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Glycyrrhizin (or glycyrrhizic acid or glycyrrhizinic acid) is the chief sweet-tasting constituent of Glycyrrhiza glabra (liquorice) root. Structurally it is a saponin and has been used as an emulsifier and gel-forming agent in foodstuff and cosmetics. Its aglycone is enoxolone and it has therefore been used as a prodrug for that compound, for example it is used in Japan to prevent liver carcinogenesis in patients with chronic hepatitis C.^[3]

Medical uses

Glycyrrhizin inhibits liver cell injury and is given intravenously for the treatment of chronic viral hepatitis and cirrhosis in Japan.^[4]^[5] In one small scale preliminary clinical trial, it was found that early treatment with glycyrrhizin might prevent disease progression in patients with acute onset autoimmune hepatitis.^[6]

Adverse effects

The most widely reported side effects of glycyrrhizin use are fluid retention. These effects are related to the inhibition of cortisol metabolism within the kidney, and the subsequent stimulation of the mineralocorticoid receptors.^[7] Other side effects include:^[8]

Headache
Paralysis
Transient visual loss
Torsades de pointes
Tachycardia
Cardiac arrest
Hypokalaemia
Reduced testosterone
Premature birth
Acute kidney failure
Muscle weakness
Myopathy
Myoglobinuria
Rhabdomyolysis
Increased body weight

Mechanism of action

It inhibits the enzyme 11β-hydroxysteroid dehydrogenase, which likely contributes to its anti-inflammatory and mineralocorticoid activity.^[8] It has a broad-spectrum of antiviral activity in vitro against:^[8]^[9]

Herpes simplex virus,^[10] which has also been confirmed in vivo.^[11]
Influenzavirus (including H5N1)^[12]
Varicella zoster virus^[13]
SARS coronavirus
HIV
Hepatitis A virus
Hepatitis B virus
Hepatitis C virus
Hepatitis E virus
Epstein–Barr virus
Human cytomegalovirus
Flavivirus
Japanese encephalitis virus

Pharmacokinetics

After oral ingestion, glycyrrhizin is first hydrolysed to 18β-glycyrrhetinic acid by intestinal bacteria. After complete absorption from the gut, β-glycyrrhetinic acid is metabolised to 3β-monoglucuronyl-18β-glycyrrhetinic acid in the liver. This metabolite then circulates in the bloodstream. Consequently, its oral bioavailability is poor. The main part is eliminated by bile and only a minor part (0.31–0.67%) by urine.^[14] 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.^[14]

Organoleptic properties

It is 30-50 times as sweet as sucrose (table sugar).^[8]^[15]

References

^ van Rossum, TG; Vulto, AG; Hop, WC; Schalm, SW (December 1999). "Pharmacokinetics of intravenous glycyrrhizin after single and multiple doses in patients with chronic hepatitis C infection.". Clinical Therapeutics. 21 (12): 2080–90. doi:10.1016/S0149-2918(00)87239-2. PMID 10645755.
^ Ploeger, B; Mensinga, T; Sips, A; Seinen, W; Meulenbelt, J; DeJongh, J (May 2001). "The pharmacokinetics of glycyrrhizic acid evaluated by physiologically based pharmacokinetic modeling.". Drug Metabolism Reviews. 33 (2): 125–47. doi:10.1081/DMR-100104400. PMID 11495500.
^ Arase, Yasuji; Ikeda, Kenji; Murashima, Naoya; Chayama, Kazuaki; Tsubota, Akihito; Koida, Isao; Suzuki, Yoshiyuki; Saitoh, Satoshi; Kobayashi, Masahiro; Kumada, Hiromitsu (15 April 1997). "The long term efficacy of glycyrrhizin in chronic hepatitis C patients". Cancer. 79 (8): 1494–1500. doi:10.1002/(SICI)1097-0142(19970415)79:8<1494::AID-CNCR8>3.0.CO;2-B.
^ Sato, H; Goto, W; Yamamura, J; Kurokawa, M; Kageyama, S; Takahara, T; Watanabe, A; Shiraki, K (May 1996). "Therapeutic basis of glycyrrhizin on chronic hepatitis B.". Antiviral Research. 30 (2-3): 171–7. doi:10.1016/0166-3542(96)00942-4. PMID 8783808.
^ van Rossum, TG; Vulto, AG; de Man, RA; Brouwer, JT; Schalm, SW (March 1998). "Review article: glycyrrhizin as a potential treatment for chronic hepatitis C." (PDF). Alimentary Pharmacology & Therapeutics. 12 (3): 199–205. doi:10.1046/j.1365-2036.1998.00309.x. PMID 9570253.
^ Yasui, S; Fujiwara, K; Tawada, A; Fukuda, Y; Nakano, M; Yokosuka, O (December 2011). "Efficacy of intravenous glycyrrhizin in the early stage of acute onset autoimmune hepatitis.". Digestive Diseases and Sciences. 56 (12): 3638–47. doi:10.1007/s10620-011-1789-5. PMID 21681505.
^ Ferrari, P.; Sansonnens, A.; Dick, B.; Frey, F. J. (2001). "In Vivo 11 -HSD-2 Activity: Variability, Salt-Sensitivity, and Effect of Licorice". Hypertension. 38 (6): 1330–6. doi:10.1161/hy1101.096112. PMID 11751713.
^ ^a ^b ^c ^d Asl, MN; Hosseinzadeh, H (June 2008). "Review of pharmacological effects of Glycyrrhiza sp. and its bioactive compounds." (PDF). Phytotherapy Research. 22 (6): 709–24. doi:10.1002/ptr.2362. PMID 18446848.
^ Shamsa, F; Ohtsuki, K; Hasanzadeh, E; Rezazadeh, S (2010). "The Anti-inflammatory and Anti-viral Effects of an Ethnic Medicine: Glycyrrhizin" (PDF). Journal of Medicinal Plants. 9 (Suppl. 2): 1389.
^ Pompei, Raffaello; Flore, Ornella; Marccialis, Maria Antonietta; Pani, Alessandra; Loddo, Bernardo (1979). "Glycyrrhizic acid inhibits virus growth and inactivates virus particles". Nature. 281 (5733): 689–90. doi:10.1038/281689a0. PMID 233133.
^ Sekizawa, T; Yanagi, K; Itoyama, Y (February 2001). "Glycyrrhizin increases survival of mice with herpes simplex encephalitis.". Acta Virologica. 45 (1): 51–4. PMID 11394578.
^ Michaelis, Martin; Geiler, Janina; Naczk, Patrizia; Sithisarn, Patchima; Leutz, Anke; Doerr, Hans Wilhelm; Cinatl, Jindrich (2011). Pekosz, Andrew, ed. "Glycyrrhizin Exerts Antioxidative Effects in H5N1 Influenza a Virus-Infected Cells and Inhibits Virus Replication and Pro-Inflammatory Gene Expression". PLoS ONE. 6 (5): e19705. doi:10.1371/journal.pone.0019705. PMC 3096629 . PMID 21611183.
^ Baba, M; Shigeta, S (February 1987). "Antiviral activity of glycyrrhizin against varicella-zoster virus in vitro.". Antiviral Research. 7 (2): 99–107. doi:10.1016/0166-3542(87)90025-8. PMID 3034150.
^ ^a ^b Kočevar Glavač, Nina; Kreft, Samo (2012). "Excretion profile of glycyrrhizin metabolite in human urine". Food Chemistry. 131: 305–308. doi:10.1016/j.foodchem.2011.08.081.
^ "Glycyrrhizic Acid". PubChem. National Institutes of Health. Retrieved 24 February 2014.

External links

CHEMICAL MODIFICATION OF GLYCYRRHIZIC ACID AS A ROUTE TO NEW BIOACTIVE COMPOUNDS FOR MEDICINE by L.A.Baltina; doi:10.2174/0929867033368538

UpToDate Contents

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1. アレルギー疾患の治療のための漢方薬 chinese herbal medicine for the treatment of allergic diseases

English Journal

Investigating herb-herb interactions: The potential attenuated toxicity mechanism of the combined use of Glycyrrhizae radix et rhizoma (Gancao) and Sophorae flavescentis radix (Kushen).

Shi L1, Tang X1, Dang X1, Wang Q1, Wang X2, He P2, Wang Q1, Liu L1, Liu X1, Zhang Y1.
Journal of ethnopharmacology.J Ethnopharmacol.2015 May 13;165:243-250. doi: 10.1016/j.jep.2015.02.022. Epub 2015 Feb 19.
ETHNOPHARMACOLOGICAL RELEVANCE: Glycyrrhizae radix et rhizoma (Gancao) is often prescribed together with Sophorae flavescentis radix (Kushen) in traditional Chinese medicinal practice to increase the efficacy on the treatment of hepatitis and hepatic fibrosis. Meanwhile, long-term single used Gancao
PMID 25701755

Determination of high-intensity sweeteners in river water and wastewater by solid-phase extraction and liquid chromatography-tandem mass spectrometry.

Arbeláez P1, Borrull F1, Pocurull E2, Marcé RM1.
Journal of chromatography. A.J Chromatogr A.2015 May 8;1393:106-14. doi: 10.1016/j.chroma.2015.03.035. Epub 2015 Mar 21.
High-intensity sweeteners have been suggested as potential organic contaminants due to their widespread use in food, drugs and sanitary products. As a consequence, they are introduced into the environment by different pathways, affecting aquatic life. In this study, a method based on solid-phase ext
PMID 25840659

Extracellular, but not intracellular HMGB1, facilitates self-DNA induced macrophage activation via promoting DNA accumulation in endosomes and contributes to the pathogenesis of lupus nephritis.

Li X1, Yue Y1, Zhu Y1, Xiong S2.
Molecular immunology.Mol Immunol.2015 May;65(1):177-88. doi: 10.1016/j.molimm.2015.01.023. Epub 2015 Feb 6.
Systemic lupus erythematosus (SLE) is a typical autoimmune disease with unclear etiology. Aberrant self-DNA recognition has been proven critical for the initiation of excessive immune responses in lupus. Consistently, we previously reported that a sort of self-DNA, activated lymphocyte-derived DNA (
PMID 25660970

Japanese Journal

The effects of 18β-glycyrrhetinic acid and glycyrrhizin on intestinal absorption of paeoniflorin using the everted rat gut sac model

Journal of natural medicines 71(1), 198-207, 2017
NAID 40021062710

C型肝炎治療薬の偽造品に関する成分分析

YAKUGAKU ZASSHI, 2017
NAID 130005808390

Bioactive Compounds from the Leaves of Lumnitzera racemosa against Acetaminophen-induced Liver damage in vitro (Special issue : Proceedings of DT ⅩⅡ : THE INTERNATIONAL CONFERENCE ON DESERT TECHNOLOGIES ⅩⅡ (DT ⅩⅡ))

沙漠研究 26(3), 183-186, 2016
NAID 130005297260

Related Pictures

archerfriendly | Licorice Root (Glycyrrhiza glabra) Lakritz - Norevo Eastern blotting profile of glycyrrhizin in rat serum after injection | Download Licorice Root Extract Powder 30% Glycyrrhizin Glycyrrhiza Glabra PREMIUM Grade 50g Liquorice-Synonyms Glycyrrhiza; Liquorice root; Glycyrrhizae radix. The proposed hepatoprotective mechanism of glycyrrhizin and omega-3 fatty acids in Chemical structure of glycyrrhizin (GA) and its derivatives. | Download Scientific Diagram

★リンクテーブル★

リンク元	「グリチルリチン」「glycyrrhizic acid」「グリチルリジン」
拡張検索	「glycyrrhizinate」「diammonium glycyrrhizinate」「monoammonium glycyrrhizinate」「glycyrrhizinic acid」

「グリチルリチン」

Glycyrrhizic acid
Clinical data
Trade names	Epigen, Glycyron
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral, intravenous
ATC code	A05BA08 (WHO) QA05BA08 (vet);
Pharmacokinetic data
Metabolism	Hepatic and by intestinal bacteria
Biological half-life	6.2-10.2 hours
Excretion	Faeces, urine (0.31-0.67%)
Identifiers
	IUPAC name (3β,20β)-20-carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-β-D-glucopyranuronosyl-α-D-glucopyranosiduronic acid;
CAS Number	1405-86-3;
PubChem CID	128229;
ChemSpider	14263 ;
UNII	6FO62043WK;
ChEBI	CHEBI:15939 ;
ChEMBL	CHEMBL441687 ;
E number	E958 (glazing agents, ...)
ECHA InfoCard	100.014.350
Chemical and physical data
Formula	C42H62O16
Molar mass	822.93 g/mol
3D model (Jmol)	Interactive image;
Solubility in water	1-10 mg/mL (20 °C)
	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 ;
	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 ; Key:LPLVUJXQOOQHMX-QWBHMCJMSA-N ;

　　[★]

英: glycyrrhizin
同: グリチルリチン酸
化: グリチルリチン酸二カリウム glycyrrhizinate dipotassium, dipotassium glycyrrhizinate
商: ノイボルミチン、強力ネオミノファーゲンシー(グリシン、L-システインとの配合剤)]]、グリチロン(アミノ酢酸、DL-メチオニンとの配合剤)
関: 甘草

特徴

甘草由来の成分

禁忌

アルドステロン症、ミオパチー、低カリウム血症

副作用

偽アルドステロン症

「glycyrrhizic acid」

　　[★]

グリチルリチン酸、グリチルリジン酸

関: diammonium glycyrrhizinate、glycyrrhizin、glycyrrhizinate、glycyrrhizinate dipotassium、glycyrrhizinic acid、monoammonium glycyrrhizinate

「グリチルリジン」

　　[★]

英: glycyrrhizin
関: グリチルリチン

「glycyrrhizinate」

　　[★]

グリチルリチン酸、グリチルリジン酸、(化合物)リチルリジン酸塩

関: diammonium glycyrrhizinate、glycyrrhizic acid、glycyrrhizinate dipotassium、glycyrrhizinic acid、monoammonium glycyrrhizinate

「diammonium glycyrrhizinate」

　　[★]

グリチルリチン酸二アンモニウム

関: glycyrrhizic acid、glycyrrhizin、glycyrrhizinate、glycyrrhizinate dipotassium、glycyrrhizinic acid、monoammonium glycyrrhizinate

「monoammonium glycyrrhizinate」

　　[★]

グリチルリチン酸モノアンモニウム

関: diammonium glycyrrhizinate、glycyrrhizic acid、glycyrrhizinate、glycyrrhizinate dipotassium

「glycyrrhizinic acid」

　　[★]

グリチルリジン酸

関: diammonium glycyrrhizinate、glycyrrhizic acid、glycyrrhizin、glycyrrhizinate

[Pharm-1] van Rossum, TG; Vulto, AG; Hop, WC; Schalm, SW (December 1999). "Pharmacokinetics of intravenous glycyrrhizin after single and multiple doses in patients with chronic hepatitis C infection.". Clinical Therapeutics. 21 (12): 2080–90. doi:10.1016/S0149-2918(00)87239-2. PMID 10645755.

[2] Ploeger, B; Mensinga, T; Sips, A; Seinen, W; Meulenbelt, J; DeJongh, J (May 2001). "The pharmacokinetics of glycyrrhizic acid evaluated by physiologically based pharmacokinetic modeling.". Drug Metabolism Reviews. 33 (2): 125–47. doi:10.1081/DMR-100104400. PMID 11495500.

[3] Arase, Yasuji; Ikeda, Kenji; Murashima, Naoya; Chayama, Kazuaki; Tsubota, Akihito; Koida, Isao; Suzuki, Yoshiyuki; Saitoh, Satoshi; Kobayashi, Masahiro; Kumada, Hiromitsu (15 April 1997). "The long term efficacy of glycyrrhizin in chronic hepatitis C patients". Cancer. 79 (8): 1494–1500. doi:10.1002/(SICI)1097-0142(19970415)79:8<1494::AID-CNCR8>3.0.CO;2-B.

[4] Sato, H; Goto, W; Yamamura, J; Kurokawa, M; Kageyama, S; Takahara, T; Watanabe, A; Shiraki, K (May 1996). "Therapeutic basis of glycyrrhizin on chronic hepatitis B.". Antiviral Research. 30 (2-3): 171–7. doi:10.1016/0166-3542(96)00942-4. PMID 8783808.

[5] van Rossum, TG; Vulto, AG; de Man, RA; Brouwer, JT; Schalm, SW (March 1998). "Review article: glycyrrhizin as a potential treatment for chronic hepatitis C." (PDF). Alimentary Pharmacology & Therapeutics. 12 (3): 199–205. doi:10.1046/j.1365-2036.1998.00309.x. PMID 9570253.

[6] Yasui, S; Fujiwara, K; Tawada, A; Fukuda, Y; Nakano, M; Yokosuka, O (December 2011). "Efficacy of intravenous glycyrrhizin in the early stage of acute onset autoimmune hepatitis.". Digestive Diseases and Sciences. 56 (12): 3638–47. doi:10.1007/s10620-011-1789-5. PMID 21681505.

[7] Ferrari, P.; Sansonnens, A.; Dick, B.; Frey, F. J. (2001). "In Vivo 11 -HSD-2 Activity: Variability, Salt-Sensitivity, and Effect of Licorice". Hypertension. 38 (6): 1330–6. doi:10.1161/hy1101.096112. PMID 11751713.

[rev-8] Asl, MN; Hosseinzadeh, H (June 2008). "Review of pharmacological effects of Glycyrrhiza sp. and its bioactive compounds." (PDF). Phytotherapy Research. 22 (6): 709–24. doi:10.1002/ptr.2362. PMID 18446848.

[9] Shamsa, F; Ohtsuki, K; Hasanzadeh, E; Rezazadeh, S (2010). "The Anti-inflammatory and Anti-viral Effects of an Ethnic Medicine: Glycyrrhizin" (PDF). Journal of Medicinal Plants. 9 (Suppl. 2): 1389.

[10] Pompei, Raffaello; Flore, Ornella; Marccialis, Maria Antonietta; Pani, Alessandra; Loddo, Bernardo (1979). "Glycyrrhizic acid inhibits virus growth and inactivates virus particles". Nature. 281 (5733): 689–90. doi:10.1038/281689a0. PMID 233133.

[11] Sekizawa, T; Yanagi, K; Itoyama, Y (February 2001). "Glycyrrhizin increases survival of mice with herpes simplex encephalitis.". Acta Virologica. 45 (1): 51–4. PMID 11394578.

[12] Michaelis, Martin; Geiler, Janina; Naczk, Patrizia; Sithisarn, Patchima; Leutz, Anke; Doerr, Hans Wilhelm; Cinatl, Jindrich (2011). Pekosz, Andrew, ed. "Glycyrrhizin Exerts Antioxidative Effects in H5N1 Influenza a Virus-Infected Cells and Inhibits Virus Replication and Pro-Inflammatory Gene Expression". PLoS ONE. 6 (5): e19705. doi:10.1371/journal.pone.0019705. PMC 3096629 . PMID 21611183.

[13] Baba, M; Shigeta, S (February 1987). "Antiviral activity of glycyrrhizin against varicella-zoster virus in vitro.". Antiviral Research. 7 (2): 99–107. doi:10.1016/0166-3542(87)90025-8. PMID 3034150.

[Kreft-14] Kočevar Glavač, Nina; Kreft, Samo (2012). "Excretion profile of glycyrrhizin metabolite in human urine". Food Chemistry. 131: 305–308. doi:10.1016/j.foodchem.2011.08.081.

[pubchem-15] "Glycyrrhizic Acid". PubChem. National Institutes of Health. Retrieved 24 February 2014.

v t e Glycosides

Bond	O-glycosidic bond N-glycosidic bond S-glycosidic bond C-glycosidic bond

Geometry	α-Glycoside β-Glycoside 1,4-Glycoside 1,6-Glycoside

Glycone	Fructoside Galactoside Glucoside Glucuronide Rhamnoside Riboside

Aglycone	Alcoholic glycoside Cardiac glycoside Bufadienolide Cardenolide Cyanogenic glycoside Glycosylamine Phenolic glycoside Anthraquinone glycoside Coumarin glycoside Flavonoid glycoside Saponin Steviol glycoside Thioglycoside

v t e Bile and liver therapy (A05)

Bile therapy	bile acid (Chenodeoxycholic acid Cholic acid Ursodeoxycholic acid) Obeticholic acid Nicotinyl methylamide Piprozolin Hymecromone Cyclobutyrol

Liver therapy	Arginine glutamate Silymarin Citiolone Epomediol Ornithine oxoglutarate Tidiacic arginine Glycyrrhizin

匿名

検索

案内

案内

glycyrrhizin