CARBENOXOLONE

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C34H50O7
Molecular Weight	570.7566
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1(C)[C@H](CC[C@@]2(C)[C@H]1CC[C@]3(C)[C@@H]2C(=O)C=C4[C@@H]5C[C@](C)(CC[C@]5(C)CC[C@@]34C)C(O)=O)OC(=O)CCC(O)=O

InChI

InChIKey=OBZHEBDUNPOCJG-WBXJDKIVSA-N

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

HIDE SMILES / InChI

Molecular Formula	C34H50O7
Molecular Weight	570.7566
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	9 / 9
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22473546
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/780088 | https://www.ncbi.nlm.nih.gov/pubmed/4564085 | https://www.ncbi.nlm.nih.gov/pubmed/3418512 | https://www.ncbi.nlm.nih.gov/pubmed/9029719 | http://onlinelibrary.wiley.com/doi/10.1111/j.2042-7158.1960.tb12629.x/pdf | http://www.hpra.ie/img/uploaded/swedocuments/2122523.PA0074_011_001.71e04f1c-dfd8-4e60-916a-6ba998cf37c0.000001Product%20Leaflet%20Approved.131003.pdf

Carbenoxolone is a glycyrrhetinic acid derivative with a steroid-like structure, similar to substances found in the flavor-ful root of the licorice plant. It influences endogenous glucocorticoids by potently inhibiting 11β-hydroxysteroid dehydrogenase. Electrolyte imbalance is a serious side effect of carbenoxolone when used systemically. Carbenoxolone is best known in cellular physiology as a modestly potent, reasonably effective, water-soluble blocker of gap junctions. It exerts anti-inflammatory activity. Carbenoxolone has used orally in the clinical treatment of peptic ulcers, now it is used topically for the treatment of lip sores and mouth ulcers.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
11-beta-hydroxysteroid dehydrogenase 3 Target ID: CHEMBL3542430 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9029719 \| https://www.ncbi.nlm.nih.gov/pubmed/8664169	Inhibitor 8504
gap junction assembly 5 Target ID: GO:0016264 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3418512	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Mouth ulcers 8 Sources: http://www.hpra.ie/img/uploaded/swedocuments/2122523.PA0074_011_001.71e04f1c-dfd8-4e60-916a-6ba998cf37c0.000001Product%20Leaflet%20Approved.131003.pdf	Primary		Approved 8583	CARBOSAN Approved Use Carbosan Gel is used for the treatment of lip sores and mouth ulcers.

PubMed

Title	Date	PubMed
Towards a systematic analysis of human short-chain dehydrogenases/reductases (SDR): Ligand identification and structure-activity relationships.	2015-06-05	25526675
Gastroprotective effects of goniothalamin against ethanol and indomethacin-induced gastric lesions in rats: Role of prostaglandins, nitric oxide and sulfhydryl compounds.	2014-12-05	25451594
Anti-diabetic and anti-inflammatory effect of a novel selective 11β-HSD1 inhibitor in the diet-induced obese mice.	2013-12-05	24135201
Resveratrol inhibits 11β-hydroxysteroid dehydrogenase type 1 activity in rat adipose microsomes.	2013-09	23814014
Structure-based design and synthesis of 1,3-oxazinan-2-one inhibitors of 11β-hydroxysteroid dehydrogenase type 1.	2011-09-08	21786805
Gastroprotective mechanisms of Citrus lemon (Rutaceae) essential oil and its majority compounds limonene and β-pinene: involvement of heat-shock protein-70, vasoactive intestinal peptide, glutathione, sulfhydryl compounds, nitric oxide and prostaglandin E₂.	2011-01-15	20934418
Gap junctions: the claymore for cancerous cells.	2011	23678415
High-content chemical and RNAi screens for suppressors of neurotoxicity in a Huntington's disease model.	2011	21909362
Pannexin 1 contributes to ATP release in airway epithelia.	2009-11	19213873
Vascular nitric oxide and superoxide anion contribute to sex-specific programmed cardiovascular physiology in mice.	2009-03	19144750
Pharmacological characterization of pannexin-1 currents expressed in mammalian cells.	2009-02	19023039
Reduction of glucocorticoid receptor ligand binding by the 11-beta hydroxysteroid dehydrogenase type 2 inhibitor, Thiram.	2006-10	16857225
Cross talk between corticosteroids and alpha-adrenergic signalling augments cardiomyocyte hypertrophy: a possible role for SGK1.	2006-06-01	16533503
Mineralocorticoid versus glucocorticoid receptor occupancy mediating aldosterone-stimulated sodium transport in a novel renal cell line.	2005-04	15743993
Some aspects of medical management of gastrointestinal disease. I.	1975-01-25	234288

Patents

Sample Use Guides

In Vivo Use Guide

Cabosan 2% w/w Gel (Carbenoxolone Sodium). Carbosan Gel is used for the treatment of lip sores and mouth ulcers.

Route of Administration: Transdermal

In Vitro Use Guide

100 uM carbenoxolone induces Connexin-43 expression in bovine aortic endothelial cells

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:12:03 GMT 2025` Edited by `admin` on `Mon Mar 31 18:12:03 GMT 2025`
Record UNII	MM6384NG73
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

CARBENOXOLONE

Official Name

English

3.BETA.-HYDROXY-11-OXOOLEAN-12-EN-30-OIC ACID HYDROGEN SUCCINATE

Preferred Name

English

OLEAN-12-EN-29-OIC ACID, 3-(3-CARBOXY-1-OXOPROPOXY)-11-OXO, (3.BETA.,20.BETA.)-

Common Name

English

carbenoxolone [INN]

Common Name

English

CARBENOXOLONE [MI]

Common Name

English

Carbenoxolone [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QA02BX71