Basic information hormone drugs Chemical Properties Uses production method Category Toxicity grading Acute toxicity Flammability and hazard characteristics Storage Characteristics Extinguishing agent Safety Supplier Related
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Betamethasone

Basic information hormone drugs Chemical Properties Uses production method Category Toxicity grading Acute toxicity Flammability and hazard characteristics Storage Characteristics Extinguishing agent Safety Supplier Related

Betamethasone Basic information

Product Name:
Betamethasone
Synonyms:
  • 17,21-trihydr
  • betamethasone standard
  • (8S,9R,10S,11S,13S,14S,16S,17R)-9-fluoro- 11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl- 6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one
  • Betamethasone Base & Salts
  • Betamethasone,9α-Fluoro-11β,17α,21-trihydroxy-16β-methylpregna-1,4-diene-3,20-dione, 9α-Fluoro-16β-methyl-11β,17α,21-trihydroxy-1,4-pregnadiene-3,20-dione, 9α-Fluoro-16β-methylprednisolone
  • Betamethasone (200 mg)
  • BetaMethasone (Celestone)
  • BetaMethasone SolutioM
CAS:
378-44-9
MF:
C22H29FO5
MW:
392.47
EINECS:
206-825-4
Product Categories:
  • CELESTONE
  • Pharmaceutical intermediate
  • Biochemistry
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Steroid and Hormone
  • Hydroxyketosteroids
  • Steroids
Mol File:
378-44-9.mol
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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.
form 
neat
pka
12.13±0.70(Predicted)
Water Solubility 
58mg/L(25 ºC)
Merck 
14,1180
CAS DataBase Reference
378-44-9(CAS DataBase Reference)
NIST Chemistry Reference
Pregna-1,4-diene-3,20-dione, 9alpha-fluoro-11beta,17alpha,21-trihydroxy-16beta-methyl-(378-44-9)
EPA Substance Registry System
Pregna-1,4-diene-3,20-dione, 9-fluoro-11,17,21-trihydroxy-16-methyl-, (11.beta.,16.beta.)- (378-44-9)
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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 Data
378-44-9(Hazardous Substances Data)
Toxicity
LD50 oral in mouse: > 4500mg/kg
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Betamethasone Usage And Synthesis

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 chemicalbook of Tian Ye.

Chemical Properties

White 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.

Uses

Hormone 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 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.

Category

Toxic substances

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.

Description

Shortly 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.

Description

Betamethasone 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 Properties

White to Off-White Solid

Originator

Celestone,Schering,US,1961

Uses

glucocorticoid, antiinflammatory

Uses

Betamethasone is a glucocorticoid used as an anti-inflammatory agent.

Uses

anti-inflammatory, immunosuppressive

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.

brand name

Celestone Syrup and Tablets (Schering).

Therapeutic Function

Glucocorticoid

General Description

Betamethasone, 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).

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.

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-.

Chemical 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.

Veterinary Drugs and Treatments

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.]

Betamethasone Preparation Products And Raw materials

Raw materials

BetamethasoneSupplier

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