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382-67-2 molecular structure
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(1R,2S,10S,11S,13R,14S,15S,17S)-1-fluoro-17-hydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one

ChemBase ID: 429
Molecular Formular: C22H29FO4
Molecular Mass: 376.4616632
Monoisotopic Mass: 376.20498763
SMILES and InChIs

SMILES:
F[C@@]12[C@H]([C@H]3[C@@]([C@H]([C@@H](C3)C)C(=O)CO)(C[C@@H]1O)C)CCC1=CC(=O)C=C[C@]21C
Canonical SMILES:
OCC(=O)[C@H]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
InChI:
InChI=1S/C22H29FO4/c1-12-8-16-15-5-4-13-9-14(25)6-7-21(13,3)22(15,23)18(27)10-20(16,2)19(12)17(26)11-24/h6-7,9,12,15-16,18-19,24,27H,4-5,8,10-11H2,1-3H3/t12-,15+,16+,18+,19-,20+,21+,22+/m1/s1
InChIKey:
VWVSBHGCDBMOOT-IIEHVVJPSA-N

Cite this record

CBID:429 http://www.chembase.cn/molecule-429.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1R,2S,10S,11S,13R,14S,15S,17S)-1-fluoro-17-hydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one
(1R,2S,10S,11S,13R,14S,15S,17S)-1-fluoro-17-hydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one
IUPAC Traditional name
desoximetasone
Brand Name
Topicort
Topicort LP
Synonyms
Desoximetasone
(11β,16α)-9-Fluoro-11,21-dihydroxy-16-methyl-pregna-1,4-diene-3,20-dione
17-Deoxydexamethasone
9-Fluoro-16α-methyl-1-corticosterone
Desoximetasone
Stidex
Topicort
Topicorte
Topisolon
Desoxymetasone
Desoximetasone
9-氟-11β,21-二羟基-16α-甲基孕甾-1,4-二烯-3,20-二酮
去羟米松
CAS Number
382-67-2
EC Number
206-845-3
MDL Number
MFCD00083301
PubChem SID
160963892
46506793
24893994
PubChem CID
5311067

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 13.440161  H Acceptors
H Donor LogD (pH = 5.5) 2.351041 
LogD (pH = 7.4) 2.3510406  Log P 2.351041 
Molar Refractivity 101.1699 cm3 Polarizability 38.960907 Å3
Polar Surface Area 74.6 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.13  LOG S -4.08 
Solubility (Water) 3.10e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
42.1 mg/L expand Show data source
Chloroform expand Show data source
Methanol expand Show data source
Apperance
Off-White Solid expand Show data source
Melting Point
213-215°C expand Show data source
Hydrophobicity(logP)
2.3 expand Show data source
Storage Condition
Refrigerator expand Show data source
RTECS
TU3834000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
20/21/22-36/37/38-40-43 expand Show data source
Safety Statements
22-26-36 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302-H312-H315-H317-H319-H332-H335-H351 expand Show data source
GHS Precautionary statements
P261-P280-P305 + P351 + P338 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank TRC TRC
DrugBank - DB00547 external link
Item Information
Drug Groups approved
Description A topical anti-inflammatory glucocorticoid used in dermatoses, skin allergies, psoriasis, etc. [PubChem]
Indication For the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.
Pharmacology Like other topical corticosteroids, desoximetasone has anti-inflammatory, antipruritic, and vasoconstrictive properties. Once absorbed through the skin, topical corticosteroids are handled through pharmacokinetic pathways similar to systemically administered corticosteroids. Desoximetasone is a potent 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 Topically applied desoximetasone 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.
Half Life The half-life of the material was 15 ± 2 hours (for urine) and 17 ± 2 hours (for feces) between the third and fifth trial day.
Protein Binding Bound to plasma proteins in varying degrees.
Elimination Corticosteroids are bound to plasma proteins in varying degrees, are metabolized primarily in the liver and excreted by the kidneys. Some of the topical corticosteroids and their metabolites are also excreted into the bile.Pharmacokinetic studies in men with Desoximetasone Cream USP, 0.25% with tagged desoximetasone showed a total of 5.2% ± 2.9% excretion in urine (4.1% ± 2.3%) and feces (1.1% ± 0.6%)
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Toronto Research Chemicals - D296970 external link
Glucocorticoid anti-inflammatory. It is also found as an impurity in Dexamethasone (D298800).

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Lee, P., et al.: Bioorg. Med. Chem. Lett., 20, 69 (2010)
  • • Schriks, M., et al.: Environ. Sci. Technol., 44, 4766 (2010)
  • • Baeck, M., et al.: Eur. J. Dermatol., 20, 102 (2010)
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PATENTS

PATENTS

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INTERNET

INTERNET

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