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| Trade names | Arthrodont, PruClair |
| AHFS/Drugs.com | International Drug Names |
| Routes of administration | Oral, topical |
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| CompTox Dashboard(EPA) | |
| ECHA InfoCard | 100.006.769 |
| Chemical and physical data | |
| Formula | C30H46O4 |
| Molar mass | 470.694 g·mol−1 |
| 3D model (JSmol) | |
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Enoxolone (INN,BAN; also known asglycyrrhetinic acid orglycyrrhetic acid) is a pentacyclictriterpenoid derivative of thebeta-amyrin type obtained from thehydrolysis ofglycyrrhizic acid, which was obtained from the herbliquorice.
The substance has a sweet taste, so it is used inflavoring to mask the bitter taste of drugs likealoe andquinine. It may have some anti-inflammatory activities.[1] One of its metabolites is responsible for the blood pressure-increasing effect of liquorice.[2]
In Turkey, enoxolone is used in an "Anzibel" lozenge in combination withbenzocaine (a local anesthetic) andchlorhexidine hydrochloride (an antibacterial).[3]
It is found in an over-the-counter "Arthrodont" toothpaste. Evidence for the ingredient's usefulness for plaque and gingivitis is lacking.[4]
In Japan, enoxolone is an active ingredient in the Salonpas brand ofpain relief patch.[3]
It is also used in the Singaporean "Vetic" cream.[3] In the United States, it is found in PruClair, a "precription medical device" indicated for genericdermatoses.[5]
Enoxolone is effective in the treatment ofpeptic ulcer and also hasexpectorant (antitussive) properties.[1] It has some additional pharmacological properties with possible antiviral, antifungal, antiprotozoal, and antibacterial activities.[6][7][8][9]
Glycyrrhetinic acid inhibits theenzymes (15-hydroxyprostaglandin dehydrogenase and delta-13-prostaglandin reductase) that metabolize theprostaglandins PGE-2 and PGF-2α to their respective, inactive 15-keto-13,14-dihydrometabolites. This increases prostaglandins in the digestive system. Prostaglandins inhibit gastric secretion, stimulatepancreatic secretion and mucous secretion in theintestines, and markedly increase intestinal motility. They also cause cell proliferation in thestomach. The effect ongastric acid secretion, and promotion of mucous secretion and cell proliferation shows why licorice has potential in treating peptic ulcers.[10]
Excessive consumption of glycyrrhetinic acid can cause a significant rise in blood pressure.[11]Liquorice root should not be consumed during pregnancy.[12]
The structure of glycyrrhetinic acid is similar to that ofcortisone. Both molecules are flat and similar at positions 3 and 11. This might be the basis for liquorice'santi-inflammatory action.[citation needed]
3-β-D-(Monoglucuronyl)-18-β-glycyrrhetinic acid, a metabolite of glycyrrhetinic acid, inhibits the conversion of 'active'cortisol to 'inactive'cortisone in thekidneys.[13] This occurs via inhibition of the enzyme11-β-hydroxysteroid dehydrogenase.[citation needed] As a result, cortisol levels become high within the collecting duct of the kidney. Cortisol has intrinsic mineralocorticoid properties (that is, it acts likealdosterone and increasessodium reabsorption) that work on ENaC channels in the collecting duct.[citation needed]Hypertension develops due to this mechanism of sodium retention. People often have high blood pressure with a lowrenin and lowaldosterone blood level.[citation needed] The increased amounts of cortisol binds to the unprotected, nonspecific mineralocorticoid receptors and induce sodium and fluid retention,hypokalaemia, high blood pressure, and inhibition of the renin-angiotensin-aldosterone system. Therefore, licorice should not be given to patients with a known history of hypertension in doses sufficient to inhibit 11-β-hydroxysteroid dehydrogenase.[2]
In glycyrrhetinic acid, thefunctional group (R) is ahydroxyl group. Research in 2005 demonstrated that with a proper functional group a very effective glycyrrhetinicartificial sweetener can be obtained.[14] WhenR is ananionic NHCO(CH2)CO2Kside chain, the sweetening effect is found to be 1200 times that ofsugar (human sensory panel data). A shorter or longerspacer reduces the sweetening effect. One explanation is that thetaste bud cellreceptor has 1.3nanometers (13angstroms) available for docking with the sweetener molecule. In addition, the sweetener molecule requires threeproton donor positions, of which two reside at the extremities, to be able to interact efficiently with the receptor cavity.
A synthetic analog,carbenoxolone, was developed in Britain.[citation needed] Both glycyrrhetinic acid and carbenoxolone have a modulatory effect on neural signaling throughgap junction channels.
Acetoxolone, theacetyl derivative of glycyrrhetinic acid, is a drug used in the treatment ofpeptic ulcer andgastroesophageal reflux disease.
Media related toEnoxolone at Wikimedia Commons