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Home> Encyclopedia >   /  Pharmaceutical  /  Pharmaceutical Intermediates  /  Hormones and synthetic substitutes  /  Organic Intermediate  /  Other Auxiliary Agent
Clobetasol propionate structure
Clobetasol propionate structure

Clobetasol propionate

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
CAS No.:25122-46-7
Molecular Weight:466.974
Introduction: Clobetasol-17-propionate is a topical corticosteroid belonging to the group-D (hydrocortisone-q-butyrate) type of steroids. View more+
1. Names and Identifiers
1.1 Name
Clobetasol propionate
1.2 Synonyms

(11Β,16Β)-21-chloro-9-fluoro-11-hydroxy-16-methyl-3,20-dioxopregna-1,4-dien-17-yl propanoate (11Β,16Β)-21-Chloro-9-fluoro-11-hydroxy-16-methyl-3,20-dioxopregna-1,4-dien-17-yl propionate (8S,9R,10S,11S,13S,14S,16S,17R)-17-(Chloracetyl)-9-fluor-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-ylpropanoat (8S,9R,10S,11S,13S,14S,16S,17R)-17-(chloroacetyl)-9-fluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl propanoate [(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 17-propionate 21-Chloro-9-fluoro-11b,17-dihydroxy-16b-methylpregna-1,4-diene-3,20-dione 17-propionate 21-Chloro-9α-fluoro-11Β,17α-dihydroxy-16Β-methyl-1,4-pregnadiene-3,20-dione 17-Propionate CCl 4725 cgp9555 clobesol Clobetasol 17- propionate solution,100ppm Clobetasol 17-Propionate CLOBETASOL 17-PROPIONATE USP Clobetasol propionate (JAN/USP) Clobetasol propionate [USAN:JAN] clobetasol-17-propionate Clobetasolpropionate CloΒsol 17-Propionate Cloβsol propionate Dermoval Dermovate Dermoxin EINECS 246-634-3 GR 2/925 GR-2/92 MFCD00058499 Olux Pregna-1,4-diene-3,20-dione, 21-chloro-9-fluoro-11-hydroxy-16-methyl-17-(1-oxopropoxy)-, (11Β,16Β)- propanoate de (8S,9R,10S,11S,13S,14S,16S,17R)-17-(chloroacétyl)-9-fluoro-11-hydroxy-10,13,16-triméthyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodécahydro-3H-cyclopenta[a]phénanthrén-17-yle Psorex Temovate

1.3 CAS No.
25122-46-7
1.4 CID
32798
1.5 EINECS(EC#)
246-634-3
1.6 Molecular Formula
C25H32ClFO5 (isomer)
1.7 Inchi
InChI=1S/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
1.8 InChkey
CBGUOGMQLZIXBE-XGQKBEPLSA-N
1.9 Canonical Smiles
CCC(=O)OC1(C(CC2C1(CC(C3(C2CCC4=CC(=O)C=CC43C)F)O)C)C)C(=O)CCl
1.10 Isomers Smiles
CCC(=O)O[C@@]1([C@H](C[C@@H]2[C@@]1(C[C@@H]([C@]3([C@H]2CCC4=CC(=O)C=C[C@@]43C)F)O)C)C)C(=O)CCl
2. Properties
3.1 Density
1.28
3.1 Melting point
195.5-197 °C
3.1 Boiling point
569 oC at 760 mmHg
3.1 Refractive index
1.56
3.1 Flash Point
297.9 oC
3.1 Vapour pressure
2.58E-15mmHg at 25°C
3.1 Precise Quality
466.19200
3.1 PSA
80.67000
3.1 logP
4.10310
3.1 Appearance
White Crystalline Powder
3.2 Chemical Properties
White or almost white, crystalline powder.
3.3 pKa
12.88±0.70(Predicted)
3.4 Water Solubility
3.860 mg/L?at 25 °C in water
3.5 StorageTemp
Keep in dark place,Sealed in dry,2-8°C
3. Use and Manufacturing
4.1 Definition
ChEBI: The 17-O-propionate ester of clobetasol. A potent corticosteroid, it is used to treat various skin disorders, including exzema and psoriasis.
4.2 GHS Classification
Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 61 companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H315 (36.07%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (36.07%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (34.43%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
H360 (59.02%): May damage fertility or the unborn child [Danger Reproductive toxicity]
H373 (59.02%): Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]
H413 (57.38%): May cause long lasting harmful effects to aquatic life [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, P261, P264, P271, P273, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P314, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501
4.3 Usage
Clobetasol-17-propionate is a topical corticosteroid belonging to the group-D (hydrocortisone-q-butyrate) type of steroids.
4. Safety and Handling
5.1 Symbol
GHS08
5.1 Hazard Codes
Xi
5.1 Signal Word
Danger
5.1 Risk Statements
R36/37/38
5.1 Safety Statements
S26;S36
5.1 Hazard Declaration
H360Df-H373-H413
5.1 RIDADR
NONH for all modes of transport
5.1 Caution Statement
P201-P260-P280-P308 + P313
5.1 WGK Germany
2
5.1 RTECS
TU3725000
5.1 Safety

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?.

5.2 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)- .

5.3 Toxicity

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.

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

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 4

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

H413 May cause long lasting harmful effects to aquatic life

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.

P273 Avoid release to the environment.

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

6. Synthesis Route
25122-46-7Total: 1 Synthesis Route
7. Precursor and Product
precursor:
1062-09-5
1062-09-5
8. Other Information
8.0 Target
Value
8.1 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.
8.2 Indications
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.
8.3 Chemical Properties
White or almost white, crystalline powder.
8.4 Originator
Dermovate,Glaxo,UK,1973
8.5 Uses
Clobetasol-17-propionate is a topical corticosteroid belonging to the group-D (hydrocortisone-q-butyrate) type of steroids.
8.6 Uses
For short-term topical treatment of the inflammatory and pruritic manifestations of moderate to severe corticosteroid-responsive dermatoses of the scalp.
8.7 Uses
Topical corticosteroid. Glucocorticoid; anti-inflammatory.
Clobetasol Propionate
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.
8.8 Definition
ChEBI: The 17-O-propionate ester of clobetasol. A potent corticosteroid, it is used to treat various skin disorders, including exzema and psoriasis.
8.9 Indications
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.
8.10 Manufacturing Process
A solution of betamethasone 21-methanesulfonate (4 g) in dimethylformamide (25 ml) was treated with lithium chloride (4 g) and the mixture heated on the steam bath for 30 minutes. Dilution with water gave the crude product which was recrystallized to afford the title compound, MP 226°C.
Clobetasol is usually converted to the propionate as the useful form by reaction with propionic anhydride.
8.11 Brand name
Clobex (Galderma); Clobex (Galderma); Embeline (Healthpoint); Olux (Connetics); Temovate (Altana).
8.12 Therapeutic Function
Corticosteroid, Antiinflammatory
9. Computational chemical data
  • Molecular Weight:466.974g/mol
  • Molecular Formula:C25H32ClFO5
  • Compound Is Canonicalized:True
  • XLogP3-AA:
  • Exact Mass:466.1922300
  • Monoisotopic Mass:466.1922300
  • Complexity:929
  • Rotatable Bond Count:5
  • Hydrogen Bond Donor Count:1
  • Hydrogen Bond Acceptor Count:6
  • Topological Polar Surface Area:80.7
  • Heavy Atom Count:32
  • Defined Atom Stereocenter Count:8
  • Undefined Atom Stereocenter Count:0
  • Defined Bond Stereocenter Count:0
  • Undefined Bond Stereocenter Count:0
  • Isotope Atom Count:0
  • Covalently-Bonded Unit Count:1
10. Question & Answer
  • Patents & Indications 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 ...
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