CARBENOXOLONE

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

[H][C@@]12C[C@](C)(CC[C@]1(C)CC[C@]3(C)C2=CC(=O)[C@]4([H])[C@@]5(C)CC[C@H](OC(=O)CCC(O)=O)C(C)(C)[C@]5([H])CC[C@@]34C)C(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

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 8297
gap junction assembly 3 Target ID: GO:0016264 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3418512	Inhibitor 8297

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 8429	CARBOSAN Approved Use Carbosan Gel is used for the treatment of lip sores and mouth ulcers.

PubMed

Title	Date	PubMed
Some aspects of medical management of gastrointestinal disease. I.	1975 Jan 25	234288
Cross talk between corticosteroids and alpha-adrenergic signalling augments cardiomyocyte hypertrophy: a possible role for SGK1.	2006 Jun 1	16533503
Reduction of glucocorticoid receptor ligand binding by the 11-beta hydroxysteroid dehydrogenase type 2 inhibitor, Thiram.	2006 Oct	16857225
Pannexin 1 contributes to ATP release in airway epithelia.	2009 Nov	19213873
Gap junctions: the claymore for cancerous cells.	2011	23678415
Anti-diabetic and anti-inflammatory effect of a novel selective 11β-HSD1 inhibitor in the diet-induced obese mice.	2013 Dec 5	24135201
Resveratrol inhibits 11β-hydroxysteroid dehydrogenase type 1 activity in rat adipose microsomes.	2013 Sep	23814014
Gastroprotective effects of goniothalamin against ethanol and indomethacin-induced gastric lesions in rats: Role of prostaglandins, nitric oxide and sulfhydryl compounds.	2014 Dec 5	25451594
Towards a systematic analysis of human short-chain dehydrogenases/reductases (SDR): Ligand identification and structure-activity relationships.	2015 Jun 5	25526675

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

Name

Type

Language

CARBENOXOLONE

Official 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

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

Common Name

English

Classification Tree Code System Code

WHO-VATC

QA02BX71