Narlaprevir | SCH-900518 | CAS#865466-24-6 | HCV NS3 protease inhibitor

MedKoo Cat#: 326781 | Name: Narlaprevir

Description:

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

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.

Chemical Structure

Narlaprevir

CAS#865466-24-6

Theoretical Analysis

MedKoo Cat#: 326781

Name: Narlaprevir

CAS#: 865466-24-6

Chemical Formula: C36H61N5O7S

Exact Mass: 707.4292

Molecular Weight: 707.97

Elemental Analysis: C, 61.08; H, 8.69; N, 9.89; O, 15.82; S, 4.53

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 #

No Data

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

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 707.97 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

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.