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

Hodoodo CAT#: H319834

CAS#: 473921-12-9

Description: Lersivirine, also known as UK-453061, is a novel second-generation non-nucleoside reverse transcriptase inhibitor (NNRTI) under development for HIV infection therapy. It binds reverse transcriptase in a distinct way leading to a unique resistance profile. In February 2013, ViiV Healthcare announced a stop of the development program investigating lersivirine.

Chemical Structure

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Lersivirine
CAS# 473921-12-9
Instruction

Theoretical Analysis

Hodoodo Cat#: H319834
Name: Lersivirine
CAS#: 473921-12-9
Chemical Formula: C17H18N4O2
Exact Mass: 310.14
Molecular Weight: 310.357
Elemental Analysis: C, 65.79; H, 5.85; N, 18.05; O, 10.31

Price and Availability

Size Price Availability Quantity
50mg USD 550 2 Weeks
100mg USD 950 2 Weeks
200mg USD 1450 2 Weeks
500mg USD 2150 2 Weeks
1g USD 3150 2 Weeks
2g USD 5650 2 Weeks
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Synonym: UK-453061; UK453061; UK 453061; UK-453,061; UK453,061; UK 453,061;Lersivirine

IUPAC/Chemical Name: 5-((3,5-diethyl-1-(2-hydroxyethyl)-1H-pyrazol-4-yl)oxy)isophthalonitrile

InChi Key: MCPUZZJBAHRIPO-UHFFFAOYSA-N

InChi Code: InChI=1S/C17H18N4O2/c1-3-15-17(16(4-2)21(20-15)5-6-22)23-14-8-12(10-18)7-13(9-14)11-19/h7-9,22H,3-6H2,1-2H3

SMILES Code: N#CC1=CC(OC2=C(CC)N(CCO)N=C2CC)=CC(C#N)=C1

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, not in water

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 310.36 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.

Recalculate based on batch purity %
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:
In vitro protocol:
In vivo protocol:

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1: DeJesus E, Fätkenheuer G, Orrell C, Wang C, Jones J, Craig C, Tawadrous M, Heera J. Efficacy and safety of lersivirine versus etravirine for the treatment of HIV-1 infection in patients with prior non-nucleoside reverse transcriptase inhibitor (NNRTI) use and evidence of NNRTI resistance: a randomized phase 2B trial. HIV Clin Trials. 2014 Sep-Oct;15(5):209-17. doi: 10.1310/hct1505-209. PubMed PMID: 25350959.

2: Houle CD, Finch GL, Mauthe RJ, Potter DM, Walisser JA, Gardner IB, DeWit RH. Effects of lersivirine on canine and rodent thyroid function. Toxicol Pathol. 2014 Jul;42(5):897-912. doi: 10.1177/0192623313503516. Epub 2013 Oct 16. PubMed PMID: 24135463.

3: Platten M, Fätkenheuer G. Lersivirine - a new drug for HIV infection therapy. Expert Opin Investig Drugs. 2013 Dec;22(12):1687-94. doi: 10.1517/13543784.2013.846325. Epub 2013 Oct 16. Review. PubMed PMID: 24128277.

4: Vourvahis M, Davis J, Langdon G, Layton G, Fang J, Choo HW, Hansson AG, Tawadrous M. Pharmacokinetic interactions between lersivirine and zidovudine, tenofovir disoproxil fumarate/emtricitabine and abacavir/lamivudine. Antivir Ther. 2013;18(6):745-54. doi: 10.3851/IMP2566. Epub 2013 Apr 4. PubMed PMID: 23558061.

5: Vernazza P, Wang C, Pozniak A, Weil E, Pulik P, Cooper DA, Kaplan R, Lazzarin A, Valdez H, Goodrich J, Mori J, Craig C, Tawadrous M. Efficacy and safety of lersivirine (UK-453,061) versus efavirenz in antiretroviral treatment-naive HIV-1-infected patients: week 48 primary analysis results from an ongoing, multicenter, randomized, double-blind, phase IIb trial. J Acquir Immune Defic Syndr. 2013 Feb 1;62(2):171-9. doi: 10.1097/QAI.0b013e31827a2ba2.. PubMed PMID: 23328090.

6: Vourvahis M, Wang R, Gruener DM, Bruce RD, Haider S, Tawadrous M. Effect of lersivirine co-administration on pharmacokinetics of methadone in healthy volunteers. Drug Alcohol Depend. 2012 Nov 1;126(1-2):183-8. doi: 10.1016/j.drugalcdep.2012.05.009. Epub 2012 Jun 8. PubMed PMID: 22682979.

7: Vourvahis M, Davis J, Wang R, Layton G, Choo HW, Chong CL, Tawadrous M. Effect of rifampin and rifabutin on the pharmacokinetics of lersivirine and effect of lersivirine on the pharmacokinetics of rifabutin and 25-O-desacetyl-rifabutin in healthy subjects. Antimicrob Agents Chemother. 2012 Aug;56(8):4303-9. doi: 10.1128/AAC.06282-11. Epub 2012 May 29. PubMed PMID: 22644026; PubMed Central PMCID: PMC3421562.

8: Kar P, Knecht V. Energetics of mutation-induced changes in potency of lersivirine against HIV-1 reverse transcriptase. J Phys Chem B. 2012 Jun 7;116(22):6269-78. doi: 10.1021/jp300818c. Epub 2012 May 22. PubMed PMID: 22574920.

9: Davis J, Langdon G, Layton G, Chong CL, Ndongo MN, Vourvahis M. The effect of lersivirine, a next-generation NNRTI, on the pharmacokinetics of midazolam and oral contraceptives in healthy subjects. Eur J Clin Pharmacol. 2012 Nov;68(11):1567-72. doi: 10.1007/s00228-012-1287-5. Epub 2012 Apr 22. PubMed PMID: 22527351.

10: Vourvahis M, Langdon G, Layton G, Labadie RR, Choo HW, Ndongo MN, Davis J. The pharmacokinetics of lersivirine (UK-453,061) and HIV-1 protease inhibitor coadministration in healthy subjects. J Acquir Immune Defic Syndr. 2012 May 1;60(1):24-32. doi: 10.1097/QAI.0b013e31824c4186. PubMed PMID: 22517413.

11: Campion SN, Bowman CJ, Cappon GD, Harrison A, Finch GL, Hurtt ME. Developmental toxicity of lersivirine in rabbits when administered throughout organogenesis and when limited to sensitive windows of axial skeletal development. Birth Defects Res B Dev Reprod Toxicol. 2012 Jun;95(3):250-61. doi: 10.1002/bdrb.21014. Epub 2012 Apr 11. PubMed PMID: 22495820.

12: Cappon GD, Bowman CJ, Campion SN, Chmielewski G, Hurtt ME, Finch GL, Lewis EM. Developmental toxicity study of lersivirine in mice. Birth Defects Res B Dev Reprod Toxicol. 2012 Jun;95(3):225-30. doi: 10.1002/bdrb.21008. Epub 2012 Mar 22. PubMed PMID: 22447726.

13: Vourvahis M, Wang R, Ndongo MN, O'Gorman M, Tawadrous M. No effect of a single supratherapeutic dose of lersivirine, a next-generation nonnucleoside reverse transcriptase inhibitor, on corrected QT interval in healthy subjects. Antimicrob Agents Chemother. 2012 May;56(5):2408-13. doi: 10.1128/AAC.05194-11. Epub 2012 Feb 27. PubMed PMID: 22371898; PubMed Central PMCID: PMC3346613.

14: Vourvahis M, Langdon G, Labadie RR, Layton G, Ndongo MN, Banerjee S, Davis J. Pharmacokinetic effects of coadministration of lersivirine with raltegravir or maraviroc in healthy subjects. Antimicrob Agents Chemother. 2012 Feb;56(2):887-92. doi: 10.1128/AAC.00572-11. Epub 2011 Nov 28. PubMed PMID: 22123705; PubMed Central PMCID: PMC3264271.

15: Langdon G, Davis J, Layton G, Chong CL, Weissgerber G, Vourvahis M. Effects of ketoconazole and valproic acid on the pharmacokinetics of the next generation NNRTI, lersivirine (UK-453,061), in healthy adult subjects. Br J Clin Pharmacol. 2012 May;73(5):768-75. doi: 10.1111/j.1365-2125.2011.04136.x. PubMed PMID: 22040521; PubMed Central PMCID: PMC3403204.

16: Jones LH, Allan G, Corbau R, Middleton DS, Mowbray CE, Newman SD, Phillips C, Webster R, Westby M. Comparison of the non-nucleoside reverse transcriptase inhibitor lersivirine with its pyrazole and imidazole isomers. Chem Biol Drug Des. 2011 May;77(5):393-7. doi: 10.1111/j.1747-0285.2011.01113.x. Epub 2011 Mar 29. PubMed PMID: 21352504.

17: Davis J, Hackman F, Ndongo MN, Choo H, Lewis D, Tawadrous M, Goodrich J, Langdon G. Safety and tolerability of lersivirine, a nonnucleoside reverse transcriptase inhibitor, during a 28-day, randomized, placebo-controlled, Phase I clinical study in healthy male volunteers. Clin Ther. 2010 Oct;32(11):1889-95. doi: 10.1016/j.clinthera.2010.10.007. PubMed PMID: 21095483.

18: Corbau R, Mori J, Phillips C, Fishburn L, Martin A, Mowbray C, Panton W, Smith-Burchnell C, Thornberry A, Ringrose H, Knöchel T, Irving S, Westby M, Wood A, Perros M. Lersivirine, a nonnucleoside reverse transcriptase inhibitor with activity against drug-resistant human immunodeficiency virus type 1. Antimicrob Agents Chemother. 2010 Oct;54(10):4451-63. doi: 10.1128/AAC.01455-09. Epub 2010 Jul 26. PubMed PMID: 20660667; PubMed Central PMCID: PMC2944613.

19: Vourvahis M, Banerjee S, LaBadie R, Gore D, Mayer H. Lack of a clinically relevant effect of an antacid on the pharmacokinetics of lersivirine. Antimicrob Agents Chemother. 2010 May;54(5):2209-11. doi: 10.1128/AAC.01110-09. Epub 2010 Feb 16. PubMed PMID: 20160047; PubMed Central PMCID: PMC2863683.

20: Vourvahis M, Gleave M, Nedderman AN, Hyland R, Gardner I, Howard M, Kempshall S, Collins C, LaBadie R. Excretion and metabolism of lersivirine (5-{[3,5-diethyl-1-(2-hydroxyethyl)(3,5-14C2)-1H-pyrazol-4-yl]oxy}benzene-1,3-dic arbonitrile), a next-generation non-nucleoside reverse transcriptase inhibitor, after administration of [14C]Lersivirine to healthy volunteers. Drug Metab Dispos. 2010 May;38(5):789-800. doi: 10.1124/dmd.109.031252. Epub 2010 Feb 2. PubMed PMID: 20124396.