carbenoxolone   Click here for help

GtoPdb Ligand ID: 4151

PDB Ligand
Compound class: Synthetic organic
Comment: Carbenoxolone is derived from licorice root, and has a steroid-like chemical structure. Formulations used clinically typically contain carbenoxolone sodium.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 117.97
Molecular weight 570.36
XLogP 6.86
No. Lipinski's rules broken 1
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Canonical SMILES O=C(OC1CCC2(C(C1(C)C)CCC1(C2C(=O)C=C2C1(C)CCC1(C2CC(C)(CC1)C(=O)O)C)C)C)CCC(=O)O
Isomeric SMILES O=C(O[C@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2C(=O)C=C2[C@@]1(C)CC[C@@]1([C@H]2C[C@](C)(CC1)C(=O)O)C)C)C)CCC(=O)O
InChI InChI=1S/C34H50O7/c1-29(2)23-10-13-34(7)27(32(23,5)12-11-24(29)41-26(38)9-8-25(36)37)22(35)18-20-21-19-31(4,28(39)40)15-14-30(21,3)16-17-33(20,34)6/h18,21,23-24,27H,8-17,19H2,1-7H3,(H,36,37)(H,39,40)/t21-,23-,24-,27+,30+,31-,32-,33+,34+/m0/s1
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Summary of Clinical Use Click here for help
Carbenoxolone is not approved by the US FDA or EMA. Its use is authorised by other national approval agencies, where it is used for the treatment of peptic, esophageal and oral ulceration and inflammation.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Carbenoxolone inhibits 11β-hydroxysteroid dehydrogenase type 1, and through this mechanism increases levels of the active glucocorticoid, cortisol. Cortisol-induced activation of the glucocorticoid receptor produces an antiinflammatory response.