EICAR (藥物)

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	開發中藥物;
識別資訊
	IUPAC命名法 1-[(3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-ethynylimidazole-4-carboxamide; ;
CAS號	118908-07-9
PubChem CID	21120184;
ChemSpider	399153;
CompTox Dashboard（英語：CompTox Chemicals Dashboard） (EPA)	DTXSID50922809 ;
化學資訊
化學式	C11H13N3O5
摩爾質量	267.24 g·mol−1
3D模型（JSmol（英語：JSmol））	交互式圖像;
	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，簡稱EICAR^{[註 1]}，是一種具有抗癌和抗病毒效果的核苷類似物藥物。其最初作為一種治療白血病藥物而被開發^[1]^[2]，但失敗於人體臨床試驗階段。其發現具有廣譜抗病毒活性，對痘病毒、塞姆利基森林病毒（英語：Semliki Forest virus）、鳩寧病毒（英語：Argentinian mammarenavirus）、呼腸孤病毒、流感病毒、麻疹病毒和人類呼吸道合胞病毒等病毒在內均有抗病毒效果^[3]^[4]^[5]，但對諸如SARS病毒等冠狀病毒無效^[6]。如此廣泛的抗病毒譜意味着EICAR以及其衍生物將繼續被研究用於治療病毒性疾病^[7]^[8]^[9]。

人們最初發現EICAR對人體中參與單磷酸鳥苷合成的肌苷-5'-單磷酸脫氫酶（英語：Inosine-5′-monophosphate dehydrogenase）（IMPDH）具有強力的抑制作用^[10]^[11]，這種作用也是抑制的抗病毒^[12]^[13] 和抗癌^[11]活性機制。

注釋

^ 英語全稱：5-Ethynyl-1-beta-D-ribofuranosylimidazole-4-carboxamide

參考文獻

^ 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] 英語全稱：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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