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66852-54-8 molecular structure
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(1R,8S,13S,14R)-14-(2-chloroacetyl)-1,8-difluoro-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: 478
Molecular Formular: C25H31ClF2O5
Molecular Mass: 484.9604464
Monoisotopic Mass: 484.18280821
SMILES and InChIs

SMILES:
ClCC(=O)[C@]1(OC(=O)CC)C2(C(C3[C@](F)(C(O)C2)C2(C(=CC(=O)C=C2)[C@@H](F)C3)C)C[C@@H]1C)C
Canonical SMILES:
CCC(=O)O[C@@]1([C@@H](C)CC2C1(C)CC(O)[C@]1(C2C[C@@H](C2=CC(=O)C=CC12C)F)F)C(=O)CCl
InChI:
InChI=1S/C25H31ClF2O5/c1-5-21(32)33-25(20(31)12-26)13(2)8-15-16-10-18(27)17-9-14(29)6-7-22(17,3)24(16,28)19(30)11-23(15,25)4/h6-7,9,13,15-16,18-19,30H,5,8,10-12H2,1-4H3/t13-,15?,16?,18-,19?,22?,23?,24-,25-/m0/s1
InChIKey:
BDSYKGHYMJNPAB-YKQIDFLYSA-N

Cite this record

CBID:478 http://www.chembase.cn/molecule-478.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1R,8S,13S,14R)-14-(2-chloroacetyl)-1,8-difluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl propanoate
IUPAC Traditional name
halobetasol propionate
Brand Name
Halobetasol
Ulobetasol Propionate
Ultravate
Synonyms
Halobetasol Propionate
CAS Number
66852-54-8
PubChem SID
46506187
160963941
PubChem CID
48175

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
DrugBank DB00596 external link
PubChem 48175 external link
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 13.545719  H Acceptors
H Donor LogD (pH = 5.5) 3.8381035 
LogD (pH = 7.4) 3.8381033  Log P 3.8381035 
Molar Refractivity 119.1457 cm3 Polarizability 46.300114 Å3
Polar Surface Area 80.67 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 3.81  LOG S -4.81 
Solubility (Water) 7.57e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Solubility
Mostly insoluble expand Show data source
Hydrophobicity(logP)
2.9 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00596 external link
Item Information
Drug Groups approved
Description Halobetasol propionate is thought to act by the induction of phospholipase A2 inhibitory proteins, collectively called lipocortins. It is postulated that these proteins control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes by inhibiting the release of their common precursor arachidonic acid. Arachidonic acid is released from membrane phospholipids by phospholipase A2. It is used for the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.
Indication For the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.
Affected Organisms
Humans and other mammals
Absorption The extent of percutaneous absorption of topical corticosteroids is determined by many factors including the vehicle and the integrity of the epidermal barrier. Inflammation and/or other disease processes in the skin may increase percutaneous absorption.
External Links
RxList
PDRhealth
Drugs.com

REFERENCES

REFERENCES

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PATENTS

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