Paritaprevir | ABT-450 | CAS#1216941-48-8 | NS3-4A Inhibitor

MedKoo Cat#: 314255 | Name: Paritaprevir

Description:

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

Paritaprevir, also known as ABT-450 or Veruprevir, is an acylsulfonamide inhibitor of the NS3-4A serine protease manufactured by Abbott Laboratories that shows promising results as a treatment of hepatitis C. When given in combination with ritonavir and ribavirin for 12 weeks, the rate of sustained virologic response at 24 weeks after treatment has been estimated to be 95% for those with hepatitis C virus genotype 1. Resistance to treatment with paritaprevir is uncommon, because it targets the binding site, but has been seen to arise due to mutations at positions 155 and 168 in NS3.

Chemical Structure

Paritaprevir

CAS#1216941-48-8

Theoretical Analysis

MedKoo Cat#: 314255

Name: Paritaprevir

CAS#: 1216941-48-8

Chemical Formula: C40H43N7O7S

Exact Mass: 765.2945

Molecular Weight: 765.88

Elemental Analysis: C, 62.73; H, 5.66; N, 12.80; O, 14.62; S, 4.19

Price and Availability

Size	Price	Availability
5mg	USD 90.00	Ready to ship
10mg	USD 150.00	Ready to ship
25mg	USD 250.00	Ready to ship
50mg	USD 450.00	Ready to ship
100mg	USD 750.00	Ready to ship
200mg	USD 1,350.00	Ready to ship
500mg	USD 2,850.00	Ready to ship

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Related CAS #

No Data

Synonym

ATB450; ABT-450; ABT 450; Paritaprevir; Veruprevir; Brand name: VIEKIRA PAK.

IUPAC/Chemical Name

(2R,6S,13aS,14aR,16aS,Z)-N-(cyclopropylsulfonyl)-6-(5-methylpyrazine-2-carboxamido)-5,16-dioxo-2-(phenanthridin-6-yloxy)-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxamide

InChi Key

UAUIUKWPKRJZJV-QPLHLKROSA-N

InChi Code

InChI=1S/C40H43N7O7S/c1-24-21-42-33(22-41-24)35(48)43-32-16-6-4-2-3-5-11-25-20-40(25,39(51)46-55(52,53)27-17-18-27)45-36(49)34-19-26(23-47(34)38(32)50)54-37-30-14-8-7-12-28(30)29-13-9-10-15-31(29)44-37/h5,7-15,21-22,25-27,32,34H,2-4,6,16-20,23H2,1H3,(H,43,48)(H,45,49)(H,46,51)/b11-5-/t25-,26-,32+,34+,40-/m1/s1

SMILES Code

O=C([C@]([C@]1([H])/C=C\CCCCC[C@@H]2NC(C3=NC=C(C)N=C3)=O)(C1)NC([C@@](C[C@@H](OC4=C5C=CC=CC5=C(C=CC=C6)C6=N4)C7)([H])N7C2=O)=O)NS(=O)(C8CC8)=O

Appearance

White to off-white powder

Purity

>97% (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

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#CRB70116

QC Data

View QC data: current batch, Lot#CRB70116

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Paritaprevir (ABT-450) is a potent non-structural protein 3/4A (NS3/4A) protease and SARS-CoV 3CLpro (IC50 of 1.31 μM.) inhibitor with EC50s of 1 and 0.21 nM against HCV 1a and 1b, respectively.

In vitro activity:

ABT-450 inhibited genotype 1a-H77 and 1b-Con1 HCV subgenomic replicons in cell culture with EC50s of 1.0 and 0.21 nM, respectively. In the presence of 40% human plasma, the EC50s increased by 17- to 24-fold (Table 1). The CC50 of ABT-450 was >37 μM, resulting in an in vitro selectivity index of ≥37,000-fold. ABT-450 demonstrated activity across multiple HCV genotypes, with an EC50 of 5.3 nM against the genotype 2a JFH-1 subgenomic replicon and EC50s of 19, 0.09, and 0.69 nM against replicons containing NS3 protease from genotypes 3a, 4a, and 6a, respectively. As has been observed for other NS3/4A protease inhibitors such as simeprevir and asunaprevir, ABT-450 has reduced potency against genotype 3a, likely caused by the presence of the NS3 polymorphism D168Q, which is commonly found in this genotype. Reference: Antimicrob Agents Chemother. 2015 Feb; 59(2): 988–997. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4335891/

In vivo activity:

TBD

	Solvent	mg/mL	mM
Solubility
	DMSO	30.0	39.20

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 765.88 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

Formulation protocol:

1. Pilot-Matias T, Tripathi R, Cohen D, Gaultier I, Dekhtyar T, Lu L, Reisch T, Irvin M, Hopkins T, Pithawalla R, Middleton T, Ng T, McDaniel K, Or YS, Menon R, Kempf D, Molla A, Collins C. In vitro and in vivo antiviral activity and resistance profile of the hepatitis C virus NS3/4A protease inhibitor ABT-450. Antimicrob Agents Chemother. 2015 Feb;59(2):988-97. doi: 10.1128/AAC.04227-14. Epub 2014 Dec 1. PMID: 25451053; PMCID: PMC4335891.

In vitro protocol:

In vivo protocol:

TBD

1: Minaei AA, Kowdley KV. ABT-450/ ritonavir and ABT-267 in combination with ABT-333 for the treatment of hepatitis C virus. Expert Opin Pharmacother. 2015 Apr;16(6):929-37. doi: 10.1517/14656566.2015.1024653. Review. PubMed PMID: 25800085. 2: Gamal N, Vitale G, Andreone P. ABT-450: a novel agent for the treatment of CHC genotype 1: focus on treatment-experienced patients. Expert Rev Anti Infect Ther. 2015 Mar;13(3):295-304. doi: 10.1586/14787210.2015.1001746. Review. PubMed PMID: 25582226. 3: Pilot-Matias T, Tripathi R, Cohen D, Gaultier I, Dekhtyar T, Lu L, Reisch T, Irvin M, Hopkins T, Pithawalla R, Middleton T, Ng T, McDaniel K, Or YS, Menon R, Kempf D, Molla A, Collins C. In vitro and in vivo antiviral activity and resistance profile of the hepatitis C virus NS3/4A protease inhibitor ABT-450. Antimicrob Agents Chemother. 2015 Feb;59(2):988-97. doi: 10.1128/AAC.04227-14. PubMed PMID: 25451053; PubMed Central PMCID: PMC4335891. 4: Lawitz E, Sullivan G, Rodriguez-Torres M, Bennett M, Poordad F, Kapoor M, Badri P, Campbell A, Rodrigues L Jr, Hu Y, Pilot-Matias T, Vilchez RA. Exploratory trial of ombitasvir and ABT-450/r with or without ribavirin for HCV genotype 1, 2, and 3 infection. J Infect. 2015 Feb;70(2):197-205. doi: 10.1016/j.jinf.2014.09.008. PubMed PMID: 25246359. 5: Badri P, Dutta S, Coakley E, Cohen D, Ding B, Podsadecki T, Bernstein B, Awni W, Menon R. Pharmacokinetics and dose recommendations for cyclosporine and tacrolimus when coadministered with ABT-450, ombitasvir, and dasabuvir. Am J Transplant. 2015 May;15(5):1313-22. doi: 10.1111/ajt.13111. PubMed PMID: 25708713; PubMed Central PMCID: PMC5024008. 6: Andreone P, Colombo MG, Enejosa JV, Koksal I, Ferenci P, Maieron A, Müllhaupt B, Horsmans Y, Weiland O, Reesink HW, Rodrigues L Jr, Hu YB, Podsadecki T, Bernstein B. ABT-450, ritonavir, ombitasvir, and dasabuvir achieves 97% and 100% sustained virologic response with or without ribavirin in treatment-experienced patients with HCV genotype 1b infection. Gastroenterology. 2014 Aug;147(2):359-365.e1. doi: 10.1053/j.gastro.2014.04.045. PubMed PMID: 24818763. 7: Zeuzem S, Jacobson IM, Baykal T, Marinho RT, Poordad F, Bourlière M, Sulkowski MS, Wedemeyer H, Tam E, Desmond P, Jensen DM, Di Bisceglie AM, Varunok P, Hassanein T, Xiong J, Pilot-Matias T, DaSilva-Tillmann B, Larsen L, Podsadecki T, Bernstein B. Retreatment of HCV with ABT-450/r-ombitasvir and dasabuvir with ribavirin. N Engl J Med. 2014 Apr 24;370(17):1604-14. doi: 10.1056/NEJMoa1401561. PubMed PMID: 24720679. 8: Carrion AF, Gutierrez J, Martin P. New antiviral agents for the treatment of hepatitis C: ABT-450. Expert Opin Pharmacother. 2014 Apr;15(5):711-6. doi: 10.1517/14656566.2014.889116. Review. PubMed PMID: 24517400. 9: Ferenci P, Bernstein D, Lalezari J, Cohen D, Luo Y, Cooper C, Tam E, Marinho RT, Tsai N, Nyberg A, Box TD, Younes Z, Enayati P, Green S, Baruch Y, Bhandari BR, Caruntu FA, Sepe T, Chulanov V, Janczewska E, Rizzardini G, Gervain J, Planas R, Moreno C, Hassanein T, Xie W, King M, Podsadecki T, Reddy KR; PEARL-III Study.; PEARL-IV Study.. ABT-450/r-ombitasvir and dasabuvir with or without ribavirin for HCV. N Engl J Med. 2014 May 22;370(21):1983-92. doi: 10.1056/NEJMoa1402338. PubMed PMID: 24795200. 10: Poordad F, Hezode C, Trinh R, Kowdley KV, Zeuzem S, Agarwal K, Shiffman ML, Wedemeyer H, Berg T, Yoshida EM, Forns X, Lovell SS, Da Silva-Tillmann B, Collins CA, Campbell AL, Podsadecki T, Bernstein B. ABT-450/r-ombitasvir and dasabuvir with ribavirin for hepatitis C with cirrhosis. N Engl J Med. 2014 May 22;370(21):1973-82. doi: 10.1056/NEJMoa1402869. PubMed PMID: 24725237. 11: Zeng QL, Zhang JY, Zhang Z, Wang LF, Wang FS. Sofosbuvir and ABT-450: terminator of hepatitis C virus? World J Gastroenterol. 2013 Jun 7;19(21):3199-206. doi: 10.3748/wjg.v19.i21.3199. Review. PubMed PMID: 23745021; PubMed Central PMCID: PMC3671071. 12: Feld JJ, Kowdley KV, Coakley E, Sigal S, Nelson DR, Crawford D, Weiland O, Aguilar H, Xiong J, Pilot-Matias T, DaSilva-Tillmann B, Larsen L, Podsadecki T, Bernstein B. Treatment of HCV with ABT-450/r-ombitasvir and dasabuvir with ribavirin. N Engl J Med. 2014 Apr 24;370(17):1594-603. doi: 10.1056/NEJMoa1315722. PubMed PMID: 24720703. 13: Gentile I, Borgia F, Buonomo AR, Zappulo E, Castaldo G, Borgia G. ABT-450: a novel protease inhibitor for the treatment of hepatitis C virus infection. Curr Med Chem. 2014;21(28):3261-70. Review. PubMed PMID: 25005190. 14: Lawitz E, Poordad F, Kowdley KV, Cohen DE, Podsadecki T, Siggelkow S, Larsen L, Menon R, Koev G, Tripathi R, Pilot-Matias T, Bernstein B. A phase 2a trial of 12-week interferon-free therapy with two direct-acting antivirals (ABT-450/r, ABT-072) and ribavirin in IL28B C/C patients with chronic hepatitis C genotype 1. J Hepatol. 2013 Jul;59(1):18-23. doi: 10.1016/j.jhep.2013.02.009. PubMed PMID: 23439262. 15: Poordad F, Agarwal K, Younes Z, Cohen D, Xie W, Podsadecki T. Low relapse rate leads to high concordance of sustained virologic response (SVR) at 12 weeks with SVR at 24 weeks after treatment with ABT-450/ritonavir, ombitasvir, and dasabuvir plus ribavirin in subjects with chronic hepatitis C virus genotype 1 infection in the AVIATOR study. Clin Infect Dis. 2015 Feb 15;60(4):608-10. doi: 10.1093/cid/ciu865. PubMed PMID: 25365973. 16: Asselah T. ABT-450 combined with ritonavir, in addition to ABT-333 and ribavirin: a race for an interferon-free regimen to cure HCV infection. J Hepatol. 2013 Oct;59(4):885-8. doi: 10.1016/j.jhep.2013.05.020. PubMed PMID: 23707374. 17: Martel-Laferrière V. ABT-450/r-ombitasvir and dasabuvir with ribavirin eliminates viraemia in most patients with HCV infection with cirrhosis. Evid Based Med. 2015 Feb;20(1):6. doi: 10.1136/ebmed-2014-110055. PubMed PMID: 25209528.