Raltegravir (MK-0518)

Catalog No.S2005

For research use only.

Raltegravir (MK-0518) is a potent integrase (IN) inhibitor for WT and S217Q PFV IN with IC50 of 90 nM and 40 nM in cell-free assays, respectively. It shows greater than 1000-fold selectivity for HIV-1 IN over several related Mg2+-dependent enzyme such as HCV polymerase, HIV reverse transcriptase, HIV RNaseH and human α-, β-, γ-polymerases.

Raltegravir (MK-0518) Chemical Structure

CAS No. 518048-05-0

Selleck's Raltegravir (MK-0518) has been cited by 52 publications

Purity & Quality Control

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Biological Activity

Description Raltegravir (MK-0518) is a potent integrase (IN) inhibitor for WT and S217Q PFV IN with IC50 of 90 nM and 40 nM in cell-free assays, respectively. It shows greater than 1000-fold selectivity for HIV-1 IN over several related Mg2+-dependent enzyme such as HCV polymerase, HIV reverse transcriptase, HIV RNaseH and human α-, β-, γ-polymerases.
Features The 1st approved human immunodeficiency virus type 1 (HIV-1) integrase inhibitor.
Targets
Integrase (S217Q PFV) [1]
(Cell-free assay)
Integrase (WT PFV) [1]
(Cell-free assay)
40 nM 90 nM
In vitro

PFV IN carrying the S217H substitution is 10-fold less susceptible to Raltegravir with IC50 of 900 nM. PFV IN displays 10% of WT activity and is inhibited by Raltegravir with an IC50 of 200 nM, indicating a ~twofold decrease in susceptibility to the IN strand transfer inhibitor (INSTI) compared with WT IN. S217Q PFV IN is as sensitive to Raltegravir as the WT enzyme. [1] Raltegravir is metabolized by glucuronidation, not hepatically. Raltegravir has potent in vitro activity against HIV-1, with a 95% inhibitory concentration of 31?0 nM, in human T lymphoid cell cultures. Raltegravir is also active against HIV-2 when Raltegravir is tested in CEMx174 cells, with an IC95 of 6 nM. Raltegravir metabolism occurs primarily through glucuronidation. Drugs that are strong inducers of the glucuronidation enzyme, UGT1A1, significantly reduce Raltegravir concentrations and should not be used. Raltegravir exhibits weak inhibitory effects on hepatic cytochrome P450 activity. Raltegravir does not induce CYP3A4 RNA expression or CYP3A4-dependent testosterone 6-β-hydroxylase activity. [2] Raltegravir cellular permeativity is reduced in the presence of magnesium and calcium. [3] Raltegravir and related HIV-1 integrase (IN) strand transfer inhibitors (INSTIs efficiently block viral replication. [4] In acutely infected human lymphoid CD4+ T-cell lines MT-4 and CEMx174, SIVmac251 replication is efficiently inhibited by Raltegravir, which shows an EC90 in the low nanomolar range. [5]

Cell Data
Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID
MT4 NE\tWnNCdnSrdnnyZYwh[XO|YYm= NYHPVGdrSW62aY\pdoFtKGGldHn2bZR6KGGpYXnud5QhUHWvYX6gbY1ufW6xZHXmbYNq\W6leTD2bZJ2eyBzIEPCJIlv\mWldHXkJIlvKGi3bXHuJG1VPCClZXzsd{Bie3Onc4Pl[EBieyCrbnjpZol1cW:wIH;mJJZqemGuIILldIxq[2G2aX;uMEBGSzVyIE2gNE4xODF2IN88UU4> MmnLQIEhfGG{Z3X0QUdg[myjbnunJIhz\WZ;J3j0eJB{Qi9xcIXicYVlNm6lYnmucoxuNm6raD7nc5YwOTh3NEG3NlYoRjF6NUSxO|I3RC:jPh?=
MT-4 NInZTXNCdnSrdnnyZYwh[XO|YYm= NYiyUmF7SW62aY\pdoFtKGGldHn2bZR6KGGpYXnud5QhUHWvYX6gbY1ufW6xZHXmbYNq\W6leTD2bZJ2eyBzIEPCJIlv\mWldHXkJIlvKGi3bXHuJG1VNTRiY3XscJMh[XO|ZYPz[YQh[XNiaX7obYJqfGmxbjDv[kB3cXKjbDDy[ZBtcWOjdHnvckwhTUN3MDC9JFAvODBzODFOwG0v M4HJZVxiKHSjcnfleF0oZ2KuYX7rK{BpemWoPTfoeJRxezpxL4D1Zo1m\C6wY3LpMo5tdS6waXiu[493NzF6MU[wOVIyLz5zOEG2NFUzOTxxYU6=
MT-4 MoDGRY51cX[rcnHsJIF{e2G7 MU\BcpRqfmm{YXygZYN1cX[rdImgZYdicW6|dDD2[ZNq[3WuYYKgd5RwdWG2aYTpd{B3cXK3czDHMZB{\XWmb4T5dIVlKEi3bXHuJIludXWwb3Tl[olkcWWwY4mgeolzfXNiaX7m[YN1\WRiaX6gbJVu[W5iTWStOEBk\WyuczDhd5Nme3OnZDDhd{BqdmirYnn0bY9vKG:oII\pdoFtKHKncHzpZ4F1cW:wLDDFR|UxKD1iMD6wNFIh|ryPLh?= NF3UOlA9[SC2YYLn[ZQ:L1:kbHHub{chcHKnZk2nbJR1eHN8Lz;weYJu\WRwbnPibU5vdG1wbnnoModwfi9zOEG2NFUzOSd-MUixOlA2OjF:L3G+
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MT-2 MXvBcpRqfmm{YXygZZN{[Xl? NHPOdGhCdnSrdnnyZYwh[WO2aY\peJkh[WejaX7zeEBJUVZzIEPCJIlv\mWldHXkJIlvKGi3bXHuJG1VNTJiY3XscJMh[nlidIfvJIZwdGRiZHnseZRqd25ibXX0bI9lKGmwIIDy[ZNmdmOnIH;mJFExLSCIQmOsJGVEPTBiPTCwMlAxOyEQvF2u MUe8ZUB1[XKpZYS9K39jdGGwazegbJJm\j1paIT0dJM7Ny:ydXLt[YQvdmOkaT7ucI0vdmmqLnfvek8yQTFyNECxNEc,OTlzMESwNVA9N2F-
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MT-4 M4XBeGFvfGm4aYLhcEBie3OjeR?= MlLGRY51cX[rcnHsJIFkfGm4aYT5JIFo[Wmwc4SgTGlXKDFiUlnOJIhiemKxcnnu[{BqdnSnZ4Lhd4Uh\2WwZTDpcoZm[3SnZDDpckBOXC12IHPlcIx{KGG|c3Xzd4VlKGG|IHnubIljcXSrb36gc4Yhfmm{dYOtbY5lfWOnZDDjfZRweGG2aHnjJIVn\mWldDDifUBOXFRiYYPzZZktKEWFNUCgQUAxNjByNjFOwG0v NInvWVA9[SC2YYLn[ZQ:L1:kbHHub{chcHKnZk2nbJR1eHN8Lz;weYJu\WRwbnPibU5vdG1wbnnoModwfi9zOEO3PFcyOyd-MUizO|g4OTN:L3G+
MT4 M2TYXmFvfGm4aYLhcEBie3OjeR?= NEnXXmtCdnSrdnnyZYwh[WO2aY\peJkh[WejaX7zeEBJUVZzIEPCJIlv\mWldHXkJIlvKGi3bXHuJG1VPCClZXzsd{Bie3Onc4Pl[EBieyCrbnjpZol1cW:wIH;mJJZqenW|LXnu[JVk\WRiY4n0c5BifGirYzDl[oZm[3RiYomgUXRVKGG|c3H5MEBGSzVyIE2gNE4xODZizszNMi=> MUi8ZUB1[XKpZYS9K39jdGGwazegbJJm\j1paIT0dJM7Ny:ydXLt[YQvdmOkaT7ucI0vdmmqLnfvek8zPDlyMEexPEc,OjR7MEC3NVg9N2F-
MT4 MljNRY51cX[rcnHsJIF{e2G7 M3PNXmFvfGm4aYLhcEBi[3Srdnn0fUBi\2GrboP0JGhKXi1zIEPCJIlv\mWldHXkJIlvKGi3bXHuJG1VPCClZXzsd{Bie3Onc4Pl[EBieyCycn;0[YN1cW:wIHHnZYlve3RidnnyeZMucW6mdXPl[EBkgXSxcHH0bIlkKGWoZnXjeEBjgSCPVGSgZZN{[XluIFXDOVAhRSByLkCwOkDPxE1w M4e3[|xiKHSjcnfleF0oZ2KuYX7rK{BpemWoPTfoeJRxezpxL4D1Zo1m\C6wY3LpMo5tdS6waXiu[493NzJ2N{mzN|YxLz5{NEe5N|M3ODxxYU6=
MT4 NFuy[2NCdnSrdnnyZYwh[XO|YYm= M2jSW2FvfGm4aYLhcEBi[3Srdnn0fUBi\2GrboP0JGh2dWGwIHntcZVvd2SnZnnjbYVv[3lidnnyeZMhOSB|QjDpcoZm[3SnZDDpckBpfW2jbjDNWFQh[2WubIOgZZN{\XO|ZXSgZZMhcW6qaXLpeIlwdiCxZjD2bZJ2eyCrbnT1Z4VlKGO7dH;wZZRpcWNiZX\m[YN1NCCHQ{WwJF0hOC5yME[xJO69VS5? NHrKO2I9[SC2YYLn[ZQ:L1:kbHHub{chcHKnZk2nbJR1eHN8Lz;weYJu\WRwbnPibU5vdG1wbnnoModwfi9{MES3PVIxPid-MkC0O|kzODZ:L3G+
MT4 NHHiVnFHfW6ldHnvckBie3OjeR?= M{XIUlEhcHJ? NV30ZVM3UW6qaXLpeIlwdiCxZjD3bYxlKHS7cHWgTGlXOSB|QjDpcoZm[3SnZDDpckBpfW2jbjDNWFQh[2WubIOgeZNqdmdiY3XscJMheHKnLXnuZ5Vj[XSnZDD3bZRpKGOxbYDveY5lKG[xcjCxJIhzKG2nYYP1doVlKDRiZHH5d{Bxd3O2II\pdoFtKGmwZnXjeIlwdiCkeTDNWHQh[XO|YYmsJGlEPTBiPTCwMlAxPjJizszNMi=> NVjLfpRDRGFidHHy[4V1RSehYnzhcosoKGi{ZX[9K4h1fHC|Oj:vdJVjdWWmLn7jZokvdmyvLn7pbE5od3ZxMkK5OlMyOzVpPkKyPVY{OTN3PD;hQi=>
MT4 M4HFW2FvfGm4aYLhcEBie3OjeR?= NXf1SpNUSW62aY\pdoFtKGGldHn2bZR6KGGpYXnud5QhUEmYMTCzRkBqdm[nY4Tl[EBqdiCqdX3hckBOXDRiY3XscJMh[XO|ZYPz[YQh[XNicnXkeYN1cW:wIH;mJJZqenW|LXnu[JVk\WRiY4n0c5BifGixZ3XubYNqfHliYomgUXRVKGG|c3H5MEBGSzVyIE2gNE4xODZ2IN88UU4> MmLNQIEhfGG{Z3X0QUdg[myjbnunJIhz\WZ;J3j0eJB{Qi9xcIXicYVlNm6lYnmucoxuNm6raD7nc5YwOTl2NEe2NlEoRjF7NES3OlIyRC:jPh?=
MT-4 MVTBcpRqfmm{YXygZZN{[Xl? MlO1RY51cX[rcnHsJIFkfGm4aYT5JIFo[Wmwc4SgTGlXKDFiTly0MlMhcGG{Yn;ybY5oKGmwdHXndoF{\SCON{TNJI12fGGwdDDpcoZm[3SnZDDpckBpfW2jbjDNWE01KGOnbHzzJIF{e2W|c3XkJIF{KGmwaHnibZRqd25ib3[geolzfXNvaX7keYNm\CCleYTvdIF1cGmlIHXm[oVkfCCkeTDNWHQh[XO|YYmsJGVEPTBiPTCwMlAxPyEQvF2u M4P3ZVxiKHSjcnfleF0oZ2KuYX7rK{BpemWoPTfoeJRxezpxL4D1Zo1m\C6wY3LpMo5tdS6waXiu[493NzF6M{e4O|E{Lz5zOEO3PFcyOzxxYU6=
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MT-4 M{\3[2FvfGm4aYLhcEBie3OjeR?= NXjPRpNZSW62aY\pdoFtKGGldHn2bZR6KGGpYXnud5QhUEmYIEGgVmlPKGijcnLvdolv\yCrboTl[5Jie2ViZ3Xu[UBqdm[nY4Tl[EBqdiCPVD20JINmdGy|IHHzd4V{e2WmIHHzJIlvcGmkaYTpc44hd2ZidnnyeZMucW6mdXPl[EBkgXSxcHH0bIlkKGWoZnXjeEBjgSCPVGSgZZN{[XliYX\0[ZIhOjBicHHzd4Fo\XNic3Xs[YN1\WRiaX6gdJJme2WwY3Wgc4Yh[2:vcH;1coQtKEWFNUCgQUAxNjBzIN88UU4> M3yyNVxiKHSjcnfleF0oZ2KuYX7rK{BpemWoPTfoeJRxezpxL4D1Zo1m\C6wY3LpMo5tdS6waXiu[493NzF6M{e4O|E{Lz5zOEO3PFcyOzxxYU6=
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U373-MAGI NYXGNHhTSW62aY\pdoFtKGG|c3H5 MXq1NEBweiBzMECgcm0> M2XKZVczKGi{cx?= NHfCVHBCdnSrdnnyZYwh[WO2aY\peJkh[WejaX7zeEBXW1ZvRzDwd4V2\G:2eYDl[EBJUVZvMTDOUFQuOyCrbn\lZ5Rm\CCrbjDoeY1idiCXM{ezMW1CT0liY3XscJMh[XO|ZYPz[YQh[XNicnXkeYN1cW:wIHnuJHU2NWejZzDs[ZZmdCCjdDC1NEBweiBzMECgcm0hdWWjc4Xy[YQh[XRiN{KgbJJ{KHCxc4SgbY5n\WO2aX;uJIJ6KHGSQ2KgcYV1cG:m M4juXFxiKHSjcnfleF0oZ2KuYX7rK{BpemWoPTfoeJRxezpxL4D1Zo1m\C6wY3LpMo5tdS6waXiu[493NzJ5MUG3NlYxLz5{N{GxO|I3ODxxYU6=
MT2 NH\nV41CdnSrdnnyZYwh[XO|YYm= MofJNUB2VQ>? NGKzN48{OCCqcoO= M1vBemFvfGm4aYLhcEBi[3Srdnn0fUBi\2GrboP0JJdqdGRvdInw[UBJUVZzIF7MOE0{KGmwZnXjeIVlKGmwZnXjeIVlKGmwIHj1cYFvKE2WMjDj[YxteyCjc4Pld5Nm\CCjczDy[YR2[3Srb36gbY4hUEmYMTDpcpRm\3KjdHXkJGRPSSCjdDCxJJVOKGGwZDDt[YF{fXKnZDDh[pRmeiB|MDDodpMheG:|dDDpcoZm[3Srb36gZpkhSWy3LVzUVkBRS1JicILveI9kd2xiYnHz[YQhdWW2aH;k MXW8ZUB1[XKpZYS9K39jdGGwazegbJJm\j1paIT0dJM7Ny:ydXLt[YQvdmOkaT7ucI0vdmmqLnfvek8{ODl7Nke4NEc,OzB7OU[3PFA9N2F-
Assay
Methods Test Index PMID
Western blot CHOP / ATF-4 / XBP-1 / Lamin B 24625618
In vivo Raltegravir induces viro-immunological improvement of nonhuman primates with progressing SIVmac251 infection. One non-human primate shows an undetectable viral load following Raltegravir monotherapy. [5]

Protocol (from reference)

Kinase Assay:

[1]

  • PFV integration assay:

    For quantitative strand transfer assays, donor DNA substrate is formed by annealing HPLC grade oligonucleotides 5′-GACTCACTATAGGGCACGCGTCAAAATTCCATGACA and 5′-ATTGTCATG GAATTTTGACGCGTGCCCTATAGTGAGTC. Reactions (40 μL) contains 0.75 μM PFV IN, 0.75 μM donor DNA, 4 nM (300 ng) supercoiled pGEM9-Zf(−) target DNA, 125 mM NaCl, 5 mM MgSO4, 4 μM ZnCl2, 10 mM DTT, 0.8% (vol/vol) DMSO, and 25 mM BisTris propane–HCl, pH 7.45. Raltegravir is added at indicated concentrations. Reactions are initiated by addition of 2 μL PFV IN diluted in 150 mM NaCl, 2 mM DTT, and 10 mM Tris-HCl, pH 7.4, and stopped after 1 hour at 37 °C by addition of 25 mM EDTA and 0.5% (wt/vol) SDS. Reaction products, deproteinized by digestion with 20 μg proteinase K for 30 minutes at 37 °C followed by ethanol precipitation, are separated in 1.5% agarose gels and visualized by staining with ethidium bromide. Integration products are quantified by quantitative real-time PCR, using Platinum SYBR Green qPCR SuperMix and three primers: 5′-CTACTTACTCTAGCTTCCCGGCAAC, 5′-TTCGCCAGTTAATAGTTTGCGCAAC, and 5′-GACTCACTATAGGGCACGCGT. PCR reactions (20 μL) contained 0.5 μM of each primer and 1 μL diluted integration reaction product. Following a 5-min denaturation step at 95 °C, 35 cycles are carried out in a CFX96 PCR instrument, using 10 seconds denaturation at 95 °C, 30 seconds annealing at 56 °C and 1 minutes extension at 68 °C. Standard curves are generated using serial dilutions of WT PFV IN reaction in the absence of INSTI.

Cell Research:

[5]

  • Cell lines: Human MT-4 cells
  • Concentrations: 0.0001-1 μM
  • Incubation Time: 5 days
  • Method:

    Human MT-4 cells are infected for 2 hours with the SIVmac251, HIV-1 (IIIB) and HIV-2 (CDC 77618) stocks at a multiplicity of infection of, approximately, 0.1. Cells are then washed three times in phosphate buffered saline, and suspended at 5 × 105/mL in fresh culture medium (to primary cells 50 units/mL of IL-2 are added) in 96-well plates, in the presence or absence of a range of triplicate raltegravir concentrations (0.0001 μM -1 μM). Untreated infected and mock-infected controls are prepared too, in order to allow comparison of the data derived from the different treatments. Viral cytopathogeniciy in MT-4 cells is quantitated by the methyl tetrazolium (MTT) method (MT-4/MTT assay) when extensive cell death in control virus-infected cell cultures is detectable microscopically as lack of capacity to re-cluster. The capability of MT-4 cells to form clusters after infection. Briefly, clusters are disrupted by pipetting; and, after 2 hours of incubation at 37 °C, the formation of new clusters is assessed by light microscopy (100 × magnification). Cell culture supernatants are collected for HIV-1 p24 and HIV-2/SIVmac251 p27 core antigen measurement by ELISA. In CEMx174-infected cell cultures, which show a propensity to form syncytia induced by the virus envelope glycoproteins, syncytia are counted, in blinded fashion, by light microscopy for each well at 5 days following infection.

Animal Research:

[5]

  • Animal Models: Indian Rhesus macaques
  • Dosages: 50 mg/kg or 100 mg/kg
  • Administration: Oral administration

Solubility (25°C)

In vitro

DMSO 88 mg/mL
(198.01 mM)
Water Insoluble
Ethanol Insoluble

In vivo

Add solvents to the product individually and in order
(Data is from Selleck tests instead of citations):
2% DMSO+40% PEG 300+2% Tween 80+ddH2O
For best results, use promptly after mixing.

8mg/mL

Chemical Information

Molecular Weight 444.42
Formula

C20H21FN6O5

CAS No. 518048-05-0
Storage 3 years -20°C powder
2 years -80°C in solvent
Smiles CC1=NN=C(O1)C(=O)NC(C)(C)C2=NC(=C(C(=O)N2C)O)C(=O)NCC3=CC=C(C=C3)F

In vivo Formulation Calculator (Clear solution)

Step 1: Enter information below (Recommended: An additional animal making an allowance for loss during the experiment)

mg/kg g μL

Step 2: Enter the in vivo formulation (This is only the calculator, not formulation. Please contact us first if there is no in vivo formulation at the solubility Section.)

% DMSO % % Tween 80 % ddH2O
%DMSO %

Calculation results:

Working concentration: mg/ml;

Method for preparing DMSO master liquid: mg drug pre-dissolved in μL DMSO ( Master liquid concentration mg/mL, Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug. )

Method for preparing in vivo formulation: Take μL DMSO master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O, mix and clarify.

Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.

Note: 1. Please make sure the liquid is clear before adding the next solvent.
2. Be sure to add the solvent(s) in order. You must ensure that the solution obtained, in the previous addition, is a clear solution before proceeding to add the next solvent. Physical methods such
as vortex, ultrasound or hot water bath can be used to aid dissolving.

Molarity Calculator

Mass Concentration Volume Molecular Weight

Clinical Trial Information

NCT Number Recruitment Interventions Conditions Sponsor/Collaborators Start Date Phases
NCT04513626 Recruiting Drug: DORAVIRINE 100 MG [Pifeltro] HIV Infections Centre de Recherches et d''Etude sur la Pathologie Tropicale et le Sida September 15 2020 Phase 2
NCT03667547 Completed Drug: Raltegravir Human Immunodeficiency Virus (HIV) Infection Merck Sharp & Dohme Corp. September 27 2018 Phase 4
NCT03174977 Recruiting Drug: 18F-Raltegravir HIV-1-infection University of California San Francisco|Merck Sharp & Dohme Corp. April 1 2018 Early Phase 1

(data from https://clinicaltrials.gov, updated on 2022-01-17)

Tech Support

Answers to questions you may have can be found in the inhibitor handling instructions. Topics include how to prepare stock solutions, how to store inhibitors, and issues that need special attention for cell-based assays and animal experiments.

Handling Instructions

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