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Betamethasone structure

Betamethasone
  • CAS：378-44-9
  • MW:392.467
  • MF：C22H29FO5
Shortly after the introduction of dexamethasone, betamethasone, which differs from dexamethasone only inconfiguration of the 16-methyl group, was made available for the treatment of rheumatic diseasesand dermatologic disorders. This analogue, which contains a 16β-methyl group, has received sufficient clinicaltrial 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 suggestthat it is best used for short-term therapy. View more+
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1. Names and Identifiers
1.1 Name
Betamethasone
1.2 Synonyms
(11b,16b)-9-fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione; (11Β,16Β)-9-Fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione; (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; (8S,9R,10S,11S,13S,14S,16S,17R)-9-fluoro-11,17-dihydroxy-17-(hydroxyacetyl)-10,13,16-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one; (8α,9β,10α,11α,13α,14β,16α,17α)-9-Fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione; 16b-Methyl-9a-fluoro-D1-hydrocortisone; 16b-Methyl-9a-fluoroprednisolone; 16Β-Methyl-1,4-pregnadiene-9α-fluoro-11Β,17α,21-triol-3,20-dione; 17,21-trihydr; 4-08-00-03501; 4-08-00-03501 (Beilstein Handbook Reference); 6beta); 9a-Fluoro-16b-methylprednisolone; 9A-FLUORO-16Β-METHYLPREDNISOLONE; 9α-Fluoro-11Β,17α,21-trihydroxy-16Β-methyl-1,4-pregnadiene-3,20-dione; 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; b-Corlan; Bebate; Becort; Bedifos; Bentelan; Betadexamethasone; Betalon; Betametasona [INN-Spanish]; Betametasone [DCIT]; betamethasone standard; Betamethasone (200 mg); BetaMethasone (Celestone); Betamethasone Base & Salts; BetaMethasone SolutioM; 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; betamethazone; Betasolon; Betnelan; Betsolan; Bifas; b-Methasone; b-Methasone alcohol; Celestene; Celestone; Cidoten; DERMABET; Diprolene; EINECS 206-825-4; Flubenisolone; GF120918A; MFCD00062969; Pertene; pregna-1,4-diene-3,20-dione, 9-fluoro-11,17,21-trihydroxy-16-methyl-, (11b,16b)-; Pregna-1,4-diene-3,20-dione, 9-fluoro-11,17,21-trihydroxy-16-methyl-, (11Β,16Β)-; Pregna-1,4-diene-3,20-dione, 9-fluoro-11,17,21-trihydroxy-16-methyl-, (8α,9β,10α,11α,13α,14β,16α,17α)-; Pregna-1,4-diene-3,20-dione, 9-fluoro-11Β,17,21-trihydroxy-16Β-methyl-; UNII-9842X06Q6M; Visubeta; Β-Corlan; Β-Methasone; Β-Methasone alcohol;
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1.3 CAS No.
378-44-9
1.4 CID
9782
1.5 EINECS
206-825-4
1.6 Molecular Formula
C22H29FO5
1.7 Inchi
InChI=1S/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-/m0/s1
1.8 InChkey
UREBDLICKHMUKA-DVTGEIKXSA-N
1.9 Canonical Smiles
CC1CC2C3CCC4=CC(=O)C=CC4(C3(C(CC2(C1(C(=O)CO)O)C)O)F)C
1.10 Isomers Smiles
C[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@@]4([C@]3([C@H](C[C@@]2([C@]1(C(=O)CO)O)C)O)F)C
2. Properties
2.1 Solubility
58mg/L(25 ºC)
2.2 AnalyticLaboratory Methods
Analyte: betamethasone;; matrix: chemical purity; procedure: liquid chromatography with detection at 240 nm and comparison to standards
2.3 Appearance
white to off-white crystalline powder
2.4 Color/Form
Powder
2.5 Odor
ODORLESS
2.6 Physical
Solid
2.7 pKa
12.13±0.70(Predicted)
2.8 Water Solubility
SPARINGLY SOL IN ACETONE AND ALC
SPARINGLY SOL IN DIOXANE, METHANOL; VERY SLIGHTLY SOL IN CHLOROFORM & ETHER
In water, 66.5 mg/l @ 25 deg C
2.9 Spectral Properties
Specific optical rotation: +63.5 deg @ 24 deg C/D (dioxane)
Specific optical rotation: +108 deg/D acetone; max UV absorption (methanol)
2.10 Stability
HYGROSCOPIC. /SODIUM PHOSPHATE/
2.11 StorageTemp
0-6°C
3. Use and Manufacturing
3.1 Description
Betamethasone is a glucocorticoid steroid with anti-inflammatory and immunosuppressive properties.Target: Glucocorticoid ReceptorBetamethasone is a potent glucocorticoid steroid with anti-inflammatory and immunosuppressive properties. Unlike other drugs with these effects, betamethasone does not cause water retention. The median (range) IC50 value for betamethasone butyrate propionate evaluated in the streptococcal pyrogenic enterotoxin A-stimulated peripheral-blood mononuclear cells was
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3.2 GHS Classification
Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 68 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H330 (50%): Fatal if inhaled [Danger Acute toxicity, inhalation]
H360 (95.59%): May damage fertility or the unborn child [Danger Reproductive toxicity]
H372 (50%): Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]
H373 (45.59%): Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]
H410 (50%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P201, P202, P260, P264, P270, P271, P273, P281, P284, P304+P340, P308+P313, P310, P314, P320, P391, P403+P233, P405, and P501
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3.3 Methods of Manufacturing
EXTRACTION OF HECOGENIN; FROM AGAVE SISALANA (SISAL PLANT), THEN TRANSFER OF 12-OXO GROUP TO C-11, BROMINATION, TREATMENT WITH SODIUM HYDROXIDE;, ACETYLATION, DEBROMINATION WITH ZINC; DUST, AND REDUCTION WITH CALCIUM;/LIQUID AMMONIA;
3.4 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
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3.5 Usage
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.
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4. Safety and Handling
4.1 Exposure Standards and Regulations
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl betamethasone acetate,betamethasone sodium phosphate, betamethasone dipropionate, and betamethasone valerate approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Betamethasone acetate,betamethasone sodium phosphate, betamethasone dipropionate, and betamethasone valerate/
Betamethasone acetate and betamethasone disodium phosphate aqueous suspension. ... It is used or intended for use by intra-articular injection of horses for the treatment of various inflammatory joint conditions; for example, acute and traumatic lameness involving the carpel and fetlock joints. ... Not for use in horses intended for food. For use only by or on the order of a licensed veterinarian. /Betamethasone acetate/
Betamethasone dipropionate and betamethasone sodium phosphate aqueous suspension. ... Conditions of use -- (1) Dogs. (i) It is used as an aid in the control of pruritus associated with dermatoses. ... (2) Horses. (i) It is used as an aid in the control of inflammation associated with various arthropathies. ... Not for use in horses intended for food. ... Restrictions. Federal law restricts this drug to use by or on the order of a licensed veterinarian. /Betamethasone dipropionate, Betamethasone sodium phosphate/
Gentamicin sulfate, betamethasone valerate otic solution. ... Conditions of use. (1) The drug is used or indicated for use in dogs in the treatment of acute and chronic otitis externa caused by bacteria sensitive to gentamicin; the drug is also used or indicated for use in dogs and cats in the treatment of superficial infected lesions caused by bacteria sensitive to gentamicin. ... For use by or on the order of a licensed veterinarian. /Betamethasone valerate/
Gentamicin sulfate, betamethasone valerate ointment. ... Conditions of use. (1) The drug is used or indicated for use in dogs in the treatment of acute and chronic canine otitis externa and canine infected superficial lesions caused by bacteria sensitive to gentamicin. ... For use by or on the order of a licensed veterinarian. /Betamethasone valerate/
Gentamicin sulfate, betamethasone valerate topical spray. ... Conditions of use. (1) The drug is used in dogs in the treatment of infected superficial lesions caused by bacteria sensitive to gentamicin. ... Federal law restricts this drug to use by or on the order of a licensed veterinarian. /Betamethasone valerate/
Gentamicin sulfate, betamethasone valerate, clotrimazole ointment. ... Indications for use. For the treatment of canine otitis externa associated with yeast (Malassezia pachydermatis, formerly Pityrosporum canis) and/or bacteria susceptible to gentamicin. ... Limitations. Federal law restricts this drug to use by or on the order of a licensed veterinarian. /Betamethasone valerate/
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392). [
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4.2 Octanol/Water Partition Coefficient
log Kow= 1.94
4.3 DisposalMethods
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
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4.4 Safety Profile
Low toxicity by ingestion. Anexperimental teratogen. Other experimental reproductiveeffects. When heated to decomposition it emits toxicfumes of F-.
4.5 Formulations/Preparations
Available commercially as the alcohol and as the 17-valerate, 17-benzoate, 17,21-dipropionate, disodium 21-phosphate salt.
beta-Corlan, Becort, Betasolon, Betnelan, Celestene, Celestone, Dermabet, Diprolene, Visubeta
Celestovet /betamethasone acetate/
Bebate, Beben, Benisone, Euvaderm, Flurobate, Parbetan, Uticort /betamethasone benzoate/
Diproderm, Diprophos, Diprosis, Diprosone, Maxivate, Rinderon-DP /betamethasone dipropioniate/
Bedremin, Betnesol-V, Betneval, Betnovate, Bextasol, Celestan-V, Celestoderm-V, Dermosol, Dermovaleas, Ecoval 70, Hormezon, Tokuderm, Valisone /betamethasone valerate/
Bentelan, Betnesol, Celestan, Durabetason, Vista-Methasone /betamethasone phosphate disodium salt/
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4.6 Safety
Low toxicity by ingestion. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits toxic fumes of F?.
4.7 Toxicity

CHEMICAL IDENTIFICATION

RTECS NUMBER :
TU4000000
CHEMICAL NAME :
Pregna-1,4-diene-3,20-dione, 9-fluoro-11-beta,17,21-trihydroxy-16-beta-methyl-
CAS REGISTRY NUMBER :
378-44-9
BEILSTEIN REFERENCE NO. :
3176546
LAST UPDATED :
199612
DATA ITEMS CITED :
11
MOLECULAR FORMULA :
C22-H29-F-O5
MOLECULAR WEIGHT :
392.51
WISWESSER LINE NOTATION :
L E5 B666 OV AHTTT&J A1 BF CQ E1 FV1Q FQ G1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>4500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YAKUD5 Gekkan Yakuji. Pharmaceuticals Monthly. (Yakugyo Jihosha, Inaoka Bldg., 2-36 Jinbo-cho, Kanda, Chiyoda-ku, Tokyo 101, Japan) V.1- 1959- Volume(issue)/page/year: 21,2117,1979 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
1200 ug/kg
SEX/DURATION :
female 18-20 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - other effects to embryo
REFERENCE :
PEREBL Pediatric Research. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1967- Volume(issue)/page/year: 33,5,1993
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
150 ug/kg
SEX/DURATION :
female 16-18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - biochemical and metabolic
REFERENCE :
JPEMAO Journal of Perinatal Medicine. (Walter de Gruyter, Inc., 200 Saw Mill River Rd., Hawthorne, NY 10532) V.1- 1973- Volume(issue)/page/year: 22,319,1993
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intramuscular
DOSE :
2 mg/kg
SEX/DURATION :
female 18-19 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - other effects
REFERENCE :
DPTHDL Developmental Pharmacology and Therapeutics. (S. Karger Pub., Inc., 79 Fifth Ave., New York, NY 10003) V.1- 1980- Volume(issue)/page/year: 18,14,1992
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intramuscular
DOSE :
600 ug/kg
SEX/DURATION :
female 20 week(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - other effects to embryo
REFERENCE :
AJOGAH American Journal of Obstetrics and Gynecology. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63146) V.1- 1920- Volume(issue)/page/year: 127,261,1977
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intramuscular
DOSE :
1600 ug/kg
SEX/DURATION :
female 18 week(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - respiratory system
REFERENCE :
ARDSBL American Review of Respiratory Disease. (American Lung Assoc., 1740 Broadway, New York, NY 10019) V.80- 1959- Volume(issue)/page/year: 117,377,1978
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intramuscular
DOSE :
1200 ug/kg
SEX/DURATION :
female 18-19 week(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - respiratory system Reproductive - Specific Developmental Abnormalities - hepatobiliary system
REFERENCE :
AJOGAH American Journal of Obstetrics and Gynecology. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63146) V.1- 1920- Volume(issue)/page/year: 133,677,1979
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intramuscular
DOSE :
5200 ug/kg
SEX/DURATION :
female 16-18 week(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - extra-embryonic structures (e.g., placenta, umbilical cord) Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - endocrine system
REFERENCE :
AJOGAH American Journal of Obstetrics and Gynecology. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63146) V.1- 1920- Volume(issue)/page/year: 133,677,1979
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
69 mg/kg
SEX/DURATION :
female 8-18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)
REFERENCE :
JIDOAA Experimental Animals. Jikken Dobutso Iho. (Nippon Jikken Dobutsu Gakkai, c/o Keio Gijuku Daigaku Igakubu Jikken Dobutsu Senta, 35 Shinano-machi, Shinjuku-ku, Tokyo 160, Japan) V.1- 1952- Volume(issue)/page/year: 35,387,1986
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
138 mg/kg
SEX/DURATION :
female 8-18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death
REFERENCE :
JIDOAA Experimental Animals. Jikken Dobutso Iho. (Nippon Jikken Dobutsu Gakkai, c/o Keio Gijuku Daigaku Igakubu Jikken Dobutsu Senta, 35 Shinano-machi, Shinjuku-ku, Tokyo 160, Japan) V.1- 1952- Volume(issue)/page/year: 35,387,1986 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - M0622 No. of Facilities: 20 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 656 (estimated) No. of Female Employees: 489 (estimated)
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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Reproductive toxicity, Category 1B

Specific target organ toxicity \u2013 repeated exposure, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Danger

Hazard statement(s)

H360 May damage fertility or the unborn child

H373 May cause damage to organs through prolonged or repeated exposure
Precautionary statement(s)
Prevention

P201 Obtain special instructions before use.

P202 Do not handle until all safety precautions have been read and understood.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P260 Do not breathe dust/fume/gas/mist/vapours/spray.

Response

P308+P313 IF exposed or concerned: Get medical advice/ attention.

P314 Get medical advice/attention if you feel unwell.

Storage

P405 Store locked up.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum
13C NMR : in DMSO-d6  
IR : KBr disc  
IR : nujol mull  
Mass  
Mass spectrum (electron ionization)  
7. Synthesis Route
378-44-9Total: 15 Synthesis Route
 
987-24-6
987-24-6 151 Suppliers
 
378-44-9
378-44-9 470 Suppliers
 
915-35-5
915-35-5 13 Suppliers
 
378-44-9
378-44-9 470 Suppliers
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8. Precursor and Product
precursor:
1879-77-2
1879-77-2
467-55-0
467-55-0
21650-83-9
21650-83-9
989-73-1
989-73-1
987-24-6
987-24-6
915-35-5
915-35-5
5593-20-4
5593-20-4
1106-20-3
1106-20-3
37414-01-0
37414-01-0
14135-32-1
14135-32-1
product:
79578-14-6
79578-14-6
2152-44-5
2152-44-5
9. Computed Properties
10.Other Information
Merck
14,1180
Target
Value
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.
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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.
View all
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.
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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.
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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).
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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.
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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.]
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12. Related Questions
What are the effects and functions of Betamethasone?It is essential to understand the effects and functions of a medication in order to better treat any corresponding symptoms that may arise in the body. Betamethasone is a medication that has been used..
Where to Find the Best Channel for Bulk Purchasing Betamethasone?Betamethasone is commonly available in the form of injections and tablets, primarily used for intramuscular and intravenous injections to treat diseases such as rheumatoid arthritis and acute leukemia..
What are the differences between Betamethasone and Dexamethasone?Corticosteroids are a class of drugs with anti-inflammatory, anti-toxic, anti-shock, anti-allergic, immune response inhibition, and airway hyperresponsiveness inhibition effects. The main long-acting ..
What are the precautions for using Betamethasone?Betamethasone is a corticosteroid drug commonly available in tablet, cream, and injection forms, primarily used for allergic and autoimmune inflammatory diseases. It possesses various pharmacological ..
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