Identification

Name
Glycyrrhizic acid
Accession Number
DB13751
Type
Small Molecule
Groups
Approved, Experimental
Description

Glycyrrhizic acid is extracted from the root of the licorice plant; Glycyrrhiza glabra.[11] It is a triterpene glycoside with glycyrrhetinic acid that possesses a wide range of pharmacological and biological activities. When extracted from the plant, it can be obtained in the form of ammonium glycyrrhizin and mono-ammonium glycyrrhizin.[8] Glycyrrhizic acid has been developed in Japan and China as a hepatoprotective drug in cases of chronic hepatitis.[1] From January 2014, glycyrrhizic acid as part of the licorice extract was approved by the FDA as an existing food sweetener.[12] It was approved by Health Canada to be used in over-the-counter products but all the products are currently on the status canceled post marketed.[10]

Structure
Thumb
Synonyms
  • 18-beta-Glycyrrhizic acid
  • Glizigen
  • Glycyrrhizin
External IDs
NSC-167409 / NSC-234419
Product Ingredients
IngredientUNIICASInChI Key
Ammonium glycyrrhizinate trihydrate78NEL3149I911217-00-0RSPXVECNDMCBGQ-YMYWBCTMSA-N
Glycyrrhizinate dipotassiumCA2Y0FE3FX68797-35-3BIVBRWYINDPWKA-VLQRKCJKSA-L
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
BAMBOO SALT Eunganggo Jook YeomGlycyrrhizinate dipotassium (0.04 g/100g) + Aminocaproic Acid (0.05 g/100g) + Curcuma xanthorrhiza oil (0.025 g/100g) + Sea salt (3 g/100g) + Silicon dioxide (20 g/100g) + Sodium fluoride (0.22 g/100g) + Ursodeoxycholic acid (0.02 g/100g)PasteDentalLg Household & Health Care Ltd.2011-03-15Not applicableUs
BAMBOO SALT Eunganggo Jook Yeom ToothpasteGlycyrrhizinate dipotassium (0.04 g/100g) + Aminocaproic Acid (0.05 g/100g) + Curcuma xanthorrhiza oil (0.025 g/100g) + Sea salt (3 g/100g) + Silicon dioxide (20 g/100g) + Sodium fluoride (0.22 g/100g) + Ursodeoxycholic acid (0.02 g/100g)PasteDentalLg Household & Health Care Ltd.2010-05-25Not applicableUs
Pulmoll PastillesGlycyrrhizic acid (7.6 mg) + Menthol (1.52 mg)LozengeOralLe Nigen N. Industries1994-12-311999-07-16Canada
Categories
UNII
6FO62043WK
CAS number
1405-86-3
Weight
Average: 822.942
Monoisotopic: 822.403785916
Chemical Formula
C42H62O16
InChI Key
LPLVUJXQOOQHMX-QWBHMCJMSA-N
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
IUPAC Name
(2S,3S,4S,5R,6S)-6-{[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-5-{[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4-dihydroxyoxane-2-carboxylic acid
SMILES
[H][C@@]12C[C@](C)(CC[C@]1(C)CC[C@]1(C)C2=CC(=O)[C@]2([H])[C@@]3(C)CC[C@H](O[C@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4O[C@@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4O)C(O)=O)C(O)=O)C(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O

Pharmacology

Indication

Glycyrrhizic acid is widely applied in foods as a natural sweetener. As a therapeutic agent, is has been used in a vast variety of formulations as it is reported to be anti-inflammatory, anti-ulcer, anti-allergic, antioxidant, anti-tumor, anti-diabetic and hepatoprotective. Due to this properties, its indications have been: treatment of premenstrual syndrome, treatment of viral infections, anti-lipidemic and antihyperglycemic.[2] It is also known to be used as a remedy for peptic ulcer and other stomach diseases.[9]

Associated Conditions
Pharmacodynamics

Glycyrrhizic acid was reported to present antiallergic, antiviral and anti-inflammatory activities as well as improvements in glucose tolerance.[1]

The effect of glycyrrhizic acid in metabolic syndrome generates a significant decrease in blood glucose, fasting blood glucose and mean serum insulin concentration.[2]

Mechanism of action

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.[1]

The antiviral activity of glycyrrhizic acid includes the inhibition of viral replication and immune regulation.[1] 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.[2]

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.[2]

TargetActionsOrganism
ACorticosteroid 11-beta-dehydrogenase isozyme 1
antagonist
Human
ATumor necrosis factor
antagonist
Human
ACaspase-3
antagonist
Human
ANuclear factor NF-kappa-B
translocation inhibitor
Human
ALipoprotein lipase
inducer
Human
Absorption

Glycyrrhizic acid is mainly absorbed after presystemic hydrolysis and formation of glycyrrhetinic acid.[3] Therefore, after oral administration of a dose of 100 mg of glycyrrhizic acid, this major metabolite appears in plasma in a concentration of 200 ng/ml while glycyrrhizic acid cannot be found. The finding of a minimal amount of glycyrrhizic acid in urine suggests the existence of a partial absorption in the gastrointestinal tract.[5]

Volume of distribution

The apparent volume of distribution of glycyrrhizic acid either in the central compartment and in steady-state are in the range of 37-64 ml/kg and 59-98 ml/kg, respectively.[5]

Protein binding

Glycyrrhizic acid does not bind to any plasma proteins as it is not absorbed systemically. On the other hand, its main active metabolite, glycyrrhetinic acid presents a very large binding to serum proteins such as albumin.[7]

Metabolism

When orally administered, glycyrrhizic acid is almost completely hydrolyzed by intestinal bacteria for the formation of glycyrrhetinic acid, which is an active metabolite and can enter systemic circulation, and two molecules of glucuronic acid.[11] This metabolite is transported and taken in the liver for its metabolization to form glucuronide and sulfate conjugates.[3]

Route of elimination

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.[4] 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.[3] 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.[6]

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.[5]

Half life

Depending on the dose, the second elimination phase in humans has a half-life of 3.5 hours.[4]

Clearance

The constant reabsorption of glycyrrhetic acid in the duodenum causes a delay in the terminal plasma clearance.[3] The reported total body clearance of glycyrrhizic acid is reported to be in the range of 16-25 ml.kg/h.[5]

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.[11]

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.[11]

Glycyrrhizic acid has been proven to not have mutagenic, genotoxic, teratogenic nor carcinogenic effects.[11]

Affected organisms
  • Humans and other mammals
  • Herpes simplex virus
  • Various viruses
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AmiodaroneGlycyrrhizic acid may decrease the excretion rate of Amiodarone which could result in a higher serum level.
AstemizoleAstemizole may decrease the excretion rate of Glycyrrhizic acid which could result in a higher serum level.
AtazanavirAtazanavir may decrease the excretion rate of Glycyrrhizic acid which could result in a higher serum level.
AtenololAtenolol may decrease the excretion rate of Glycyrrhizic acid which could result in a higher serum level.
AtorvastatinAtorvastatin may decrease the excretion rate of Glycyrrhizic acid which could result in a higher serum level.
AtropineAtropine may decrease the excretion rate of Glycyrrhizic acid which could result in a higher serum level.
BenzbromaroneBenzbromarone may decrease the excretion rate of Glycyrrhizic acid which could result in a higher serum level.
BosentanBosentan may decrease the excretion rate of Glycyrrhizic acid which could result in a higher serum level.
BudesonideBudesonide may decrease the excretion rate of Glycyrrhizic acid which could result in a higher serum level.
CefaclorCefaclor may decrease the excretion rate of Glycyrrhizic acid which could result in a higher serum level.
Food Interactions
Not Available

References

General References
  1. Li JY, Cao HY, Liu P, Cheng GH, Sun MY: Glycyrrhizic acid in the treatment of liver diseases: literature review. Biomed Res Int. 2014;2014:872139. doi: 10.1155/2014/872139. Epub 2014 May 13. [PubMed:24963489]
  2. Ming LJ, Yin AC: Therapeutic effects of glycyrrhizic acid. Nat Prod Commun. 2013 Mar;8(3):415-8. [PubMed:23678825]
  3. 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 . [PubMed:11495500]
  4. Krahenbuhl S, Hasler F, Krapf R: Analysis and pharmacokinetics of glycyrrhizic acid and glycyrrhetinic acid in humans and experimental animals. Steroids. 1994 Feb;59(2):121-6. [PubMed:8191540]
  5. 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. [PubMed:1432618]
  6. Ploeger BA, Meulenbelt J, DeJongh J: Physiologically based pharmacokinetic modeling of glycyrrhizic acid, a compound subject to presystemic metabolism and enterohepatic cycling. Toxicol Appl Pharmacol. 2000 Feb 1;162(3):177-88. doi: 10.1006/taap.1999.8843. [PubMed:10652246]
  7. Ishida S, Ichikawa T, Sakiya Y: Binding of glycyrrhetinic acid to rat plasma, rat serum albumin, human serum, and human serum albumin. Chem Pharm Bull (Tokyo). 1988 Jan;36(1):440-3. [PubMed:3378305]
  8. Gloria M. (2003). Encyclopedia of food sciences and nutrition (2nd ed.). Academic Press.
  9. Sharma M., Dwivedi P., Singh A. and Dwivedi A. (2016). Nutraceuticals. Academic Press.
  10. Health Canada [Link]
  11. FDA records [File]
  12. FDA food aditives [File]
External Links
KEGG Drug
D00157
KEGG Compound
C02284
ChemSpider
14263
BindingDB
50185127
ChEBI
15939
ChEMBL
CHEMBL441687
Wikipedia
Glycyrrhizin
ATC Codes
A05BA08 — Glycyrrhizic acid
MSDS
Download (47.6 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
PasteDental
LozengeOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)220 ºC (Decomposes at 200 ºC)'MSDS'
boiling point (°C)Decomposes at 200 ºC'MSDS'
water solubilityEasily soluble in hot water'MSDS'
logP2.8'MSDS'
Predicted Properties
PropertyValueSource
Water Solubility0.0545 mg/mLALOGPS
logP2.78ALOGPS
logP3.13ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)2.96ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area267.04 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity198.83 m3·mol-1ChemAxon
Polarizability86.31 Å3ChemAxon
Number of Rings7ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00di-0000000090-4ce2b1a1894e31a4b583
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00di-0000000090-05cf6f9c95233e0b6093
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00di-0000000090-b7273d4a3c7ac5053507
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00di-0000000090-380d12d32657ccb592bc
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00di-0102000090-bed09978385e89f7fa03
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-00di-0101000090-e2103026d03012f4386b
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-00di-0002000090-301b760e1a43241eb03d
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-00di-0202000090-f5911cc6b21dd8fa08fa
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-00di-0002000090-8620dc60deae22ab4b96
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-00di-0000000090-f5c5cfd754bfd69139d6
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-00di-0000000090-ec1596ab8cbd06c136c1
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-0w29-0709000000-3a40dbcd4a9e24a4e64a
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-00di-0000000090-00d5155c760746cee29c
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-00di-0001000090-5fd4d3fb6b71940d3e21
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-0fk9-0104000090-35df1ca6b0cc93c2681b
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-0uk9-0309000050-ce67083e8ed48da875b9
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-006x-0000000090-8cd630bf15ce35555075
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0fk9-0000702090-b0ba25c87ff68dd3b767
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udi-0000901000-57104f23e3197f427a1d
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udi-0000900000-537381840e9d1d1c4253
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udi-0000900000-ed766c3b16a4efad6b09
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0000901000-115bc1eeeaff2bc6cf94
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0000901000-22da39f178b78eb4cafe

Taxonomy

Description
This compound belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Terpene glycosides
Direct Parent
Triterpene saponins
Alternative Parents
Triterpenoids / O-glucuronides / Disaccharides / O-glycosyl compounds / Tricarboxylic acids and derivatives / Beta hydroxy acids and derivatives / Cyclohexenones / Pyrans / Oxanes / Secondary alcohols
show 6 more
Substituents
Triterpene saponin / Triterpenoid / 1-o-glucuronide / O-glucuronide / Glucuronic acid or derivatives / Disaccharide / Glycosyl compound / O-glycosyl compound / Tricarboxylic acid or derivatives / Beta-hydroxy acid
show 19 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
enone, tricarboxylic acid, glucosiduronic acid, triterpenoid saponin, pentacyclic triterpenoid (CHEBI:15939)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
11-beta-hydroxysteroid dehydrogenase [nad(p)] activity
Specific Function
Catalyzes reversibly the conversion of cortisol to the inactive metabolite cortisone. Catalyzes reversibly the conversion of 7-ketocholesterol to 7-beta-hydroxycholesterol. In intact cells, the rea...
Gene Name
HSD11B1
Uniprot ID
P28845
Uniprot Name
Corticosteroid 11-beta-dehydrogenase isozyme 1
Molecular Weight
32400.665 Da
References
  1. FDA records [File]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Tumor necrosis factor receptor binding
Specific Function
Cytokine that binds to TNFRSF1A/TNFR1 and TNFRSF1B/TNFBR. It is mainly secreted by macrophages and can induce cell death of certain tumor cell lines. It is potent pyrogen causing fever by direct ac...
Gene Name
TNF
Uniprot ID
P01375
Uniprot Name
Tumor necrosis factor
Molecular Weight
25644.15 Da
References
  1. Li JY, Cao HY, Liu P, Cheng GH, Sun MY: Glycyrrhizic acid in the treatment of liver diseases: literature review. Biomed Res Int. 2014;2014:872139. doi: 10.1155/2014/872139. Epub 2014 May 13. [PubMed:24963489]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Phospholipase a2 activator activity
Specific Function
Involved in the activation cascade of caspases responsible for apoptosis execution. At the onset of apoptosis it proteolytically cleaves poly(ADP-ribose) polymerase (PARP) at a '216-Asp-|-Gly-217' ...
Gene Name
CASP3
Uniprot ID
P42574
Uniprot Name
Caspase-3
Molecular Weight
31607.58 Da
References
  1. Li JY, Cao HY, Liu P, Cheng GH, Sun MY: Glycyrrhizic acid in the treatment of liver diseases: literature review. Biomed Res Int. 2014;2014:872139. doi: 10.1155/2014/872139. Epub 2014 May 13. [PubMed:24963489]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Translocation inhibitor
General Function
Transcriptional activator activity, rna polymerase ii core promoter proximal region sequence-specific binding
Specific Function
NF-kappa-B is a pleiotropic transcription factor present in almost all cell types and is the endpoint of a series of signal transduction events that are initiated by a vast array of stimuli related...
Gene Name
NFKB2
Uniprot ID
Q00653
Uniprot Name
Nuclear factor NF-kappa-B p100 subunit
Molecular Weight
96748.355 Da
References
  1. Li JY, Cao HY, Liu P, Cheng GH, Sun MY: Glycyrrhizic acid in the treatment of liver diseases: literature review. Biomed Res Int. 2014;2014:872139. doi: 10.1155/2014/872139. Epub 2014 May 13. [PubMed:24963489]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inducer
General Function
Triglyceride lipase activity
Specific Function
The primary function of this lipase is the hydrolysis of triglycerides of circulating chylomicrons and very low density lipoproteins (VLDL). Binding to heparin sulfate proteogylcans at the cell sur...
Gene Name
LPL
Uniprot ID
P06858
Uniprot Name
Lipoprotein lipase
Molecular Weight
53162.07 Da
References
  1. Ming LJ, Yin AC: Therapeutic effects of glycyrrhizic acid. Nat Prod Commun. 2013 Mar;8(3):415-8. [PubMed:23678825]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Retinal dehydrogenase activity
Specific Function
Catalyzes the transformation of the potent androgen dihydrotestosterone (DHT) into the less active form, 5-alpha-androstan-3-alpha,17-beta-diol (3-alpha-diol). Also has some 20-alpha-hydroxysteroid...
Gene Name
AKR1C4
Uniprot ID
P17516
Uniprot Name
Aldo-keto reductase family 1 member C4
Molecular Weight
37066.52 Da
References
  1. Ploeger BA, Meulenbelt J, DeJongh J: Physiologically based pharmacokinetic modeling of glycyrrhizic acid, a compound subject to presystemic metabolism and enterohepatic cycling. Toxicol Appl Pharmacol. 2000 Feb 1;162(3):177-88. doi: 10.1006/taap.1999.8843. [PubMed:10652246]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase activity
Specific Function
Catalyzes the conversion of aldehydes and ketones to alcohols. Catalyzes the reduction of prostaglandin (PG) D2, PGH2 and phenanthrenequinone (PQ) and the oxidation of 9-alpha,11-beta-PGF2 to PGD2....
Gene Name
AKR1C3
Uniprot ID
P42330
Uniprot Name
Aldo-keto reductase family 1 member C3
Molecular Weight
36852.89 Da
References
  1. Ploeger BA, Meulenbelt J, DeJongh J: Physiologically based pharmacokinetic modeling of glycyrrhizic acid, a compound subject to presystemic metabolism and enterohepatic cycling. Toxicol Appl Pharmacol. 2000 Feb 1;162(3):177-88. doi: 10.1006/taap.1999.8843. [PubMed:10652246]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase activity
Specific Function
Works in concert with the 5-alpha/5-beta-steroid reductases to convert steroid hormones into the 3-alpha/5-alpha and 3-alpha/5-beta-tetrahydrosteroids. Catalyzes the inactivation of the most potent...
Gene Name
AKR1C2
Uniprot ID
P52895
Uniprot Name
Aldo-keto reductase family 1 member C2
Molecular Weight
36734.97 Da
References
  1. Ploeger BA, Meulenbelt J, DeJongh J: Physiologically based pharmacokinetic modeling of glycyrrhizic acid, a compound subject to presystemic metabolism and enterohepatic cycling. Toxicol Appl Pharmacol. 2000 Feb 1;162(3):177-88. doi: 10.1006/taap.1999.8843. [PubMed:10652246]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Substrate
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Ishida S, Ichikawa T, Sakiya Y: Binding of glycyrrhetinic acid to rat plasma, rat serum albumin, human serum, and human serum albumin. Chem Pharm Bull (Tokyo). 1988 Jan;36(1):440-3. [PubMed:3378305]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Transporter activity
Specific Function
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name
ABCB11
Uniprot ID
O95342
Uniprot Name
Bile salt export pump
Molecular Weight
146405.83 Da
References
  1. Pedersen JM, Matsson P, Bergstrom CA, Hoogstraate J, Noren A, LeCluyse EL, Artursson P: Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43. doi: 10.1093/toxsci/kft197. Epub 2013 Sep 6. [PubMed:24014644]

Drug created on June 23, 2017 14:47 / Updated on November 02, 2018 09:14