甘草酸

甘草酸
临床资料
商品名（英语：Drug nomenclature）	Epigen, Glycyron
AHFS/Drugs.com	国际药品名称
给药途径	口服、静脉注射
ATC码	A05BA08 (WHO) QA05BA08 (vet);
药物动力学数据
药物代谢	肝脏和肠道细菌
生物半衰期	6.2-10.2 h
排泄途径	粪便、尿液 (0.31-0.67%)
识别信息
	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号	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编码	E958 (glazing agents, ...)
CompTox Dashboard（英语：CompTox Chemicals Dashboard） (EPA)	DTXSID8047006 ;
ECHA InfoCard	100.014.350
化学信息
化学式	C42H62O16
摩尔质量	822.93 g/mol
3D模型（JSmol（英语：JSmol））	交互式图像;
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）又称甘草皂苷、甘草甜素（Glycyrrhizin），是甘草（Glycyrrhiza glabra）根的主要甜味成分；在结构上是一种皂苷。可用作食品和化妆品中的乳化剂和凝胶形成剂。其糖苷配基是甘草次酸，在日本被用于降低慢性丙型肝炎患者患肝癌的风险的前体药物。^[3] ^[4]

不良影响

通过食用黑甘草使用甘草酸的最广泛报道的副作用是降低血钾水平，对体液平衡和神经功能有影响。^[5] ^[6] 长期服用黑甘草，即使是适量，也会导致血压升高， ^[6]可能导致心律不齐，以及与处方药的不良反应。 ^[5]

其对体液的影响与肾脏内皮质醇代谢的抑制，和随后对盐皮质激素受体的刺激， ^[7]以及血液中肾素、钾和醛固酮的水平降低有关，这些因素共同导致血压升高。 ^[6]

根据摄取黑甘草的量和频率，其他副作用可能包括： ^[5] ^[8]

水肿
嗜睡
头痛
瘫痪
瞬时失明
扭转性室速
心动过速
心脏骤停
睾酮减少
早产
急性肾衰竭
肌肉无力
肌病
肌红蛋白尿
横纹肌溶解
体重增加

研究

正在对甘草酸进行实验室和初步临床研究，以确定其对常见病毒（如丙型肝炎）的可能活性。^[4] 甘草甜素在体外抑制酶11β-羟基类固醇脱氢酶。 ^[8]

药代动力学

口服摄入后，甘草酸首先被肠道细菌水解为18β-甘草次酸（Enoxolone）。从肠道完全吸收后，18β-甘草次酸被代谢成肝脏中的3β-单葡糖醛酸-18β-甘草次酸。然后该代谢物在血流中循环。主要部分被胆汁清除，只有一小部分（0.31-0.67％）被尿液清除。 ^[9] 口服摄入600mg甘草酸后，1.5至14小时后尿液中出现代谢物。1.5至39小时后达到最大浓度（0.49至2.69mg / l），并且在2至4天后仍可在尿液中检测到代谢物。^[9]

调味特性

甘草酸是甘草根浸提后，在水中煮沸而得的提取物。^[10] 甘草提取物（甘草酸）在美国作为液体、糊剂或喷雾干燥粉末出售。 ^[10] 当在规定量范围时，它被批准用作制造食品，饮料，糖果，膳食补充剂和调味品中的香料和香味剂。 ^[10]它的甜度是蔗糖（食糖）的30至50倍。 ^[8] ^[11]

请参见

参考文献

^ 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.
^ 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.
^ 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.
^ ^4.0 ^4.1 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.
^ ^5.0 ^5.1 ^5.2 Black Licorice: Trick or Treat?. US Food and Drug Administration. 30 October 2017 [15 December 2017]. （原始内容存档于2017-06-30）. 引用错误：带有name属性“fda-cons”的<ref>标签用不同内容定义了多次
^ ^6.0 ^6.1 ^6.2 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.
^ 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.
^ ^8.0 ^8.1 ^8.2 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.
^ ^9.0 ^9.1 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.
^ ^10.0 ^10.1 ^10.2 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]. （原始内容存档于2021-01-22）.
^ Glycyrrhizic Acid. PubChem. National Institutes of Health. [24 February 2014]. （原始内容存档于2014-03-11）.

外部链接

维基共享资源上的相关多媒体资源：甘草酸

[Pharm-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.

[fiore-4] 4.0 ^4.1 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] 5.0 ^5.1 ^5.2 Black Licorice: Trick or Treat?. US Food and Drug Administration. 30 October 2017 [15 December 2017]. （原始内容存档于2017-06-30）. 引用错误：带有name属性“fda-cons”的<ref>标签用不同内容定义了多次

[jhh-6] 6.0 ^6.1 ^6.2 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.

[rev-8] 8.0 ^8.1 ^8.2 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] 9.0 ^9.1 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] 10.0 ^10.1 ^10.2 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]. （原始内容存档于2021-01-22）.

[pubchem-11] Glycyrrhizic Acid. PubChem. National Institutes of Health. [24 February 2014]. （原始内容存档于2014-03-11）.

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