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Details

Stereochemistry ABSOLUTE
Molecular Formula C34H48O7.2Na
Molecular Weight 614.7203
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARBENOXOLONE SODIUM

SMILES

[Na+].[Na+].[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=BQENDLAVTKRQMS-SBBGFIFASA-L
InChI=1S/C34H50O7.2Na/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);;/q;2*+1/p-2/t21-,23-,24-,27+,30+,31-,32-,33+,34+;;/m0../s1

HIDE SMILES / InChI
Molecular Formula C34H48O7
Molecular Weight 568.7407
Charge -2
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 9
E/Z Centers 0
Optical Activity UNSPECIFIED
Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Originator

Approval Year

2016
495
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
CARBOSAN

Approved Use

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

PubMed

TitleDatePubMed
Some aspects of medical management of gastrointestinal disease. I.
1975 Jan 25
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
Reduction of glucocorticoid receptor ligand binding by the 11-beta hydroxysteroid dehydrogenase type 2 inhibitor, Thiram.
2006 Oct
Pharmacological characterization of pannexin-1 currents expressed in mammalian cells.
2009 Feb
Vascular nitric oxide and superoxide anion contribute to sex-specific programmed cardiovascular physiology in mice.
2009 Mar
Pannexin 1 contributes to ATP release in airway epithelia.
2009 Nov
Gap junctions: the claymore for cancerous cells.
2011
High-content chemical and RNAi screens for suppressors of neurotoxicity in a Huntington's disease model.
2011
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 Jan 15
Structure-based design and synthesis of 1,3-oxazinan-2-one inhibitors of 11β-hydroxysteroid dehydrogenase type 1.
2011 Sep 8
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

Patents

DE2936046A1
2
JPS61165348A
2
US20170014425
2

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 15:09:27 GMT 2023
Edited
by admin
on Fri Dec 15 15:09:27 GMT 2023
Record UNII
F1MP7242Z5
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CARBENOXOLONE SODIUM
JAN   MART.   USAN   WHO-DD  
USAN  
Official Name English
SODIUM CARBENOXOLONE
Common Name English
CARBENOXOLONE SODIUM [JAN]
Common Name English
20.BETA.-OLEAN-12-EN-29-OIC ACID, 3(.BETA.)-(3-CARBOXY-1-OXOPROPOXY)-11-OXO-, DISODIUM SALT
Common Name English
Carbenoxolone sodium [WHO-DD]
Common Name English
BIORAL
Brand Name English
BIOGASTRONE
Brand Name English
SANODIN
Brand Name English
3β-Hydroxy-11-oxoolean-12-en-30-oic acid hydrogen succinate disodium salt
Common Name English
DISODIUM 3-SUCCINYLOXY-.BETA.-GLYCYRRHETINATE
Common Name English
CARBENOXOLONE DISODIUM SALT
MI  
Common Name English
DISODIUM SUCCINOYL GLYCYRRHETINATE
INCI  
INCI  
Official Name English
NSC-758146
Code English
CARBENOXOLONE SODIUM [USAN]
Common Name English
CARBENOXOLONE SODIUM [MART.]
Common Name English
OLEAN-12-EN-29-OIC ACID, 3-(3-CARBOXY-1-OXOPROPOXY)-11-OXO-, SODIUM SALT (1:2), (3.BETA.,20.BETA.)-
Common Name English
ULCUS-TABLINEN
Brand Name English
CARBENOXOLONE DISODIUM SALT [MI]
Common Name English
DISODIUM SUCCINOYL GLYCYRRHETINATE [INCI]
Common Name English
NEOGEL
Brand Name English
OLEAN-12-EN-29-OIC ACID, 3-(3-CARBOXY-1-OXOPROPOXY)-11-OXO, DISODIUM SALT, (3.BETA.,20.BETA.)-
Common Name English
BIOPLEX
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C54678
Created by admin on Fri Dec 15 15:09:27 GMT 2023 , Edited by admin on Fri Dec 15 15:09:27 GMT 2023
Code System Code Type Description
EVMPD
SUB01042MIG
Created by admin on Fri Dec 15 15:09:27 GMT 2023 , Edited by admin on Fri Dec 15 15:09:27 GMT 2023
PRIMARY
ECHA (EC/EINECS)
231-044-0
Created by admin on Fri Dec 15 15:09:27 GMT 2023 , Edited by admin on Fri Dec 15 15:09:27 GMT 2023
PRIMARY
RXCUI
2018
Created by admin on Fri Dec 15 15:09:27 GMT 2023 , Edited by admin on Fri Dec 15 15:09:27 GMT 2023
PRIMARY RxNorm
CAS
7421-40-1
Created by admin on Fri Dec 15 15:09:27 GMT 2023 , Edited by admin on Fri Dec 15 15:09:27 GMT 2023
PRIMARY
SMS_ID
100000084870
Created by admin on Fri Dec 15 15:09:27 GMT 2023 , Edited by admin on Fri Dec 15 15:09:27 GMT 2023
PRIMARY
EPA CompTox
DTXSID7045572
Created by admin on Fri Dec 15 15:09:27 GMT 2023 , Edited by admin on Fri Dec 15 15:09:27 GMT 2023
PRIMARY
NSC
758146
Created by admin on Fri Dec 15 15:09:27 GMT 2023 , Edited by admin on Fri Dec 15 15:09:27 GMT 2023
PRIMARY
DRUG BANK
DBSALT001875
Created by admin on Fri Dec 15 15:09:27 GMT 2023 , Edited by admin on Fri Dec 15 15:09:27 GMT 2023
PRIMARY
DAILYMED
F1MP7242Z5
Created by admin on Fri Dec 15 15:09:27 GMT 2023 , Edited by admin on Fri Dec 15 15:09:27 GMT 2023
PRIMARY
MERCK INDEX
m3064
Created by admin on Fri Dec 15 15:09:27 GMT 2023 , Edited by admin on Fri Dec 15 15:09:27 GMT 2023
PRIMARY Merck Index
FDA UNII
F1MP7242Z5
Created by admin on Fri Dec 15 15:09:27 GMT 2023 , Edited by admin on Fri Dec 15 15:09:27 GMT 2023
PRIMARY
NCI_THESAURUS
C82597
Created by admin on Fri Dec 15 15:09:27 GMT 2023 , Edited by admin on Fri Dec 15 15:09:27 GMT 2023
PRIMARY
ChEMBL
CHEMBL499915
Created by admin on Fri Dec 15 15:09:27 GMT 2023 , Edited by admin on Fri Dec 15 15:09:27 GMT 2023
PRIMARY
PUBCHEM
636402
Created by admin on Fri Dec 15 15:09:27 GMT 2023 , Edited by admin on Fri Dec 15 15:09:27 GMT 2023
PRIMARY
Related Record Type Details
Structure of CARBENOXOLONE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of CARBENOXOLONE
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