EICAR (antiviral)

EICAR (antiviral)
Clinical data
Trade names	EICAR
Legal status
Legal status	US: Investigational New Drug ;
Identifiers
	IUPAC name 1-[(3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-ethynylimidazole-4-carboxamide;
CAS Number	118908-07-9;
PubChem CID	21120184;
ChemSpider	399153;
Chemical and physical data
Formula	C11H13N3O5
Molar mass	267.24 g·mol−1
3D model (JSmol)	Interactive image;
	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;

EICAR is a drug which acts as an inhibitor of the enzyme IMP dehydrogenase.[1][2] It is a nucleoside derivative which has both anti-cancer and antiviral effects, and was originally developed for the treatment of leukemia,[3][4] but was unsuccessful in human clinical trials. It has broad spectrum antiviral effects with activity against pox viruses, Semliki forest virus, Junin virus, reovirus, influenza, measles virus and respiratory syncytial virus among others,[5][6][7] although it is not active against coronaviridae such as SARS-CoV-1.[8] This useful spectrum of activity means that EICAR and related derivatives continue to be investigated for the treatment of viral diseases.[9][10][11]

References

Balzarini J, Karlsson A, Wang L, Bohman C, Horská K, Votruba I, et al. (25 November 1993). "Eicar (5-ethynyl-1-beta-D-ribofuranosylimidazole-4-carboxamide). A novel potent inhibitor of inosinate dehydrogenase activity and guanylate biosynthesis" (PDF). The Journal of Biological Chemistry. 268 (33): 24591–8. PMID 7901217.
Minakawa N, Matsuda A (July 1999). "Mechanism-based design of inosine 5-monophosphate dehydrogenase inhibitors: synthesis and biological activities of 5-ethynyl-1-beta-D-ribofuranosylimidazole-4-carboxamide (EICAR) and its derivatives". Current Medicinal Chemistry. 6 (7): 615–28. PMID 10390604.
Matsuda A, Minakawa N, Sasaki T, Ueda T (July 1988). "The design, synthesis and antileukemic activity of 5-alkynyl-1-beta-D-ribofuranosylimidazole-4-carboxamides". Chemical & Pharmaceutical Bulletin. 36 (7): 2730–3. doi:10.1248/cpb.36.2730. PMID 3272143.
Minakawa N, Takeda T, Sasaki T, Matsuda A, Ueda T (February 1991). "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. 34 (2): 778–86. doi:10.1021/jm00106a045. PMID 1995901.
De Clercq E, Cools M, Balzarini J, Snoeck R, Andrei G, Hosoya M, et al. (April 1991). "Antiviral activities of 5-ethynyl-1-beta-D-ribofuranosylimidazole-4- carboxamide and related compounds". Antimicrobial Agents and Chemotherapy. 35 (4): 679–84. doi:10.1128/aac.35.4.679. PMC 245078. PMID 2069373.
Jashés M, González M, López-Lastra M, De Clercq E, Sandino A (March 1996). "Inhibitors of infectious pancreatic necrosis virus (IPNV) replication". Antiviral Research. 29 (2–3): 309–12. doi:10.1016/0166-3542(96)80226-9. PMID 8739609.
Dal Pozzo F, Galligioni V, Vaccari F, Gallina L, Battilani M, Scagliarini A (April 2010). "Antiviral efficacy of EICAR against canine distemper virus (CDV) in vitro". Research in Veterinary Science. 88 (2): 339–44. doi:10.1016/j.rvsc.2009.08.010. PMID 19781726.
Barnard DL, Day CW, Bailey K, Heiner M, Montgomery R, Lauridsen L, et al. (August 2006). "Enhancement of the infectivity of SARS-CoV in BALB/c mice by IMP dehydrogenase inhibitors, including ribavirin". Antiviral Research. 71 (1): 53–63. doi:10.1016/j.antiviral.2006.03.001. PMC 7114261. PMID 16621037.
De Clercq E (2015). "Curious (Old and New) Antiviral Nucleoside Analogues with Intriguing Therapeutic Potential". Current Medicinal Chemistry. 22 (34): 3866–80. doi:10.2174/0929867322666150625094705. PMID 26112146.
Okano Y, Saito-Tarashima N, Kurosawa M, Iwabu A, Ota M, Watanabe T, et al. (June 2019). "Synthesis and biological evaluation of novel imidazole nucleosides as potential anti-dengue virus agents". Bioorganic & Medicinal Chemistry. 27 (11): 2181–2186. doi:10.1016/j.bmc.2019.04.015. PMID 31003866.
De Clercq E (November 2019). "New Nucleoside Analogues for the Treatment of Hemorrhagic Fever Virus Infections". Chemistry, an Asian Journal. 14 (22): 3962–3968. doi:10.1002/asia.201900841. PMC 7159701. PMID 31389664.

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[1] Balzarini J, Karlsson A, Wang L, Bohman C, Horská K, Votruba I, et al. (25 November 1993). "Eicar (5-ethynyl-1-beta-D-ribofuranosylimidazole-4-carboxamide). A novel potent inhibitor of inosinate dehydrogenase activity and guanylate biosynthesis" (PDF). The Journal of Biological Chemistry. 268 (33): 24591–8. PMID 7901217.

[2] Minakawa N, Matsuda A (July 1999). "Mechanism-based design of inosine 5-monophosphate dehydrogenase inhibitors: synthesis and biological activities of 5-ethynyl-1-beta-D-ribofuranosylimidazole-4-carboxamide (EICAR) and its derivatives". Current Medicinal Chemistry. 6 (7): 615–28. PMID 10390604.

[3] Matsuda A, Minakawa N, Sasaki T, Ueda T (July 1988). "The design, synthesis and antileukemic activity of 5-alkynyl-1-beta-D-ribofuranosylimidazole-4-carboxamides". Chemical & Pharmaceutical Bulletin. 36 (7): 2730–3. doi:10.1248/cpb.36.2730. PMID 3272143.

[4] Minakawa N, Takeda T, Sasaki T, Matsuda A, Ueda T (February 1991). "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. 34 (2): 778–86. doi:10.1021/jm00106a045. PMID 1995901.

[5] De Clercq E, Cools M, Balzarini J, Snoeck R, Andrei G, Hosoya M, et al. (April 1991). "Antiviral activities of 5-ethynyl-1-beta-D-ribofuranosylimidazole-4- carboxamide and related compounds". Antimicrobial Agents and Chemotherapy. 35 (4): 679–84. doi:10.1128/aac.35.4.679. PMC 245078. PMID 2069373.

[6] Jashés M, González M, López-Lastra M, De Clercq E, Sandino A (March 1996). "Inhibitors of infectious pancreatic necrosis virus (IPNV) replication". Antiviral Research. 29 (2–3): 309–12. doi:10.1016/0166-3542(96)80226-9. PMID 8739609.

[7] Dal Pozzo F, Galligioni V, Vaccari F, Gallina L, Battilani M, Scagliarini A (April 2010). "Antiviral efficacy of EICAR against canine distemper virus (CDV) in vitro". Research in Veterinary Science. 88 (2): 339–44. doi:10.1016/j.rvsc.2009.08.010. PMID 19781726.

[8] Barnard DL, Day CW, Bailey K, Heiner M, Montgomery R, Lauridsen L, et al. (August 2006). "Enhancement of the infectivity of SARS-CoV in BALB/c mice by IMP dehydrogenase inhibitors, including ribavirin". Antiviral Research. 71 (1): 53–63. doi:10.1016/j.antiviral.2006.03.001. PMC 7114261. PMID 16621037.

[9] De Clercq E (2015). "Curious (Old and New) Antiviral Nucleoside Analogues with Intriguing Therapeutic Potential". Current Medicinal Chemistry. 22 (34): 3866–80. doi:10.2174/0929867322666150625094705. PMID 26112146.

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

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