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25122-46-7

Basic Information
CAS No.: 25122-46-7
Name: Clobetasol propionate
Article Data: 8
Molecular Structure:
Molecular Structure of 25122-46-7 (Clobetasol propionate)
Formula: C25H32ClFO5
Molecular Weight: 466.977
Synonyms: Pregna-1,4-diene-3,20-dione,21-chloro-9-fluoro-11b,17-dihydroxy-16b-methyl-,17-propionate (8CI);21-Chloro-21-deoxybetamethasone 17-propionate;CCl 4725;CGP 9555;Clobederm;Clobesol;Clobetasol 17-propionate;Clobex;Dermoval;Dermovate;Dermoxinale;GR 2/925;Karison;Olux;Skin Cap;Temovate;Pregna-1,4-diene-3,20-dione,21-chloro-9-fluoro-11-hydroxy-16-methyl-17-(1-oxopropoxy)-, (11b,16b)-;
EINECS: 246-634-3
Density: 1.28 g/cm3
Melting Point: 195.5-197 °C
Boiling Point: 569 °C at 760 mmHg
Flash Point: 297.9 °C
Appearance: White crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36
PSA: 80.67000
LogP: 4.10310
Synthetic route

C25H31ClO5

25122-46-7

clobetasol-17-propionate

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

C25H31ClO5

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%
1062-09-5

Betamethasone 17α,21-ethyl orthopropanoate

25122-46-7

clobetasol-17-propionate

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

C22H26O2

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

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

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

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
116846-77-6

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

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
25122-46-7

clobetasol-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
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Chemistry


IUPAC Name: [(8S,9R,10S,11S,13S,14S,16S,17R)-17-(2-Chloroacetyl)-9-fluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate
Molecular Weight: 466.969983 [g/mol]
Molecular Formula: C25H32ClFO5
XLogP3: 3.8
H-Bond Donor: 1
H-Bond Acceptor: 6 
EINECS: 246-634-3
Product Categories: Organics; Intermediates & Fine Chemicals; Pharmaceuticals 
Index of Refraction: 1.56
Molar Refractivity: 117.75 cm3
Molar Volume: 364.1 cm3
Surface Tension: 48.9 dyne/cm
Density: 1.28 g/cm3
Flash Point: 297.9 °C
Enthalpy of Vaporization: 98.07 kJ/mol
Boiling Point: 569 °C at 760 mmHg
Vapour Pressure: 2.58E-15 mmHg at 25 °C
Water Solubility: 3.860 mg/L at 25 °C
Appearance: White Crystalline Powder
Melting Point: 195.5-197 °C
Classification Code of Clobetasol propionate (CAS NO.25122-46-7): Anti-inflammatory; Drug / Therapeutic Agent; Hormone; Reproductive Effect

Uses

 Clobetasol propionate (CAS NO.25122-46-7) is used for the treatment of various skin disorders including eczema, psoriasis, and lichen sclerosus. It is also used to treat several auto-immune diseases including alopecia areata, vitiligo and lichen planus (auto immune skin nodules).

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 118mg/kg (118mg/kg)   Drugs in Japan Vol. 6, Pg. 241, 1982.
mouse LD50 oral > 3gm/kg (3000mg/kg)   Drugs in Japan Vol. 6, Pg. 241, 1982.
mouse LD50 subcutaneous 81700ug/kg (81.7mg/kg)   Drugs in Japan Vol. 6, Pg. 241, 1982.
rat LD50 intraperitoneal 351mg/kg (351mg/kg)   Drugs in Japan Vol. 6, Pg. 241, 1982.
rat LD50 oral > 3gm/kg (3000mg/kg)   Drugs in Japan Vol. 6, Pg. 241, 1982.
rat LD50 subcutaneous 366mg/kg (366mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 9, Pg. 1066, 1978.

Safety Profile

Hazard Codes:Xi
Risk Statements:36/37/38
36/37/38:Irritating to eyes, respiratory system and skin  
Safety Statements:26-36
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
36:Wear suitable protective clothing
Poison by subcutaneous and intraperitoneal routes. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of F and Cl.

Specification

  Clobetasol propionate (CAS NO.25122-46-7), its Synonyms are 21-Chloro-9-fluoro-11-hydroxy-16-methyl-17-(1-oxopropoxy)pregna-1,4-diene-3,20-dione (11beta,16beta)- ; 21-Chloro-9-fluoro-11beta,17-dihydroxy-16beta-methylpregna-1,4-diene-3,20-dione 17-propionate ; Butavate ; Clobesol ; Clobetasol 17-propionate ; Clobex ; Cormax ; Dermoval ; Dermovate ; Dermoxinale ; Embeline ; Embeline E ; Olux-E ; Temovate ; Temovate E ; Pregna-1,4-diene-3,20-dione, 21-chloro-9-fluoro-11-beta,17-dihydroxy-16-beta-methyl-, 17-propionate ; Pregna-1,4-diene-3,20-dione, 21-chloro-9-fluoro-11-hydroxy-16-methyl-17-(1-oxopropoxy)-, (11beta,16beta)- .

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