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MedKoo Cat#: 555786 | Name: EICAR

Description:

WARNING: This product is for research use only, not for human or veterinary use.

EICAR is a drug which acts as an inhibitor of the enzyme IMP dehydrogenase. It is a nucleoside derivative which has both anti-cancer and antiviral effects, and was originally developed for the treatment of leukemia, but was unsuccessful in human clinical trials. It has broad spectrum antiviral effects with activity against vaccinia virus, Semliki forest virus, Junin virus, reovirus, influenza, measles virus and respiratory syncytial virus among others, although it is not active against SARS. This useful spectrum of activity means that EICAR and related derivatives continue to be investigated for the treatment of viral diseases.

Chemical Structure

EICAR
EICAR
CAS#118908-07-9

Theoretical Analysis

MedKoo Cat#: 555786

Name: EICAR

CAS#: 118908-07-9

Chemical Formula: C11H13N3O5

Exact Mass: 267.0855

Molecular Weight: 267.24

Elemental Analysis: C, 49.44; H, 4.90; N, 15.72; O, 29.93

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
EICAR; 5-Erfic;
IUPAC/Chemical Name
5-Ethynyl-1-beta-D-ribofuranosylimidazole-4-carboxamide
InChi Key
SWQQELWGJDXCFT-PNHWDRBUSA-N
InChi Code
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
SMILES Code
O=C(C1=C(C#C)N([C@H]2[C@@H]([C@@H]([C@@H](CO)O2)O)O)C=N1)N
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 267.24 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
This message contains search results from the National Center for Biotechnology Information (NCBI) at the U.S. National Library of Medicine (NLM). Do not reply directly to this message Sent On: Wed May 13 15:13:48 2020 20 selected items PubMed Results Items 1-20 of 20 (Display the 20 citations in PubMed) 1: De Clercq E. New Nucleoside Analogues for the Treatment of Hemorrhagic Fever Virus Infections. Chem Asian J. 2019 Nov 18;14(22):3962-3968. doi: 10.1002/asia.201900841. Epub 2019 Aug 7. PMID: 31389664; PMCID: PMC7159701. 2: 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. Bioorg Med Chem. 2019 Jun 1;27(11):2181-2186. doi: 10.1016/j.bmc.2019.04.015. Epub 2019 Apr 8. PMID: 31003866. 3: Smee DF, Hurst BL, Evans WJ, Clyde N, Wright S, Peterson C, Jung KH, Day CW. Evaluation of cell viability dyes in antiviral assays with RNA viruses that exhibit different cytopathogenic properties. J Virol Methods. 2017 Aug;246:51-57. doi: 10.1016/j.jviromet.2017.03.012. Epub 2017 Mar 27. PMID: 28359770; PMCID: PMC5479350. 4: Koopen AM, Groen AK, Nieuwdorp M. Human microbiome as therapeutic intervention target to reduce cardiovascular disease risk. Curr Opin Lipidol. 2016 Dec;27(6):615-622. doi: 10.1097/MOL.0000000000000357. PMID: 27676197. 5: Kok M, Mihl C, Hendriks BM, Altintas S, Eijsvoogel NG, Kietselaer BL, Wildberger JE, Das M. Patient Comfort During Contrast Media Injection in Coronary Computed Tomographic Angiography Using Varying Contrast Media Concentrations and Flow Rates: Results From the EICAR Trial. Invest Radiol. 2016 Dec;51(12):810-815. doi: 10.1097/RLI.0000000000000284. PMID: 27164459. 6: De Clercq E. Curious (Old and New) Antiviral Nucleoside Analogues with Intriguing Therapeutic Potential. Curr Med Chem. 2015;22(34):3866-80. doi: 10.2174/0929867322666150625094705. PMID: 26112146. 7: Debing Y, Emerson SU, Wang Y, Pan Q, Balzarini J, Dallmeier K, Neyts J. Ribavirin inhibits in vitro hepatitis E virus replication through depletion of cellular GTP pools and is moderately synergistic with alpha interferon. Antimicrob Agents Chemother. 2014;58(1):267-73. doi: 10.1128/AAC.01795-13. Epub 2013 Oct 21. PMID: 24145541; PMCID: PMC3910773. 8: Ölschläger S, Neyts J, Günther S. Depletion of GTP pool is not the predominant mechanism by which ribavirin exerts its antiviral effect on Lassa virus. Antiviral Res. 2011 Aug;91(2):89-93. doi: 10.1016/j.antiviral.2011.05.006. Epub 2011 May 17. PMID: 21616094. 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. Res Vet Sci. 2010 Apr;88(2):339-44. doi: 10.1016/j.rvsc.2009.08.010. Epub 2009 Sep 24. PMID: 19781726. 10: Ostrowski T, Zeidler J. Synthesis of 5-ethynyl-1-beta-D- ribofuranosyl-1H-[1,2,3]triazole-4-carboxylic acid amide (isosteric to EICAR) and its derivatives. Nucleic Acids Symp Ser (Oxf). 2008;(52):585-6. doi: 10.1093/nass/nrn296. PMID: 18776515. 11: Georges-Courbot MC, Contamin H, Faure C, Loth P, Baize S, Leyssen P, Neyts J, Deubel V. Poly(I)-poly(C12U) but not ribavirin prevents death in a hamster model of Nipah virus infection. Antimicrob Agents Chemother. 2006 May;50(5):1768-72. doi: 10.1128/AAC.50.5.1768-1772.2006. PMID: 16641448; PMCID: PMC1472238. 12: 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 Res. 2006 Aug;71(1):53-63. doi: 10.1016/j.antiviral.2006.03.001. Epub 2006 Mar 24. PMID: 16621037; PMCID: PMC7114261. 13: Leyssen P, De Clercq E, Neyts J. The anti-yellow fever virus activity of ribavirin is independent of error-prone replication. Mol Pharmacol. 2006 Apr;69(4):1461-7. doi: 10.1124/mol.105.020057. Epub 2006 Jan 18. PMID: 16421290. 14: Wu Q, Qu F, Wan J, Xia Y, Peng L. Photolabeling probes of ribavirin and EICAR. Nucleosides Nucleotides Nucleic Acids. 2005;24(5-7):999-1008. doi: 10.1081/ncn-200060336. PMID: 16248080. 15: Leyssen P, Balzarini J, De Clercq E, Neyts J. The predominant mechanism by which ribavirin exerts its antiviral activity in vitro against flaviviruses and paramyxoviruses is mediated by inhibition of IMP dehydrogenase. J Virol. 2005 Feb;79(3):1943-7. doi: 10.1128/JVI.79.3.1943-1947.2005. PMID: 15650220; PMCID: PMC544097. 16: Benarroch D, Egloff MP, Mulard L, Guerreiro C, Romette JL, Canard B. A structural basis for the inhibition of the NS5 dengue virus mRNA 2'-O-methyltransferase domain by ribavirin 5'-triphosphate. J Biol Chem. 2004 Aug 20;279(34):35638-43. doi: 10.1074/jbc.M400460200. Epub 2004 May 19. PMID: 15152003. 17: Wang G, Sakthivel K, Rajappan V, Bruice TW, Tucker K, Fagan P, Brooks JL, Hurd T, Leeds JM, Cook PD. Synthesis of azole nucleoside 5'-monophosphate mimics (P1Ms) and their inhibitory properties of IMP dehydrogenases. Nucleosides Nucleotides Nucleic Acids. 2004;23(1-2):317-37. doi: 10.1081/ncn-120027838. PMID: 15043157. 18: De Clercq E. Vaccinia virus inhibitors as a paradigm for the chemotherapy of poxvirus infections. Clin Microbiol Rev. 2001 Apr;14(2):382-97. doi: 10.1128/CMR.14.2.382-397.2001. PMID: 11292644; PMCID: PMC88980. 19: Moya J, Pizarro H, Jashés M, De Clercq E, Sandino AM. In vivo effect of EICAR (5-ethynyl-1-beta-D-ribofuranosylimidazole-carboxamide) on experimental infected rainbow trout (Oncorhynchus mykiss) and coho salmon (Oncorhynchus kisutch) fry with infectious pancreatic necrosis virus. Antiviral Res. 2000 Nov;48(2):125-30. doi: 10.1016/s0166-3542(00)00122-4. PMID: 11114414. 20: Shigeta S. Recent progress in antiviral chemotherapy for respiratory syncytial virus infections. Expert Opin Investig Drugs. 2000 Feb;9(2):221-35. doi: 10.1517/13543784.9.2.221. PMID: 11060673.

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