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甘草酸

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甘草酸
臨床資料
商品名英语Drug nomenclatureEpigen, Glycyron
AHFS/Drugs.com国际药品名称
给药途径口服、静脉注射
ATC碼
藥物動力學數據
药物代谢肝脏和肠道细菌
生物半衰期6.2-10.2 h[1]
排泄途徑粪便、尿液 (0.31-0.67%)[2]
识别信息
  • (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
ChemSpider
UNII
ChEBI
ChEMBL
E编码E958 (glazing agents, ...) 編輯維基數據鏈接
CompTox Dashboard英语CompTox Chemicals Dashboard (EPA)
ECHA InfoCard100.014.350 編輯維基數據鏈接
化学信息
化学式C42H62O16
摩尔质量822.93 g/mol
3D模型(JSmol英语JSmol
水溶性1-10 mg/mL (20 °C)
  • 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=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 checkY
  • Key:LPLVUJXQOOQHMX-QWBHMCJMSA-N checkY

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凝胶形成剂。其糖苷配基甘草次酸,在日本被用于降低慢性丙型肝炎患者肝癌的风险的前体药物[3] [4]

不良影响

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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]

研究

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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

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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

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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

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参考文献

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

外部链接

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