ursolic acid
Glycyrrhizin, a component of Chinese medicine licorice root. In Japan glycyrrhizin has been used for more than 20 years as treatment for chronic hepatitis and improves liver function with occasional complete recovery from hepatitis. In randomized controlled trials, glycyrrhizin induced a significant reduction of serum aminotransferases and an improvement in liver histology compared to placebo. Intravenous glycyrrhizin can be used safely and be useful for patients with difficult-to-diagnose acute liver disease as an 'initial' treatment tool to improve liver inflammation before starting disease-specific treatments. The mechanism of anti-inflammatory effect of glycyrrhizin most probably does not involve ROS and this major constituent is not responsible for the inhibition effects of liquorice extract on neutrophil functions. — NCATS
Clinical trial activity
11 trials · 11 clinical orgs · 0 marketing orgs
Earliest trial started Feb 1, 2002 (NCT00759525)
Timeline
Indications
Approved for
Studied for
- Cholangitis, Sclerosing · Phase 1
- Depressive Disorder · Phase 1/Phase 2
- Erythema · Phase 1
- Hepatitis, Autoimmune · Phase 1
- Hepatitis C, Chronic · Phase 3
- Insulin Resistance · Phase 2
- Kidney Failure, Chronic · Phase 2
- Metabolic Syndrome · Phase 2
- Muscle Hypotonia · Phase 2
- Muscular Atrophy · Phase 2
- Paraplegia · Phase 2
- Pharmacology · Early Phase 1
- Prostatic Neoplasms · Early Phase 1
- Quadriplegia · Phase 2
- Sarcopenia · Phase 2/Phase 3
- Spinal Cord Injuries · Phase 2
- Steroids · Phase 2/Phase 3
Mechanism of action
- Unspecified targetUnclear
unclear
Chemistry & pharmacology
SMILES
CC1(C)[C@@H](O[C@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O)CC[C@]2(C)[C@H]3C(=O)C=C4[C@@H]5C[C@@](C)(C(=O)O)CC[C@]5(C)CC[C@@]4(C)[C@]3(C)CC[C@@H]12- Mol. weight
- 822.94 g/mol
- Lipinski Ro5
- 3 violation(s)
- Rule of 3
- No
- Chirality
- Single Stereoisomer
- Inorganic
- No
- Polymer
- No
Oral
No
Parenteral
No
Topical
No
Sources
- ChEMBLCHEMBL441687 ↗
- WikipediaEnoxolone ↗
- NCATSP540XA09DR ↗
- WikipediaUrsolic acid ↗
- ChEMBLCHEMBL169 ↗
- ChEMBLCHEMBL230006 ↗
- ChEMBLCHEMBL1923952 ↗
Also known as
- 18beta-glycyrrhizic acid
- (3 beta)-3-hydroxyurs-12-en-28-oic acid
- 3-epi-ursolic acid
- arthrodont
- biosone
- e958
- e958
- enoxolone
- enoxolone
- enoxolone
- enoxolone
- enoxolone
- enoxolone
- enoxolone
- glycyron
- glycyrrhetic acid
- glycyrrhetic acid
- glycyrrhetic acid
- glycyrrhetic acid
- glycyrrhetic acid
- glycyrrhetin
- glycyrrhetin
- glycyrrhetinic acid
- glycyrrhetinic acid
- glycyrrhetinic acid
- glycyrrhetinic acid
- glycyrrhetinic acid glycoside
- glycyrrhizic acid
- glycyrrhizic acid
- glycyrrhizic acid
- glycyrrhizic acid
- glycyrrhizin
- glycyrrhizin
- glycyrrhizin
- glycyrrhizin
- glycyrrhizin
- glycyrrhizin
- glycyrrhizinate dipotassium
- glycyrrhizinic acid
- glycyrrhizinic acid
- glycyrrhizinic acid
- merotaine
- nsc-35347
- nsc-35347
- nsc-35350
- nsc-35350
- rhetinic acid
- rhetinic acid
- subglycyrrhelinic acid
- uralenic acid
- uralenic acid
- uralenic acid
- ursolic acid
- ursolic acid
- ursolic acid
- ursolic acid, (3beta)-isomer, 2-(14)c-labeled
- ursolic acid, (3beta)-isomer, monopotassium salt
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT05776862 | Phase 2 | Mar 27, 2023 | University of Miami |
| NCT05570110 | Phase 1/Phase 2 (Phase 2) | Sep 23, 2022 | Philipps University of Marburg, Slovak Academy of Sciences |
| NCT05987722 | N/A | Jul 30, 2021 | Kaohsiung Medical University |
| NCT04403568 | Early Phase 1 (Phase 1) | Jun 30, 2020 | University of Texas, San Antonio |
| NCT04421716 | Early Phase 1 (Phase 1) | Jun 30, 2020 | University of Texas, San Antonio |
| NCT03216876 | Phase 1 | Sep 30, 2017 | University of California, Davis |
| NCT02401113 | Phase 2/Phase 3 (Phase 3) | Nov 1, 2014 | Pusan National University |
| NCT02337933 | Phase 2 | Sep 1, 2014 | University of Guadalajara |
| NCT00686881 | Phase 3 | Dec 1, 2006 | Merck |
| NCT00384384 | Phase 2 | Aug 1, 2006 | University of Bern |
| NCT00759525 | Phase 2/Phase 3 (Phase 3) | Feb 1, 2002 | Harvard University |
Organizations
Research & Development (11)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| University of Texas, San Antonio | Academic/Hospital | 2 | 2 | 1 | 2020 |
| Harvard University | Academic/Hospital | 1 | 1 | 1 | 2002 |
| Kaohsiung Medical University | Academic/Hospital | 1 | 1 | 1 | 2021 |
| Merck | For profit | 1 | 1 | 1 | 2006 |
| Philipps University of Marburg | Academic/Hospital | 1 | 1 | 1 | 2022 |
| Pusan National University | Academic/Hospital | 1 | 1 | 1 | 2014 |
| Slovak Academy of Sciences | Government | 1 | 0 | 1 | 2022 |
| University of Bern | Academic/Hospital | 1 | 1 | 1 | 2006 |
| University of California, Davis | Academic/Hospital | 1 | 1 | 1 | 2017 |
| University of Guadalajara | Academic/Hospital | 1 | 1 | 1 | 2014 |
| University of Miami | Academic/Hospital | 1 | 1 | 1 | 2023 |