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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 of CARBENOXOLONE

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
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

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
CARBOSAN

Approved Use

Carbosan Gel is used for the treatment of lip sores and mouth ulcers.
PubMed

PubMed

TitleDatePubMed
Mineralocorticoid versus glucocorticoid receptor occupancy mediating aldosterone-stimulated sodium transport in a novel renal cell line.
2005 Apr
Cross talk between corticosteroids and alpha-adrenergic signalling augments cardiomyocyte hypertrophy: a possible role for SGK1.
2006 Jun 1
Pannexin 1 contributes to ATP release in airway epithelia.
2009 Nov
Anti-diabetic and anti-inflammatory effect of a novel selective 11β-HSD1 inhibitor in the diet-induced obese mice.
2013 Dec 5
Resveratrol inhibits 11β-hydroxysteroid dehydrogenase type 1 activity in rat adipose microsomes.
2013 Sep
Gastroprotective effects of goniothalamin against ethanol and indomethacin-induced gastric lesions in rats: Role of prostaglandins, nitric oxide and sulfhydryl compounds.
2014 Dec 5
Towards a systematic analysis of human short-chain dehydrogenases/reductases (SDR): Ligand identification and structure-activity relationships.
2015 Jun 5
Patents

Sample Use Guides

Cabosan 2% w/w Gel (Carbenoxolone Sodium). Carbosan Gel is used for the treatment of lip sores and mouth ulcers.
Route of Administration: Transdermal
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
  • Download
Name Type Language
CARBENOXOLONE
INN   MI   WHO-DD  
INN  
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
Created by admin on Fri Dec 15 15:53:07 GMT 2023 , Edited by admin on Fri Dec 15 15:53:07 GMT 2023
NCI_THESAURUS C54678
Created by admin on Fri Dec 15 15:53:07 GMT 2023 , Edited by admin on Fri Dec 15 15:53:07 GMT 2023
FDA ORPHAN DRUG 429414
Created by admin on Fri Dec 15 15:53:07 GMT 2023 , Edited by admin on Fri Dec 15 15:53:07 GMT 2023
WHO-ATC A02BX71
Created by admin on Fri Dec 15 15:53:07 GMT 2023 , Edited by admin on Fri Dec 15 15:53:07 GMT 2023
WHO-VATC QA02BX01
Created by admin on Fri Dec 15 15:53:07 GMT 2023 , Edited by admin on Fri Dec 15 15:53:07 GMT 2023
WHO-ATC A02BX51
Created by admin on Fri Dec 15 15:53:07 GMT 2023 , Edited by admin on Fri Dec 15 15:53:07 GMT 2023
WHO-ATC A02BX01
Created by admin on Fri Dec 15 15:53:07 GMT 2023 , Edited by admin on Fri Dec 15 15:53:07 GMT 2023
Code System Code Type Description
DRUG CENTRAL
493
Created by admin on Fri Dec 15 15:53:07 GMT 2023 , Edited by admin on Fri Dec 15 15:53:07 GMT 2023
PRIMARY
RXCUI
2017
Created by admin on Fri Dec 15 15:53:07 GMT 2023 , Edited by admin on Fri Dec 15 15:53:07 GMT 2023
PRIMARY RxNorm
FDA UNII
MM6384NG73
Created by admin on Fri Dec 15 15:53:07 GMT 2023 , Edited by admin on Fri Dec 15 15:53:07 GMT 2023
PRIMARY
INN
1789
Created by admin on Fri Dec 15 15:53:07 GMT 2023 , Edited by admin on Fri Dec 15 15:53:07 GMT 2023
PRIMARY
EVMPD
SUB06123MIG
Created by admin on Fri Dec 15 15:53:07 GMT 2023 , Edited by admin on Fri Dec 15 15:53:07 GMT 2023
PRIMARY
ECHA (EC/EINECS)
227-174-2
Created by admin on Fri Dec 15 15:53:07 GMT 2023 , Edited by admin on Fri Dec 15 15:53:07 GMT 2023
PRIMARY
DRUG BANK
DB02329
Created by admin on Fri Dec 15 15:53:07 GMT 2023 , Edited by admin on Fri Dec 15 15:53:07 GMT 2023
PRIMARY
WIKIPEDIA
CARBENOXOLONE
Created by admin on Fri Dec 15 15:53:07 GMT 2023 , Edited by admin on Fri Dec 15 15:53:07 GMT 2023
PRIMARY
MERCK INDEX
m3064
Created by admin on Fri Dec 15 15:53:07 GMT 2023 , Edited by admin on Fri Dec 15 15:53:07 GMT 2023
PRIMARY Merck Index
PUBCHEM
636403
Created by admin on Fri Dec 15 15:53:07 GMT 2023 , Edited by admin on Fri Dec 15 15:53:07 GMT 2023
PRIMARY
ChEMBL
CHEMBL499915
Created by admin on Fri Dec 15 15:53:07 GMT 2023 , Edited by admin on Fri Dec 15 15:53:07 GMT 2023
PRIMARY
NCI_THESAURUS
C63669
Created by admin on Fri Dec 15 15:53:07 GMT 2023 , Edited by admin on Fri Dec 15 15:53:07 GMT 2023
PRIMARY
SMS_ID
100000081319
Created by admin on Fri Dec 15 15:53:07 GMT 2023 , Edited by admin on Fri Dec 15 15:53:07 GMT 2023
PRIMARY
EPA CompTox
DTXSID4022733
Created by admin on Fri Dec 15 15:53:07 GMT 2023 , Edited by admin on Fri Dec 15 15:53:07 GMT 2023
PRIMARY
CAS
5697-56-3
Created by admin on Fri Dec 15 15:53:07 GMT 2023 , Edited by admin on Fri Dec 15 15:53:07 GMT 2023
PRIMARY
MESH
D002229
Created by admin on Fri Dec 15 15:53:07 GMT 2023 , Edited by admin on Fri Dec 15 15:53:07 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY