n-MCT

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

MedKoo CAT#: 208108

CAS#: 156126-12-4

Description: n-MCT is a potent and selective nucleoside antiviral agent effective as therapy for acute and recurrent genital HSV-2 disease.

Chemical Structure

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n-MCT
CAS# 156126-12-4
Instruction

Theoretical Analysis

MedKoo Cat#: 208108
Name: n-MCT
CAS#: 156126-12-4
Chemical Formula: C12H16N2O4
Exact Mass: 252.11
Molecular Weight: 252.270
Elemental Analysis: C, 57.13; H, 6.39; N, 11.10; O, 25.37

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: n-MCT; n MCT; nMCT

IUPAC/Chemical Name: 1-((1S,2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)bicyclo[3.1.0]hexan-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

InChi Key: NOWRLNPOENZFHP-ARHDFHRDSA-N

InChi Code: InChI=1S/C12H16N2O4/c1-6-4-14(11(18)13-10(6)17)8-2-9(16)12(5-15)3-7(8)12/h4,7-9,15-16H,2-3,5H2,1H3,(H,13,17,18)/t7-,8+,9+,12+/m1/s1

SMILES Code: OC[C@]12[C@@H](O)C[C@H](N3C=C(C)C(NC3=O)=O)[C@H]1C2

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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 252.27 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Bernstein DI, Bravo FJ, Pullum DA, Shen H, Wang M, Rahman A, Glazer RI, Cardin RD. Efficacy of N-methanocarbathymidine against genital herpes simplex virus type 2 shedding and infection in guinea pigs. Antivir Chem Chemother. 2015 Feb;24(1):19-27. doi: 10.1177/2040206614566581. PMID: 26149263; PMCID: PMC5890498.
2: Jung ME, Dwight TA, Vigant F, Østergaard ME, Swayze EE, Seth PP. Synthesis and duplex-stabilizing properties of fluorinated N-methanocarbathymidine analogues locked in the C3'-endo conformation. Angew Chem Int Ed Engl. 2014 Sep 8;53(37):9893-7. doi: 10.1002/anie.201405283. Epub 2014 Jul 15. PMID: 25044699.
3: Kołodziej M, Joniec J, Bartoszcze M, Gryko R, Kocik J, Knap J. Research on substances with activity against orthopoxviruses. Ann Agric Environ Med. 2013;20(1):1-7. PMID: 23540204.
4: Thompson A, Marquez VE. Synthesis of a North-methanocarba-thymidine (N-MCT) analog. Curr Protoc Nucleic Acid Chem. 2012 Dec;Chapter 1:Unit1.29. doi: 10.1002/0471142700.nc0129s51. PMID: 23255201; PMCID: PMC7477758.
5: De Clercq E. Highlights in antiviral drug research: antivirals at the horizon. Med Res Rev. 2013 Nov;33(6):1215-48. doi: 10.1002/med.21256. Epub 2012 May 2. PMID: 22553111; PMCID: PMC7168470.
6: Quenelle DC, Collins DJ, Rice TL, Rahman A, Glazer R. Efficacy of orally administered low dose N-methanocarbathymidine against lethal herpes simplex virus type-2 infections of mice. Antivir Chem Chemother. 2011 Nov 17;22(3):131-7. doi: 10.3851/IMP1901. PMID: 22095521.
7: Bernstein DI, Bravo FJ, Clark JR, Earwood JD, Rahman A, Glazer R, Cardin RD. N-Methanocarbathymidine is more effective than acyclovir for treating neonatal herpes simplex virus infection in guinea pigs. Antiviral Res. 2011 Nov;92(2):386-8. doi: 10.1016/j.antiviral.2011.08.021. Epub 2011 Sep 7. PMID: 21924293; PMCID: PMC3202067.
8: Ludek OR, Marquez VE. A greener enantioselective synthesis of the antiviral agent North-methanocarbathymidine (N-MCT) from 2-deoxy-d-ribose. Tetrahedron. 2009 Oct 10;65(41):8461-8467. doi: 10.1016/j.tet.2009.08.035. PMID: 20625519; PMCID: PMC2900805.
9: Smee DF. Progress in the discovery of compounds inhibiting orthopoxviruses in animal models. Antivir Chem Chemother. 2008;19(3):115-24. doi: 10.1177/095632020801900302. PMID: 19024628.
10: Smee DF, Humphreys DE, Hurst BL, Barnard DL. Antiviral activities and phosphorylation of 5-halo-2'-deoxyuridines and N-methanocarbathymidine in cells infected with vaccinia virus. Antivir Chem Chemother. 2008;19(1):15-24. doi: 10.1177/095632020801900103. PMID: 18610554.
11: Comin MJ, Vu BC, Boyer PL, Liao C, Hughes SH, Marquez VE. D-(+)-iso- methanocarbathymidine: a high-affinity substrate for herpes simplex virus 1 thymidine kinase. ChemMedChem. 2008 Jul;3(7):1129-34. doi: 10.1002/cmdc.200800027. PMID: 18399509; PMCID: PMC2727455.
12: Prichard MN, Kern ER, Quenelle DC, Keith KA, Moyer RW, Turner PC. Vaccinia virus lacking the deoxyuridine triphosphatase gene (F2L) replicates well in vitro and in vivo, but is hypersensitive to the antiviral drug (N)-methanocarbathymidine. Virol J. 2008 Mar 5;5:39. doi: 10.1186/1743-422X-5-39. PMID: 18321387; PMCID: PMC2276199.
13: Smee DF, Hurst BL, Wong MH, Glazer RI, Rahman A, Sidwell RW. Efficacy of N-methanocarbathymidine in treating mice infected intranasally with the IHD and WR strains of vaccinia virus. Antiviral Res. 2007 Nov;76(2):124-9. doi: 10.1016/j.antiviral.2007.06.005. Epub 2007 Jul 10. PMID: 17658623; PMCID: PMC2268765.
14: Marquez VE, Hughes SH, Sei S, Agbaria R. The history of N-methanocarbathymidine: the investigation of a conformational concept leads to the discovery of a potent and selective nucleoside antiviral agent. Antiviral Res. 2006 Sep;71(2-3):268-75. doi: 10.1016/j.antiviral.2006.04.012. Epub 2006 May 6. PMID: 16730077.
15: Smee DF, Wandersee MK, Bailey KW, Wong MH, Chu CK, Gadthula S, Sidwell RW. Cell line dependency for antiviral activity and in vivo efficacy of N-methanocarbathymidine against orthopoxvirus infections in mice. Antiviral Res. 2007 Jan;73(1):69-77. doi: 10.1016/j.antiviral.2006.04.010. Epub 2006 May 5. PMID: 16712967.
16: Dvir-Ginzberg M, Konson A, Cohen S, Agbaria R. Entrapment of retroviral vector producer cells in three-dimensional alginate scaffolds for potential use in cancer gene therapy. J Biomed Mater Res B Appl Biomater. 2007 Jan;80(1):59-66. doi: 10.1002/jbm.b.30568. PMID: 16680730.
17: Prichard MN, Keith KA, Quenelle DC, Kern ER. Activity and mechanism of action of N-methanocarbathymidine against herpesvirus and orthopoxvirus infections. Antimicrob Agents Chemother. 2006 Apr;50(4):1336-41. doi: 10.1128/AAC.50.4.1336-1341.2006. PMID: 16569849; PMCID: PMC1426929.
18: Zhu W, Burnette A, Dorjsuren D, Roberts PE, Huleihel M, Shoemaker RH, Marquez VE, Agbaria R, Sei S. Potent antiviral activity of north- methanocarbathymidine against Kaposi's sarcoma-associated herpesvirus. Antimicrob Agents Chemother. 2005 Dec;49(12):4965-73. doi: 10.1128/AAC.49.12.4965-4973.2005. PMID: 16304159; PMCID: PMC1315933.
19: Huleihel M, Talishanisky M, Ford H Jr, Marquez VE, Kelley JA, Johns DG, Agbaria R. Dynamics of the antiviral activity of N-methanocarbathymidine against herpes simplex virus type 1 in cell culture. Int J Antimicrob Agents. 2005 May;25(5):427-32. doi: 10.1016/j.ijantimicag.2005.01.013. PMID: 15848299.
20: Schelling P, Claus MT, Johner R, Marquez VE, Schulz GE, Scapozza L. Biochemical and structural characterization of (South)-methanocarbathymidine that specifically inhibits growth of herpes simplex virus type 1 thymidine kinase-transduced osteosarcoma cells. J Biol Chem. 2004 Jul 30;279(31):32832-8. doi: 10.1074/jbc.M313343200. Epub 2004 May 25. PMID: 15163659.