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25122-46-7

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  • Top Quality Raw Material Clobetasol Propionate 25122-46-7

    Cas No: 25122-46-7

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25122-46-7 Usage

Mechanism of Action

Clobetasol Propionate is the propionate salt form of clobetasol, a topical synthetic corticosteroid with anti-inflammatory, anti-pruritic, and vasoconstrictive properties. Clobetasol propionate exerts its effect by binding to cytoplasmic glucocorticoid receptors and subsequently activates glucocorticoid receptor mediated gene expression. This results in the synthesis of certain anti-inflammatory proteins, while inhibiting the synthesis of certain inflammatory mediators. Specifically, clobetasol propionate appears to induce phospholipase A2 inhibitory proteins, thereby controlling the release of the inflammatory precursor arachidonic acid from membrane phospholipids by phospholipase A2.

Indications

Different sources of media describe the Indications of 25122-46-7 differently. You can refer to the following data:
1. Clobetasol propionate is the 17-O-propionate ester of clobetasol and it derives from a clobetasol and a propionic acid. A potent corticosteroid, it is used to treat various skin disorders, including exzema and psoriasis. Clobetasol propionate was patented in 1968 and came into medical use in 1978. It is available as a generic medication. Clobetasol propionate is used for the treatment of various skin disorders including eczema, herpes labialis, psoriasis, and lichen sclerosus. It is also used to treat several auto-immune diseases, including alopecia areata, lichen planus (auto immune skin nodules), and mycosis fungoides (T-cell skin lymphoma). It is used as first-line treatment for both acute and chronic GVHD of the skin.
2. Clobetasol propionate (Cormax, Temovate, Embeline, Olux) is one of the most potent of the currently available agents and is indicated for short-term treatment of inflammatory or hyperplastic disorders. It is a synthetic fluorinated corticosteroid. It may cause a more rapid or prolonged response than other topical corticosteroids. It is recommended that clobetasol have a maximum application of 60 g/week for no longer than 14 days without occlusion and that it should not be used in children below age 12.

Chemical Properties

White or almost white, crystalline powder.

Uses

Different sources of media describe the Uses of 25122-46-7 differently. You can refer to the following data:
1. Clobetasol-17-propionate is a topical corticosteroid belonging to the group-D (hydrocortisone-q-butyrate) type of steroids.
2. For short-term topical treatment of the inflammatory and pruritic manifestations of moderate to severe corticosteroid-responsive dermatoses of the scalp.
3. Topical corticosteroid. Glucocorticoid; anti-inflammatory. Clobetasol propionate (Cormax, Temovate, Embeline, Olux) is one of the most potent of the currently available agents and is indicated for short-term treatment of inflammatory or hyperplastic disorders. It is a synthetic fluorinated corticosteroid. It may cause a more rapid or prolonged response than other topical corticosteroids. It is recommended that clobetasol have a maximum application of 60 g/week for no longer than 14 days without occlusion and that it should not be used in children below age 12.

Definition

ChEBI: The 17-O-propionate ester of clobetasol. A potent corticosteroid, it is used to treat various skin disorders, including exzema and psoriasis.

Check Digit Verification of cas no

The CAS Registry Mumber 25122-46-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,5,1,2 and 2 respectively; the second part has 2 digits, 4 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 25122-46:
(7*2)+(6*5)+(5*1)+(4*2)+(3*2)+(2*4)+(1*6)=77
77 % 10 = 7
So 25122-46-7 is a valid CAS Registry Number.
InChI:InChI=1/C25H32ClFO5/c1-5-21(31)32-25(20(30)13-26)14(2)10-18-17-7-6-15-11-16(28)8-9-22(15,3)24(17,27)19(29)12-23(18,25)4/h8-9,11,14,17-19,29H,5-7,10,12-13H2,1-4H3/t14-,17?,18?,19-,22-,23-,24-,25-/m0/s1

25122-46-7 Well-known Company Product Price

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  • TCI America

  • (C2612)  Clobetasol 17-Propionate  >98.0%(HPLC)(T)

  • 25122-46-7

  • 1g

  • 495.00CNY

  • Detail
  • TCI America

  • (C2612)  Clobetasol 17-Propionate  >98.0%(HPLC)(T)

  • 25122-46-7

  • 5g

  • 1,650.00CNY

  • Detail
  • Sigma-Aldrich

  • (Y0000570)  Clobetasol for peak identification  European Pharmacopoeia (EP) Reference Standard

  • 25122-46-7

  • Y0000570

  • 1,880.19CNY

  • Detail
  • Sigma-Aldrich

  • (Y0000559)  Clobetasolpropionate  European Pharmacopoeia (EP) Reference Standard

  • 25122-46-7

  • Y0000559

  • 1,880.19CNY

  • Detail
  • USP

  • (1138405)  Clobetasolpropionate  United States Pharmacopeia (USP) Reference Standard

  • 25122-46-7

  • 1138405-200MG

  • 4,662.45CNY

  • Detail

25122-46-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name clobetasol propionate

1.2 Other means of identification

Product number -
Other names Olux

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:25122-46-7 SDS

25122-46-7Synthetic route

C25H31ClO5

C25H31ClO5

clobetasol-17-propionate
25122-46-7

clobetasol-17-propionate

Conditions
ConditionsYield
With hydrogen fluoride; potassium hydroxide In water; acetone at -40 - -30℃; for 6h; Temperature;95%
C25H31ClO5

C25H31ClO5

clobetasol-17-propionate
25122-46-7

clobetasol-17-propionate

Conditions
ConditionsYield
With hydrogen fluoride In tetrahydrofuran; water at -5 - 0℃; Solvent;94.3%
With hydrogen fluoride In chloroform; water at -40℃;84%
Betamethasone 17α,21-ethyl orthopropanoate
1062-09-5

Betamethasone 17α,21-ethyl orthopropanoate

clobetasol-17-propionate
25122-46-7

clobetasol-17-propionate

Conditions
ConditionsYield
With chloro-trimethyl-silane In N,N-dimethyl-formamide
C22H26O2

C22H26O2

clobetasol-17-propionate
25122-46-7

clobetasol-17-propionate

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: sodium hydroxide / -5 - 5 °C
1.2: 20 °C / Darkness
1.3: 20 °C
2.1: toluene-4-sulfonic acid / dichloromethane / 20 °C
3.1: tert.-butylhydroperoxide; N-benzyl-trimethylammonium hydroxide / tetrahydrofuran / 20 °C
4.1: hydrogen bromide / dichloromethane / 20 °C
4.2: Raney nickel / 20 °C
5.1: triethylamine; dmap / chloroform / 50 °C
6.1: 5,5-dibromohydantoin; perchloric acid / acetone / -5 - 5 °C
7.1: hydrogen fluoride / chloroform; water / -40 °C
View Scheme
C24H31ClO3

C24H31ClO3

clobetasol-17-propionate
25122-46-7

clobetasol-17-propionate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: toluene-4-sulfonic acid / dichloromethane / 20 °C
2.1: tert.-butylhydroperoxide; N-benzyl-trimethylammonium hydroxide / tetrahydrofuran / 20 °C
3.1: hydrogen bromide / dichloromethane / 20 °C
3.2: Raney nickel / 20 °C
4.1: triethylamine; dmap / chloroform / 50 °C
5.1: 5,5-dibromohydantoin; perchloric acid / acetone / -5 - 5 °C
6.1: hydrogen fluoride / chloroform; water / -40 °C
View Scheme
C22H25ClO2

C22H25ClO2

clobetasol-17-propionate
25122-46-7

clobetasol-17-propionate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: tert.-butylhydroperoxide; N-benzyl-trimethylammonium hydroxide / tetrahydrofuran / 20 °C
2.1: hydrogen bromide / dichloromethane / 20 °C
2.2: Raney nickel / 20 °C
3.1: triethylamine; dmap / chloroform / 50 °C
4.1: 5,5-dibromohydantoin; perchloric acid / acetone / -5 - 5 °C
5.1: hydrogen fluoride / chloroform; water / -40 °C
View Scheme
C22H25ClO3

C22H25ClO3

clobetasol-17-propionate
25122-46-7

clobetasol-17-propionate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: hydrogen bromide / dichloromethane / 20 °C
1.2: Raney nickel / 20 °C
2.1: triethylamine; dmap / chloroform / 50 °C
3.1: 5,5-dibromohydantoin; perchloric acid / acetone / -5 - 5 °C
4.1: hydrogen fluoride / chloroform; water / -40 °C
View Scheme
21-Chloro-17α-hydroxy-16β-methylpregna-1,4,9(11)-triene-3,20-dione
116846-77-6

21-Chloro-17α-hydroxy-16β-methylpregna-1,4,9(11)-triene-3,20-dione

clobetasol-17-propionate
25122-46-7

clobetasol-17-propionate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine; dmap / chloroform / 50 °C
2: 5,5-dibromohydantoin; perchloric acid / acetone / -5 - 5 °C
3: hydrogen fluoride / chloroform; water / -40 °C
View Scheme
clobetasol-17-propionate
25122-46-7

clobetasol-17-propionate

21-chloro-9α-fluoro-16β-methyl-11β,17α-dihydroxy-5β-pregnane-3,20-dione 17-propionate
80042-35-9

21-chloro-9α-fluoro-16β-methyl-11β,17α-dihydroxy-5β-pregnane-3,20-dione 17-propionate

Conditions
ConditionsYield
palladium In 4,4-dichlorobutan-2-one; ethyl acetate
palladium In 4,4-dichlorobutan-2-one; ethyl acetate

25122-46-7Downstream Products

25122-46-7Relevant articles and documents

Clobetasol propionate intermediate and preparation method thereof

-

Paragraph 0048-0049; 0057-0061; 0070-0075; 0083-0087, (2020/12/15)

The invention provides a clobetasol propionate intermediate and a preparation method thereof. The preparation method of clobetasol propionate comprises the following steps: A) in a protective atmosphere, reacting a compound DB11 with a chlorination reagent in an organic solution in the presence of a first catalyst to obtain a system containing an intermediate shown as a formula V; b) adding a second catalyst into the system containing the intermediate shown in the formula V, and continuously reacting to obtain a system containing an intermediate shown in a formula VI; c) adding an organic basecatalyst and a propionylation reagent into the system containing the intermediate shown in the formula VI, continuously reacting, performing standing for layering after the reaction is finished, extracting, concentrating and filtering to obtain an intermediate shown in a formula VII; and d) slowly adding the intermediate shown in the formula VII into a solvent for reaction, and crystallizing thereaction solution to obtain a clobetasol propionate crude product. The reaction route is as follows. The preparation method disclosed by the invention is efficient, green and environment-friendly, andthe purity and yield of the clobetasol propionate product are high.

Preparation method of clobetasol propionate

-

Paragraph 0065-0067, (2018/03/25)

The invention provides a brand new synthesis route for preparation of clobetasol propionate; adopted raw materials are cheaper and are easier to obtain, reactive raw materials are hydroxylated and then chloridized, carbonyl protection groups are removed, five-membered ring double bonds are subjected to selective oxidation and reduction, after esterification, six-membered ring double bonds are subjected to epoxidation, and then fluorination ring opening is performed to obtain the clobetasol propionate product. The reaction process is easy to operate, the yield of each step is relatively high, the purity of the obtained product is higher, the formation of by-products is effectively avoided, the production cost is reduced and industrialized production is facilitated.

Composition for the topical treatment of poison ivy and other forms of contact dermatitis

-

, (2008/06/13)

Composition for topical administration comprising (a) a corticosteroid, and (b) a drying agent.

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