carbenoxolone

Carbenoxolone (CBX) is a glycyrrhetinic acid derivative with a steroid-like structure, similar to substances found in the root of the licorice plant. Carbenoxolone is used for the treatment of peptic, esophageal and oral ulceration and inflammation. Electrolyte imbalance is a serious side effect of carbenoxolone when used systemically.

Chemical data

Formula: C34H50O7
Molecular weight: 570.8 g/mol
IUPAC name: (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-10-(3-carboxypropanoyloxy)-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylic acid
SMILES: C[C@]12CC[C@](C[C@H]1C3=CC(=O)[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)OC(=O)CCC(=O)O)C)(C)C(=O)O
InChIKey: OBZHEBDUNPOCJG-WBXJDKIVSA-N
XLogP: 6.4
Polar surface area: 118 Å²
H-bond donors: 2
H-bond acceptors: 7
Formal charge: 0

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Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
Admin. routes: oral
Indications: gastroesophageal reflux disease, Peptic ulcer

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Research

1,881 papers

Analgesic and anti-inflammatory properties of carbenoxolone: a review.Inflammopharmacology · 2025
Carbenoxolone disodium suppresses the migration of gastric cancer by targeting HDAC6.Future medicinal chemistry · 2023
Carbenoxolone: a review of its pharmacological properties and therapeutic efficacy in peptic ulcer disease.Drugs · 1976
Systematic review of neurological diseases and carbenoxolone: A double-edged sword?European journal of pharmacology · 2025
Carbenoxolone Ameliorates Allergic Airway Inflammation through NF-κB/NLRP3 Pathway in Mice.Biological & pharmaceutical bulletin · 2022

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Wikidata facts

Mass: 570.356

Show 5 more facts

chemical formula: C₃₄H₅₀O₇
isomeric SMILES: C[C@]12CC[C@](C[C@H]1C3=CC(=O)[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)OC(=O)CCC(=O)O)C)(C)C(=O)O
canonical SMILES: CC1(C2CCC3(C(C2(CCC1OC(=O)CCC(=O)O)C)C(=O)C=C4C3(CCC5(C4CC(CC5)(C)C(=O)O)C)C)C)C
Commons category: Carbenoxolone
subject has role: nootropic

Sources (3)

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Encyclopedic overview

3 sections

Contents

Nootropic effects
See also
References

Carbenoxolone reversibly inhibits the conversion of inactive cortisone to cortisol by blocking 11β-hydroxysteroid dehydrogenase (11β-HSD). 11β-HSD also reversibly catalyzes the conversion of 7-ketocholesterol to 7-beta-hydroxycholesterol.

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