378-44-9 Usage
Description
Betamethasone, also known as 9-fluoro-11β,17,21-trihydroxy-16β-methylpregna-1,4-diene-3,20-dione, is a synthetic corticosteroid that belongs to the glucocorticoid class. It is available in various ester derivatives, such as Betamethasone valerate, Betamethasone acetate, Betamethasone sodium phosphate, and Betamethasone dipropionate. This white crystalline powder is odorless and has a melting point of 231-234°C. It is similar in function to dexamethasone but has a stronger anti-inflammatory effect and fewer side effects.
Uses
1. Used in Pharmaceutical Industry:
Betamethasone is used as a hormone drug for anti-inflammatory and anti-allergic purposes. It is particularly suitable for treating rheumatoid arthritis and various skin diseases.
2. Used in Medical Treatment:
Betamethasone is used as an anti-inflammatory agent, providing relief from inflammation and reducing the immune system's response.
3. Used in Immunosuppressive Therapy:
Betamethasone is used as an immunosuppressive agent, helping to suppress the immune system and prevent organ transplant rejection.
4. Used in Obstetrics:
Betamethasone is used to accelerate fetal lung maturation, which has been shown to decrease neonatal mortality and morbidity in infants born before 34 weeks of gestation.
5. Used in Branded Medications:
Betamethasone is the active ingredient in Celestone Syrup and Tablets, a brand manufactured by Schering, which is used for various medical conditions requiring anti-inflammatory and immunosuppressive effects.
hormone drugs
Betamethasone, belongs to adrenal corticosteroids, it is a isomer of dexamethasone , and the role of betamethasone is similiar to prednisolone and dexamethasone , it has anti-inflammatory, anti-rheumatic, anti-allergic and suppression of the immune and other pharmacological effects, its anti-inflammatory effect is stronger than dexamethasone, triamcinolone, hydrocortisone etc. , it can reduce and prevent tissue response to inflammation and eliminate heat, redness and swelling caused by local non-infectious inflammation, thereby reducing the performance of inflammation, anti-inflammatory effect of this product 0.3mg is equal to dexamethasone 0.75mg, prednisone 5mg or 25mg cortisone .
Betamethasone sodium retention effect is a hundred times more than hydrocortisone, in primary adrenal hypofunction, it can be used together with glucocorticoid for replacement therapy ,and it is used for preventing or inhibiting cell-mediated immune response, delaying allergic reactions and reducing the primary immune response expansion ,it is used for low renin and low aldosterone syndrome and autonomic neuropathy induced orthostatic hypotension.
Currently betamethasone is also used for the treatment of active rheumatoid arthritis, rheumatoid arthritis, lupus, severe bronchial asthma, severe dermatitis, acute leukemia, atopic dermatitis, eczema, neurodermatitis, seborrheic dermatitis, and pruritus and comprehensive treatment of certain infections.
The product is contraindicated in severe psychiatric history, active duodenal ulcer, recent gastrointestinal anastomosis, heavier osteoporosis, overt diabetes, severe hypertension, virus , bacterial, fungal infections which are failed to control by the use of antimicrobial agents , thrombophlebitis, skin infections, such as impetigo, tinea, jock itch and so on.
The above information is edited by the lookchem of Tian Ye.
production method
According to U.S. Patent No. 3,164,618, betamethasone acetate is dealt with hydrochloric acid in methanol-chloroform-water mixture , it can be converted to betamethasone.
Toxicity grading
Middle toxic
Acute toxicity
Oral-mouse LD50:> 4500 mg/kg
Flammability and hazard characteristics
Combustible;Its combustion produces toxic fumes of fluoride.
Storage Characteristics
Ventilated, low-temperature ,dry storeroom.
Extinguishing agent
Dry powder , foam, sand, carbon dioxide, water spray.
Originator
Celestone,Schering,US,1961
Manufacturing Process
Betamethasone acetate is converted to betamethasone by means of
hydrochloric acid in a methanol-chloroform-water mixture as described in US
Patent 3,164,618.
Therapeutic Function
Glucocorticoid
Flammability and Explosibility
Nonflammable
Biochem/physiol Actions
Betamethasone, an?isomer?of dexamethasone is also termed as 9α-fluoro-16β-methyl-11 β,17,21-trihydroxypregna-1,4-dien-3,20-dione or 9α-fluoro-16β-methylprednisolone (27.1.52). It can be used as an anti-itch agent and treating dermatitis?and?eczema.
Clinical Use
Corticosteroid:
Suppression of inflammatory and allergic disorders
Congenital adrenal hyperplasia
Side effects
Toxic side effects, such as increased appetite, weight gain, and
facial mooning, occur with prolonged use.
Safety Profile
Low toxicity by ingestion. Anexperimental teratogen. Other experimental reproductiveeffects. When heated to decomposition it emits toxicfumes of F-.
Synthesis
Betamethasone is 9α-fluoro-16β-methyl-11 β,17,21-trihydroxypregna-
1,4-dien-3,20-dione, or simply 9α-fluoro-16β-methylprednisolone (27.1.52). As seen from
the chemical name of the drug, betamethasone only differs from dexamethasone in the orientation
of the methyl group at C16. The proposed method of synthesis differs from the other
method in a number of details and successive reactions besides the first stage, in particular
concerning the addition of the methyl group at C16 of the steroid ring. Betamethasone, like
dexamethasone, is synthesized from 3α-acetoxy-16-pregnen-11,20-dione; however, the
methyl group at C16 of the steroid ring is not reacted with methylbromide, but rather is
reacted with diazomethane followed by hydrogenation of the double bond between carbon
atoms C16–C17 of the steroid ring using a palladium on carbon catalyst, which results in the
corresponding β-orientation of the introduced methyl group.
Drug interactions
Potentially hazardous interactions with other drugs
Aldesleukin: avoid concomitant use.
Antibacterials: metabolism accelerated by rifampicin;
metabolism possibly inhibited by erythromycin;
concentration of isoniazid possibly reduced.
Anticoagulants: efficacy of coumarins and
phenindione may be altered.
Antiepileptics: metabolism accelerated by
carbamazepine, fosphenytoin, phenobarbital,
phenytoin and primidone.
Antifungals: increased risk of hypokalaemia with
amphotericin - avoid; metabolism possibly inhibited
by itraconazole and ketoconazole.
Antivirals: concentration possibly increased by
ritonavir.
Ciclosporin: rare reports of convulsions in patients
on ciclosporin and high-dose corticosteroids.
Cobicistat: concentration of betamethasone possibly
increased.
Diuretics: enhanced hypokalaemic effects of
acetazolamide, loop diuretics and thiazide diuretics.
Vaccines: high dose corticosteroids can impair
immune response to vaccines; avoid with live
vaccines.
Metabolism
Corticosteroids are metabolised mainly in the liver
but also in other tissues, and are excreted in the urine.
The slower metabolism of the synthetic corticosteroids
with their lower protein-binding affinity may account
for their increased potency compared with the natural
corticosteroids.
Purification Methods
Betamethasone crystallises from ethyl acetate, and has max at 238nm (log 4.18) in MeOH. The 21-acetate [287-24-6] crystallises from Me2CO/Et2O (charcoal) m 196-201o (205-208o) and has [] D 20 +140o (CHCl3). [Taub et al. J Am Chem Soc 82 4012 1960, Olivetto et al. J Am Chem Soc 80 6688 1958, Beilstein 8 IV 3501.]
references
[1] pharmacology review(s)-fda.
Check Digit Verification of cas no
The CAS Registry Mumber 378-44-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,7 and 8 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 378-44:
(5*3)+(4*7)+(3*8)+(2*4)+(1*4)=79
79 % 10 = 9
So 378-44-9 is a valid CAS Registry Number.
InChI:InChI=1/C22H29FO5/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+/m1/s1
378-44-9Relevant articles and documents
A variation of Mattox rearrangement mechanism under alkaline condition
Li, Min,Chen, Bin,Lin, Mingxiang,Chan, Tze-Ming,Fu, Xiaoyong,Rustum, Abu
, p. 3901 - 3905 (2007)
A variation of the Mattox rearrangement, a key degradation pathway under acidic conditions for corticosteroids possessing the 1,3-dihydroxyacetone side chain, has been found to occur for the 17,21-diesters of these corticosteroids but under the alkaline condition. The mechanism of this variation of the original Mattox rearrangement is proposed.
A 17, 21 - double-hydroxy steroid derivatives of synthetic method
-
, (2018/04/02)
The invention relates to a method of preparing 17, 21-double-hydroxyl steroid derivatives by using 6, 9-substituted silyl steroid enol ether compound I as an initiator.
Ring opening and fluoridation method and device of steroidal epoxy compound
-
Paragraph 0038; 0039; 0041, (2017/07/22)
The invention discloses a method of preparing a compound II, which is as shown as the following reaction formula as shown in the specification. A 9 alpha-fluorine-11 beta -hydroxyl steroidal compound II is prepared via epoxy compound ring opening and fluoridation of a steroidal epoxy compound I by taking hydrogen fluoride as a fluorination reagent in a solvent consisting of arene and water. In the formula, R is CH3, CH2OH or CH2OAc; R1 is OH; R2 is alpha-CH3 or beta-CH3; and R3 is F or H. A continuous reaction device as shown in Figure 1 can be used in the method.