(1R,2S,10S,11S,13S,14R,15S,17S)-14-(2-chloroacetyl)-1-fluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl propanoate

• ChemBase ID: 886
• Molecular Formular: C25H32ClFO5
• Molecular Mass: 466.9699832
• Monoisotopic Mass: 466.19223002
• SMILES: ClCC(=O)[C@]1(OC(=O)CC)[C@@]2([C@H]([C@H]3[C@](F)([C@@H](O)C2)[C@@]2(C(=CC(=O)C=C2)CC3)C)C[C@@H]1C)C
• Canonical SMILES: CCC(=O)O[C@@]1([C@@H](C)C[C@@H]2[C@]1(C)C[C@H](O)[C@]1([C@H]2CCC2=CC(=O)C=C[C@]12C)F)C(=O)CCl
• 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
• InChIKey: CBGUOGMQLZIXBE-XGQKBEPLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,10S,11S,13S,14R,15S,17S)-14-(2-chloroacetyl)-1-fluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl propanoate; (1R,2S,10S,11S,13S,14R,15S,17S)-14-(2-chloroacetyl)-1-fluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl propanoate
• IUPAC Traditional name: clobetasol; temovate
• Brand Name: Clobesol; Clobetasol Propionate; Clobetasol propionate [USAN:JAN]; Clobetasole propionate; Clobetasolpropionat mikron.; Clobex; Dermovate; Embeline; Embeline E; Olux; Temovate; Temovate E
• Synonyms: Clobetasol propionate; Clobetasol; Clobetasol propionate; (11β,16β)-21-Chloro-9-fluoro-11-hydroxy-16-methyl-17-(1-oxopropoxy)pregna-1,4-diene-3,20-dione; 21-Chloro-21-deoxybetamethasone 17-Propionate; Clobederm; Clobesol; Clobex; Dermoval; Dermovate; Dermoxin; Dermoxinale; GR 2/925; Karison; Olux; Skin Cap; Temovate; Clobetasol 17-Propionate; 丙酸氯倍他索

Database IDs

• CAS Number: 25122-46-7
• EC Number: 246-634-3
• MDL Number: MFCD00058499
• PubChem SID: 160964349; 24893013
• PubChem CID: 32798

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.626671
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 4.1778226
• LogD (pH = 7.4): 4.1778226
• Log P: 4.1778226
• Molar Refractivity: 119.3223 cm^3
• Polarizability: 46.51583 Å^3
• Polar Surface Area: 80.67 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.49
• LOG S: -5.05
• Solubility (Water): 4.13e-03 g/l

PROPERTIES

Physical Property

• Solubility: 3.86 mg/L; Dioxane; DMSO
• Apperance: White Solid
• Melting Point: 191-193°C
• Hydrophobicity(logP): 3

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• RTECS: TU3725000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 2
• Risk Statements: 61-48/20/21-53-62
• Safety Statements: 53-36/37-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H360Df-H373-H413
• GHS Precautionary statements: P201-P308 + P313
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: rat ... Nr3c1(24413)
• Target Organ: Adrenal gland, Immune system

Product Information

• Purity: ≥98%
• Grade: analytical standard
• Salt Data: propionate

DETAILS

DrugBank - DB01013

• Drug Groups: approved
• Description: A derivative of prednisolone with high glucocorticoid activity and low mineralocorticoid activity. Absorbed through the skin faster than fluocinonide, it is used topically in treatment of psoriasis but may cause marked adrenocortical suppression. [PubChem]
• Indication: For short-term topical treatment of the inflammatory and pruritic manifestations of moderate to severe corticosteroid-responsive dermatoses of the scalp.
• Pharmacology: Like other topical corticosteroids, clobetasol has anti-inflammatory, antipruritic, and vasoconstrictive properties. It is a very high potency topical corticosteroid that should not be used with occlusive dressings. It is recommended that treatment should be limited to 2 consecutive weeks and therapy should be discontinued when adequate results have been achieved.
• Toxicity: Oral LD₅₀ in rat and mouse is >3000 mg/kg. Topically applied clobetasol can be absorbed in sufficient amounts to produce systemic effects. Symptoms of overdose include thinning of skin and suppression of adrenal cortex (decreased ability to respond to stress).
• Affected Organisms: Humans and other mammals
• Biotransformation: Metabolized, primarily in the liver, and then excreted by the kidneys.
• Absorption: Topical corticosteroids can be absorbed from intact healthy skin. The extent of percutaneous absorption of topical corticosteroids is determined by many factors, including the vehicle and the integrity of the epidermal barrier. Occlusion, inflammation and/or other disease processes in the skin may also increase percutaneous absorption.
• Elimination: Corticosteroids are metabolized primarily in the liver and are then excreted by the kidneys. Some of the topical corticosteroids, including clobetasol propionate and its metabolites, are also excreted into the bile.
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Selleck Chemicals - S2584

Research Area: Inflammation
Biological Activity:
Clobetasol propionate is a anti-inflammatory corticosteroid used to treat various skin disorders including eczema and psoriasis. Clobetasol propionate is also highly effective for contact dermatitis caused by exposure to poison ivy/oak. Clobetasol belongs to US Class I (Europe: class IV) of the corticosteroids, making it one of the most potent available. Clobetasol propionate has very high potency and typically should not be used with occlusive dressings, or for extended continuous use (beyond two weeks). Clobetasol propionate is also used to treat several auto-immune diseases including alopecia areata, vitiligo and lichen planus. [1][2]References on Clobetasol propionate[1] http://en.wikipedia.org/wiki/Clobetasol_propionate, , [2] Forensic Sci Int. , 2011 Apr 5,

Sigma Aldrich - C8037

Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C8037.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - C583500

Topical corticosteroid. Glucocorticoid; anti-inflammatory.

REFERENCES

• Nam YS et al. Forensic Sci Int. 2011 Apr 5
• Olsen, E.A., et al.: J. Am. Acad. Dermatol., 15, 246 (1986)