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Purity: ≥98%
Enoxolone (Glycyrrhetin; NSC 35347; Enoxolone; Glycyrrhetic acid; BRN-2229654; NSC-35347) is a novel, potent, pentacyclic triterpenoid derivative of the beta-amyrin type with potential liver-protecting effects. It was obtained from the hydrolysis of glycyrrhizic acid, which can be extracted from the herb liquorice.
| ln Vitro |
The primary bioactive ingredient of Glycyrrhizae Radix, 18β-Glycyrrhetinic acid, has anti-inflammatory, anti-ulcer, and anti-proliferative properties. The MTS experiment demonstrated that a 24-hour treatment with 18β-Glycyrrhetinic acid decreased cell proliferation in both cell lines in a dose-dependent way. The proportion of viable cells was considerably decreased by 18β-Glycyrrhetinic acid at 160 μM, to about 40.5±10.5% in A549 and 38.3±4.6% in NCI-H460 (p < 0.01, respectively). Greater inhibition of cell growth was seen when cells treated with 320 μM 18β-Glycyrrhetinic acid; the proportion of viable cells was less than 30% when compared to untreated controls (p<0.001). Following treatment with 160 μM and 320 μM 18β-Glycyrrhetinic acid, full-length PARP levels decreased while cleaved PARP levels rose [1].
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| ln Vivo |
The three serum parameters of rats given low-dose 18β-Glycyrrhetinic acid (50 mg/kg) were considerably lower than those of TP rats in the 18β-Glycyrrhetinic acid + triptolide (TP) group. Three liver enzyme levels somewhat dropped in rats in the 18β-Glycyrrhetinic acid + TP group after they were given a high dose of the drug (100 mg/kg). In contrast to the TP group, there was no statistically significant decline. On the other hand, mice were spared TP-induced liver damage when low dosages of 18β-Glycyrrhetinic acid were administered beforehand. By contrast, the production of the four cytokines mentioned above was considerably suppressed by low-dose 18β-Glycyrrhetinic acid (50 mg/kg) [3].
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| Additional Infomation |
Glycyrrhetinic acid is a pentacyclic triterpenoid that is olean-12-ene substituted by a hydroxy group at position 3, an oxo group at position 11 and a carboxy group at position 30. It has a role as an immunomodulator and a plant metabolite. It is a pentacyclic triterpenoid, a cyclic terpene ketone and a hydroxy monocarboxylic acid. It is a conjugate acid of a glycyrrhetinate. It derives from a hydride of an oleanane.
Enoxolone (glycyrrhetic acid) has been investigated for the basic science of Apparent Mineralocorticoid Excess (AME). Enoxolone has been reported in Glycyrrhiza uralensis, Glycyrrhiza, and other organisms with data available. Enoxolone is a pentacyclic triterpenoid aglycone metabolite of glycyrrhizin, which is a product of the plant Glycyrrhiza glabra (licorice), with potential expectorant, and gastrokinetic activities. After administration, enoxolone inhibits the metabolism of prostaglandins by both 15-hydroxyprostaglandin dehydrogenase [NAD(+)] and prostaglandin reductase 2. Therefore, this agent potentiates the activity of prostaglandin E2 and F2alpha, which inhibits gastric secretion while stimulating pancreatic secretion and the secretion of intestinal and respiratory mucus, leading to increased intestinal motility and antitussive effects. Additionally, this agent inhibits 11 beta-hydroxysteroid dehydrogenase and other enzymes involved in the conversion of cortisol to cortisone in the kidneys. An oleanolic acid from GLYCYRRHIZA that has some antiallergic, antibacterial, and antiviral properties. It is used topically for allergic or infectious skin inflammation and orally for its aldosterone effects in electrolyte regulation. See also: Glycyrrhizin (is active moiety of); Ammonium Glycyrrhizate (is active moiety of); Glycyrrhiza Glabra (part of). |
| Molecular Formula |
C30H46O4
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| Molecular Weight |
470.68
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| Exact Mass |
470.339
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| CAS # |
471-53-4
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| Related CAS # |
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| PubChem CID |
10114
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| Appearance |
White to off-white solid powder
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
588.3±50.0 °C at 760 mmHg
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| Melting Point |
292 - 295ºC
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| Flash Point |
323.7±26.6 °C
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| Vapour Pressure |
0.0±3.7 mmHg at 25°C
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| Index of Refraction |
1.563
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| LogP |
6.57
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
34
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| Complexity |
965
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| Defined Atom Stereocenter Count |
9
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| SMILES |
CC1(C)[C@@H](O)CC[C@]([C@@]1([H])CC[C@@]([C@@]2(CC[C@]3(CC[C@](C(O)=O)(C[C@]3(C2=C4)[H])C)C)C)5C)(C)[C@@]5([H])C4=O
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| InChi Key |
MPDGHEJMBKOTSU-YKLVYJNSSA-N
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| InChi Code |
InChI=1S/C30H46O4/c1-25(2)21-8-11-30(7)23(28(21,5)10-9-22(25)32)20(31)16-18-19-17-27(4,24(33)34)13-12-26(19,3)14-15-29(18,30)6/h16,19,21-23,32H,8-15,17H2,1-7H3,(H,33,34)/t19-,21-,22-,23+,26+,27-,28-,29+,30+/m0/s1
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| Chemical Name |
(2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylic acid
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| Synonyms |
Glycyrrhetin; Enoxolone; Glycyrrhetic acid; BRN 2229654; NSC 35347; NSC-35347; BRN-2229654; BRN2229654; NSC35347
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
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| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.17 mg/mL (4.61 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 21.7 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.17 mg/mL (4.61 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 21.7 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. View More
Solubility in Formulation 3: 2% DMSO+30% PEG 300+5% Tween 80+ddH2O: 10mg/mL |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.1246 mL | 10.6229 mL | 21.2459 mL | |
| 5 mM | 0.4249 mL | 2.1246 mL | 4.2492 mL | |
| 10 mM | 0.2125 mL | 1.0623 mL | 2.1246 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT05987722 | Completed | Other: Enoxolone Other: Sensodyne |
Periodontal Surgery | Kaohsiung Medical University Chung-Ho Memorial Hospital |
July 30, 2021 | Not Applicable |
| NCT05570110 | Recruiting | Drug: Enoxolone | Unipolar Depression | Philipps University Marburg Medical Center |
September 23, 2022 | Phase 1 Phase 2 |
| NCT03874949 | Completed | Device: SEALITE Regular Device: SEALITE Ultra |
Root Canal Obturation | ACTEON Group | April 2, 2019 | Not Applicable |
| NCT00384384 | Completed | Drug: oral 18B Glycyrrhetinic acid versus placebo |
End Stage Renal Disease | Insel Gruppe AG, University Hospital Bern |
August 2006 | Phase 2 |
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