Raltegravir

Summary

Raltegravir (CHEMBL254316) is an approved small-molecule antiviral drug (ATC J05AJ01); indicated across 12 conditions including viral infectious disease and hiv infectious disease.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: J05AJ01
• Indications: 12 conditions
• Clinical trials: 172
• Chemistry: 444.4 Da · C20H21FN6O5

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL254316
Name	Raltegravir
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	54671008
ChEBI	CHEBI:82960
ATC	J05AJ01
Molecular formula	C20H21FN6O5
Molecular weight	444.4
InChIKey	CZFFBEXEKNGXKS-UHFFFAOYSA-N

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

IUPAC name: N-[2-[4-[(4-fluorophenyl)methylcarbamoyl]-5-hydroxy-1-methyl-6-oxopyrimidin-2-yl]propan-2-yl]-5-methyl-1,3,4-oxadiazole-2-carboxamide

ChEBI definition: A pyrimidone that is pyrimidin-4(3H)-one in which the hydrogens at positions 2, 3, 5 and 6 are replaced by 2-[(5-methyl-1,3,4-oxadiazole-2-carbonyl)amino]propan-2-yl, methyl, hydroxy, and N-[(4-fluorophenyl)methyl]aminoacyl groups, respectively. It is an antiretroviral drug used for treatment of HIV infection.

Pharmacological roles (ChEBI): antiviral drug, HIV-1 integrase inhibitor.

Also known as: L-000900612, L000900612, Raltegravir, raltegravir, Reltegravir, SID124896574, SID170466888, RALTEGRAVIR, RALTEGRAVIR (MK-0518), Raltegravir (MK-0518)

Parent form; salt/anhydrous children: CHEMBL460566, CHEMBL518520, CHEMBL1162988, CHEMBL4567874

Patent coverage: 3,311 distinct patent families (12,743 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 2 (assay-derived). Sample: Voltage-gated potassium channel, IKs; KCNQ1(Kv7.1)/KCNE1(MinK), C-C chemokine receptor type 1.

Bioactivity

ChEMBL activities: 1 potent at pChembl ≥ 5 of 2 total. Top 100 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
CCR1	8.3	Ki	5	nM	CHEMBL_ACT_12149759

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

8 diseases in clinical trials (phase 1–3, investigational — not approved indications). Highest ChEMBL trial phase per disease; a non-cancer approved use is occasionally logged at phase 3 here.

Disease (in trials)	Phase	MONDO	EFO
viral infectious disease	3	MONDO:0005108	EFO:0000763
HIV infectious disease	3	MONDO:0005109	EFO:0000764
AIDS	3	MONDO:0012268	EFO:0000765
relapsing-remitting multiple sclerosis	2	MONDO:0005314	EFO:0003929
human T-lymphotropic virus 1 infectious disease	2	MONDO:0005801	EFO:0007316
primary biliary cholangitis	2	MONDO:0005388	EFO:1001486
hepatitis C virus infection	1	MONDO:0005231	EFO:0003047
T-cell acute lymphoblastic leukemia	1	MONDO:0004963	EFO:0000209

2 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 172.

Phase distribution

Phase	Trials
PHASE4	45
Not specified	39
PHASE1	34
PHASE3	25
PHASE2	19
PHASE2/PHASE3	4
PHASE1/PHASE2	3
EARLY_PHASE1	3

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00564772	PHASE4	COMPLETED	Raltegravir Kaletra Pharmacokinetics
NCT00594646	PHASE4	COMPLETED	HIV Non Occupational Post-Exposure Prophylaxis (PEP)
NCT00631449	PHASE4	COMPLETED	Raltegravir Intensification in HIV-infected Patients
NCT00632970	PHASE4	TERMINATED	Raltegravir vs. Lopinavir/Ritonavir, Both in Combination With Truvada, in HIV+ Treatment Naive Individuals
NCT00666705	PHASE4	COMPLETED	A Study To Evaluate An Interaction Between Maraviroc And Raltegravir In Healthy Subjects
NCT00677300	PHASE4	COMPLETED	Raltegravir And Darunavir Antiretroviral in Antiretroviral Naive Patients
NCT00751153	PHASE4	UNKNOWN	Raltegravir and Atazanavir Replacing Current Suppressive Treatment Because of Side Effects in Current Treatment
NCT00762892	PHASE4	COMPLETED	Raltegravir vs. Atazanavir in Combination With Truvada® for the Treatment of Antiretroviral naïve HIV Infected Patients
NCT00772590	PHASE4	COMPLETED	Antiretroviral Therapy Intensification With Raltegravir or Addition of Hyper-immune Bovine Colostrum in HIV-1 Infected Patients With Suboptimal CD4+ T Cell Response
NCT00773708	PHASE4	COMPLETED	Pilot Opened Trial in HIV-infected Patients Including an Investigational Marketed Product
NCT00781287	PHASE4	TERMINATED	Raltegravir (Isentress/MK-0518) and HIV-1 Infected CD4 Cells During Acute/Early HIV-1
NCT00843713	PHASE4	COMPLETED	Effect of Raltegravir on Endothelial Function in HIV-Infected Patients
NCT00931463	PHASE4	COMPLETED	A Trial of 2 Options for Second Line Combination Antiretroviral Therapy Following Virological Failure of a Standard Non-nucleoside Reverse Transcriptase Inhibitor (NNRTI)+2N(t)RTI First Line Regimen
NCT00931801	PHASE4	COMPLETED	BATAR: Individuals Currently Taking Boosted Atazanavir as Part of an HIV Treatment Regimen Will be Evaluated to See if Substituting Raltegravir for Nucleoside Transcriptase Inhibitors Will be Safe and Well Tolerated.
NCT00939874	PHASE4	COMPLETED	Switch From Tenofovir to Raltegravir for Low Bone Mineral Density
NCT00995241	PHASE4	COMPLETED	Pilot Study to Compare the Pharmacokinetics Parameters in Plasma and Intracellular of Raltegravir Administered Once a Day in Adult Patients Infected With HIV
NCT01013987	PHASE4	UNKNOWN	Maraviroc (Celsentri) With Raltegravir and Darunavir/Ritonavir for the Treatment of Triple Class Failure in Adult HIV-1 Infected Patients
NCT01087840	PHASE4	COMPLETED	Raltegravir Use as Nonoccupational Postexposure Prophylaxis (NPEP) in Men Who Have Sex With Men
NCT01105611	PHASE4	UNKNOWN	Safety and Efficacy Study Comparing Raltegravir to a Protease Inhibitor in Treatment-naïve, HIV/Hepatitis C Drug Users
NCT01121809	PHASE4	COMPLETED	Plasma and Intracellular Concentrations of Raltegravir and Etravirine Administered Once Daily
NCT01147107	PHASE4	COMPLETED	Hepatic Safety of Raltegravir Versus Efavirenz as HIV Therapy for Patients With HIV and HCV Coinfection
NCT01201239	PHASE4	UNKNOWN	Efficacy and Safety of Raltegravir (RAL) in Treatment-experienced HIV-1 Infected Adult Chinese Patients
NCT01214759	PHASE4	COMPLETED	Truvada Plus Raltegravir for Nonoccupational Post-exposure Prophylaxis (nPEP)
NCT01225705	PHASE4	WITHDRAWN	Safety Study of Raltegravir in HIV/HCV Co-infected Patients
NCT01245101	PHASE4	TERMINATED	Addition of Raltegravir to Established Antiretroviral Suppressive Therapy
NCT01270802	PHASE4	COMPLETED	Effects of Switching Efavirenz to Raltegravir on Vascular Function and Bone Markers in HIV-infected Patients
NCT01285050	PHASE4	COMPLETED	Interferon Alfa Sensitivity in HIV/HCV Persons Before and After HIV Meds
NCT01332227	PHASE4	COMPLETED	Atazanavir/Ritonavir, Once Daily + Raltegravir, Twice Daily, Switch Study in HIV-1-Infected Patients
NCT01335620	PHASE4	COMPLETED	The Safety, Pharmacokinetic Profile and Efficacy of Raltegravir in HIV-infected Patients at Least 60 Years of Age
NCT01448486	PHASE4	TERMINATED	A Study of the Neurological Effects of Adding Raltegravir to HAART Regimen in Patients With HIV
NCT01453933	PHASE4	UNKNOWN	RAltegravir Switch STudy: Effects on Endothelial Recovery
NCT01513122	PHASE4	COMPLETED	Bone and Body Comp: A Sub Study of the SECOND-LINE Study
NCT01576731	PHASE4	COMPLETED	Study Comparing Two Alternatives of Antiretroviral Therapy as Post-exposure Prophylaxis to HIV-1: Tenofovir + Emtricitabine + Lopinavir/Ritonavir Versus Tenofovir + Emtricitabine + Raltegravir (RAL-PEP)
NCT01618305	PHASE4	COMPLETED	Evaluating the Response to Two Antiretroviral Medication Regimens in HIV-Infected Pregnant Women, Who Begin Antiretroviral Therapy Between 20 and 36 Weeks of Pregnancy, for the Prevention of Mother-to-Child Transmission
NCT01641367	PHASE4	COMPLETED	A5288/MULTI-OCTAVE: Management Using Latest Technologies to Optimize Combination Therapy After Viral Failure
NCT01679964	PHASE4	COMPLETED	Sustained Virological Suppression and Improvement of Adverse Events of Switching to Raltegravir Study
NCT01829802	PHASE4	UNKNOWN	RAL+ATV/r in Comparison With TDF/FTC (or 3TC) +ATV/r in HIV Infected Patients
NCT01900015	PHASE4	COMPLETED	Changes in Liver Steatosis After Switching to Raltegravir in HIV/HCV Coinfection
NCT01902186	PHASE4	TERMINATED	Bone Mineral Density Changes in HIV-positive Females With Osteopenia Switching to Raltegravir
NCT01989910	PHASE4	COMPLETED	Compare the Efficacy and Safety of Raltegravir Versus Efavirenz Combination Therapy in Treatment-naïve HIV-1 Patients
NCT02383355	PHASE4	COMPLETED	Effects of Raltegravir Based Regimen on Platelet Reactivity, Platelet-monocyte Aggregation and Immune Activation
NCT02577042	PHASE4	COMPLETED	Study of the Effect of Atorvastatin for Reducing Aging-related Complication in HIV-infected Patients Older Than 45 Years Receiving a Protease Inhibitor-based Regimen Versus a Raltegravir-based Regimen
NCT03374358	PHASE4	COMPLETED	Effect on Liver Fat and Metabolic Parameters When Switching a Protease Inhibitor or Efavirenz to Raltegravir
NCT03667547	PHASE4	COMPLETED	Safety, Tolerability, and Pharmacokinetics of Raltegravir (MK-0518) in Healthy Japanese Male Participants (MK-0518-851)
NCT03732625	PHASE4	UNKNOWN	Neuropsyquiatric Evolution After Introduction of Raltegravir QD in Substitution of Dolutegravir: NEAR QD Study
NCT00443729	PHASE3	TERMINATED	MK0518 in the Treatment of HIV-Infected Patients Switched From a Protease Inhibitor Regimen (0518-033)(TERMINATED)
NCT00528892	PHASE3	COMPLETED	Switching From PI to RALtegravir in HIV Stable Patients
NCT00529243	PHASE3	COMPLETED	Evaluating the Effect of CHanging EnfuvirtidE to Raltegravir in HIV Infected Subjects
NCT00537394	PHASE3	COMPLETED	Optimizing Treatment for Treatment-Experienced, HIV-Infected People
NCT00562510	PHASE3	TERMINATED	Raltegravir Added to Stable HAART in HIV-1 Infected Subjects With Viral Suppression and Low CD4 Recovery
NCT00708162	PHASE3	COMPLETED	Multicenter, Randomized, Double-Blind, Double-Dummy, Phase 3 Study of the Safety and Efficacy of Elvitegravir Versus Raltegravir
NCT00711009	PHASE3	COMPLETED	Study Comparing Lopinavir/Ritonavir (LPV/r) + Emtricitabine/Tenofovir Disoproxil Fumarate (FTC/TDF) With a Nucleoside Sparing Regimen Consisting of Lopinavir/Ritonavir + Raltegravir (RAL)
NCT00729924	PHASE2/PHASE3	COMPLETED	Genetic Predictors of Raltegravir Penetration Into Cerebrospinal Fluid
NCT00764946	PHASE3	COMPLETED	A Study of Raltegravir in a Diverse Cohort of HIV-Infected Patients (0518-055)
NCT00808002	PHASE3	COMPLETED	Efficacy of Treatment Intensification With Maraviroc on HIV-1 Viral Latency in Recently Infected Hiv-1 naïve Patients Starting Raltegravir Plus Tenofovir/Emtricitabine
NCT00811954	PHASE3	COMPLETED	Comparative Study of Three NNRTI-Sparing HAART Regimens
NCT00887653	PHASE3	COMPLETED	Changes in Lipids and Safety of Raltegravir in HIV+ Patients With Hyperlipidemia While on Current Standard Therapy
NCT00988039	PHASE3	COMPLETED	Europe-Africa Research Network for Evaluation of Second-line Therapy
NCT01114425	PHASE3	COMPLETED	Safety Study of Isentress® + Truvada® in Post-exposure Treatment of HIV Infection
NCT01154673	PHASE2/PHASE3	COMPLETED	Effects of Intensive cART During Acute/Early HIV Infection
NCT01195467	PHASE3	COMPLETED	Atripla to Raltegravir Switch Study for CNS Toxicity
NCT01227824	PHASE3	COMPLETED	A Trial Comparing GSK1349572 50mg Once Daily to Raltegravir 400mg Twice Daily
NCT01231516	PHASE3	COMPLETED	A Study of GSK1349572 Versus Raltegravir (RAL) With Investigator Selected Background Regimen in Antiretroviral-Experienced, Integrase Inhibitor-Naive Adults
NCT01352715	PHASE3	COMPLETED	Study of Options for Second-Line Effective Combination Therapy (SELECT)
NCT01453192	PHASE3	COMPLETED	Renal Transplantation and Raltegravir in HIV-Infected Patients
NCT01825031	PHASE3	COMPLETED	Reduction of EArly mortaLITY in HIV-infected Adults and Children Starting Antiretroviral Therapy
NCT01854762	PHASE2/PHASE3	TERMINATED	Antiretroviral Regimens Containing Raltegravir for Prophylaxis of Mother-to-child-transmission of HIV Infection
NCT02131233	PHASE3	COMPLETED	Evaluation of the Safety and Efficacy of Reformulated Raltegravir (MK-0518) 1200 mg Once Daily in Combination With TRUVADA™ in Human Immunodeficiency Virus (HIV)-1 Infected, Treatment-Naive Participants (MK-0518-292)
NCT02150993	PHASE2/PHASE3	COMPLETED	First-Line Treatment for HIV-2
NCT02273765	PHASE3	COMPLETED	Raltegravir Versus Efavirenz in Naive HIV-1-infected Patients Receiving Rifampin for Active Tuberculosis
NCT02284035	PHASE3	COMPLETED	Safety & Efficacy of Dual Therapy With Raltegravir/Lamivudine
NCT03029689	PHASE3	COMPLETED	Clinical Trial to Evaluate the Effect of Raltegravir Intensification (1.200 mg QD) on the Gut Microbiota of Chronically HIV-1 Infected Subject Over Time: THE RAGTIME STUDY
NCT03311945	PHASE3	COMPLETED	Simplification Study of HIV-1 Infected Patients With Virological Suppression Under the Combination of Lamivudine (150 mg BID) Plus Raltegravir (400 mg BID) Switching to Lamivudine (300 mg QD) Plus Raltegravir (1200 mg QD) : Roll-over Study of the RALAM
NCT03333083	PHASE3	TERMINATED	Study With Dual Therapy Including Lamivudine (300 mg QD) Plus Raltegravir (1200 mg QD) in Virologically Suppressed HIV-1 Infected Patients Experiencing Inconvenience, Toxicity, Negative Impact on Co-morbidities or Risk of Drug-drug Interactions With Their Current Regimen
NCT02140255	PHASE1/PHASE2	RECRUITING	Very Early Intensive Treatment of Infants Living With HIV to Achieve HIV Remission
NCT00515827	PHASE2	COMPLETED	Effect of Addition of Raltegravir (MK-0518) to PI- or NNRTI-Based ART Regimens in HIV Infected Subjects With Undetectable Viral Load
NCT00520897	PHASE2	COMPLETED	Integrase Inhibitor (MK-0518) Viral Decay
NCT00656175	PHASE2	COMPLETED	Raltegravir Therapy for Women With HIV and Fat Accumulation
NCT00768989	PHASE2	TERMINATED	Phase IIB Pilot of Atazanavir + Raltegravir
NCT00807443	PHASE2	COMPLETED	Effect Of An Integrase Inhibitor On The Latency And Reservoir Of HIV-1
NCT00822315	PHASE2	COMPLETED	Efficacy and Safety of 2 Raltegravir Doses in Naive HIV-1-infected Patients Receiving Rifampin for Active Tuberculosis
NCT00830804	PHASE2	COMPLETED	Safety and Effectiveness of Raltegravir Plus Darunavir/Ritonavir in Treatment-Naive HIV-Infected Adults
NCT01000285	PHASE1/PHASE2	COMPLETED	EPOCH Chemotherapy and Bortezomib for Associated T-Cell Leukemia Lymphoma
NCT01159132	PHASE2	COMPLETED	Pharmacokinetics of Low Dose Raltegravir
NCT01231685	PHASE2	COMPLETED	Raltegravir Switch Study to Reduce Liver Fibrosis Progression in HIV-Hepatitis C Co-infection
NCT01291459	PHASE2	UNKNOWN	Pilot Study of Maraviroc/Raltegravir for Naive HIV-1 Patients
NCT01384734	PHASE2	COMPLETED	HIV Attachment Inhibitor to Treat Human Immunodeficiency Virus 1 (HIV-1) Infections
NCT01601626	PHASE2	TERMINATED	Rifampin-Based Tuberculosis Treatment Versus Rifabutin-Based Tuberculosis Treatment in Persons With HIV
NCT01620736	PHASE2	WITHDRAWN	Trial to Assess Effect of Raltegravir on HTLV-1 Proviral Load
NCT01751568	PHASE1/PHASE2	COMPLETED	Safety, Tolerance and Pharmacokinetics of Raltegravir-Containing Antiretroviral Therapy in Infants, Children Infected With HIV and TB
NCT01767701	PHASE2	COMPLETED	Raltegravir (Isentress) Pilot Study in Relapsing Multiple Sclerosis
NCT02097108	PHASE2	COMPLETED	Changes in Lipids and Lipoproteins in HIV Infected Women After Switch From Protease Inhibitor to Raltegravir
NCT02116660	PHASE2	TERMINATED	Evaluation of Renal Function, Efficacy, and Safety When Switching From Tenofovir/Emtricitabine Plus a Protease Inhibitor/Ritonavir, to a Combination of Raltegravir (MK-0518) Plus Nevirapine Plus Lamivudine in HIV-1 Participants With Suppressed Viremia and Impaired Renal Function (MK-0518-284)
NCT02212379	PHASE2	COMPLETED	Capacity of the Dual Combination Raltegravir/Etravirine to Maintain Virological Success in HIV-1 Infected Patients of at Least 45 Years of Age- ANRS 163 ETRAL
NCT02336074	PHASE2	COMPLETED	Research In Viral Eradication of HIV Reservoirs
NCT03954327	PHASE2	COMPLETED	Combination Antiretroviral Therapy (cART) for PBC
NCT00518297	PHASE1	COMPLETED	DDI HV (ATV - Merck)
NCT00618241	PHASE1	COMPLETED	Pharmacokinetic Study on Raltegravir and Lamotrigine
NCT00660972	PHASE1	COMPLETED	Study of Viral Load Decay Rates in HIV Infected Participants Starting Treatment With Raltegravir (RAL) and Emtricitabine/Tenofovir Disoproxil Fumarate (TDF)
NCT00665717	PHASE1	COMPLETED	The Influence of Raltegravir on Pravastatin Pharmacokinetics(GRAPPA)

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline, but PharmGKB curates 0 clinical and 12 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).