res.2015 Nov 16. [Epub ahead of print]
PURPOSE: The aim of this work was to evaluate the effect of two different dry powder inhalers, of the NGI induction port and Alberta throat and of the actual inspiratory profiles of asthmatic patients on in-vitro drug inhalation performances.METHODS: The two devices considered were a reservoir multi
PMID 26572643

Beclomethasone dipropionate hydrofluoroalkane for the treatment of allergic rhinitis.

Ferrante G1, Montalbano L2, Cilluffo G3, Malizia V4, Grutta S4.
Expert review of clinical immunology.Expert Rev Clin Immunol.2015 Nov 11. [Epub ahead of print]
Allergic rhinitis (AR) is a common respiratory disease and its prevalence is increasing all over the world, both in adults and in children. Patients experience symptoms that may negatively impact on physical, social and psychological well-being. Hence, if left untreated, allergic rhinitis may signif
PMID 26558604

Japanese Journal

乳児の好酸球性膿疱性毛包炎の 1 例

西日本皮膚科 77(5), 469-472, 2015
NAID 130005137630

吸入ステロイド喘息治療剤HFA-BDP(キュバール)の小児における特別調査

アレルギ-・免疫 18(8), 1216-1230, 2011-08
NAID 40018936682

小児気管支喘息患者におけるシクレソニドの定量噴霧式エアゾール剤（ＢＴＲ‐１５）の有効性及び安全性の検討―用量確認試験―

日本小児アレルギー学会誌 25(2), 138-150, 2011
NAID 130004504234

「ベクロメタゾン」

Beclometasone dipropionate
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.com	International Drug Names
Pregnancy cat.	B3 (AU)
Legal status	Pharmacy Only (S2) (AU) POM (UK)
Routes	Oral & nasal inhalation, topical
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	?
Identifiers
CAS number	5534-09-8
ATC code	A07EA07 D07AC15, R01AD01, R03BA01
PubChem	CID 21700
DrugBank	DB00394
ChemSpider	20396
UNII	5B307S63B2
ChEBI	CHEBI:3002
ChEMBL	CHEMBL1200500
Chemical data
Formula	C28H37ClO7
Mol. mass	521.042 g/mol
	SMILES O=C(OCC(=O)[C@]3(OC(=O)CC)[C@]2(C[C@H](O)[C@]4(Cl)[C@@]/1(\C(=C/C(=O)\C=C\1)CC[C@H]4[C@@H]2C[C@@H]3C)C)C)CC;
	InChI InChI=1S/C28H37ClO7/c1-6-23(33)35-15-22(32)28(36-24(34)7-2)16(3)12-20-19-9-8-17-13-18(30)10-11-25(17,4)27(19,29)21(31)14-26(20,28)5/h10-11,13,16,19-21,31H,6-9,12,14-15H2,1-5H3/t16-,19-,20-,21-,25-,26-,27-,28-/m0/s1 ; Key:KUVIULQEHSCUHY-XYWKZLDCSA-N ;
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