| Drug Name: | Glycyrrhizic acid |
| Iupac Name: | (3β,20β)-20-carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-β-D-glucopyranuronosyl-α-D-glucopyranosiduronic acid |
| Width: | 280px |
| Width2: | 250px |
| Tradename: | Epigen, Glycyron |
| Routes Of Administration: | Oral, intravenous |
| Metabolism: | Hepatic and by intestinal bacteria |
| Elimination Half-Life: | 6.2–10.2 hours[1] |
| Excretion: | Faeces, urine (0.31–0.67%)[2] |
| Unii: | 6FO62043WK |
| Kegg: | D00157 |
| Pubchem: | 128229 |
| Stdinchi: | 1S/C42H62O16/c1-37(2)21-8-11-42(7)31(20(43)16-18-19-17-39(4,36(53)54)13-12-38(19,3)14-15-41(18,42)6)40(21,5)10-9-22(37)55-35-30(26(47)25(46)29(57-35)33(51)52)58-34-27(48)23(44)24(45)28(56-34)32(49)50/h16,19,21-31,34-35,44-48H,8-15,17H2,1-7H3,(H,49,50)(H,51,52)(H,53,54)/t19-,21-,22-,23-,24-,25-,26-,27+,28-,29-,30+,31+,34-,35-,38+,39-,40-,41+,42+/m0/s1 |
| Stdinchikey: | LPLVUJXQOOQHMX-QWBHMCJMSA-N |
| Cas Number: | 1405-86-3 |
| Cas Supplemental: | (α-D-Glucopyranosiduronic acid), (β-D-Glucopyranosiduronic acid) |
| Chemspiderid: | 14263 |
| Chembl: | 441687 |
| Chebi: | 15939 |
| Atc Prefix: | A05 |
| Atc Suffix: | BA08 |
| Atc Supplemental: | QA05BA08 (vet) |
| C: | 42 |
| H: | 62 |
| O: | 16 |
| Solubility: | 1–10 |
| Smiles: | O=C(O)[C@H]7O[C@@H](O[C@@H]6[C@@H](O)[C@H](O)[C@H](O[C@@H]6O[C@@H]2C(C)(C)[C@@H]3CC[C@@]1(C)[C@]5(C(=C/C(=O)[C@@H]1[C@@]3(C)CC2)\[C@@H]4C[C@](C(=O)O)(C)CC[C@]4(C)CC5)C)C(=O)O)[C@H](O)[C@@H](O)[C@@H]7O |
Glycyrrhizin (glycyrrhizic acid or glycyrrhizinic acid) is the chief sweet-tasting constituent of Glycyrrhiza glabra (liquorice) root. Structurally, it is a saponin used as an emulsifier and gel-forming agent in foodstuffs and cosmetics. Its aglycone is enoxolone.
After oral ingestion, glycyrrhizin is hydrolysed to 18β-glycyrrhetinic acid (enoxolone) by intestinal bacteria. After absorption from the gut, 18β-glycyrrhetinic acid is metabolised to 3β-monoglucuronyl-18β-glycyrrhetinic acid in the liver. This metabolite circulates in the bloodstream. Consequently, its oral bioavailability is poor. Most of it is eliminated by bile and only a minor part (0.31–0.67%) by urine.[3] After oral ingestion of 600 mg of glycyrrhizin the metabolite appeared in urine after 1.5 to 14 hours. Maximal concentrations (0.49 to 2.69 mg/L) were achieved after 1.5 to 39 hours and metabolite can be detected in the urine after 2 to 4 days.[3]
Glycyrrhizin is obtained as an extract from licorice root after maceration and boiling in water.[4] Licorice extract (glycyrrhizin) is sold in the United States as a liquid, paste, or spray-dried powder.[4] When in specified amounts, it is approved for use as a flavor and aroma in manufactured foods, beverages, candies, dietary supplements, and seasonings.[4] It is 30 to 50 times as sweet as sucrose (table sugar).[5]
The most widely reported side effect of glycyrrhizin use via consumption of black liquorice is reduction of blood potassium levels, which can affect body fluid balance and function of nerves.[6] [7] Chronic consumption of black licorice, even in moderate amounts, is associated with an increase in blood pressure,[7] may cause irregular heart rhythm, and may have adverse interactions with prescription drugs.[6] In extreme cases, death can occur as a result of excess consumption.[8] [9]