prednicarbate   

GtoPdb Ligand ID: 7605

Synonyms: Dermatop® | Hoe 777 | Hoe-777 | S-770777
prednicarbate is an approved drug (FDA (1991))
Compound class: Synthetic organic
Comment: Prednicarbate is a nonhalogenated derivative of prednisolone.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 8
Hydrogen bond donors 1
Rotatable bonds 9
Topological polar surface area 116.2
Molecular weight 488.24
XLogP 2.92
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CCOC(=O)OC1(CCC2C1(C)CC(O)C1C2CCC2=CC(=O)C=CC12C)C(=O)COC(=O)CC
Isomeric SMILES CCOC(=O)O[C@@]1(CC[C@@H]2[C@]1(C)C[C@H](O)[C@H]1[C@H]2CCC2=CC(=O)C=C[C@]12C)C(=O)COC(=O)CC
InChI InChI=1S/C27H36O8/c1-5-22(31)34-15-21(30)27(35-24(32)33-6-2)12-10-19-18-8-7-16-13-17(28)9-11-25(16,3)23(18)20(29)14-26(19,27)4/h9,11,13,18-20,23,29H,5-8,10,12,14-15H2,1-4H3/t18-,19-,20-,23+,25-,26-,27-/m0/s1
InChI Key FNPXMHRZILFCKX-KAJVQRHHSA-N
No information available.
Summary of Clinical Use
Prednicarbate is a topical corticosteroid drug [1]. It is used to relieve inflammatory and pruritic symptoms of corticosteroid-responsive skin conditions such as seborrheic or atopic dermatitis, localized neurodermatitis, psoriasis, the late phase of allergic contact dermatitis and the inflammatory phase of xerosis cutis. Prednicarbate is claimed to have low atrophogenic potential compared to other glucocorticoids [2-3].
Mechanism Of Action and Pharmacodynamic Effects
Glucocorticoids cause their effects by binding to the glucocorticoid receptor (GR). The GR-drug complex translocates to the nucleus where it transactivates the expression of genes containing glucocorticoid response elements (GREs). Target genes include those for anti-inflammatory proteins and the net effect is a reduction of prostaglandin and leukotriene biosynthesis.
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