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

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 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
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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:53:07 GMT 2023` Edited by `admin` on `Fri Dec 15 15:53:07 GMT 2023`
Record UNII	MM6384NG73
Record Status	`Validated (UNII)`
Record Version

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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