甘草酸

甘草酸
臨床資料
商品名（英語：Drug nomenclature）	Epigen, Glycyron
AHFS/Drugs.com	國際藥品名稱
給藥途徑	口服、靜脈注射
ATC碼	A05BA08 (WHO) QA05BA08 (vet);
藥物動力學數據
藥物代謝	肝臟和腸道細菌
生物半衰期	6.2-10.2 h
排泄途徑	糞便、尿液 (0.31-0.67%)
識別資訊
	IUPAC命名法 (3β,20β)-20-carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-β-D-glucopyranuronosyl-α-D-glucopyranosiduronic acid; OR; (1R,2S,5S,8S,10R,14R,15S,18S,20R)-18-{[(2S,3R,4S,5S,6S)-6-carboxy-3-{[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}-1,2,5,8,15,19,19-heptamethyl-13-oxopentacyclo[12.8.0.02,11.05,10.015,20]docos-11-ene-8-carboxylic acid; ;
CAS號	1405-86-3（α-D-Glucopyranosiduronic acid）; 103000-77-7（β-D-Glucopyranosiduronic acid）
PubChem CID	128229;
ChemSpider	14263 ;
UNII	6FO62043WK;
ChEBI	CHEBI:15939 ;
ChEMBL	ChEMBL441687 ;
E編碼	E958 (glazing agents, ...)
CompTox Dashboard（英語：CompTox Chemicals Dashboard） (EPA)	DTXSID8047006 ;
ECHA InfoCard	100.014.350
化學資訊
化學式	C42H62O16
摩爾質量	822.93 g/mol
3D模型（JSmol（英語：JSmol））	交互式圖像;
水溶性	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 ;

甘草酸（Glycyrrhizic acid 或 glycyrrhizinic acid）又稱甘草皂苷、甘草甜素（Glycyrrhizin），是甘草（Glycyrrhiza glabra）根的主要甜味成分；在結構上是一種皂苷。可用作食品和化妝品中的乳化劑和凝膠形成劑。其糖苷配基是甘草次酸，在日本被用於降低慢性C型肝炎患者患肝癌的風險的前體藥物。^[3] ^[4]

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不良影響

通過食用黑甘草使用甘草酸的最廣泛報道的副作用是降低血鉀水平，對體液平衡和神經功能有影響。^[5] ^[6] 長期服用黑甘草，即使是適量，也會導致血壓升高， ^[6]可能導致心律不齊，以及與處方藥的不良反應。 ^[5]

其對體液的影響與腎臟內皮質醇代謝的抑制，和隨後對鹽皮質激素受體的刺激， ^[7]以及血液中腎素、鉀和醛固酮的水平降低有關，這些因素共同導致血壓升高。 ^[6]

根據攝取黑甘草的量和頻率，其他副作用可能包括： ^[5] ^[8]

水腫
嗜睡
頭痛
癱瘓
瞬時失明
扭轉性室速
心動過速
心臟驟停
睪酮減少
早產
急性腎衰竭
肌肉無力
肌病
肌紅蛋白尿
橫紋肌溶解
體重增加

研究

正在對甘草酸進行實驗室和初步臨床研究，以確定其對常見病毒（如C型肝炎）的可能活性。^[4] 甘草甜素在體外抑制酶11β-羥基類固醇脫氫酶。 ^[8]

藥代動力學

口服攝入後，甘草酸首先被腸道細菌水解為18β-甘草次酸（Enoxolone）。從腸道完全吸收後，18β-甘草次酸被代謝成肝臟中的3β-單葡糖醛酸-18β-甘草次酸。然後該代謝物在血流中循環。主要部分被膽汁清除，只有一小部分（0.31-0.67％）被尿液清除。 ^[9] 口服攝入600mg甘草酸後，1.5至14小時後尿液中出現代謝物。1.5至39小時後達到最大濃度（0.49至2.69mg / l），並且在2至4天後仍可在尿液中檢測到代謝物。^[9]

調味特性

甘草酸是甘草根浸提後，在水中煮沸而得的提取物。^[10] 甘草提取物（甘草酸）在美國作為液體、糊劑或噴霧乾燥粉末出售。 ^[10] 當在規定量範圍時，它被批准用作製造食品，飲料，糖果，膳食補充劑和調味品中的香料和香味劑。 ^[10]它的甜度是蔗糖（食糖）的30至50倍。 ^[8] ^[11]

請參見

參考文獻

[1]
van Rossum, TG; Vulto, AG; Hop, WC; Schalm, SW. Pharmacokinetics of intravenous glycyrrhizin after single and multiple doses in patients with chronic hepatitis C infection.. Clinical Therapeutics. December 1999, 21 (12): 2080–90. PMID 10645755. doi:10.1016/S0149-2918(00)87239-2. hdl:1765/73160.
[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 Metabolism Reviews. May 2001, 33 (2): 125–47. PMID 11495500. doi:10.1081/DMR-100104400.
[3]
Arase, Yasuji; Ikeda, Kenji; Murashima, Naoya; Chayama, Kazuaki; Tsubota, Akihito; Koida, Isao; Suzuki, Yoshiyuki; Saitoh, Satoshi; Kobayashi, Masahiro. The long term efficacy of glycyrrhizin in chronic hepatitis C patients. Cancer. 15 April 1997, 79 (8): 1494–1500. doi:10.1002/(SICI)1097-0142(19970415)79:8<1494::AID-CNCR8>3.0.CO;2-B.
[4]
Fiore, C; Eisenhut, M; Krausse, R; Ragazzi, E; Pellati, D; Armanini, D; Bielenberg, J. Antiviral effects of Glycyrrhiza species. Phytotherapy Research. 2008, 22 (2): 141–8. PMID 17886224. doi:10.1002/ptr.2295.
[5]
Black Licorice: Trick or Treat?. US Food and Drug Administration. 30 October 2017 [15 December 2017]. （原始內容存檔於2017-06-30）. 引用錯誤：帶有name屬性「fda-cons」的<ref>標籤用不同內容定義了多次
[6]
Penninkilampi, R; Eslick, E. M; Eslick, G. D. The association between consistent licorice ingestion, hypertension and hypokalaemia: A systematic review and meta-analysis. Journal of Human Hypertension. 2017, 31 (11): 699–707. PMID 28660884. doi:10.1038/jhh.2017.45.
[7]
Ferrari, P.; Sansonnens, A.; Dick, B.; Frey, F. J. In Vivo 11 -HSD-2 Activity: Variability, Salt-Sensitivity, and Effect of Licorice. Hypertension. 2001, 38 (6): 1330–6. PMID 11751713. doi:10.1161/hy1101.096112.
[8]
Asl, MN; Hosseinzadeh, H. Review of pharmacological effects of Glycyrrhiza sp. and its bioactive compounds.. Phytotherapy Research. 1 June 2008, 22 (6): 709–24. PMID 18446848. doi:10.1002/ptr.2362.
[9]
Kočevar Glavač, Nina; Kreft, Samo. Excretion profile of glycyrrhizin metabolite in human urine. Food Chemistry. 2012, 131: 305–308. doi:10.1016/j.foodchem.2011.08.081.
[10]
Sec. 184.1408 Licorice and licorice derivatives. US Food and Drug Administration, Code of Federal Regulations Title 21, 21CFR184.1408. 1 April 2017 [15 December 2017]. （原始內容存檔於2021-01-22）.
[11]
Glycyrrhizic Acid. PubChem. National Institutes of Health. [24 February 2014]. （原始內容存檔於2014-03-11）.

外部連結

維基共享資源上的相關多媒體資源：甘草酸

[Pharm-1] [1]
van Rossum, TG; Vulto, AG; Hop, WC; Schalm, SW. Pharmacokinetics of intravenous glycyrrhizin after single and multiple doses in patients with chronic hepatitis C infection.. Clinical Therapeutics. December 1999, 21 (12): 2080–90. PMID 10645755. doi:10.1016/S0149-2918(00)87239-2. hdl:1765/73160.

[2] [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 Metabolism Reviews. May 2001, 33 (2): 125–47. PMID 11495500. doi:10.1081/DMR-100104400.

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

[fiore-4] [4]
Fiore, C; Eisenhut, M; Krausse, R; Ragazzi, E; Pellati, D; Armanini, D; Bielenberg, J. Antiviral effects of Glycyrrhiza species. Phytotherapy Research. 2008, 22 (2): 141–8. PMID 17886224. doi:10.1002/ptr.2295.

[fda-cons-5] [5]
Black Licorice: Trick or Treat?. US Food and Drug Administration. 30 October 2017 [15 December 2017]. （原始內容存檔於2017-06-30）. 引用錯誤：帶有name屬性「fda-cons」的<ref>標籤用不同內容定義了多次

[jhh-6] [6]
Penninkilampi, R; Eslick, E. M; Eslick, G. D. The association between consistent licorice ingestion, hypertension and hypokalaemia: A systematic review and meta-analysis. Journal of Human Hypertension. 2017, 31 (11): 699–707. PMID 28660884. doi:10.1038/jhh.2017.45.

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

[rev-8] [8]
Asl, MN; Hosseinzadeh, H. Review of pharmacological effects of Glycyrrhiza sp. and its bioactive compounds.. Phytotherapy Research. 1 June 2008, 22 (6): 709–24. PMID 18446848. doi:10.1002/ptr.2362.

[Kreft-9] [9]
Kočevar Glavač, Nina; Kreft, Samo. Excretion profile of glycyrrhizin metabolite in human urine. Food Chemistry. 2012, 131: 305–308. doi:10.1016/j.foodchem.2011.08.081.

[fda-10] [10]
Sec. 184.1408 Licorice and licorice derivatives. US Food and Drug Administration, Code of Federal Regulations Title 21, 21CFR184.1408. 1 April 2017 [15 December 2017]. （原始內容存檔於2021-01-22）.

[pubchem-11] [11]
Glycyrrhizic Acid. PubChem. National Institutes of Health. [24 February 2014]. （原始內容存檔於2014-03-11）.

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