Narlaprevir

Modify Date: 2024-01-02 19:51:11

Narlaprevir structure	Common Name	Narlaprevir
	CAS Number	865466-24-6	Molecular Weight	707.964
	Density	1.2±0.1 g/cm3	Boiling Point	N/A
	Molecular Formula	C₃₆H₆₁N₅O₇S	Melting Point	N/A
	MSDS	N/A	Flash Point	N/A

Use of Narlaprevir

Narlaprevir is a potent, selective, orally bioavailable NS3 protease inhibitor(Ki=6 nM; EC90=40 nM)IC50 Value: 6 nM (Ki)Target: HCV NS3/4A Protease; HCVNarlaprevir (SCH 900518) is a potent inhibitor of the hepatitis C virus (HCV) nonstructural protein 3 serine protease that is primarily metabolized by the cytochrome P450-3A4 system. Narlaprevir administration resulted in a robust HCV-RNA decline and high SVR rates when followed by standard of care in both treatment-experienced and treatment-naive HCV genotype 1-infected patients.

Name	(1R,2S,5S)-3-[(2S)-2-[[1-(tert-butylsulfonylmethyl)cyclohexyl]carbamoylamino]-3,3-dimethylbutanoyl]-N-[(3S)-1-(cyclopropylamino)-1,2-dioxoheptan-3-yl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide
Synonym	More Synonyms

Description	Narlaprevir is a potent, selective, orally bioavailable NS3 protease inhibitor(Ki=6 nM; EC90=40 nM)IC50 Value: 6 nM (Ki)Target: HCV NS3/4A Protease; HCVNarlaprevir (SCH 900518) is a potent inhibitor of the hepatitis C virus (HCV) nonstructural protein 3 serine protease that is primarily metabolized by the cytochrome P450-3A4 system. Narlaprevir administration resulted in a robust HCV-RNA decline and high SVR rates when followed by standard of care in both treatment-experienced and treatment-naive HCV genotype 1-infected patients.
Related Catalog	Signaling Pathways >> Metabolic Enzyme/Protease >> HCV Protease Signaling Pathways >> Anti-infection >> HCV Research Areas >> Infection
References	[1]. Ashok Arasappan, et al. Discovery of Narlaprevir (SCH 900518): A Potent, Second Generation HCV NS3 Serine Protease Inhibitor. ACS Med. Chem. Lett., 2010, 1 (2), pp 64–69 [2]. 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. Epub 2010 Mar 22. [3]. 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. [4]. 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. [5]. Tomillero A, Moral MA.Gateways to clinical trials.Methods Find Exp Clin Pharmacol. 2010 Nov;32(9):675-703.

Description

Related Catalog

Signaling Pathways >> Metabolic Enzyme/Protease >> HCV Protease

Signaling Pathways >> Anti-infection >> HCV

Research Areas >> Infection

References

[1]. Ashok Arasappan, et al. Discovery of Narlaprevir (SCH 900518): A Potent, Second Generation HCV NS3 Serine Protease Inhibitor. ACS Med. Chem. Lett., 2010, 1 (2), pp 64–69

[2]. 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. Epub 2010 Mar 22.

[3]. 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.

[4]. 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.

[5]. Tomillero A, Moral MA.Gateways to clinical trials.Methods Find Exp Clin Pharmacol. 2010 Nov;32(9):675-703.

Density	1.2±0.1 g/cm3
Molecular Formula	C₃₆H₆₁N₅O₇S
Molecular Weight	707.964
Exact Mass	707.429199
PSA	186.21000
LogP	3.61
Index of Refraction	1.558

Precursor 8
CAS#:110-62-3 Valeraldehyde CAS#:4630-82-4 Methyl cyclohex... CAS#:18999-28-5 Hept-2-enoic acid CAS#:40195-26-4 cyclohexylidene...
CAS#:254438-52-3 (2S,3S)-tert-bu... CAS#:1184928-27-5 (2S,3S)-3-(benz... CAS#:1208245-90-2 (1R,2S,5S)-3-[(... CAS#:108-94-1 Cyclohexanone
DownStream 0

(1R,2S,5S)-3-((S)-2-(3-(1-(tert-butylsulfonylmethyl)cyclohexyl)ureido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxoheptan-3-yl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide

(1R,2S,5S)-N-[(3S)-1-(Cyclopropylamino)-1,2-dioxo-3-heptanyl]-6,6-dimethyl-3-{3-methyl-N-[(1-{[(2-methyl-2-propanyl)sulfonyl]methyl}cyclohexyl)carbamoyl]-L-valyl}-3-azabicyclo[3.1.0]hexane-2-carboxamide

CS-0445

Narlaprevir (USAN/INN)

Narlaprevir

(1R,5S)-N-[1(S)-[2-(cyclopropylamino)-1,2-dioxoethyl]pentyl]-3-[2(S)-[[[[1-[[(1,1-dimethylethyl)sulfonyl]methyl]cyclohexyl]amino]carbonyl]amino]-3,3-dimethyl-1-oxobutyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2(S)-carboxamide

3-Azabicyclo[3.1.0]hexane-2-carboxamide, N-[(1S)-1-[2-(cyclopropylamino)-1,2-dioxoethyl]pentyl]-3-[(2S)-2-[[[[1-[[(1,1-dimethylethyl)sulfonyl]methyl]cyclohexyl]amino]carbonyl]amino]-3,3-dimethyl-1-oxobutyl]-6,6-dimethyl-, (1R,2S,5S)-

DC Chemicals Limited
China
Product Name: Narlaprevir
Price: $100.0/100mg $200.0/250mg $400.0/1g
Purity: 98.0%
Stocking Period: 3 Day
Contact: Tony Cao

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Price: $737/10mM*1mLinDMSO

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Narlaprevir

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