NM-107 | CAS#20724-73-6 | anti-viral

MedKoo Cat#: 206746 | Name: NM-107

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Description:

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

NM-107, also known as 2'-C-Methylcytidine; 2'-C-MeC; 2-CMC; mCyd ; 2'CMeC; 2CMC, is a a potent and selective anti-viral drug. NM-107 showed activity to inhibit the replication of foot-and-mouth disease virus. NM-107 exerts potent anti-DENV activity in DENV subgenomic RNA replicon and infectious systems, with an IC50 value of 11.2±0.3μM. NM-107 may be a promising compound for the development of direct-acting antivirals against DENV infection.

Chemical Structure

NM-107

CAS#20724-73-6

Theoretical Analysis

MedKoo Cat#: 206746

Name: NM-107

CAS#: 20724-73-6

Chemical Formula: C10H15N3O5

Exact Mass: 257.1012

Molecular Weight: 257.25

Elemental Analysis: C, 46.69; H, 5.88; N, 16.33; O, 31.10

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 220.00
25mg	USD 530.00

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Synonym

NM-107; NM 107; NM107; 2'-C-Methylcytidine; 2'-C-MeC; 2-CMC; mCyd ; 2'CMeC; 2CMC.

IUPAC/Chemical Name

4-amino-1-((2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)pyrimidin-2(1H)-one

InChi Key

PPUDLEUZKVJXSZ-VPCXQMTMSA-N

InChi Code

InChI=1S/C10H15N3O5/c1-10(17)7(15)5(4-14)18-8(10)13-3-2-6(11)12-9(13)16/h2-3,5,7-8,14-15,17H,4H2,1H3,(H2,11,12,16)/t5-,7-,8-,10-/m1/s1

SMILES Code

OC[C@@H]1[C@H]([C@@]([C@H](N2C(N=C(C=C2)N)=O)O1)(C)O)O

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

>2 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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

NM107 (2'-C-Methylcytidine) is an nucleoside inhibitor of the hepatitis C virus (HCV) NS5B polymerase, the EC50 of NM107 in the wild-type replicon cells is 1.85 μM.

In vitro activity:

Treatment of FMDV-infected BHK-21 cells with 77 microM 2'-C-MetCyt resulted in a (1.6-3.2)x10(3)-fold reduction of infectious virus yield. Time-of-drug addition experiments suggest that 2'-C-MetCyt interacts with viral replication at a time point that coincides with the onset of intracellular viral RNA synthesis. Reference: Antiviral Res. 2007 Mar;73(3):161-8. https://pubmed.ncbi.nlm.nih.gov/17055073/

In vivo activity:

This study established a mouse model for persistent norovirus infection (using the mouse norovirus MNV.CR6 strain). The nucleoside viral polymerase inhibitor 2'-C-methylcytidine (2CMC), but not favipiravir (T-705), reduced viral shedding to undetectable levels. Viral rebound was observed after stopping treatment, which was again effectively controlled by treatment with 2CMC. Reference: Antimicrob Agents Chemother. 2015 Dec 28;60(3):1907-11. https://pubmed.ncbi.nlm.nih.gov/26711754/

	Solvent	mg/mL	mM
Solubility
	DMF	10.0	38.87
	DMSO	60.0	233.24
	PBS (pH 7.2)	10.0	38.87
	Water	50.0	194.37

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 257.25 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.

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

Formulation protocol:

1. Lanko K, Ma Y, Delang L, Mirabelli C, Neyts J. Antiviral effects of selected nucleoside analogues against human parechoviruses A1 and A3. Antiviral Res. 2019 Feb;162:51-53. doi: 10.1016/j.antiviral.2018.12.009. Epub 2018 Dec 12. PMID: 30550798. 2. Goris N, De Palma A, Toussaint JF, Musch I, Neyts J, De Clercq K. 2'-C-methylcytidine as a potent and selective inhibitor of the replication of foot-and-mouth disease virus. Antiviral Res. 2007 Mar;73(3):161-8. doi: 10.1016/j.antiviral.2006.09.007. Epub 2006 Oct 10. PMID: 17055073. 3. Jin Z, Tucker K, Lin X, Kao CC, Shaw K, Tan H, Symons J, Behera I, Rajwanshi VK, Dyatkina N, Wang G, Beigelman L, Deval J. Biochemical Evaluation of the Inhibition Properties of Favipiravir and 2'-C-Methyl-Cytidine Triphosphates against Human and Mouse Norovirus RNA Polymerases. Antimicrob Agents Chemother. 2015 Dec;59(12):7504-16. doi: 10.1128/AAC.01391-15. Epub 2015 Sep 21. PMID: 26392512; PMCID: PMC4649231. 4. Rocha-Pereira J, Van Dycke J, Neyts J. Treatment with a Nucleoside Polymerase Inhibitor Reduces Shedding of Murine Norovirus in Stool to Undetectable Levels without Emergence of Drug-Resistant Variants. Antimicrob Agents Chemother. 2015 Dec 28;60(3):1907-11. doi: 10.1128/AAC.02198-15. PMID: 26711754; PMCID: PMC4776014.

In vitro protocol:

In vivo protocol:

1. Jin Z, Tucker K, Lin X, Kao CC, Shaw K, Tan H, Symons J, Behera I, Rajwanshi VK, Dyatkina N, Wang G, Beigelman L, Deval J. Biochemical Evaluation of the Inhibition Properties of Favipiravir and 2'-C-Methyl-Cytidine Triphosphates against Human and Mouse Norovirus RNA Polymerases. Antimicrob Agents Chemother. 2015 Dec;59(12):7504-16. doi: 10.1128/AAC.01391-15. Epub 2015 Sep 21. PMID: 26392512; PMCID: PMC4649231. 2. Rocha-Pereira J, Van Dycke J, Neyts J. Treatment with a Nucleoside Polymerase Inhibitor Reduces Shedding of Murine Norovirus in Stool to Undetectable Levels without Emergence of Drug-Resistant Variants. Antimicrob Agents Chemother. 2015 Dec 28;60(3):1907-11. doi: 10.1128/AAC.02198-15. PMID: 26711754; PMCID: PMC4776014.

1: Lee JC, Tseng CK, Wu YH, Kaushik-Basu N, Lin CK, Chen WC, Wu HN. Characterization of the activity of 2'-C-methylcytidine against dengue virus replication. Antiviral Res. 2015 Apr;116:1-9. doi: 10.1016/j.antiviral.2015.01.002. PubMed PMID: 25614455. 2: Rocha-Pereira J, Jochmans D, Neyts J. Prophylactic treatment with the nucleoside analogue 2'-C-methylcytidine completely prevents transmission of norovirus. J Antimicrob Chemother. 2015 Jan;70(1):190-7. doi: 10.1093/jac/dku363. PubMed PMID: 25228588. 3: Rocha-Pereira J, Jochmans D, Debing Y, Verbeken E, Nascimento MS, Neyts J. The viral polymerase inhibitor 2'-C-methylcytidine inhibits Norwalk virus replication and protects against norovirus-induced diarrhea and mortality in a mouse model. J Virol. 2013 Nov;87(21):11798-805. doi: 10.1128/JVI.02064-13. PubMed PMID: 23986582; PubMed Central PMCID: PMC3807313. 4: Lefebvre DJ, De Vleeschauwer AR, Goris N, Kollanur D, Billiet A, Murao L, Neyts J, De Clercq K. Proof of concept for the inhibition of foot-and-mouth disease virus replication by the anti-viral drug 2'-C-methylcytidine in severe combined immunodeficient mice. Transbound Emerg Dis. 2014 Dec;61(6):e89-91. doi: 10.1111/tbed.12069. PubMed PMID: 23480064. 5: Rocha-Pereira J, Jochmans D, Dallmeier K, Leyssen P, Cunha R, Costa I, Nascimento MS, Neyts J. Inhibition of norovirus replication by the nucleoside analogue 2'-C-methylcytidine. Biochem Biophys Res Commun. 2012 Nov 2;427(4):796-800. doi: 10.1016/j.bbrc.2012.10.003. PubMed PMID: 23063849. 6: Carroll SS, Koeplinger K, Vavrek M, Zhang NR, Handt L, MacCoss M, Olsen DB, Reddy KR, Sun Z, van Poelje PD, Fujitaki JM, Boyer SH, Linemeyer DL, Hecker SJ, Erion MD. Antiviral efficacy upon administration of a HepDirect prodrug of 2'-C-methylcytidine to hepatitis C virus-infected chimpanzees. Antimicrob Agents Chemother. 2011 Aug;55(8):3854-60. doi: 10.1128/AAC.01152-10. PubMed PMID: 21628542; PubMed Central PMCID: PMC3147631. 7: Julander JG, Jha AK, Choi JA, Jung KH, Smee DF, Morrey JD, Chu CK. Efficacy of 2'-C-methylcytidine against yellow fever virus in cell culture and in a hamster model. Antiviral Res. 2010 Jun;86(3):261-7. doi: 10.1016/j.antiviral.2010.03.004. PubMed PMID: 20227442; PubMed Central PMCID: PMC2871769. 8: Gardelli C, Attenni B, Donghi M, Meppen M, Pacini B, Harper S, Di Marco A, Fiore F, Giuliano C, Pucci V, Laufer R, Gennari N, Marcucci I, Leone JF, Olsen DB, MacCoss M, Rowley M, Narjes F. Phosphoramidate prodrugs of 2'-C-methylcytidine for therapy of hepatitis C virus infection. J Med Chem. 2009 Sep 10;52(17):5394-407. doi: 10.1021/jm900447q. PubMed PMID: 19725579. 9: Meppen M, Pacini B, Bazzo R, Koch U, Leone JF, Koeplinger KA, Rowley M, Altamura S, Di Marco A, Fiore F, Giuliano C, Gonzalez-Paz O, Laufer R, Pucci V, Narjes F, Gardelli C. Cyclic phosphoramidates as prodrugs of 2'-C-methylcytidine. Eur J Med Chem. 2009 Sep;44(9):3765-70. doi: 10.1016/j.ejmech.2009.04.043. PubMed PMID: 19493593. 10: Bassit L, Grier J, Bennett M, Schinazi RF. Combinations of 2'-C-methylcytidine analogues with interferon-alpha2b and triple combination with ribavirin in the hepatitis C virus replicon system. Antivir Chem Chemother. 2008;19(1):25-31. PubMed PMID: 18610555; PubMed Central PMCID: PMC2742417. 11: Murakami E, Niu C, Bao H, Micolochick Steuer HM, Whitaker T, Nachman T, Sofia MA, Wang P, Otto MJ, Furman PA. The mechanism of action of beta-D-2'-deoxy-2'-fluoro-2'-C-methylcytidine involves a second metabolic pathway leading to beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine 5'-triphosphate, a potent inhibitor of the hepatitis C virus RNA-dependent RNA polymerase. Antimicrob Agents Chemother. 2008 Feb;52(2):458-64. PubMed PMID: 17999967; PubMed Central PMCID: PMC2224766. 12: Ma H, Jiang WR, Robledo N, Leveque V, Ali S, Lara-Jaime T, Masjedizadeh M, Smith DB, Cammack N, Klumpp K, Symons J. Characterization of the metabolic activation of hepatitis C virus nucleoside inhibitor beta-D-2'-Deoxy-2'-fluoro-2'-C-methylcytidine (PSI-6130) and identification of a novel active 5'-triphosphate species. J Biol Chem. 2007 Oct 12;282(41):29812-20. PubMed PMID: 17698842. 13: Asif G, Hurwitz SJ, Shi J, Hernandez-Santiago BI, Schinazi RF. Pharmacokinetics of the antiviral agent beta-D-2'-deoxy-2'-fluoro-2'-C-methylcytidine in rhesus monkeys. Antimicrob Agents Chemother. 2007 Aug;51(8):2877-82. PubMed PMID: 17562805; PubMed Central PMCID: PMC1932527. 14: Murakami E, Bao H, Ramesh M, McBrayer TR, Whitaker T, Micolochick Steuer HM, Schinazi RF, Stuyver LJ, Obikhod A, Otto MJ, Furman PA. Mechanism of activation of beta-D-2'-deoxy-2'-fluoro-2'-c-methylcytidine and inhibition of hepatitis C virus NS5B RNA polymerase. Antimicrob Agents Chemother. 2007 Feb;51(2):503-9. PubMed PMID: 17101674; PubMed Central PMCID: PMC1797721. 15: Pierra C, Amador A, Benzaria S, Cretton-Scott E, D'Amours M, Mao J, Mathieu S, Moussa A, Bridges EG, Standring DN, Sommadossi JP, Storer R, Gosselin G. Synthesis and pharmacokinetics of valopicitabine (NM283), an efficient prodrug of the potent anti-HCV agent 2'-C-methylcytidine. J Med Chem. 2006 Nov 2;49(22):6614-20. PubMed PMID: 17064080. 16: Goris N, De Palma A, Toussaint JF, Musch I, Neyts J, De Clercq K. 2'-C-methylcytidine as a potent and selective inhibitor of the replication of foot-and-mouth disease virus. Antiviral Res. 2007 Mar;73(3):161-8. PubMed PMID: 17055073. 17: Stuyver LJ, McBrayer TR, Tharnish PM, Clark J, Hollecker L, Lostia S, Nachman T, Grier J, Bennett MA, Xie MY, Schinazi RF, Morrey JD, Julander JL, Furman PA, Otto MJ. Inhibition of hepatitis C replicon RNA synthesis by beta-D-2'-deoxy-2'-fluoro-2'-C-methylcytidine: a specific inhibitor of hepatitis C virus replication. Antivir Chem Chemother. 2006;17(2):79-87. PubMed PMID: 17042329. 18: Coelmont L, Paeshuyse J, Windisch MP, De Clercq E, Bartenschlager R, Neyts J. Ribavirin antagonizes the in vitro anti-hepatitis C virus activity of 2'-C-methylcytidine, the active component of valopicitabine. Antimicrob Agents Chemother. 2006 Oct;50(10):3444-6. PubMed PMID: 17005827; PubMed Central PMCID: PMC1610077. 19: Pierra C, Benzaria S, Amador A, Moussa A, Mathieu S, Storer R, Gosselin G. Nm 283, an efficient prodrug of the potent anti-HCV agent 2'-C-methylcytidine. Nucleosides Nucleotides Nucleic Acids. 2005;24(5-7):767-70. PubMed PMID: 16248033. 20: Clark JL, Hollecker L, Mason JC, Stuyver LJ, Tharnish PM, Lostia S, McBrayer TR, Schinazi RF, Watanabe KA, Otto MJ, Furman PA, Stec WJ, Patterson SE, Pankiewicz KW. Design, synthesis, and antiviral activity of 2'-deoxy-2'-fluoro-2'-C-methylcytidine, a potent inhibitor of hepatitis C virus replication. J Med Chem. 2005 Aug 25;48(17):5504-8. PubMed PMID: 16107149.