Ulobetasol propionateProduct ingredient for Ulobetasol

Name
Ulobetasol propionate
Drug Entry
Ulobetasol

Ulobetasol (as ulobetasol 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.

Accession Number
DBSALT001867
Structure
Thumb
Synonyms
Halobetasol propionate / Miracorten
External IDs
BMY-30056 / CGP-14,458 / CGP-14458
UNII
91A0K1TY3Z
CAS Number
66852-54-8
Weight
Average: 484.96
Monoisotopic: 484.1828081
Chemical Formula
C25H31ClF2O5
InChI Key
BDSYKGHYMJNPAB-LICBFIPMSA-N
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
IUPAC Name
(1R,2S,8S,10S,11S,13S,14R,15S,17S)-14-(2-chloroacetyl)-1,8-difluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-14-yl propanoate
SMILES
[H][C@@]12C[C@H](C)[C@](OC(=O)CC)(C(=O)CCl)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])C[C@H](F)C2=CC(=O)C=C[C@]12C
External Links
ChemSpider
5293389
ChEBI
135782
ChEMBL
CHEMBL1200908
Wikipedia
Ulobetasol_propionate
Predicted Properties
PropertyValueSource
Water Solubility0.00757 mg/mLALOGPS
logP3.81ALOGPS
logP3.84ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)13.55ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area80.67 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity119.15 m3·mol-1ChemAxon
Polarizability48.1 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon