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5593-20-4

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5593-20-4 Usage

Chemical Properties

Betamethasone 17,21-dipropionate is Pale Yellow Foam

Originator

Betnovate,Glaxo,UK,1961

Uses

Different sources of media describe the Uses of 5593-20-4 differently. You can refer to the following data:
1. Betamethasone 17,21-dipropionate is used as anti-inflammatory and antibacterial ointment for dermatosis.
2. antiviral
3. Cortico Steroids

Definition

Betamethasone 17,21-dipropionate is a steroid ester that is betamethasone in which the hydroxy hydrogens at positions 17 and 21 are replaced by propanoyl groups. It is used in combination with calcipotriene hydrate, a synthetic vitamin D analogue, for the topical treatment of plaque psoriasi in adult patients.

Manufacturing Process

A solution of 9α-fluoro-11β-hydroxy-16β-methyl-17α,21-(1'-ethyl-1'- ethoxymethylenedioxy)pregna-1,4-diene-3,20-dione (538 mg) in acetic acid (20 ml), containing 2 drops of water, was allowed to stand at room temperature for 5 hours. Dilution of the mixture with water gave a white solid (457 mg) which, after being filtered off and dried, was recrystallized from acetone to afford 9α-fluoro-11β,21-dihydroxy-16β-methyl-17α- propionyloxypregna-1,4-diene-3, 20-dione (361 mg), MP 230°-235°C. Bethmethasone 17-propionate (812 mg) in pyridine (10 ml) was treated with propionyl chloride (0.21 ml) at 0°C for 1 hour. Dilution with water and acidification with dilute hydrochloric acid gave the crude diester. Recrystallization from acetone-petroleum ether afforded betamethasone 17,21-dipropionate (649 mg), MP 117°C (decomposition).

Brand name

Alphatrex (Savage); Diprolene (Schering).

Therapeutic Function

Glucocorticoid

Biochem/physiol Actions

Betamethasone 17,21-dipropionate is a glucocorticoid with anti-inflammatory and immunosuppressive activity.

Safety Profile

Poison by subcutaneous andintraperitoneal routes. An experimental teratogen. Otherexperimental reproductive effects. When heated todecomposition it emits toxic fumes of F-.

Check Digit Verification of cas no

The CAS Registry Mumber 5593-20-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,5,9 and 3 respectively; the second part has 2 digits, 2 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 5593-20:
(6*5)+(5*5)+(4*9)+(3*3)+(2*2)+(1*0)=104
104 % 10 = 4
So 5593-20-4 is a valid CAS Registry Number.
InChI:InChI=1/C27H34ClFO7/c1-5-22(33)35-14-21(32)27(36-23(34)13-28)15(2)10-19-18-7-6-16-11-17(30)8-9-24(16,3)26(18,29)20(31)12-25(19,27)4/h8-9,11,15,18-20,31H,5-7,10,12-14H2,1-4H3/t15-,18-,19-,20-,24-,25-,26?,27-/m0/s1

5593-20-4 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (B3166)  Betamethasone 17,21-Dipropionate  >97.0%(HPLC)

  • 5593-20-4

  • 1g

  • 490.00CNY

  • Detail
  • TCI America

  • (B3166)  Betamethasone 17,21-Dipropionate  >97.0%(HPLC)

  • 5593-20-4

  • 5g

  • 1,650.00CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1399)  Betamethasone Dipropionate  pharmaceutical secondary standard; traceable to USP and PhEur

  • 5593-20-4

  • PHR1399-1G

  • 862.41CNY

  • Detail
  • Sigma-Aldrich

  • (B1040000)  Betamethasone dipropionate  European Pharmacopoeia (EP) Reference Standard

  • 5593-20-4

  • B1040000

  • 1,880.19CNY

  • Detail
  • Sigma-Aldrich

  • (Y0001416)  Betamethasone dipropionate for peak identification  European Pharmacopoeia (EP) Reference Standard

  • 5593-20-4

  • Y0001416

  • 1,880.19CNY

  • Detail
  • Sigma-Aldrich

  • (Y0001418)  Betamethasone dipropionate for system suitability  European Pharmacopoeia (EP) Reference Standard

  • 5593-20-4

  • Y0001418

  • 1,880.19CNY

  • Detail
  • USP

  • (1067704)  Betamethasone dipropionate  United States Pharmacopeia (USP) Reference Standard

  • 5593-20-4

  • 1067704-125MG

  • 3,720.60CNY

  • Detail

5593-20-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name betamethasone dipropionate

1.2 Other means of identification

Product number -
Other names Psorion

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5593-20-4 SDS

5593-20-4Synthetic route

betamethasone
378-44-9

betamethasone

betamethasone dipropionate
5593-20-4

betamethasone dipropionate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: toluene-4-sulfonic acid / tetrahydrofuran / 2 h / 15 - 20 °C / Inert atmosphere
2: aluminum (III) chloride / 16.5 h / 10 - 30 °C
3: tetrahydrofuran; water / 8 h / 50 - 80 °C / 450.05 Torr
View Scheme
Betamethasone propionate
5534-13-4

Betamethasone propionate

betamethasone dipropionate
5593-20-4

betamethasone dipropionate

Conditions
ConditionsYield
In tetrahydrofuran; water at 50 - 80℃; under 450.045 Torr; for 8h;
betamethasone dipropionate
5593-20-4

betamethasone dipropionate

17α,21-dihydroxy-9α-fluoro-16β-methylpregna-1,4,11(12)-triene-3,20-dione 17,21-dipropionate
65669-64-9

17α,21-dihydroxy-9α-fluoro-16β-methylpregna-1,4,11(12)-triene-3,20-dione 17,21-dipropionate

Conditions
ConditionsYield
With (diethylamido)sulfur trifluoride In dichloromethane for 16h; Ambient temperature;93%
P2 S5

P2 S5

betamethasone dipropionate
5593-20-4

betamethasone dipropionate

9α-Fluoro-16β-methyl-11,17,21-trihydroxypregna-1,4-dien-20-one-3-thione 17,21-dipropionate

9α-Fluoro-16β-methyl-11,17,21-trihydroxypregna-1,4-dien-20-one-3-thione 17,21-dipropionate

Conditions
ConditionsYield
In toluene60%
betamethasone dipropionate
5593-20-4

betamethasone dipropionate

9α-fluoro-6β,11β,17α,21-tetrahydroxy-16β-methyl-1,4-pregnadiene-3,20-dione 17,21-dipropionate
72559-81-0

9α-fluoro-6β,11β,17α,21-tetrahydroxy-16β-methyl-1,4-pregnadiene-3,20-dione 17,21-dipropionate

Conditions
ConditionsYield
With selenious acid In 1,4-dioxane at 100℃; for 72h;44.2%
With selenium(IV) oxide In 1,4-dioxane at 110℃; for 2.5h;25%
Multi-step reaction with 2 steps
1: pyridine / 18 h / 60 °C
2: oxygen / CHCl3 / 3 h
View Scheme
betamethasone dipropionate
5593-20-4

betamethasone dipropionate

A

betamethasone
378-44-9

betamethasone

B

Betamethasone propionate
5534-13-4

Betamethasone propionate

C

6β-hydroxybetamethasone
24703-00-2

6β-hydroxybetamethasone

D

6β-hydroxybetamethasone 17-propionate
78144-00-0

6β-hydroxybetamethasone 17-propionate

Conditions
ConditionsYield
With phosphate buffer; air; plasma of 20 d pregnant Sprague-Dawley rat at 37℃; for 1h; Product distribution; metabolism with tissues (plasma, liver, brain, placenta) from mothers and fetuses of Sprague-Dawley rats sacrificed on day 20 of pregnancy and mice on day 17 of pregnancy, further in vivo;A 14.8 % Chromat.
B 67.8 % Chromat.
C 1.4 % Chromat.
D 2.3 % Chromat.
betamethasone dipropionate
5593-20-4

betamethasone dipropionate

Betamethasone propionate
5534-13-4

Betamethasone propionate

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 6h; Ambient temperature;
betamethasone dipropionate
5593-20-4

betamethasone dipropionate

benzoyl chloride
98-88-4

benzoyl chloride

9α-fluoro-3,11β,17α,21-tetrahydroxy-16β-methyl-1,3,5-pregnatriene-20-one 3-benzoate 17,21-dipropionate
82926-64-5

9α-fluoro-3,11β,17α,21-tetrahydroxy-16β-methyl-1,3,5-pregnatriene-20-one 3-benzoate 17,21-dipropionate

Conditions
ConditionsYield
In pyridine at 60℃; for 18h;
betamethasone dipropionate
5593-20-4

betamethasone dipropionate

A

betamethasone
378-44-9

betamethasone

B

Betamethasone propionate
5534-13-4

Betamethasone propionate

C

betamethasone 21-monopropionate

betamethasone 21-monopropionate

Conditions
ConditionsYield
With sulfuric acid In acetonitrile at 20℃; for 20h; Product distribution; Further Variations:; Temperatures;
betamethasone dipropionate
5593-20-4

betamethasone dipropionate

A

(Z)-betamethasone 20-hydroxy-17(20)-en-21-aldehyde

(Z)-betamethasone 20-hydroxy-17(20)-en-21-aldehyde

B

(E)-betamethasone 20-hydroxy-17(20)-en-21-aldehyde

(E)-betamethasone 20-hydroxy-17(20)-en-21-aldehyde

Conditions
ConditionsYield
With sodium hydroxide In acetonitrile at 20℃; for 0.333333h; Mattox rearrangement;A 30 % Chromat.
B 10 % Chromat.
With sodium hydroxide In water; acetonitrile at 20℃; for 0.333333h; Mattox rearrangement;
betamethasone dipropionate
5593-20-4

betamethasone dipropionate

9α-fluoro-11β,17α,21-trihydroxy-16β-methyl-1,4-pregnadiene-3,6,20-trione 17,21-dipropionate
72559-88-7

9α-fluoro-11β,17α,21-trihydroxy-16β-methyl-1,4-pregnadiene-3,6,20-trione 17,21-dipropionate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: pyridine / 18 h / 60 °C
2: oxygen / CHCl3 / 3 h
3: 77 percent / pyridne/ CF3COOH/ 1-cyclohexyl-3-(2-morpholinoethyl) carbodiimide metho-p-toluenesulfonate / dimethylsulfoxide; benzene / 2 h / Ambient temperature
View Scheme
betamethasone dipropionate
5593-20-4

betamethasone dipropionate

9α-fluoro-6,11β,17α,21-tetrahydroxy-16β-methyl-1,4,6-pregnatriene-3,20-dione 6-acetate 17,21-dipropionate
72559-27-4

9α-fluoro-6,11β,17α,21-tetrahydroxy-16β-methyl-1,4,6-pregnatriene-3,20-dione 6-acetate 17,21-dipropionate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: pyridine / 18 h / 60 °C
2: oxygen / CHCl3 / 3 h
3: 77 percent / pyridne/ CF3COOH/ 1-cyclohexyl-3-(2-morpholinoethyl) carbodiimide metho-p-toluenesulfonate / dimethylsulfoxide; benzene / 2 h / Ambient temperature
4: 51 percent / pyridine / 5 h / Ambient temperature
View Scheme
betamethasone dipropionate
5593-20-4

betamethasone dipropionate

9α-fluoro-6,11β,17α,21-tetrahydroxy-16β-methyl-1,4,6-pregnatriene-3,20-dione 6-isobutyrate 17,21-dipropionate
72559-99-0

9α-fluoro-6,11β,17α,21-tetrahydroxy-16β-methyl-1,4,6-pregnatriene-3,20-dione 6-isobutyrate 17,21-dipropionate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: pyridine / 18 h / 60 °C
2: oxygen / CHCl3 / 3 h
3: 77 percent / pyridne/ CF3COOH/ 1-cyclohexyl-3-(2-morpholinoethyl) carbodiimide metho-p-toluenesulfonate / dimethylsulfoxide; benzene / 2 h / Ambient temperature
4: 63 percent / pyridine / 5 h / Ambient temperature
View Scheme
betamethasone dipropionate
5593-20-4

betamethasone dipropionate

9α-fluoro-6,11β,17α,21-tetrahydroxy-16β-methyl-1,4,6-pregnatriene-3,20-dione 6-valerate 17,21-dipropionate
72560-00-0

9α-fluoro-6,11β,17α,21-tetrahydroxy-16β-methyl-1,4,6-pregnatriene-3,20-dione 6-valerate 17,21-dipropionate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: pyridine / 18 h / 60 °C
2: oxygen / CHCl3 / 3 h
3: 77 percent / pyridne/ CF3COOH/ 1-cyclohexyl-3-(2-morpholinoethyl) carbodiimide metho-p-toluenesulfonate / dimethylsulfoxide; benzene / 2 h / Ambient temperature
4: 58 percent / pyridine / 5 h / Ambient temperature
View Scheme
betamethasone dipropionate
5593-20-4

betamethasone dipropionate

9α-fluoro-6,11β,17α,21-tetrahydroxy-16β-methyl-1,4,6-pregnatriene-3,20-dione 6-trimethylacetate 17,21-dipropionate
72559-32-1

9α-fluoro-6,11β,17α,21-tetrahydroxy-16β-methyl-1,4,6-pregnatriene-3,20-dione 6-trimethylacetate 17,21-dipropionate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: pyridine / 18 h / 60 °C
2: oxygen / CHCl3 / 3 h
3: 77 percent / pyridne/ CF3COOH/ 1-cyclohexyl-3-(2-morpholinoethyl) carbodiimide metho-p-toluenesulfonate / dimethylsulfoxide; benzene / 2 h / Ambient temperature
4: 56 percent / various solvent(s) / 5 h / Ambient temperature
View Scheme
betamethasone dipropionate
5593-20-4

betamethasone dipropionate

9α-fluoro-6,11β,17α,21-tetrahydroxy-16β-methyl-1,4,6-pregnatriene-3,20-dione 6-benzoate 17,21-dipropionate
72559-98-9

9α-fluoro-6,11β,17α,21-tetrahydroxy-16β-methyl-1,4,6-pregnatriene-3,20-dione 6-benzoate 17,21-dipropionate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: pyridine / 18 h / 60 °C
2: oxygen / CHCl3 / 3 h
3: 77 percent / pyridne/ CF3COOH/ 1-cyclohexyl-3-(2-morpholinoethyl) carbodiimide metho-p-toluenesulfonate / dimethylsulfoxide; benzene / 2 h / Ambient temperature
4: 70 percent / pyridine / 5 h / Ambient temperature
View Scheme
betamethasone dipropionate
5593-20-4

betamethasone dipropionate

9α-fluoro-6,11β,17α,21-tetrahydroxy-16β-methyl-1,4,6-pregnatriene-3,20-dione 6-methanesulfonate 17,21-dipropionate
82934-60-9

9α-fluoro-6,11β,17α,21-tetrahydroxy-16β-methyl-1,4,6-pregnatriene-3,20-dione 6-methanesulfonate 17,21-dipropionate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: pyridine / 18 h / 60 °C
2: oxygen / CHCl3 / 3 h
3: 77 percent / pyridne/ CF3COOH/ 1-cyclohexyl-3-(2-morpholinoethyl) carbodiimide metho-p-toluenesulfonate / dimethylsulfoxide; benzene / 2 h / Ambient temperature
4: 41 percent / pyridine / 5 h / Ambient temperature
View Scheme
betamethasone dipropionate
5593-20-4

betamethasone dipropionate

17α,21-dihydroxy-9α-fluoro-16β-methylpregna-1,4,11(12)-triene-3,20-dione
127034-59-7

17α,21-dihydroxy-9α-fluoro-16β-methylpregna-1,4,11(12)-triene-3,20-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 93 percent / (diethylamido)sulfur trifluoride (DAST) / CH2Cl2 / 16 h / Ambient temperature
2: 88 percent / NaHCO3 / methanol / 1 h / Heating
View Scheme
betamethasone dipropionate
5593-20-4

betamethasone dipropionate

16β-methyl-12β,17α,21-trihydroxypregna-1,4,9(11)-triene-3,20-dione
127034-60-0

16β-methyl-12β,17α,21-trihydroxypregna-1,4,9(11)-triene-3,20-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 93 percent / (diethylamido)sulfur trifluoride (DAST) / CH2Cl2 / 16 h / Ambient temperature
2: 88 percent / NaHCO3 / methanol / 1 h / Heating
3: 57 percent / 48percent aq. HF / 1.5 h / 22 °C
View Scheme
betamethasone dipropionate
5593-20-4

betamethasone dipropionate

16β-methyl-12α,17α,21-trihydroxypregna-1,4,9(11)-triene-3,20-dione
127034-61-1

16β-methyl-12α,17α,21-trihydroxypregna-1,4,9(11)-triene-3,20-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 93 percent / (diethylamido)sulfur trifluoride (DAST) / CH2Cl2 / 16 h / Ambient temperature
2: 88 percent / NaHCO3 / methanol / 1 h / Heating
3: 19 percent / 48percent aq. HF / 1.5 h / 22 °C
View Scheme
p-TSA hydrate

p-TSA hydrate

betamethasone dipropionate
5593-20-4

betamethasone dipropionate

9α-Fluoro-11β,17α,21-trihydroxy-16β-methyl-5β-pregnane-3,20-dione 17,21-dipropionate
80226-13-7

9α-Fluoro-11β,17α,21-trihydroxy-16β-methyl-5β-pregnane-3,20-dione 17,21-dipropionate

Conditions
ConditionsYield
palladium In dichloromethane; 4,4-dichlorobutan-2-one; acetone
palladium In dichloromethane; 4,4-dichlorobutan-2-one; acetone
betamethasone dipropionate
5593-20-4

betamethasone dipropionate

9α-Fluoro-16β-methyl-11,17-21-trihydroxypregna-1,4-dien-20-one-3-thione
64681-07-8

9α-Fluoro-16β-methyl-11,17-21-trihydroxypregna-1,4-dien-20-one-3-thione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: toluene
2: sodium hydroxide; acetic acid / methanol
View Scheme

5593-20-4Relevant articles and documents

Preparation method of betamethasone dipropionate

-

Paragraph 0009; 0044-0062, (2021/05/29)

The invention belongs to the technical field of chemical synthesis, and particularly relates to a preparation method of betamethasone dipropionate. According to the method, betamethason-17-propionate is taken as a raw material, propionic anhydride is taken as a raw material, under the condition that 4-dimethylaminopyridine is taken as a catalyst, betamethasone dipropionate is generated through reaction, and high-purity betamethasone dipropionate is obtained through refining by adopting absolute ethyl alcohol, dichloromethane and normal hexane. The preparation process is simple, the reaction temperature is moderate, and ultralow-temperature or high-temperature reaction is avoided; the solvent or reagent used in the preparation is cheap and easy to obtain, convenient to charge and easy to transport and store; the method has the advantages of small dosage of reaction catalyst, high yield, less generated waste liquid, environmental friendliness and suitability for commercial production.

Pharmaceutical composition

-

, (2008/06/13)

A pharmaceutical composition for dermal use, wherein the composition has a first pharmacologically active component A consisting of at least one vitamin D or vitamin D analogue, and a second pharmacologically active component B consisting of at least one corticosteroid, wherein the difference between the maximum stability pH of said first component A and the maximum stability pH of said second component B is at least 1. The composition can also have at least one solvent component C, where component C is compounds of the general formula R3(OCH2C(R1)H)xOR2(I), wherein x is in the range of 2-60, R1in each of the x units independently is H or CH3, R2is straight chain or branched C1-20alkyl or benzoyl, and R3is H or phenylcarbonyloxy; di-(straight or branched)-C4-10alkyl esters of C4-C8dicarboxylic acids; straight or branched C12-18-alkyl benzoates; straight or branched C2-4-alkyl esters of straight or branched C10-18-alkanoic or -alkenoic acids; propylenglycol diesters with C8-14-alkanoic acids; and branched primary C18-24alkanols.

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