Narlaprevir

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

MedKoo CAT#: 326781

CAS#: 865466-24-6

Description: Narlaprevir, also known as SCH-900518, is a potent and second generation inhibitor of HCV NS3 protease with Ki value of 6 nM. Narlaprevir forms a reversible covalent bond with the active-site serine. It has an overall inhibition constant (K*(i)) of 7 nM and a dissociation half-life of 1 to 2 h. SCH 900518 inhibited replicon RNA at a 90% effective concentration (EC(90)) of 40 nM.


Price and Availability

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Narlaprevir 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#: 326781
Name: Narlaprevir
CAS#: 865466-24-6
Chemical Formula: C36H61N5O7S
Exact Mass: 707.4292
Molecular Weight: 707.972
Elemental Analysis: C, 61.08; H, 8.69; N, 9.89; O, 15.82; S, 4.53


Synonym: SCH-900518; SCH 900518; SCH900518; Narlaprevir

IUPAC/Chemical Name: (1R,2S,5S)-3-(N-(((1-((tert-butylsulfonyl)methyl)cyclohexyl)amino)carbonyl)-3-methyl-l- valyl)-N-((1s)-1-((cyclopropylamino)(oxo)acetyl)pentyl)-6,6-dimethyl-3- azabicyclo(3.1.0)hexane-2-carboxamide

InChi Key: RICZEKWVNZFTNZ-LFGITCQGSA-N

InChi Code: InChI=1S/C36H61N5O7S/c1-10-11-15-24(27(42)30(44)37-22-16-17-22)38-29(43)26-25-23(35(25,8)9)20-41(26)31(45)28(33(2,3)4)39-32(46)40-36(18-13-12-14-19-36)21-49(47,48)34(5,6)7/h22-26,28H,10-21H2,1-9H3,(H,37,44)(H,38,43)(H2,39,40,46)/t23-,24-,25-,26-,28+/m0/s1

SMILES Code: O=C([C@@H]1[C@@]2([H])C(C)(C)[C@@]2([H])CN1C([C@H](C(C)(C)C)NC(NC3(CS(=O)(C(C)(C)C)=O)CCCCC3)=O)=O)N[C@H](C(C(NC4CC4)=O)=O)CCCC


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: Wang H, Geng L, Chen BZ, Ji M. Computational study on the molecular mechanisms of drug resistance of Narlaprevir due to V36M, R155K, V36M+R155K, T54A, and A156T mutations of HCV NS3/4A protease. Biochem Cell Biol. 2014 Oct;92(5):357-69. doi: 10.1139/bcb-2014-0039. Epub 2014 Jul 23. PubMed PMID: 25178998.

2: de Bruijne J, Thomas XV, Rebers SP, Weegink CJ, Treitel MA, Hughes E, Bergmann JF, de Knegt RJ, Janssen HL, Reesink HW, Molenkamp R, Schinkel J. Evolutionary dynamics of hepatitis C virus NS3 protease domain during and following treatment with narlaprevir, a potent NS3 protease inhibitor. J Viral Hepat. 2013 Nov;20(11):779-89. doi: 10.1111/jvh.12104. Epub 2013 Jun 27. PubMed PMID: 24168257.

3: Hotho DM, de Bruijne J, Spaan M, Treitel MA, Boonstra A, de Knegt RJ, Janssen HL, Reesink HW. Sustained virologic response after therapy with the HCV protease inhibitor narlaprevir in combination with peginterferon and ribavirin is durable through long-term follow-up. J Viral Hepat. 2013 Apr;20(4):e78-81. doi: 10.1111/jvh.12012. Epub 2013 Jan 7. PubMed PMID: 23490393.

4: Zhu J, Li Y, Yu H, Zhang L, Mao X, Hou T. Insight into the structural requirements of narlaprevir-type inhibitors of NS3/NS4A protease based on HQSAR and molecular field analyses. Comb Chem High Throughput Screen. 2012 Jul;15(6):439-50. PubMed PMID: 22263860.

5: de Bruijne J, Bergmann JF, Reesink HW, Weegink CJ, Molenkamp R, Schinkel J, Tong X, Li J, Treitel MA, Hughes EA, van Lier JJ, van Vliet AA, Janssen HL, de Knegt RJ. Antiviral activity of narlaprevir combined with ritonavir and pegylated interferon in chronic hepatitis C patients. Hepatology. 2010 Nov;52(5):1590-9. doi: 10.1002/hep.23899. PubMed PMID: 20938912.

6: Arasappan A, Bennett F, Bogen SL, Venkatraman S, Blackman M, Chen KX, Hendrata S, Huang Y, Huelgas RM, Nair L, Padilla AI, Pan W, Pike R, Pinto P, Ruan S, Sannigrahi M, Velazquez F, Vibulbhan B, Wu W, Yang W, Saksena AK, Girijavallabhan V, Shih NY, Kong J, Meng T, Jin Y, Wong J, McNamara P, Prongay A, Madison V, Piwinski JJ, Cheng KC, Morrison R, Malcolm B, Tong X, Ralston R, Njoroge FG. Discovery of Narlaprevir (SCH 900518): A Potent, Second Generation HCV NS3 Serine Protease Inhibitor. ACS Med Chem Lett. 2010 Feb 15;1(2):64-9. doi: 10.1021/ml9000276. eCollection 2010 May 13. PubMed PMID: 24900178; PubMed Central PMCID: PMC4007962.

7: Tong X, Arasappan A, Bennett F, Chase R, Feld B, Guo Z, Hart A, Madison V, Malcolm B, Pichardo J, Prongay A, Ralston R, Skelton A, Xia E, Zhang R, Njoroge FG. Preclinical characterization of the antiviral activity of SCH 900518 (narlaprevir), a novel mechanism-based inhibitor of hepatitis C virus NS3 protease. Antimicrob Agents Chemother. 2010 Jun;54(6):2365-70. doi: 10.1128/AAC.00135-10. Epub 2010 Mar 22. PubMed PMID: 20308381; PubMed Central PMCID: PMC2876368.