3D Mol Similar

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; Modify Date.: 2022-11-25 02:23; Introduction: Clobetasol-17-propionate is a topical corticosteroid belonging to the group-D (hydrocortisone-q-butyrate) type of steroids. View more+

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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; View all

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 InChIkey: 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

2.1 Density: 1.28

2.1 Melting point: 195.5-197 °C

2.1 Boiling point: 569 oC at 760 mmHg

2.1 Refractive index: 1.56

2.1 Flash Point: 297.9 oC

2.1 Precise Quality: 466.19200

2.1 PSA: 80.67000

2.1 logP: 4.10310

2.1 Appearance: White Crystalline Powder

2.2 Chemical Properties: White or almost white, crystalline powder.

2.3 pKa: 12.88±0.70(Predicted)

2.4 Water Solubility: 3.860 mg/L?at 25 °C in water

2.5 StorageTemp: Keep in dark place,Sealed in dry,2-8°C

3. Use and Manufacturing

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

3.2 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; View all

3.3 Usage: Clobetasol-17-propionate is a topical corticosteroid belonging to the group-D (hydrocortisone-q-butyrate) type of steroids.

4. Safety and Handling

4.1 Symbol: GHS08

4.1 Hazard Codes: Xi

4.1 Signal Word: Danger

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: S26;S36

4.1 Hazard Declaration: H360Df-H373-H413

4.1 RIDADR: NONH for all modes of transport

4.1 Caution Statement: P201-P260-P280-P308 + P313

4.1 WGK Germany: 2

4.1 RTECS: TU3725000

4.1 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^?.

4.2 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)- .

4.3 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.

View all

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

View all

6. Synthesis Route

25122-46-7Total: 1 Synthesis Route

1062-09-5 2 Suppliers

25122-46-7 430 Suppliers

Literatures:
CH609709DE2613875 , ; Chem.Abstr., , vol. 86, # 90137
Yield: null

7. Precursor and Product

precursor:

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 (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

8.13 Collision Cross Section: 205.1 ?2 [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

8.14 Mesh: A group of CORTICOSTEROIDS that affect carbohydrate metabolism (GLUCONEOGENESIS, liver glycogen deposition, elevation of BLOOD SUGAR), inhibit ADRENOCORTICOTROPIC HORMONE secretion, and possess pronounced anti-inflammatory activity. They also play a role in fat and protein metabolism, maintenance of arterial blood pressure, alteration of the connective tissue response to injury, reduction in the number of circulating lymphocytes, and functioning of the central nervous system. (See all compounds classified as Glucocorticoids.)|Substances that reduce or suppress INFLAMMATION. (See all compounds classified as Anti-Inflammatory Agents.)

8.15 Absorption: Twice daily application of clobetasol foam leads to a C_max of 59±36pg/mL with a T_max of 5 hours. Clobetasol cream showed an increase in clobetasol concentrations from 50.7±96.0pg/mL to 56.3±104.7pg/mL.|Corticosteroids are eliminated predominantly in the urine.|Data regarding the volume of distribution of clobetasole propionate are not readily available.|Data regarding the clearance of clobetasol propionate are not readily available.

8.16 Metabolism: The metabolism of clobetasol propionate is not well studied but it does induce metabolic enzymes, even when delivered topically. The metabolism of clobetasol propionate is predicted to follow similar metabolic pathways to other corticosteroids including the addition of oxygen, hydrogen, glucuronides, and sulfates to form water soluble metabolites.

8.17 Biological Half Life: Data regarding the half life of clobetasol propionate are not readily available.

8.18 Use Classification: Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Pharmaceuticals

9. Computational chemical data

Molecular Weight: 466.974g/mol
Molecular Formula: C₂₅H₃₂ClFO₅
Compound Is Canonicalized: True
XLogP3-AA: null
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
CACTVS Substructure Key Fingerprint: AAADcfB4OQAEAAAAAAAAAAAAAAAAAYAAAAAwYIAAAAAAAGDAAAAAGwIACAAAD1eggEICCAAABgCIAqDSCAIAAAAgAAAICAFAAkhAEBIBAQQCQAAEgAAIAYPIzPDPgAAAAAAAAADAAAYAADAAAYAADAAAAA==

10. Question & Answer

What is Clobetasol propionate? Sep 11 2024
Overview Clobetasol propionate is a topical steroid medication known for its anti-inflammatory, antipruritic, vasoconstrictive, and immunomodulatory properties. It is commonly prescribed to treat vari..
What is Clobetasol propionate and its benefits? May 15 2024
Clobetasol propionate, also known as Clobetasol propionate, is an organic compound that belongs to the class of anti-inflammatory corticosteroids. It is 112.5 times more potent in its anti-inflammator..
What is Clobetasol propionate and how is it used? Jan 07 2023
Clobetasol propionate is a corticosteroid that comes in the form of a white or slightly yellow crystalline powder. It has anti-inflammatory, anti-allergic, and immune-suppressing properties. It can re..
Can Clobetasol propionate be used for a long time? Nov 21 2022
The treatment effect of Clobetasol propionate is very good, and it can be used to treat a wide range of skin diseases such as chronic eczema, neurodermatitis, psoriasis, and lichen planus. The effects..

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