General
Preferred name
glycyrrhizic acid
Synonyms
GLYCYRRHIZIN ()
AMGZ ()
Glycyram ()
Glycamil ()
Monoammonium glycyrrhizinate hydrate ()
Ammonium Glycyrrhizate ()
Glycyrram ()
Ammonium Glycyrrhizinate ()
Diammonium Glycyrrhizinate ()
Glycyrrhizic Acid (ammonium salt) ()
Dipotassium glycyrrhizinate ()
Monoammonium glycyrrhizinate ()
Glycyrrhizic acid (dipotassium) ()
Dipotassium glycyrrhizate ()
Glycyrrhizinic acid ()
Glycyrrhizin (NSC 167409) ()
AMGZ, Glycyram, Glycyrrhizin ammonium salt, Glycyrrhizic acid ammonium salt ()
Glycamil, Glycyrram ()
Neubormitin ()
E958 ()
.beta.-glycyrrhizin ()
Glycyrrhizinate ()
Potenlini ()
Glycyrrhizate ()
18.beta.-glycyrrhizic acid ()
Glycyrrhetinic acid ()
NSC-167409 ()
NSC-234419 ()
Glycyron ()
Glycyrrhizic acid dipotassium ()
GLYCYRRHIZINATE DIPOTASSIUM ()
P&D ID
PD014506
CAS
1407-03-0
79165-06-3
68797-35-3
53956-04-0
139014-59-8
132215-36-2
1405-86-3
Tags
available
natural product
drug
drug candidate
nuisance
Approved by
FDA
Drug indication
Influenza virus infection
Drug Status
investigational
approved
experimental
Max Phase
2.0
Probe control
Probe control not defined
Orthogonal probes
0
No orthogonal probes found
Similar probes
0
No structurally similar probes found
Structure
P&D probe-likeness score
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
PHARMACODYNAMICS
Glycyrrhizic acid was reported to present antiallergic, antiviral and anti-inflammatory activities as well as improvements in glucose tolerance.[A33062] ; ; The effect of glycyrrhizic acid in metabolic syndrome generates a significant decrease in blood glucose, fasting blood glucose and mean serum insulin concentration.[A33063]
MOA
Glycyrrhizic acid can be found in the alpha and beta forms. The alpha form is predominant in the liver and duodenum and thus, it is thought that the anti-inflammatory liver effect of this drug are mainly due to the action of this isomer. Glycyrrhizic acid anti-inflammatory effect is generated via suppression of TNF alpha and caspase 3. It also inhibits the translocation of NFkB into the nuclei and conjugates free radicals. Some studies have shown a glycyrrhizic-driven inhibition of CD4+ T cell proliferation via JNK, ERK and PI3K/AKT.[A33062]; ; The antiviral activity of glycyrrhizic acid includes the inhibition of viral replication and immune regulation.[A33062] The antiviral activity of glycyrrhizic acid seems to be of a broad spectrum and be able to cover several different viral types such as vaccinia virus, herpes simplex virus, Newcastle disease virus and vesicular stomatitis virus.[A33063]; ; The effect of glycyrrhizic acid on metabolism is thought to be related to its inhibitory activity towards 11-beta-hydroxysteroid dehydrogenase type 1 which in turn decreases the activity of hexose-6-phosphate dehydrogenase. On the other hand, some studies have shown a potential lipoprotein lipase induction in non-hepatic tissues and thus it is suggested to enhance dyslipidemic conditions.[A33063]
TOXICITY
Glycyrrhizic acid is thought to generate inhibition of 11-beta-hydroxysteroid dehydrogenase in the kidney which leads to elevated cortisol levels in the kidney. Intravenous administration of the ammoniated form was shown to produce convulsions and hemolysis.[F79]; ; Preclinical overdose studies have been shown to produce mineralocorticoid excess. The LD50 in preclinical studies was reported to be in the range of 308-12700 mg/kg.[F79] ; ; Glycyrrhizic acid has been proven to not have mutagenic, genotoxic, teratogenic nor carcinogenic effects.[F79]
ROE
Glycyrrhizic acid presents a biphasic elimination from the central compartment with a dose-dependent second elimination phase. The majority of the administered dose is eliminated by the bile in which glycyrrhizic acid can be eliminated unchanged and undergoes enterohepatic cycling.[A33066] On the other hand, the major metabolite, glycyrrhetinic acid, forms glucuronide and sulfate conjugates. These conjugates are efficiently transported into the bile and duodenum where commensal bacteria hydrolizes the conjugate for the formation of glycyrrhetinic acid and further reabsorption.[A33064] This reabsorption behavior seems to be related to the activity of 3-alpha-hydroxysteroid dehydrogenase which transports very efficiently the metabolite from the plasma to the bile.[A33068]; ; About 1.1-2.5% of the administered dose of glycyrrhizic acid can be found in urine which corresponds to the minimal cycling and reabsorption of this compound.[A33067]
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Cell lines
2
Organisms
3
Compound Sets
22
Cayman Chemical Bioactives
ChEMBL Drugs
Concise Guide to Pharmacology 2017/18
Concise Guide to Pharmacology 2019/20
Concise Guide to Pharmacology 2021/22
Concise Guide to Pharmacology 2023/24
Drug Repurposing Hub
DrugBank
DrugBank Approved Drugs
DrugCentral
DrugCentral Approved Drugs
DrugMAP
Guide to Pharmacology
LSP-MoA library (Laboratory of Systems Pharmacology)
Novartis Chemogenetic Library (NIBR MoA Box)
NPC Screening Collection
Nuisance compounds in cellular assays
ReFrame library
Selleckchem Bioactive Compound Library
[[ a.name ]]
[[ ligand_id ]]
free of charge
External IDs
99
Molecular Weight
822.4
Hydrogen Bond Acceptors
13
Hydrogen Bond Donors
8
Rotatable Bonds
7
Ring Count
7
Aromatic Ring Count
0
cLogP
2.25
TPSA
267.04
Fraction CSP3
0.86
Chiral centers
19.0
Largest ring
6.0
QED
0.17
Structural alerts
1
Saponin/tannin
Detergent-like effects
Nuisance compounds in cellular assays
Related compounds
Custom attributes
(extracted from source data)
Pathway
Metabolism
Neuroscience
Immunology/Inflammation
Anti-infection
Target
11-beta-hydroxysteroid dehydrogenase
Dehydrogenase
MAO
HSD11B1, HSD11B2, SLCO1B1, SLCO1B3
Virus Protease
Dehydrogenase,High-mobility Group
Dehydrogenase,High-mobility Group,MAO
Immunology & Inflammation related
MOA
Dehydrogenase inhibitor
Inhibitors of Blood Coagulation Pathways
thrombin inhibitors
Antioxidants
Cell Adhesion Inhibitors
Thrombin inhibitor
Member status
member
Indication
cosmetic
Source data
