EICAR (药物)

EICAR
臨床資料
其他名稱	5-乙炔基-4-胺甲酰基-1-β-D-呋喃核糖基咪唑
法律規範狀態
法律規範	开发中药物;
识别信息
	IUPAC命名法 1-[(3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-ethynylimidazole-4-carboxamide; ;
CAS号	118908-07-9
PubChem CID	21120184;
ChemSpider	399153;
CompTox Dashboard（英语：CompTox Chemicals Dashboard） (EPA)	DTXSID50922809 ;
化学信息
化学式	C11H13N3O5
摩尔质量	267.24 g·mol−1
3D模型（JSmol（英语：JSmol））	交互式图像;
	SMILES NC(=O)c1ncn(c1C#C)C2[C@H](O)[C@H](O)[C@H](O2)CO;
	InChI InChI=1S/C11H13N3O5/c1-2-5-7(10(12)18)13-4-14(5)11-9(17)8(16)6(3-15)19-11/h1,4,6,8-9,11,15-17H,3H2,(H2,12,18)/t6-,8-,9-,11?/m1/s1; Key:SWQQELWGJDXCFT-ABHRNEANSA-N;

5-乙炔基-4-胺甲酰基-1-β-D-呋喃核糖基咪唑，简称EICAR^{[註 1]}，是一种具有抗癌和抗病毒效果的核苷类似物药物。其最初作为一种治疗白血病药物而被开发^[1]^[2]，但失败于人体临床试验阶段。其发现具有广谱抗病毒活性，对痘病毒、塞姆利基森林病毒（英语：Semliki Forest virus）、鸠宁病毒（英语：Argentinian mammarenavirus）、呼肠孤病毒、流感病毒、麻疹病毒和人类呼吸道合胞病毒等病毒在内均有抗病毒效果^[3]^[4]^[5]，但对诸如SARS病毒等冠状病毒无效^[6]。如此广泛的抗病毒谱意味着EICAR以及其衍生物将继续被研究用于治疗病毒性疾病^[7]^[8]^[9]。

人们最初发现EICAR对人体中参与单磷酸鸟苷合成的肌苷-5'-单磷酸脱氢酶（英语：Inosine-5′-monophosphate dehydrogenase）（IMPDH）具有强力的抑制作用^[10]^[11]，这种作用也是抑制的抗病毒^[12]^[13] 和抗癌^[11]活性机制。

注释

^ 英语全称：5-Ethynyl-1-beta-D-ribofuranosylimidazole-4-carboxamide

参考文献

^ Matsuda A, Minakawa N, Sasaki T, Ueda T. The design, synthesis and antileukemic activity of 5-alkynyl-1-beta-D-ribofuranosylimidazole-4-carboxamides. Chemical & Pharmaceutical Bulletin. July 1988, 36 (7): 2730–2733. PMID 3272143. doi:10.1248/cpb.36.2730 .
^ Minakawa N, Takeda T, Sasaki T, Matsuda A, Ueda T. Nucleosides and nucleotides. 96. Synthesis and antitumor activity of 5-ethynyl-1-beta-D-ribofuranosylimidazole-4-carboxamide (EICAR) and its derivatives. Journal of Medicinal Chemistry. February 1991, 34 (2): 778–786. PMID 1995901. doi:10.1021/jm00106a045.
^ De Clercq E, Cools M, Balzarini J, Snoeck R, Andrei G, Hosoya M, Shigeta S, Ueda T, Minakawa N, Matsuda A. Antiviral activities of 5-ethynyl-1-beta-D-ribofuranosylimidazole-4- carboxamide and related compounds. Antimicrobial Agents and Chemotherapy. April 1991, 35 (4): 679–684. PMC 245078 . PMID 2069373. doi:10.1128/aac.35.4.679.
^ Jashés M, González M, López-Lastra M, De Clercq E, Sandino A. Inhibitors of infectious pancreatic necrosis virus (IPNV) replication. Antiviral Research. March 1996, 29 (2–3): 309–312. PMID 8739609. doi:10.1016/0166-3542(96)80226-9.
^ Dal Pozzo F, Galligioni V, Vaccari F, Gallina L, Battilani M, Scagliarini A. Antiviral efficacy of EICAR against canine distemper virus (CDV) in vitro. Research in Veterinary Science. April 2010, 88 (2): 339–344. PMID 19781726. doi:10.1016/j.rvsc.2009.08.010.
^ Barnard DL, Day CW, Bailey K, Heiner M, Montgomery R, Lauridsen L, Winslow S, Hoopes J, Li JK, Lee J, Carson DA, Cottam HB, Sidwell RW. Enhancement of the infectivity of SARS-CoV in BALB/c mice by IMP dehydrogenase inhibitors, including ribavirin. Antiviral Research. August 2006, 71 (1): 53–63. PMC 7114261 . PMID 16621037. doi:10.1016/j.antiviral.2006.03.001 .
^ De Clercq E. Curious (Old and New) Antiviral Nucleoside Analogues with Intriguing Therapeutic Potential. Current Medicinal Chemistry. 2015, 22 (34): 3866–3880. PMID 26112146. doi:10.2174/0929867322666150625094705.
^ Okano Y, Saito-Tarashima N, Kurosawa M, Iwabu A, Ota M, Watanabe T, Kato F, Hishiki T, Fujimuro M, Minakawa N. Synthesis and biological evaluation of novel imidazole nucleosides as potential anti-dengue virus agents. Bioorganic & Medicinal Chemistry. June 2019, 27 (11): 2181–2186. PMID 31003866. S2CID 124129370. doi:10.1016/j.bmc.2019.04.015.
^ De Clercq E. New Nucleoside Analogues for the Treatment of Hemorrhagic Fever Virus Infections. Chemistry: An Asian Journal. November 2019, 14 (22): 3962–3968. PMC 7159701 . PMID 31389664. doi:10.1002/asia.201900841.
^ Qian X, Liu H, Xu D, Xu L, Huang F, He W, Qi J, Zhu Y, Xu D. Functional outcomes and complications following B-TURP versus HoLEP for the treatment of benign prostatic hyperplasia: a review of the literature and Meta-analysis. The Aging Male. September 2017, 20 (3): 184–191. PMID 28368238. S2CID 25963580. doi:10.1080/13685538.2017.1295436.
^ ^11.0 ^11.1 Balzarini J, Karlsson A, Wang L, Bohman C, Horská K, Votruba I, Fridland A, Van Aerschot A, Herdewijn P, De Clercq E. Eicar (5-ethynyl-1-beta-D-ribofuranosylimidazole-4-carboxamide). A novel potent inhibitor of inosinate dehydrogenase activity and guanylate biosynthesis. The Journal of Biological Chemistry. November 1993, 268 (33): 24591–24598. PMID 7901217. doi:10.1016/S0021-9258(19)74507-4 .
^ Jashés M, Mlynarz G, De Clercq E, Sandino AM. Inhibitory effects of EICAR on infectious pancreatic necrosis virus replication. Antiviral Research. January 2000, 45 (1): 9–17. PMID 10774586. doi:10.1016/S0166-3542(99)00071-6.
^ Dal Pozzo F, Galligioni V, Vaccari F, Gallina L, Battilani M, Scagliarini A. Antiviral efficacy of EICAR against canine distemper virus (CDV) in vitro. Research in Veterinary Science. April 2010, 88 (2): 339–344. PMID 19781726. doi:10.1016/j.rvsc.2009.08.010.

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[1] 英语全称：5-Ethynyl-1-beta-D-ribofuranosylimidazole-4-carboxamide

[2] Matsuda A, Minakawa N, Sasaki T, Ueda T. The design, synthesis and antileukemic activity of 5-alkynyl-1-beta-D-ribofuranosylimidazole-4-carboxamides. Chemical & Pharmaceutical Bulletin. July 1988, 36 (7): 2730–2733. PMID 3272143. doi:10.1248/cpb.36.2730 .

[3] Minakawa N, Takeda T, Sasaki T, Matsuda A, Ueda T. Nucleosides and nucleotides. 96. Synthesis and antitumor activity of 5-ethynyl-1-beta-D-ribofuranosylimidazole-4-carboxamide (EICAR) and its derivatives. Journal of Medicinal Chemistry. February 1991, 34 (2): 778–786. PMID 1995901. doi:10.1021/jm00106a045.

[4] De Clercq E, Cools M, Balzarini J, Snoeck R, Andrei G, Hosoya M, Shigeta S, Ueda T, Minakawa N, Matsuda A. Antiviral activities of 5-ethynyl-1-beta-D-ribofuranosylimidazole-4- carboxamide and related compounds. Antimicrobial Agents and Chemotherapy. April 1991, 35 (4): 679–684. PMC 245078 . PMID 2069373. doi:10.1128/aac.35.4.679.

[5] Jashés M, González M, López-Lastra M, De Clercq E, Sandino A. Inhibitors of infectious pancreatic necrosis virus (IPNV) replication. Antiviral Research. March 1996, 29 (2–3): 309–312. PMID 8739609. doi:10.1016/0166-3542(96)80226-9.

[6] Dal Pozzo F, Galligioni V, Vaccari F, Gallina L, Battilani M, Scagliarini A. Antiviral efficacy of EICAR against canine distemper virus (CDV) in vitro. Research in Veterinary Science. April 2010, 88 (2): 339–344. PMID 19781726. doi:10.1016/j.rvsc.2009.08.010.

[7] Barnard DL, Day CW, Bailey K, Heiner M, Montgomery R, Lauridsen L, Winslow S, Hoopes J, Li JK, Lee J, Carson DA, Cottam HB, Sidwell RW. Enhancement of the infectivity of SARS-CoV in BALB/c mice by IMP dehydrogenase inhibitors, including ribavirin. Antiviral Research. August 2006, 71 (1): 53–63. PMC 7114261 . PMID 16621037. doi:10.1016/j.antiviral.2006.03.001 .

[8] De Clercq E. Curious (Old and New) Antiviral Nucleoside Analogues with Intriguing Therapeutic Potential. Current Medicinal Chemistry. 2015, 22 (34): 3866–3880. PMID 26112146. doi:10.2174/0929867322666150625094705.

[9] Okano Y, Saito-Tarashima N, Kurosawa M, Iwabu A, Ota M, Watanabe T, Kato F, Hishiki T, Fujimuro M, Minakawa N. Synthesis and biological evaluation of novel imidazole nucleosides as potential anti-dengue virus agents. Bioorganic & Medicinal Chemistry. June 2019, 27 (11): 2181–2186. PMID 31003866. S2CID 124129370. doi:10.1016/j.bmc.2019.04.015.

[10] De Clercq E. New Nucleoside Analogues for the Treatment of Hemorrhagic Fever Virus Infections. Chemistry: An Asian Journal. November 2019, 14 (22): 3962–3968. PMC 7159701 . PMID 31389664. doi:10.1002/asia.201900841.

[11] Qian X, Liu H, Xu D, Xu L, Huang F, He W, Qi J, Zhu Y, Xu D. Functional outcomes and complications following B-TURP versus HoLEP for the treatment of benign prostatic hyperplasia: a review of the literature and Meta-analysis. The Aging Male. September 2017, 20 (3): 184–191. PMID 28368238. S2CID 25963580. doi:10.1080/13685538.2017.1295436.

[p7901217-12] 11.0 ^11.1 Balzarini J, Karlsson A, Wang L, Bohman C, Horská K, Votruba I, Fridland A, Van Aerschot A, Herdewijn P, De Clercq E. Eicar (5-ethynyl-1-beta-D-ribofuranosylimidazole-4-carboxamide). A novel potent inhibitor of inosinate dehydrogenase activity and guanylate biosynthesis. The Journal of Biological Chemistry. November 1993, 268 (33): 24591–24598. PMID 7901217. doi:10.1016/S0021-9258(19)74507-4 .

[13] Jashés M, Mlynarz G, De Clercq E, Sandino AM. Inhibitory effects of EICAR on infectious pancreatic necrosis virus replication. Antiviral Research. January 2000, 45 (1): 9–17. PMID 10774586. doi:10.1016/S0166-3542(99)00071-6.

[14] Dal Pozzo F, Galligioni V, Vaccari F, Gallina L, Battilani M, Scagliarini A. Antiviral efficacy of EICAR against canine distemper virus (CDV) in vitro. Research in Veterinary Science. April 2010, 88 (2): 339–344. PMID 19781726. doi:10.1016/j.rvsc.2009.08.010.

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