関: beclometasone dipropionate、beclomethasone、beclomethasone dipropionate

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/04/13 18:55:42」(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) or nasal aerosol (e.g. Qnasl), 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.

English Journal

Development and validation of simultaneous spectrophotometric and TLC-spectrodensitometric methods for determination of beclomethasone dipropionate and salbutamol in combined dosage form.

Samir A1, Lotfy HM2, Salem H3, Abdelkawy M2.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.Spectrochim Acta A Mol Biomol Spectrosc.2014 Jul 15;128:127-36. doi: 10.1016/j.saa.2014.02.044. Epub 2014 Mar 3.
Spectrophotometric and TLC-spectrodensitometric methods were developed and validated for the simultaneous determination of beclomethasone dipropionate (BEC) and salbutamol (SAL). The spectrophotometric methods include dual wavelength, ratio difference, constant center coupled with a novel method nam
PMID 24662761

Oral beclomethasone dipropionate in chronic refractory pouchitis.

Gionchetti P1, Calabrese C2, Calafiore A2, Praticò C2, Poggioli G2, Laureti S2, Capozzi N2, Campieri M2, Rizzello F2.
Journal of Crohn's & colitis.J Crohns Colitis.2014 Jul 1;8(7):649-53. doi: 10.1016/j.crohns.2013.12.001. Epub 2014 Jan 3.
BACKGROUND: Pouchitis is the major long-term complication after ileal-pouch anal-anastomosis for ulcerative colitis. Ten to 15% of patients develop chronic pouchitis, either treatment responsive or treatment refractory.AIM: To evaluate the efficacy of oral beclomethasone dipropionate in inducing rem
PMID 24394806

Effects of representative glucocorticoids on TNFα- and CD40L-induced NF-κB activation in sensor cells.

Cechin SR1, Buchwald P2.
Steroids.Steroids.2014 Jul;85:36-43. doi: 10.1016/j.steroids.2014.04.003. Epub 2014 Apr 18.
Glucocorticoids are an important class of anti-inflammatory/immunosuppressive drugs. A crucial part of their anti-inflammatory action results from their ability to repress proinflammatory transcription factors such as nuclear factor-κB (NF-κB) and activator protein-1 (AP-1) upon binding to the glu
PMID 24747770

Japanese Journal

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

蜂谷啓之,薮野孝,池嶋能達 [他]
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―

西牟田敏之,米澤博,西間三馨
日本小児アレルギー学会誌 25(2), 138-150, 2011
小児気管支喘息患者（5～15歳）167名を対象として多施設共同，無作為化，群間比較により，シクレソニドの加圧噴霧式定量吸入器（以下，BTR-15）50μg/日, 100μg/日及び200 μg/日（1日1回）の8週間投与時の有効性及び安全性を，HFA-BDP 100μg/日（1日2回）を参照薬として比較検討した．本試験には217例が組み入れられ，解析対象は167例（女：69例，男：98例），年齢 …
NAID 130004504234

Analysis of Inhaled Corticosteroid Selection in Patients with Bronchial Asthma Using a Questionnaire Survey -Effects of Age, Gender, and Disease Severity-

, , , , , , , , ,
Allergology International 58(3), 365-371, 2009
… Results: Of 2852 cases, 2279 (79.9%) were ICS users, and 1513 (66.4% of ICS users) were classified as being in the fluticasone propionate (FP) group, 438 (19.2%) in the budesonide (BUD) group, and 240 (10.5%) in the hydrofluoroalkane-beclometasone (HFA-BDP) group, indicating that FP was a standard ICS in this study. …
NAID 130004477053

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リンク元

「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	monograph
MedlinePlus	a681047
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	Biliary (60%), Renal (12%)
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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英: beclomethasone、(欧州)beclometasone
化: プロピオン酸ベクロメタゾン、beclometasone dipropionate beclomethasone dipropionate
商: ベコタイド(吸入)、アルデシン(エアゾル)、リノコート(鼻腔用吸入カプセル)、Beconase AQ; アルデシン、アルベゾン、アルロイヤー、キュバール、サルコート、タウナスアクア、ナイスピー、ナナドラ、プロパデルム、ベクラシン、ベクローゼ、ペンブリン、マイリー、リノコート
関: ジプロピオン酸ベクロメタゾン; 耳鼻科用剤

[1] 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.

[2] 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.

[3] 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.

[4] 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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beclometasone