4419-39-0 Usage
Chemical Properties
White to Off-White Solid
Originator
Propaderm,Kyowa Hakko,Japan,1972
Uses
Different sources of media describe the Uses of 4419-39-0 differently. You can refer to the following data:
1. Beclomethasone has been used in MS?MS (mass spectrometry) methods for the analysis of β-agonists, corticosteroids, chloramphenicol and penicillins. It has also been used to find the differential response of glucocorticoids in larval regeneration model.
2. Glucocorticoid. Beclomethasone is used in chronic asthma and allergic rhinitis. Antiallergic, antiasthmatic (inhalant). Anti-inflammatory (topical).
Definition
ChEBI: A 17alpha-hydroxy steroid that is prednisolone in which the hydrogens at the 9alpha and 16beta positions are substituted by a chlorine and a methyl group, respectively.
Manufacturing Process
6 grams of 6β-methyl-1,4-pregnadiene-11β,17α,21-triol-3,20-dione-21-acetate
is dissolved in a mixture of 35 ml of dimethylformamide and 6 ml of pyridine.
To the resulting solution is added 2.5 ml of methanesulfonyl chloride and the
reaction mixture maintained at 80°-85°C for about 1 hour. The resulting red
solution is cooled in an ice bath and treated successively with 55 ml of
methanol, 240 ml of 5% aqueous sodium bicarbonate and finally with 360 ml
of water. The resulting reaction mixture is then allowed to stand at room
temperature overnight after which the precipitated product is removed by
filtration, washed repeatedly with water and dried to a constant weight in air
at about 50°C to produce 6β-methyl-1,4,9(11)-pregnadiene-11α,21-diol-3,20-
dione-21-acetate.
Hydrolysis of the acetate ester with alkali, e.g., sodium methoxide in
methanol, affords the free alcohol, 16β-methyl-1,4,9(11)-pregnadiene-17α,21-
diol-3,20-dione. To a suspension of 3 grams of 6β-methyl-1,4,9(11)-
pregnadiene-17α,21-diol-3,20-dione-21-acetate 40 ml of acetone is added at
0°C with stirring 2 grams of N-chlorosuccinimide and then 7 ml of a perchloric
acid solution prepared by dissolving 0.548 ml of 70% perchloric acid in 33 ml
of water. The resulting reaction mixture is stirred at 0° for about 4 hours 45
minutes.
The excess of N-chlorosuccinimide is destroyed by the addition of about 15
drops of allyl alcohol and 180 ml of water is then added with stirring. This
mixture is held at 0°C for about one hour. The precipitated 16β-methyl-1,4-
pregnadiene-9α-chloro-11β,17α,21-triol-3,20-dione-21-acetate is recovered
filtration. A solution of 250 mg of the chlorohydrin in 5 ml of 0.25N perchloric
acid in methanol is stirred for about 18 hours at room temperature to produce
16β-methyl-9α-chloro-11β,17α,21-trihydroxy-1,4-pregnadiene-3,20-dione
which is recovered by adding water to the reaction mixture and allowing the
product to crystallize. Propionic anhydride is then used to convert this material
to the dipropionate.
Brand name
Beclovent (GlaxoSmithKline);
Beconase (GlaxoSmithKline); Qvar (3M
Pharmaceuticals); Vanceril (Schering).
Therapeutic Function
Topical antiinflammatory, Glucocorticoid
Biological Functions
The topical anti-inflammatory potency for beclomethasone dipropionate (BDP) is approximately 5,000 times greater than hydrocortisone, 500 times greater than
betamethasone or dexamethasone, and approximately five times greater than fluocinolone acetonide or
triamcinolone acetonide, as measured by vasoconstrictor assay.
Biochem/physiol Actions
Beclomethasone is an anti-inflammatory glucocorticoid.It helps to decrease airway hyperresponsiveness. It also helps to regulate symptoms of asthma.
Clinical Use
Beclomethasone, a 9α-chloro analogue of betamethasone, is a potent glucocorticoid with
approximately half the potency of its fluoro analogue. It is used topically as its dipropionate derivative in
inhalation aerosol therapy for asthma and rhinitis but not for
treatment of steroid-responsive dermatoses.
Check Digit Verification of cas no
The CAS Registry Mumber 4419-39-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,4,1 and 9 respectively; the second part has 2 digits, 3 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 4419-39:
(6*4)+(5*4)+(4*1)+(3*9)+(2*3)+(1*9)=90
90 % 10 = 0
So 4419-39-0 is a valid CAS Registry Number.
InChI:InChI=1/C22H29ClO5/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,23)17(26)10-20(16,3)22(12,28)18(27)11-24/h6-7,9,12,15-17,24,26,28H,4-5,8,10-11H2,1-3H3/t12-,15-,16?,17-,19-,20-,21?,22?/m0/s1
4419-39-0Relevant articles and documents
Efficient Interfacially Driven Vehiculization of Corticosteroids by Pulmonary Surfactant
Hidalgo, Alberto,Salomone, Fabrizio,Fresno, Nieves,Orellana, Guillermo,Cruz, Antonio,Perez-Gil, Jesus
, p. 7929 - 7939 (2017)
Pulmonary surfactant is a crucial system to stabilize the respiratory air-liquid interface. Furthermore, pulmonary surfactant has been proposed as an effective method for targeting drugs to the lungs. However, few studies have examined in detail the mechanisms of incorporation of drugs into surfactant, the impact of the presence of drugs on pulmonary surfactant performance at the interface under physiologically meaningful conditions, or the ability of pulmonary surfactant to use the air-liquid interface to vehiculise drugs to long distances. This study focuses on the ability of pulmonary surfactant to interfacially vehiculize corticosteroids such as beclomethasone dipropionate (BDP) or Budesonide (BUD) as model drugs. The main objectives have been to (a) characterize the incorporation of corticosteroids into natural and synthetic surfactants, (b) evaluate whether the presence of corticosteroids affects surfactant functionality, and (c) determine whether surfactant preparations enable the efficient spreading and distribution of BDP and BUD along the air-liquid interface. We have compared the performance of a purified surfactant from porcine lungs and two clinical surfactants: Poractant alfa, a natural surfactant of animal origin extensively used to treat premature babies, and CHF5633, a new synthetic surfactant preparation currently under clinical trials. Both, natural and clinical surfactants spontaneously incorporated corticosteroids up to at least 10% by mass with respect to phospholipid content. The presence of the drugs did not interfere with their ability to efficiently adsorb into air-liquid interfaces and form surface active films able to reach and sustain very low surface tensions (2 mN/m) under compression-expansion cycling mimicking breathing dynamics. Furthermore, the combination of clinical surfactant with corticosteroids efficiently promoted the active diffusion of the drug to long distances along the air-liquid interface. This effect could not be mimicked by vehiculisation of corticosteroids in liposomes or in micellar emulsions similar to the formulations currently in use to deliver anti-inflammatory corticosteroids through inhalation.
Method for reducing or preventing transplant rejection in the eye and intraocular implants for use therefor
-
, (2008/06/13)
Methods for reducing or preventing transplant rejection in the eye of an individual are described, comprising: a) performing an ocular transplant procedure; and b) implanting in the eye a bioerodible drug delivery system comprising an immunosuppressive agent and a bioerodible polymer.
Suspension aerosol formulations of pharmaceutical products
-
, (2008/06/13)
Pharmaceutical preparations for producing powder aerosols using propellant gases which use TG 227, and possibly also TG 11, TG 12, TGH 114, propane, butane, pentane or DME.
