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Beclomethasone Dipropionate

HCID 21700
노트반응
기본 정보이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
5534-09-8
표준 SMILES
CCC(=O)OCC(=O)[C@@]1(OC(=O)CC)[C@@H](C)C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O)C[C@@]21C
InChIKey
KUVIULQEHSCUHY-XYWKZLDCSA-N
분자식
C28H37ClO7
평균 분자량
521 g/mol
단동위원소 질량
520.2227812

이름 및 식별자

우선 이름
Beclomethasone Dipropionate
IUPAC
[2-[(8S,9R,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-oxoethyl] propanoate
영어명
Beclomethasone dipropionate
분자식
C28H37ClO7
분자량
521.04

이름 및 동의어

BECLOMETHASONE DIPROPIONATEBeclometasone dipropionate5534-09-8BecloventVancenaseSanasthmaxAerobecBeclacinBeclometBecotideEntydermaKorbutone
이름 더 보기
DipropionateBeclomethasone propionatebp2BeconaseBeclotide
PropadermVancerilQvarBecloforteSanasthmylViaroxPropaderm ForteRino-clenil

데이터베이스 식별자

CAS
5534-09-8
PubChem CID
21700
DTXSID
DTXSID3048730
ChEMBL
CHEMBL1200500
ChEBI
CHEBI:3002
UNII
5B307S63B2
EC Number
226-886-0
Nikkaji
J7.992H

물성

구조 계산 물성

XLogP
3
극성 표면적
107 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
7
회전 가능 결합 수
8
무거운 원자 수
36
형식 전하
0
복잡도
1,050

실험 및 물리화학적 성질

LogP · 2건

3.49

1.3

Solubility2.08e-03 g/L
Melting Point · 2건

208-210

117 - 120 °C

Physical DescriptionSolid

물리화학적 성질

녹는점
117 · 117-120 C
끓는 점
613.3 °C · 613.3°C (rough estimate)
밀도
1.0766 · 1.0766 (rough estimate)
굴절률
1.4429 · 1.4429 (estimate)
저장 조건
2 · Sealed in dry,2-8°C
용해도
클로로포름(약간 용해됨), 디옥산(약간 용해됨, 초음파처리), 메탄올(약간 용해됨, 가열)
물리적 상태
고체
산도 계수 (pKa)
13.02 · 13.02±0.70(Predicted)
색상
하얀색
Merck
14 · 14,1019
주요 응용
법의학 및 독성학수의사
InChIKey
KUVIULQEHSCUHY-NHOFSDNKNA-N

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 5건

Danger

H360 (76.4%): May damage fertility or the unborn child [Danger Reproductive toxicity];H361fd (16.4%): Suspected of damaging fertility; Suspected of damaging the unborn child [Warning Reproductive toxicity];H373 (53.6%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]

P203, P260, P280, P318, P319, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 110 reports by companies from 18 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

유해성 정보

Regulatory Information · 2건

Hazard Traits - Developmental Toxicity;Authoritative List - Prop 65;Report - regardless of intended function of ingredient in the product

Beclomethasone dipropionate: Does not have an individual approval but may be used under an appropriate group standard

Other Safety Information · 1건

IMAP assessments - Pregna-1,4-diene-3,20-dione, 9-chloro-11-hydroxy-16-methyl-17,21-bis(1-oxopropoxy)-, (11.beta.,16.beta.)-: Environment tier I assessment;IMAP assessments - Pregna-1,4-diene-3,20-dione, 9-chloro-11-hydroxy-16-methyl-17,21-bis(1-oxopropoxy)-, (11.beta.,16.beta.)-: Human health tier I assessment

Hazard Classes and CategoriesRepr. 1B (76.4%);Repr. 2 (16.4%);STOT RE 2 (53.6%)

규제 정보

화학 및 산업

약리 정보

Protein BindingBased on the findings of _in vitro_ studies, the protein binding of the main active metabolite, beclomethasone-17-monopropionate (17-BMP), was 94-96% over the concentration range of 1000 to 5000 pg/mL.
Pharmacodynamics · 1건

Inflammatory conditions, including asthma, dermatoses, and allergic rhinitis, involve the activation of cascades by inflammatory mediators. Inflammation is a primary defense mechanism and the homeostatic response of the immune system; however, a prolonged inflammatory response in certain disorders may lead to tissue damage, pain, and swelling. Beclomethasone dipropionate works by attenuating the inflammatory responses associated with asthma, allergic rhinitis, nasal polyps, and corticosteroid-responsive dermatoses. It suppresses the actions of inflammatory cells, such as mast cells, eosinophils, basophils, lymphocytes, macrophages, and neutrophils. It also inhibits the release of inflammatory mediators, such as histamine, eicosanoids, leukotrienes, and cytokines. Beclomethasone dipropionate is reported to exhibit potent topical activity while possessing low systemic effects. Beclomethasone dipropionate is a corticosteroid drug with anti-inflammatory and vasoconstrictive effects used to treat chronic inflammatory processes such as asthma, allergic rhinitis, corticosteroid-responsive dermatoses. When inhaled, it improves lung function, decreases airway hyper-reactivity, and reduces the severity of asthmatic symptoms. Although inhaled corticosteroids, including beclomethasone dipropionate, are reported to mainly act locally in the lungs, systemic effects such as disruption of hypothalamic-pituitary-adrenal (HPA) axis function, bone turnover, osteoporosis, and growth suppression may still be observed with chronic use or high dose administration. There were varying findings from clinical studies examining the effect of beclomethasone dipropionate on growth suppression in pediatric patients. It was shown to suppress the hypothalamo-pituitary-adrenal (HPA) axis in a dose-dependent manner. HPA axis is a central hormonal response system to stress and activation of HPA axis leads to the production of endogenous steroid hormone production. Long-term use of high-dose systemic

Mechanism of Action · 1건

Beclomethasone dipropionate is a corticosteroid and prodrug that is rapidly activated by hydrolysis to the active monoester, 17 monopropionate (17-BMP), which mediates anti-inflammatory actions. 17-BMP has been shown _in vitro_ to exhibit a binding affinity for the human glucocorticoid receptor which is approximately 13 times that of dexamethasone and 25 times that of beclomethasone dipropionate. Upon binding of the ligand, the glucocorticoid receptors dimerize and translocate into the nucleus, where they subsequently bind to glucocorticoid response elements (GRE) on glucocorticoid-responsive genes, leading to changes in transcription. There are several proposed mechanisms for the anti-inflammatory action of corticosteroids. Corticosteroids may work by increasing the transcription of genes coding for anti-inflammatory proteins, including lipocortin-1 and interleukin-10. Corticosteroids were also shown to inhibit the expression of multiple genes that encode pro-inflammatory factors, such as cytokines, chemokines, and adhesion molecules, that are activated during the chronic inflammatory process. This is thought to be due to the direct inhibitory interaction between activated glucocorticoid receptors and activated pro-inflammatory transcription factors, such as nuclear factor-kappa B and activator protein-1. Chronic inflammation is often characterized by enhanced expression of these transcription factors that bind to and activate coactivator molecules, which then acetylate core histones to switch on gene transcription to further amplify the inflammatory process. Corticosteroids suppress the multiple inflammatory gene expression by promoting histone deacetylation, resulting in tighter coiling of DNA and reduced access of transcription factors to their binding sites.

관련 반응

4건
반응 기록 만들기
HRID 28105 반응식
HRID 28105반응물로uspto-grants-1980_09
HRID 28106 반응식
HRID 28106반응물로uspto-grants-1980_09
HRID 1091230 반응식
HRID 1091230반응물로uspto-grants-2012_03
HRID 1875287 반응식
HRID 1875287반응물로uspto-grants-2012_11

화합물 노트

불러오는 중…

이 페이지에서기본 정보이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
SMILES
[C@@]1(OC(=O)CC)(C(=O)COC(=O)CC)[C@@H](C)C[C@@]2([H])[C@]3([H])CCC4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O)C[C@]12C |&1:0,14,17,19,29,31,33,36,r|

화학적 성질

The light yellow solid has low solubility in water, but high solubility in chloroform. It can easily dissolve in acetone and ethanol.

Regulatory Information · 2건

Hazard Traits - Developmental Toxicity;Authoritative List - Prop 65;Report - regardless of intended function of ingredient in the product

Beclomethasone dipropionate: Does not have an individual approval but may be used under an appropriate group standard

안전 데이터

wgk
3
rtecs
TU3805000
독성
LD50 oral in rat: > 3750mg/kg
HS 번호
29372100
risk_code
60-61-36/37/38-20/21/22
hazard_code
T,Xn
safety_code
53-36/37/39-45-36-26
Hazard Classifications
Repr. 2STOT RE 2
스토리지 클래스
11 - Combustible Solids
Biological Half-Life · 1건

Following intravenous administration, the half life of beclomethasone dipropionate was 0.5 hours while the half life of the active metabolite 17-BMP was 2.7 hours. Following oral and intranasal administration, the half life of 17-BMP was 8.8 and 5.7 hours, respectively.

Metabolism/Metabolites · 1건

During absorption, beclomethasone dipropionate is undergoes rapid and extensive hydrolysis mediated by esterases CYP3A to form beclomethasone-17-monopropionate (17-BMP), beclomethasone-21-monopropionate (21-BMP), and beclomethasone (BOH). 17-BMP is the major active metabolite with the most potent anti-inflammatory activity. About 95% of the total beclomethasone dipropionate administered via oral inhalation undergoes presystemic conversion to form 17-BMP in the lung.

FDA Pharmacological Classification · 4건

BECLOMETHASONE DIPROPIONATE

Corticosteroid [EPC]; Corticosteroid Hormone Receptor Agonists [MoA]

BECLOMETHASONE DIPROPIONATE HFA

Corticosteroid [EPC]; Corticosteroid Hormone Receptor Agonists [MoA]

MeSH Pharmacological Classification · 3건

Substances that reduce or suppress INFLAMMATION.

A group of CORTICOSTEROIDS that affect carbohydrate metabolism (GLUCONEOGENESIS, liver glycogen deposition, elevation of BLOOD SUGAR), inhibit ADRENOCORTICOTROPIC HORMONE secretion, and possess pronounced anti-inflammatory activity. They also play a role in fat and protein metabolism, maintenance of arterial blood pressure, alteration of the connective tissue response to injury, reduction in the number of circulating lymphocytes, and functioning of the central nervous system.

Drugs that are used to treat asthma.

Absorption, Distribution and Excretion · 4건

Following oral inhalation of 320 mcg of beclomethasone dipropionate (BDP), the Cmax was 88 pg/mL and it was reached after 0.5 at post-administration. The mean Cmax of the major and most active metabolite, beclomethasone-17-monopropionate (17-BMP), was 1419 pg/mL at 0.7 hour post-dosing. In another pharmacokinetic study, the AUC of BDP and 17-BMP were 6660 and 6185 pgxh/mL, respectively. The Cmax was 35356 pg/mL for BDP and 2633 pg/mL for 17-BMP, and and the median time to reach these concentrations (Tmax) was 0.2 hours. In the same study, the AUC of 17-BMP following oral and intranasal administration were 10158 and 3660 pgxh/mL, respectively. The Cmax of 17-BMP following oral and intranasal administration were 703 and 310 pg/mL, respectively, and the Tmax was 4 hours. The total bioavailability of 17-BMP following oral and intranasal administration were 41% and 44%, respectively.

Regardless of the route of administration, beclomethasone dipropionate and its metabolites are predominantly excreted in the feces, with less than 10% of the drug and its metabolites being excreted in the urine.

Following intravenous administration, the steady-state volume of distribution was 20 L for beclomethasone dipropionate and 424 L for the active metabolite, beclomethasone-17-monopropionate.

Following intravenous administration, the clearance of beclomethasone dipropionate and 17-BMP were 150 L/h and 120 L/h, respectively.

Cellular LocationsCytoplasm;Extracellular;Membrane
응용 분야 · 2건

용도Beclomethasone dipropionate is a topically active corticosteroid used as an adjuvant in the control of chronic asthma when given by inhalation as an aerosol. It is also used as a topical anti-inflammatory.

일반 설명Beclomethasone dipropionate (Beclovent, Beconase, Vanceril, Vancenase) (BDP) is rapidly converted in the lungs to beclomethasone 17-monopropionate (17-BMP), the metabolite that provides the bulk of the anti-inflammatory activity. The monopropionate also has a higher affinity for the GR than either the dipropionate or beclomethasone. The portion of BDP that is swallowed is rapidly hydrolyzed to 17-BMP, 21-BMP (which arises by a transesterification reaction from 17-BMP), and beclomethasone itself. Beclomethasone has much less GC activity than the monopropionate. It is used in nasal sprays and aerosol formulations totreat allergic rhinitis and asthma.

제조 방법

Micronized beclomethasone dipropionate is prepared via antisolvent precipitation in the presence of hydroxypropyl methylcellulose (HPMC)[6].

상·하류 제품 정보

상류 원료

N-클로로숙신이미드메틸산 나트륨메탄설포닐 클로라이드과염소산

하류 제품

베타메타손9,11-에폭사이드17,21-디프로피오네이트

공급사106 곳

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INTATRADE GmbH+49 3493/605464 · [email protected]
湖北研科时代科技有限公司15780669880 · [email protected]
Baoji Guokang Healthchem co.,ltd+8615604608665 15604608665 · [email protected]
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MedChemexpress LLC021-58955995 · [email protected]
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孝感深远化工有限公司15527621225; 15527621225 · [email protected]
Xiamen AmoyChem Co., Ltd+86-86-5926051114 · [email protected]
斯百全化学(上海)有限公司021-021-021-67601398-809-809-809 15221380277 · [email protected]
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Wuhan Biocar Bio-Pharm Co., Ltd.86 15387057351 · [email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
上海昕凯医药科技有限公司21-619849051-1 18521059765 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
上海波以尔化工有限公司021-50182298 021-50180596 · [email protected]
厦门志信化学有限公司+86-5922680277 +86-13806087780 · [email protected]
湖北世腾化工科技有限公司18971850150 19086915685 · [email protected]
Standardpharm Co. Ltd.86-714-3992388 · [email protected]
sgtlifesciences pvt ltd+91-8790379245 · [email protected]
Qiuxian Baitai New Material Co., LTD+86-19932103556 · [email protected]
추가 설명 · 1건

정의ChEBI: Beclomethasone dipropionate is a steroid ester comprising beclomethasone having propionyl groups at the 17- and 21-positions. It has a role as an anti-inflammatory drug, an anti-asthmatic drug, a prodrug and an anti-arrhythmia drug. It is a steroid ester, an enone, a 20-oxo steroid, an 11beta-hydroxy steroid, a propanoate ester, a corticosteroid, a glucocorticoid, a 3-oxo-Delta(1),Delta(4)-steroid and a chlorinated steroid. It is functionally related to a beclomethasone.