Details of the Drug

General Information of Drug (ID: DM8M2N3)

Drug Name
GLYCYRRHIZIN
Synonyms
Glycyrrhizic acid; glycyrrhizin; Glycyrrhizinic acid; 1405-86-3; Glycyron; Glycyrrhetinic acid glycoside; glyzyrrhizin; 18-beta-Glycyrrhizic acid; Glycyrrizin; Liquorice; UNII-6FO62043WK; Rizinsan K2 A2 (free acid); HSDB 496; EINECS 215-785-7; C42H62O16; Glycyrrhizin [JAN]; NSC 167409; NSC 234419; BRN 0077922; CHEMBL441687; NSC 2800; beta-Glycyrrhizin; CHEBI:15939; 6FO62043WK; DSSTox_RID_82047; DSSTox_CID_27006; DSSTox_GSID_47006; Glycyram; alpha-D-Glucopyranosiduronic acid, (3beta,20beta)-20-carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-
Indication
Disease Entry ICD 11 Status REF
Influenza virus infection 1E30-1E32 Phase 3 [1]
Affected Organisms
Humans and other mammalsHerpes simplex virusVarious viruses
ATC Code
A05BA08: GLYCYRRHIZIN
A05BA: Liver therapy
A05B: LIVER THERAPY, LIPOTROPICS
A05: BILE AND LIVER THERAPY
A: ALIMENTARY TRACT AND METABOLISM
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 3 Molecular Weight (mw) 822.9
Logarithm of the Partition Coefficient (xlogp) 3.7
Rotatable Bond Count (rotbonds) 7
Hydrogen Bond Donor Count (hbonddonor) 8
Hydrogen Bond Acceptor Count (hbondacc) 16
ADMET Property
Clearance
The total body clearance of drug is 16-25 mL/h/kg [2]
Elimination
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 [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 3.5 hours [3]
Metabolism
The drug is metabolized via the intestinal bacteria for the formation of glycyrrhetinic acid []
Vd
The volume of distribution (Vd) of drug is 0.037-0.064 L/kg [4]
Chemical Identifiers
Formula
C42H62O16
IUPAC Name
(2S,3S,4S,5R,6R)-6-[(2S,3R,4S,5S,6S)-2-[[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1H-picen-3-yl]oxy]-6-carboxy-4,5-dihydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
Canonical SMILES
C[C@]12CC[C@](C[C@H]1C3=CC(=O)[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)O[C@@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)O)O)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)C(=O)O)O)O)O)C)(C)C(=O)O
InChI
InChI=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
InChIKey
LPLVUJXQOOQHMX-QWBHMCJMSA-N
Cross-matching ID
PubChem CID
14982
ChEBI ID
CHEMBL441687
CAS Number
1405-86-3
UNII
6FO62043WK
DrugBank ID
DB13751
TTD ID
D0T8QB
VARIDT ID
DR00914
INTEDE ID
DR0786
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Corticosteroid 11-beta-dehydrogenase 1 (HSD11B1) TTN7BL9 DHI1_HUMAN Inhibitor [5]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Multidrug resistance-associated protein 3 (ABCC3) DTQ3ZHF MRP3_HUMAN Substrate [6]
Multidrug resistance-associated protein 2 (ABCC2) DTFI42L MRP2_HUMAN Substrate [7]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [8]
Cytochrome P450 3A5 (CYP3A5) DEIBDNY CP3A5_HUMAN Substrate [8]
Cytochrome P450 3A7 (CYP3A7) DERD86B CP3A7_HUMAN Substrate [8]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Actin, aortic smooth muscle (ACTA2) OTEDLG8E ACTA_HUMAN Gene/Protein Processing [9]
Bcl2-associated agonist of cell death (BAD) OT63ERYM BAD_HUMAN Gene/Protein Processing [10]
Bile salt export pump (ABCB11) OTRU7THO ABCBB_HUMAN Gene/Protein Processing [11]
Cadherin-1 (CDH1) OTFJMXPM CADH1_HUMAN Gene/Protein Processing [9]
Cyclin-dependent kinase inhibitor 1 (CDKN1A) OTQWHCZE CDN1A_HUMAN Gene/Protein Processing [10]
Mothers against decapentaplegic homolog 4 (SMAD4) OTWQWCKG SMAD4_HUMAN Gene/Protein Processing [9]
Neurogenic locus notch homolog protein 1 (NOTCH1) OTI1WADQ NOTC1_HUMAN Gene/Protein Processing [10]
Nuclear receptor subfamily 1 group I member 2 (NR1I2) OTC5U0N5 NR1I2_HUMAN Gene/Protein Processing [12]
Protein jagged-1 (JAG1) OT3LGT6K JAG1_HUMAN Gene/Protein Processing [10]
Renin (REN) OT52GZR2 RENI_HUMAN Gene/Protein Processing [13]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Influenza virus infection
ICD Disease Classification 1E30-1E32
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Corticosteroid 11-beta-dehydrogenase 1 (HSD11B1) DTT HSD11B1 2.03E-01 -0.01 -0.08
Multidrug resistance-associated protein 3 (ABCC3) DTP MRP3 9.87E-01 -1.86E-01 -4.71E-01
Multidrug resistance-associated protein 2 (ABCC2) DTP MRP2 7.65E-01 -2.63E-02 -1.32E-01
Cytochrome P450 3A5 (CYP3A5) DME CYP3A5 8.58E-01 -3.73E-03 -1.00E-02
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 2.76E-01 -4.64E-01 -9.16E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4688).
2 Ploeger B, Mensinga T, Sips A, Seinen W, Meulenbelt J, DeJongh J: The pharmacokinetics of glycyrrhizic acid evaluated by physiologically based pharmacokinetic modeling. Drug Metab Rev. 2001 May;33(2):125-47. doi: 10.1081/DMR-100104400 .
3 Analysis and pharmacokinetics of glycyrrhizic acid and glycyrrhetinic acid in humans and experimental animals. Steroids. 1994 Feb;59(2):121-6.
4 Yamamura Y, Kawakami J, Santa T, Kotaki H, Uchino K, Sawada Y, Tanaka N, Iga T: Pharmacokinetic profile of glycyrrhizin in healthy volunteers by a new high-performance liquid chromatographic method. J Pharm Sci. 1992 Oct;81(10):1042-6.
5 Discovery of novel dual functional agent as PPARgamma agonist and 11beta-HSD1 inhibitor for the treatment of diabetes. Bioorg Med Chem. 2009 Aug 1;17(15):5722-32.
6 The combination of glycyrrhizin and lamivudine can reverse the cisplatin resistance in hepatocellular carcinoma cells through inhibition of multidrug resistance-associated proteins. Int J Oncol. 2007 Dec;31(6):1465-72.
7 Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.
8 Effect of glycyrrhizin on the activity of CYP3A enzyme in humans. Eur J Clin Pharmacol. 2010 Aug;66(8):805-810.
9 Verbascoside inhibits the epithelial-mesenchymal transition of prostate cancer cells through high-mobility group box 1/receptor for advanced glycation end-products/TGF- pathway. Environ Toxicol. 2021 Jun;36(6):1080-1089. doi: 10.1002/tox.23107. Epub 2021 Feb 1.
10 Antiproliferative and apoptotic potential of Glycyrrhizin against HPV16+?Caski cervical cancer cells: A plausible association with downreguation of HPV E6 and E7 oncogenes and Notch signaling pathway. Saudi J Biol Sci. 2022 May;29(5):3264-3275. doi: 10.1016/j.sjbs.2022.01.054. Epub 2022 Jan 31.
11 Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43.
12 Pregnane X receptor mediated-transcription regulation of CYP3A by glycyrrhizin: a possible mechanism for its hepatoprotective property against lithocholic acid-induced injury. Chem Biol Interact. 2012 Oct 25;200(1):11-20.
13 Inhibition of human renin activity by saponins. Biomed Res. 2010 Apr;31(2):155-9. doi: 10.2220/biomedres.31.155.