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[(6S,9R,16S,17R)-17-(2-chloroacetyl)-6,9-difluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate

HCID 48175
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Basic information

CAS
66852-54-8
Standard SMILES
CCC(=O)O[C@]1(C(=O)CCl)[C@@H](C)CC2C3C[C@H](F)C4=CC(=O)C=CC4(C)[C@@]3(F)C(O)CC21C
InChIKey
BDSYKGHYMJNPAB-YKQIDFLYSA-N
Molecular formula
C25H31ClF2O5
Average molar mass
485 g/mol
Monoisotopic mass
484.1828081

Overview

Halobetasol Propionate can cause developmental toxicity according to state or federal government labeling requirements.

Names & identifiers

Preferred name
[(6S,9R,16S,17R)-17-(2-chloroacetyl)-6,9-difluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate
IUPAC
[(6S,9R,16S,17R)-17-(2-chloroacetyl)-6,9-difluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate
English name
Halobetasol propionate
Molecular formula
C25H31ClF2O5
Molecular weight
484.96

Names & synonyms

[(6S,9R,16S,17R)-17-(2-chloroacetyl)-6,9-difluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoateC25H31ClF2O5NCGC00167451-01orb1300689orb3025489SCHEMBL1650038CHEMBL1876307AKOS037748810AS-14150T6529Q20817068CGP-14458
Show more names
BMY-30056UltravateMiracortenulobetasol propionateUiobetasol PropionateHalobatasol ProionateHALOBETASOL PROPIONATEHalobetasolPropionate>Halobetasol propionate-d3

Database identifiers

CAS
66852-54-8
PubChem CID

Properties

Computed structural properties

XLogP
3.7
Topological polar surface area
80.7 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
7
Rotatable bonds
5
Heavy atoms
33
Formal charge
0
Complexity
964

Experimental & physicochemical properties

LogP2.9
Solubility7.57e-03 g/L
Physical DescriptionSolid

Physicochemical properties

Melting point
213 · 213-215°C
Boiling point
570.7 · 570.7±50.0 °C(Predicted)
Density
1.31 · 1.31±0.1 g/cm3(Predicted)
storage temp.
Refrigerator
solubility
Dioxane (Sparingly), DMSO (Slightly), Methanol (Slightly)
form
Solid
pka
12.55 · 12.55±0.70(Predicted)
color
White to Off-White
Major Application
pharmaceutical (small molecule)
InChIKey
BDSYKGHYMJNPAB-QNGYMBKVNA-N
SMILES
O([C@@]1([C@H](C[C@@]2([H])[C@]3([H])C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]12C)C)C(=O)CCl)C(=O)CC |&1:1,2,4,6,9,17,19,21,24,r|

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

wgk
WGK 3
hs_code
2937220000
Signal word
Danger
Symbol(GHS)
GHS08
Storage Class
11 - Combustible Solids
Hazard statements
H372-H341-H361
Precautionary statements
P260-P264-P270-P314-P501-P201-P202-P281-P308+P313-P405-P501-P201-P202-P281-P308+P313-P405-P501

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm
Applications · 2 items

DescriptionHalobetasol propionate is a new ultra-potent topical corticosteroid exhibiting both antiinflammatory and antihyperplasia properties. The compound is recommended for the treatment of moderate to severe corticosteroid-responsive dermatoses and appears to be particularly effective in patients with plaque psoriasis. It inhibits dermatitis induced by ultraviolet light in guinea pigs (ED50 = 1.45 μg/animal) and by oxazolone in mice (ED50 = 0.8 μg/animal). Halobetasol propionate also has anti-inflammatory effects on croton oil-induced ear edema in rats (ED50s = 10 μg/ml and 0.5 μg/ear) and mice (ED50s = 1.2 and <0.32 μg/ear after 6 and 24 hours of treatment, respectively). Topical formulations containing halobetasol propionate have been used for inflammatory and pruritic dermatitis.

UsesHalobetasol propionate is a corticosteroid (cortisone-like medicine or steroid). As an anti-inflammatory drug, halobetasol topical is used to help relieve redness, itching, swelling, or other discomfort caused by certain skin conditions. It is also used to treat plaque psoriasis.This medicine is available only with doctor's prescription.

Upstream & downstream products

Upstream raw materials

AcetylacetoneMethanesulfonyl chlorideLithium chloride6α,9α-difluoro-11β,17,21-trihydroxy-16β-methylpregna-1,4-diene-3,20-dione, 21-propionateDiflorasone 17-propionate

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
48175
ChEMBL
CHEMBL1876307
CAS DataBase Reference
66852 · 66852-54-8(CAS DataBase Reference)
FDA UNII
91 A0K1TY3Z · 91A0K1TY3Z
Proposition 65 List
Halobetasol Propionate
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
Symbol(GHS)
8 · GHS08
Signal word
Danger
Hazard statements
372 · H372-H341-H361
Precautionary statements
260 · P260-P264-P270-P314-P501-P201-P202-P281-P308+P313-P405-P501-P201-P202-P281-P308+P313-P405-P501
WGK Germany
3 · WGK 3
HS Code
2937220000 · 2937220000
Storage Class
11 · 11 - Combustible Solids
Diflorasone 17-propionate-21-mesylate
HALOBETASOL
Diflorasone

Additional notes

DefinitionChEBI: Ulobetasol propionate is a corticosteroid hormone.