Maribavir

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

MedKoo CAT#: 328006

CAS#: 176161-24-3

Description: Maribavir, also known as 1263W-94; BW-1263W-94; GW-1263; GW-257406X; SHP-620; VP-41263; BW-1263W94, is an UL97 kinase inhibitor potentially for the treatment of cytomegalovirus (CMV) infection. The mechanism by which maribavir inhibits HCMV replication is by inhibition of an HCMV encoded protein kinase enzyme called UL97 or pUL97.


Price and Availability

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Maribavir is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 328006
Name: Maribavir
CAS#: 176161-24-3
Chemical Formula: C15H19Cl2N3O4
Exact Mass: 375.0753
Molecular Weight: 376.234
Elemental Analysis: C, 47.89; H, 5.09; Cl, 18.84; N, 11.17; O, 17.01


Synonym: Maribavir; 1263W-94; BW-1263W-94; GW-1263; GW-257406X; SHP-620; VP-41263; BW-1263W94; 1263W94; BW1263W-94; GW1263; GW257406X; SHP620; VP41263; BW1263W94

IUPAC/Chemical Name: 5,6-Dichloro-2-(isopropylamino)-1-beta-L-ribofuranosyl-1H-benzimidazole

InChi Key: KJFBVJALEQWJBS-XUXIUFHCSA-N

InChi Code: InChI=1S/C15H19Cl2N3O4/c1-6(2)18-15-19-9-3-7(16)8(17)4-10(9)20(15)14-13(23)12(22)11(5-21)24-14/h3-4,6,11-14,21-23H,5H2,1-2H3,(H,18,19)/t11-,12-,13-,14-/m0/s1

SMILES Code: O[C@@H]1[C@@H](N2C3=CC(Cl)=C(Cl)C=C3N=C2NC(C)C)O[C@@H](CO)[C@@H]1O


Technical Data

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).

Harmonized System Code:
293490


References

1: Houldcroft CJ, Bryant JM, Depledge DP, Margetts BK, Simmonds J, Nicolaou S, Tutill HJ, Williams R, Worth AJ, Marks SD, Veys P, Whittaker E, Breuer J. Detection of Low Frequency Multi-Drug Resistance and Novel Putative Maribavir Resistance in Immunocompromised Pediatric Patients with Cytomegalovirus. Front Microbiol. 2016 Sep 9;7:1317. doi: 10.3389/fmicb.2016.01317. eCollection 2016. PubMed PMID: 27667983; PubMed Central PMCID: PMC5016526.

2: Stachel D, Stevens-Ayers T, Boeckh M. In vitro studies of the impact of maribavir on CMV-specific cellular immune responses. J Clin Virol. 2016 Feb;75:53-9. doi: 10.1016/j.jcv.2015.12.012. Epub 2015 Dec 31. PubMed PMID: 26780109.

3: Zegrí Reiriz I, Gómez-Bueno M, Segovia Cubero J. Successful Use of Maribavir for Drug-resistant Cytomegalovirus Colitis in a Heart Transplant Recipient. Rev Esp Cardiol (Engl Ed). 2015 Oct;68(10):908-9. doi: 10.1016/j.rec.2015.06.017. Epub 2015 Aug 22. PubMed PMID: 26304135.

4: Verdier MC, Patrat-Delon S, Lemaitre F, Revest M, Rivalan J, Michelet C, Bellissant E. Suspicion of interaction between maribavir and everolimus in a renal transplant recipient. Transplantation. 2014 Aug 15;98(3):e20-1. doi: 10.1097/TP.0000000000000275. PubMed PMID: 25089341.

5: Webel R, Hakki M, Prichard MN, Rawlinson WD, Marschall M, Chou S. Differential properties of cytomegalovirus pUL97 kinase isoforms affect viral replication and maribavir susceptibility. J Virol. 2014 May;88(9):4776-85. doi: 10.1128/JVI.00192-14. Epub 2014 Feb 12. PubMed PMID: 24522923; PubMed Central PMCID: PMC3993794.

6: Reitsma JM, Terhune SS. Inhibition of cellular STAT3 synergizes with the cytomegalovirus kinase inhibitor maribavir to disrupt infection. Antiviral Res. 2013 Nov;100(2):321-7. doi: 10.1016/j.antiviral.2013.09.011. Epub 2013 Sep 23. PubMed PMID: 24070820; PubMed Central PMCID: PMC3845884.

7: Schubert A, Ehlert K, Schuler-Luettmann S, Gentner E, Mertens T, Michel D. Fast selection of maribavir resistant cytomegalovirus in a bone marrow transplant recipient. BMC Infect Dis. 2013 Jul 19;13:330. doi: 10.1186/1471-2334-13-330. PubMed PMID: 23870704; PubMed Central PMCID: PMC3720178.

8: Alain S, Revest M, Veyer D, Essig M, Rerolles JP, Rawlinson W, Mengelle C, Huynh A, Kamar N, Garrigue I, Kaminski H, Segard C, Presne C, Mazeron MC, Avettant-Fenoël V, Lecuit M, Lortholary O, Coaquette A, Hantz S, Leruez-Ville M, Ploy MC. Maribavir use in practice for cytomegalovirus infection in French transplantation centers. Transplant Proc. 2013 May;45(4):1603-7. doi: 10.1016/j.transproceed.2013.01.082. PubMed PMID: 23726629.

9: Whitehurst CB, Sanders MK, Law M, Wang FZ, Xiong J, Dittmer DP, Pagano JS. Maribavir inhibits Epstein-Barr virus transcription through the EBV protein kinase. J Virol. 2013 May;87(9):5311-5. doi: 10.1128/JVI.03505-12. Epub 2013 Feb 28. PubMed PMID: 23449792; PubMed Central PMCID: PMC3624302.

10: Winston DJ, Saliba F, Blumberg E, Abouljoud M, Garcia-Diaz JB, Goss JA, Clough L, Avery R, Limaye AP, Ericzon BG, Navasa M, Troisi RI, Chen H, Villano SA, Uknis ME; 1263-301 Clinical Study Group. Efficacy and safety of maribavir dosed at 100 mg orally twice daily for the prevention of cytomegalovirus disease in liver transplant recipients: a randomized, double-blind, multicenter controlled trial. Am J Transplant. 2012 Nov;12(11):3021-30. doi: 10.1111/j.1600-6143.2012.04231.x. Epub 2012 Sep 4. Erratum in: Am J Transplant. 2013 Feb;13(2):529. PubMed PMID: 22947426.

11: Chou S, Hakki M, Villano S. Effects on maribavir susceptibility of cytomegalovirus UL97 kinase ATP binding region mutations detected after drug exposure in vitro and in vivo. Antiviral Res. 2012 Aug;95(2):88-92. doi: 10.1016/j.antiviral.2012.05.013. Epub 2012 Jun 1. PubMed PMID: 22664236; PubMed Central PMCID: PMC3398170.

12: Marty FM, Boeckh M. Maribavir and human cytomegalovirus-what happened in the clinical trials and why might the drug have failed? Curr Opin Virol. 2011 Dec;1(6):555-62. doi: 10.1016/j.coviro.2011.10.011. Epub 2011 Nov 4. Review. PubMed PMID: 22440913.

13: Hakki M, Drummond C, Houser B, Marousek G, Chou S. Resistance to maribavir is associated with the exclusion of pUL27 from nucleoli during human cytomegalovirus infection. Antiviral Res. 2011 Nov;92(2):313-8. doi: 10.1016/j.antiviral.2011.08.019. Epub 2011 Sep 1. PubMed PMID: 21906628; PubMed Central PMCID: PMC3232008.

14: Boutolleau D, Burrel S, Agut H. Genotypic characterization of human cytomegalovirus UL97 phosphotransferase natural polymorphism in the era of ganciclovir and maribavir. Antiviral Res. 2011 Jul;91(1):32-5. doi: 10.1016/j.antiviral.2011.04.015. Epub 2011 May 4. PubMed PMID: 21570426.

15: Snydman DR. Why did maribavir fail in stem-cell transplants? Lancet Infect Dis. 2011 Apr;11(4):255-7. doi: 10.1016/S1473-3099(11)70033-0. Epub 2011 Mar 15. PubMed PMID: 21414844.

16: Marty FM, Ljungman P, Papanicolaou GA, Winston DJ, Chemaly RF, Strasfeld L, Young JA, Rodriguez T, Maertens J, Schmitt M, Einsele H, Ferrant A, Lipton JH, Villano SA, Chen H, Boeckh M; Maribavir 1263-300 Clinical Study Group. Maribavir prophylaxis for prevention of cytomegalovirus disease in recipients of allogeneic stem-cell transplants: a phase 3, double-blind, placebo-controlled, randomised trial. Lancet Infect Dis. 2011 Apr;11(4):284-92. doi: 10.1016/S1473-3099(11)70024-X. Epub 2011 Mar 21. Erratum in: Lancet Infect Dis. 2011 May;11(5):343. PubMed PMID: 21414843.

17: Avery RK, Marty FM, Strasfeld L, Lee I, Arrieta A, Chou S, Tatarowicz W, Villano S. Oral maribavir for treatment of refractory or resistant cytomegalovirus infections in transplant recipients. Transpl Infect Dis. 2010 Dec;12(6):489-96. doi: 10.1111/j.1399-3062.2010.00550.x. PubMed PMID: 20682012.

18: Gentry BG, Kamil JP, Coen DM, Zemlicka J, Drach JC. Stereoselective phosphorylation of cyclopropavir by pUL97 and competitive inhibition by maribavir. Antimicrob Agents Chemother. 2010 Aug;54(8):3093-8. doi: 10.1128/AAC.00468-10. Epub 2010 Jun 14. PubMed PMID: 20547817; PubMed Central PMCID: PMC2916337.

19: Strasfeld L, Lee I, Tatarowicz W, Villano S, Chou S. Virologic characterization of multidrug-resistant cytomegalovirus infection in 2 transplant recipients treated with maribavir. J Infect Dis. 2010 Jul 1;202(1):104-8. doi: 10.1086/653122. PubMed PMID: 20504236.

20: Shannon-Lowe CD, Emery VC. The effects of maribavir on the autophosphorylation of ganciclovir resistant mutants of the cytomegalovirus UL97 protein. Herpesviridae. 2010 Dec 7;1(1):4. doi: 10.1186/2042-4280-1-4. PubMed PMID: 21429239; PubMed Central PMCID: PMC3050433.