Betamethasone

Betamethasone Basic information
hormone drugs Chemical Properties Uses production method Category Toxicity grading Acute toxicity Flammability and hazard characteristics Storage Characteristics Extinguishing agent
Product Name:Betamethasone
Synonyms:Betamethasone valerate impurity A (PhEur);Betamethasone solution,100ppm;(8S,10S,11S,13S,14S,16S,17R)-9-fluoro-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;BETAMETHASONE;BETADEXAMETHASONE;(11beta,16beta)-9-Fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione;16-beta-methyl-1,4-pregnadiene-9-alpha-fluoro-11-beta,17-alpha,21-triol-3,20;16-beta-Methyl-1,4-pregnadiene-9-alpha-fluoro-11-beta,17-alpha,21-triol-3,20-dione
CAS:378-44-9
MF:C22H29FO5
MW:392.47
EINECS:206-825-4
Product Categories:CELESTONE;Pharmaceutical intermediate;Steroid and Hormone;Intermediates & Fine Chemicals;Pharmaceuticals;Biochemistry;Hydroxyketosteroids;Steroids;API;378-44-9
Mol File:378-44-9.mol
Betamethasone Structure
Betamethasone Chemical Properties
Melting point 235-237°C
alpha D +108° (acetone)
Boiling point 568.2±50.0 °C(Predicted)
density 1.1283 (estimate)
refractive index 118 ° (C=1, Dioxane)
storage temp. 0-6°C
solubility Practically insoluble in water, sparingly soluble in anhydrous ethanol, very slightly soluble in methylene chloride.
pka12.13±0.70(Predicted)
form neat
color White to Off-White
Water Solubility 58mg/L(25 ºC)
Merck 14,1180
LogP2.01 at 25℃
CAS DataBase Reference378-44-9(CAS DataBase Reference)
NIST Chemistry ReferencePregna-1,4-diene-3,20-dione, 9alpha-fluoro-11beta,17alpha,21-trihydroxy-16beta-methyl-(378-44-9)
EPA Substance Registry SystemPregna-1,4-diene-3,20-dione, 9-fluoro-11,17,21-trihydroxy-16-methyl-, (11.beta.,16.beta.)- (378-44-9)
Safety Information
Hazard Codes Xi,Xn,T
Risk Statements 40-48/20/21-61
Safety Statements 22-36-45-53
WGK Germany 2
RTECS TU4000000
HS Code 29379000
Hazardous Substances Data378-44-9(Hazardous Substances Data)
ToxicityLD50 oral in mouse: > 4500mg/kg
MSDS Information
Betamethasone Usage And Synthesis
hormone drugsBetamethasone, 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 chemicalbook of Tian Ye.



Chemical PropertiesWhite crystalline powder. Mp 231-234 deg.] C (decomposition). Odorless. Acetate Betamethasone ([987-24-6]) is also white crystalline powder, melting point 205-208 ℃, slightly soluble in alcohol, ethanol, and very slightly soluble in chloroform or ether, insoluble in water, odorless.
UsesHormone drugs.It is mainly used for anti-inflammatory and anti-allergic. It is suitable for rheumatoid arthritis and various skin diseases. Betamethasone role is similiar to dexamethasone, its anti-inflammatory effect is stronger than dexamethasone, triamcinolone, hydrocortisone and it has few side effects.
production methodAccording 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.
CategoryToxic substances
Toxicity gradingMiddle toxic
Acute toxicityOral-mouse LD50:> 4500 mg/kg
Flammability and hazard characteristicsCombustible;Its combustion produces toxic fumes of fluoride.
Storage CharacteristicsVentilated, low-temperature ,dry storeroom.
Extinguishing agentDry powder , foam, sand, carbon dioxide, water spray.
DescriptionShortly after the introduction of dexamethasone, betamethasone, which differs from dexamethasone only in configuration of the 16-methyl group, was made available for the treatment of rheumatic diseases and dermatologic disorders. This analogue, which contains a 16β-methyl group, has received sufficient clinical trial examination to indicate that it is as effective as dexamethasone or, perhaps, even slightly more active. Although this drug has been reported to be less toxic than other steroids, some clinical investigators suggest that it is best used for short-term therapy.
DescriptionBetamethasone is a synthetic corticosteroid. Like other corticosteroids, betamethasone has anti-inflammatory actions. Betamethasone also accelerates fetal lung maturation and has been used to decrease neonatal mortality and morbidity in infants born before 34 weeks of gestation.
Chemical PropertiesWhite to Off-White Solid
OriginatorCelestone,Schering,US,1961
Usesanti-inflammatory, immunosuppressive
Usesglucocorticoid, antiinflammatory
UsesBetamethasone is a glucocorticoid used as an anti-inflammatory agent.
DefinitionChEBI: Betamethasone is a glucocorticoid, a 20-oxo steroid, a 21-hydroxy steroid, a 17alpha-hydroxy steroid, a fluorinated steroid, an 11beta-hydroxy steroid, a 3-oxo-Delta(1),Delta(4)-steroid, a primary alpha-hydroxy ketone and a tertiary alpha-hydroxy ketone. It has a role as an anti-inflammatory drug, an anti-asthmatic agent and an immunosuppressive agent. It derives from a hydride of a pregnane.
Manufacturing ProcessBetamethasone acetate is converted to betamethasone by means of hydrochloric acid in a methanol-chloroform-water mixture as described in US Patent 3,164,618.
Brand nameCelestone Syrup and Tablets (Schering).
Therapeutic FunctionGlucocorticoid
General DescriptionBetamethasone, 9-fluoro-11β,17,21-trihydroxy-16β-methylpregna-1,4-diene-3,20-dione,is available as a variety of ester derivatives.
Betamethasone valerate, USP (17-valerate)
Betamethasone acetate, USP (21-acetate)
Betamethasone sodium phosphate, USP (21-sodiumphosphate)
Betamethasone dipropionate, USP (17-propionate,21-propionate).



Flammability and ExplosibilityNonflammable
Biochem/physiol ActionsBetamethasone, 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 UseCorticosteroid:

Suppression of inflammatory and allergic disorders

Congenital adrenal hyperplasia

Side effectsToxic side effects, such as increased appetite, weight gain, and facial mooning, occur with prolonged use.
Safety ProfileLow toxicity by ingestion. Anexperimental teratogen. Other experimental reproductiveeffects. When heated to decomposition it emits toxicfumes of F-.
SynthesisBetamethasone 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 interactionsPotentially 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.
MetabolismCorticosteroids 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 MethodsBetamethasone 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.
Diflorasone BETAMETHASONE DIPROPIONATE MM(CRM STANDARD),BETAMETHASONE DIPROPIONATE USP(CRM STANDARD) Hydroxy silicone oil 1,4-PREGNADIEN-9-ALPHA-FLUORO-16-BETA-METHYL-11-BETA, 17,21-TRIOL-3,20-DIONE 21-HEMISUCCINATE BETAMETHASONE ACETATE [1,2,4-3H] BETAMETHASONE BENZOATE USP(CRM STANDARD) Diflorasone diacetate 9-fluoro-11beta,17-dihydroxy-16beta-methylpregna-1,4-diene-3,20-dione 21-[tricyclo[3.3.1.13,7]dec-1-ylformate] BETAMETHASONE, [1,2,4-3H] Betamethasone-21-sodium phosphate [(8S,10S,11S,13S,14S,16S,17R)-9-fluoro-11-hydroxy-17-(2-methoxyacetyl)-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate BETAMETHASONE BUTYRATE PROPIONATE BETAMETHASONE(REAGENT / STANDARD GRADE) fluoro jade Camptothecin Series--10-hydroxycamptothecin BETAMETHASONE VALERATE ACETATE 9-fluoro-11beta,17,21-trihydroxy-16beta-methylpregna-1,4-diene-3,20-dione 17,21-di(valerate) Betamethasone valerate BP/USP

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