Fluticasone Propionate

FLOVENT · Fluticasone propionate for impurity C identification CRS · CUTIVATE · Fluticasone propionate for impurity C identification · Zoflut · flutide · FLUNASE · FLONASE

https://huagongshe.com/ko/chemical/444036

식별자 및 물리적 특성

CAS No.	80474-14-2
분자식	C25H31F3O5S
평균 분자량	500.6 g/mol
단동위원소 질량	500.18442975 g/mol
SMILES	CCC(=O)O[C@]1(C(=O)SCF)[C@H](C)C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C
InChIKey	WMWTYOKRWGGJOA-CENSZEJFSA-N
PubChem CID	444036
ChEMBL	CHEMBL1473
ChEBI	CHEBI:31441
EC No.	617-082-4
DTXSID	DTXSID8045511

화학 및 물리적 성질

XLogP	4
극성 표면적	106
수소 결합 공여자 수	1
수소 결합 수용자 수	9
회전 가능 결합 수	6
무거운 원자 수	34
형식 전하	0
복잡도	984
의약품	Pharmaceuticals -> Dermatologicals -> Corticosteroids, dermatological preparationsPharmaceuticals -> Listed in ZINC15
용해도	InsolubleDMSO: ≥10 mg/mL
Human Drugs	FDA approved drugs -> Active ingredientPharmaceuticals
Endocrine Disruptors	Potential endocrine disrupting compound
녹는점	261-273 °C275 °C
Physical Description	Solid
끓는 점	568.3±50.0 °C(Predicted)
밀도	1.32±0.1 g/cm3(Predicted)
굴절률	31 ° (C=1, Dioxane)
저장 조건	Store at RT
pKa(산도 계수)	12.53±0.70(Predicted)
물리적 상태	고체
색상	하얀색
Merck	14,4211
InChIKey	WMWTYOKRWGGJOA-CENSZEJFSA-N
SMILES	[C@]1(C(=O)SCF)(OC(=O)CC)[C@H](C)C[C@@]2([H])[C@]3([H])C[C@@H](C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]12C)F \|&1:0,11,14,16,19,26,28,30,33,r\|
EPA	Androsta-1,4-diene-17-carbothioic acid, 6,9-difluoro-11-hydroxy-16-methyl-3-oxo-17-(1-oxopropoxy)-,S-(fluoromethyl) ester, (6.alpha.,11.beta.,16.alpha.,17.alpha.)- (80474-14-2)

화학적 성질

Fluticasone propionate is a white to off-white powder with a molecular weight of 500.6, and 17 the empirical formula is C25H31F3O5S. It is practically insoluble in water, freely soluble in 18 dimethyl sulfoxide and dimethylformamide, and slightly soluble in methanol and 95% ethanol.

안전 및 규제

GHS 분류	This chemical does not meet GHS hazard criteria for 10% (2 of 20) of reports.DangerH302 (20%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P233, P260, P261, P264, P270, P271, P272, P273, P280, P284, P301+P317, P302+P352, P304+P340, P318, P319, P321, P330, P333+P317, P342+P316, P362+P364, P391, P403, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 20 reports by companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
규제 정보	Hazard Traits - Developmental ToxicityFluticasone propionate: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and Categories	Acute Tox. 4 (20%)
수질 위해 등급(WGK)	2
RTECS 번호	BV7980000
독성	LD50 oral in rat: > 2gm/kg
관세 코드	29372900
안전 문구(S)	22-24/25
위험 등급	Repr. 2STOT RE 2
저장 분류	11 - Combustible Solids

용도

Fluticasone Propionate is a derivative of Flumethasone, a glucocorticoid that has antiallergic, anti-asthmatic, and anti-inflammatory properties. It is used in the treatment of seasonal rhinitis and asthma. Compared to beclomethasone dipropionate, fluticasone propionate is reported to have a comparable side effect profile, but twice the activity in the treatment of asthma.

일반 설명

Fluticasone Propionate is the propionate salt form of fluticasone, a synthetic trifluorinated glucocorticoid receptor agonist with antiallergic, antiinflammatory and antipruritic effects. Binding and activation of the glucocorticoid receptor results in the activation of lipocortin that in turn inhibits cytosolic phospholipase A2, which triggers cascade of reactions involved in synthesis of inflammatory mediators, such as prostaglandins and leukotrienes. Secondly, mitogen-activated protein kinase (MAPK) phosphatase 1 is induced, thereby leads to dephosphorylation and inactivation of Jun N-terminal kinase directly inhibiting c-Jun mediated transcription. Finally, transcriptional activity of nuclear factor (NF)-kappa-B is blocked, thereby inhibits the transcription of cyclooxygenase 2, which is essential for prostaglandin production.

제조 및 합성 방법

제조 방법

Fluticasone propionate, synthesized by Glaxo Wellcome and launched in 1993, is a trifluorinated glucocorticosteroid. It shows good topical antiinflammatory activity and is commonly used as a safe and effective inhaled treatment for asthma and allergic rhinitis.Fluticasone propionate can be synthesized from 9 by using BrCH2F,2a ClCH2F,5a or S-(monofluoromethyl) diarylsulfonium tetrafluoroborate 5f,g directly. Using BrCH2F can get an ideal yield; however, BrCH2F is costly and will destroy to the ozone layer. In addition, 9 reacted with BrCH2Cl or Br2CH2 and then by an anion exchange with AgF,2c,5e KF, or tetrabutylammonium fluoride5b to afford 1 in a low yield.Improved Synthesis of Fluticasone Propionate