Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C23H23ClFNO5 |
| Molecular Weight | 447.884 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC2=C(C=C1CC3=CC=CC(Cl)=C3F)C(=O)C(=CN2[C@H](CO)C(C)C)C(O)=O
InChI
InChIKey=JUZYLCPPVHEVSV-LJQANCHMSA-N
InChI=1S/C23H23ClFNO5/c1-12(2)19(11-27)26-10-16(23(29)30)22(28)15-8-14(20(31-3)9-18(15)26)7-13-5-4-6-17(24)21(13)25/h4-6,8-10,12,19,27H,7,11H2,1-3H3,(H,29,30)/t19-/m1/s1
| Molecular Formula | C23H23ClFNO5 |
| Molecular Weight | 447.884 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Elvitegravir is a human immunodeficiency virus type 1 (HIV-1) integrase strand transfer inhibitor used in combination with cobicistat, emtricitabine and tenofovir alafenamid (GENVOYA®) for the treatment of HIV-1 infection in antiretroviral treatment-experienced adults. Because integrase is necessary for viral replication, inhibition prevents the integration of HIV-1 DNA into the host genome and thereby blocks the formation of the HIV-1 provirus and resulting propagation of the viral infection.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
| 0.004 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | GENVOYA Approved UseGENVOYA is indicated as a complete regimen for the treatment of HIV-1 infection in
adults and pediatric patients 12 years of age and older who have no antiretroviral treatment history or to replace the current antiretroviral regimen in those who are virologically-suppressed (HIV-1 RNA less than 50 copies per mL) on a stable antiretroviral regimen for at least 6 months with no history of treatment failure and no known substitutions associated with resistance to the individual components of GENVOYA. Launch Date2015 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.5 μg/mL |
150 mg 1 times / day steady-state, oral dose: 150 mg route of administration: Oral experiment type: STEADY-STATE co-administered: RITONAVIR |
ELVITEGRAVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
1470 ng/mL |
150 mg 1 times / day steady-state, oral dose: 150 mg route of administration: Oral experiment type: STEADY-STATE co-administered: RITONAVIR |
ELVITEGRAVIR plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
2130 ng/mL |
150 mg 1 times / day steady-state, oral dose: 150 mg route of administration: Oral experiment type: STEADY-STATE co-administered: RITONAVIR |
ELVITEGRAVIR plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
164.1 ng/mL |
100 mg 2 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered: RITONAVIR |
ELVITEGRAVIR plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
1826.4 ng/mL |
100 mg 2 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered: RITONAVIR |
ELVITEGRAVIR plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
1.2 μg/mL |
85 mg 1 times / day steady-state, oral dose: 85 mg route of administration: Oral experiment type: STEADY-STATE co-administered: RITONAVIR |
ELVITEGRAVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
18 μg × h/mL |
150 mg 1 times / day steady-state, oral dose: 150 mg route of administration: Oral experiment type: STEADY-STATE co-administered: RITONAVIR |
ELVITEGRAVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
18300 ng × h/mL |
150 mg 1 times / day steady-state, oral dose: 150 mg route of administration: Oral experiment type: STEADY-STATE co-administered: RITONAVIR |
ELVITEGRAVIR plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
22100 ng × h/mL |
150 mg 1 times / day steady-state, oral dose: 150 mg route of administration: Oral experiment type: STEADY-STATE co-administered: RITONAVIR |
ELVITEGRAVIR plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
719.3 ng × h/mL |
100 mg 2 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered: RITONAVIR |
ELVITEGRAVIR plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
14302 ng × h/mL |
100 mg 2 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered: RITONAVIR |
ELVITEGRAVIR plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
18 μg × h/mL |
85 mg 1 times / day steady-state, oral dose: 85 mg route of administration: Oral experiment type: STEADY-STATE co-administered: RITONAVIR |
ELVITEGRAVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
8.7 h |
150 mg 1 times / day steady-state, oral dose: 150 mg route of administration: Oral experiment type: STEADY-STATE co-administered: RITONAVIR |
ELVITEGRAVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
3.5 h |
100 mg 2 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered: RITONAVIR |
ELVITEGRAVIR plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
9.5 h |
100 mg 2 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered: RITONAVIR |
ELVITEGRAVIR plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
8.7 h |
85 mg 1 times / day steady-state, oral dose: 85 mg route of administration: Oral experiment type: STEADY-STATE co-administered: RITONAVIR |
ELVITEGRAVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1% |
150 mg 1 times / day steady-state, oral dose: 150 mg route of administration: Oral experiment type: STEADY-STATE co-administered: RITONAVIR |
ELVITEGRAVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
1% |
85 mg 1 times / day steady-state, oral dose: 85 mg route of administration: Oral experiment type: STEADY-STATE co-administered: RITONAVIR |
ELVITEGRAVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
800 mg 2 times / day steady, oral Highest studied dose Dose: 800 mg, 2 times / day Route: oral Route: steady Dose: 800 mg, 2 times / day Sources: |
unhealthy, 39 years Health Status: unhealthy Age Group: 39 years Sex: M+F Sources: |
Other AEs: Muscle spasm... |
85 mg 1 times / day steady, oral Recommended Dose: 85 mg, 1 times / day Route: oral Route: steady Dose: 85 mg, 1 times / day Sources: |
unhealthy, 45 years (range: 19–78 years) Health Status: unhealthy Age Group: 45 years (range: 19–78 years) Sex: M+F Sources: |
Disc. AE: Diarrhea... AEs leading to discontinuation/dose reduction: Diarrhea Sources: |
800 mg single, oral Highest studied dose Dose: 800 mg Route: oral Route: single Dose: 800 mg Sources: |
healthy |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Muscle spasm | grade 3, 1 patient | 800 mg 2 times / day steady, oral Highest studied dose Dose: 800 mg, 2 times / day Route: oral Route: steady Dose: 800 mg, 2 times / day Sources: |
unhealthy, 39 years Health Status: unhealthy Age Group: 39 years Sex: M+F Sources: |
| Diarrhea | Disc. AE | 85 mg 1 times / day steady, oral Recommended Dose: 85 mg, 1 times / day Route: oral Route: steady Dose: 85 mg, 1 times / day Sources: |
unhealthy, 45 years (range: 19–78 years) Health Status: unhealthy Age Group: 45 years (range: 19–78 years) Sex: M+F Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Pharmacology of HIV integrase inhibitors. | 2012-09 |
|
| Elvitegravir: a once-daily inhibitor of HIV-1 integrase. | 2012-03 |
|
| Review of the safety, efficacy, and pharmacokinetics of elvitegravir with an emphasis on resource-limited settings. | 2012 |
|
| Elvitegravir overcomes resistance to raltegravir induced by integrase mutation Y143. | 2011-06-01 |
|
| HIV-1 integrase strand-transfer inhibitors: design, synthesis and molecular modeling investigation. | 2011-02 |
|
| The HIV-1 integrase α4-helix involved in LTR-DNA recognition is also a highly antigenic peptide element. | 2010-12-30 |
|
| Comparison of the Mechanisms of Drug Resistance among HIV, Hepatitis B, and Hepatitis C. | 2010-12-01 |
|
| Modeling the HIV-1 Intasome: A Prototype View of the Target of Integrase Inhibitors. | 2010-12 |
|
| Polymorphisms of HIV-2 integrase and selection of resistance to raltegravir. | 2010-11-29 |
|
| Specific HIV-1 integrase polymorphisms change their prevalence in untreated versus antiretroviral-treated HIV-1-infected patients, all naive to integrase inhibitors. | 2010-11 |
|
| Mutation Q95K enhances N155H-mediated integrase inhibitor resistance and improves viral replication capacity. | 2010-11 |
|
| Pharmacokinetics and bioavailability of an integrase and novel pharmacoenhancer-containing single-tablet fixed-dose combination regimen for the treatment of HIV. | 2010-11 |
|
| Development of integrase inhibitors of quinolone acid derivatives for treatment of AIDS: an overview. | 2010-10 |
|
| Physical trapping of HIV-1 synaptic complex by different structural classes of integrase strand transfer inhibitors. | 2010-09-28 |
|
| Bunyaviridae RNA polymerases (L-protein) have an N-terminal, influenza-like endonuclease domain, essential for viral cap-dependent transcription. | 2010-09-16 |
|
| Novel antiretroviral combinations in treatment-experienced patients with HIV infection: rationale and results. | 2010-09-10 |
|
| HIV-1 subtype B and C integrase enzymes exhibit differential patterns of resistance to integrase inhibitors in biochemical assays. | 2010-09-10 |
|
| Novel integrase inhibitors for HIV. | 2010-09 |
|
| Identification of novel mutations responsible for resistance to MK-2048, a second-generation HIV-1 integrase inhibitor. | 2010-09 |
|
| Susceptibility of the human retrovirus XMRV to antiretroviral inhibitors. | 2010-08-31 |
|
| Evolution of integrase resistance during failure of integrase inhibitor-based antiretroviral therapy. | 2010-08 |
|
| Primary mutations selected in vitro with raltegravir confer large fold changes in susceptibility to first-generation integrase inhibitors, but minor fold changes to inhibitors with second-generation resistance profiles. | 2010-07-05 |
|
| Resistance to integrase inhibitors. | 2010-06-25 |
|
| Raltegravir: The evidence of its therapeutic value in HIV-1 infection. | 2010-06-15 |
|
| Anticipating and blocking HIV-1 escape by second generation antiviral shRNAs. | 2010-06-08 |
|
| 5th International AIDS Society Conference on HIV Pathogenesis, Treatment and Prevention: summary of key research and implications for policy and practice - clinical sciences. | 2010-06-01 |
|
| HIV-1 resistance patterns to integrase inhibitors in antiretroviral-experienced patients with virological failure on raltegravir-containing regimens. | 2010-06 |
|
| Biochemical and pharmacological analyses of HIV-1 integrase flexible loop mutants resistant to raltegravir. | 2010-05-04 |
|
| Retrovirus Integrase-DNA Structure Elucidates Concerted Integration Mechanisms. | 2010-05-01 |
|
| The HIV-1 integrase mutations Y143C/R are an alternative pathway for resistance to Raltegravir and impact the enzyme functions. | 2010-04-26 |
|
| Resistance to HIV-1 integrase inhibitors: A structural perspective. | 2010-04-17 |
|
| [Analysis of HIV-1 integrase gene polymorphism in an HIV-infected population from the nosocomial outbreak of HIV infection in the south of Russia in 1989]. | 2010-04-07 |
|
| Natural polymorphisms of integrase among HIV type 1-infected South African patients. | 2010-04 |
|
| Response of a simian immunodeficiency virus (SIVmac251) to raltegravir: a basis for a new treatment for simian AIDS and an animal model for studying lentiviral persistence during antiretroviral therapy. | 2010-03-16 |
|
| Activity of elvitegravir, a once-daily integrase inhibitor, against resistant HIV Type 1: results of a phase 2, randomized, controlled, dose-ranging clinical trial. | 2010-03-15 |
|
| Pharmacokinetics and pharmacodynamics of GS-9350: a novel pharmacokinetic enhancer without anti-HIV activity. | 2010-03 |
|
| Pharmacokinetic interaction of ritonavir-boosted elvitegravir and maraviroc. | 2010-02 |
|
| Genetic diversity on the integrase region of the pol gene among HIV type 1-infected patients naive for integrase inhibitors in São Paulo City, Brazil. | 2010-01 |
|
| Improving first-line antiretroviral therapy in resource-limited settings. | 2010-01 |
|
| Integrase inhibitors: a novel class of antiretroviral agents. | 2010-01 |
|
| Strand transfer inhibitors of HIV-1 integrase: bringing IN a new era of antiretroviral therapy. | 2010-01 |
|
| Role of etravirine in the management of treatment-experienced patients with human immunodeficiency virus type 1. | 2010 |
|
| Extended use of raltegravir in the treatment of HIV-1 infection: optimizing therapy. | 2010 |
|
| Comparative biochemical analysis of HIV-1 subtype B and C integrase enzymes. | 2009-11-11 |
|
| Resistance to novel drug classes. | 2009-11 |
|
| Integrase inhibitors in salvage therapy regimens for HIV-1 infection. | 2009-11 |
|
| Elvitegravir: a new HIV integrase inhibitor. | 2009-10-19 |
|
| In search of second-generation HIV integrase inhibitors: targeting integration beyond strand transfer. | 2009-10 |
|
| Raltegravir in the management of HIV-infected patients. | 2009-02-06 |
|
| Pharmacologic and nonpharmacologic options for the management of HIV infection during pregnancy. | 2009 |
Sample Use Guides
One GENVOYA® tablet taken orally once daily with food.
Route of Administration:
Oral
It was found that integrase inhibitor elvitegravir interfered with the physiological functions of RAG1, a critical enzyme involved in V(D)J recombination. Circular dichroism studies demonstrated a distinct change in the secondary structure of RAG1 central domain (RAG1 shares DDE motif amino acids with integrases), and when incubated with elvitegravir, an equilibrium dissociation constant (Kd) of 32.53±2.9 uM was determined by biolayer interferometry, leading to inhibition of its binding to DNA. Besides, using extrachromosomal assays, it was shown that elvitegravir inhibited both coding and signal joint formation in pre-B cells. Importantly, treatment with elvitegravir resulted in significant reduction of mature B lymphocytes in 70% of mice studied.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Apr 02 10:00:32 GMT 2025
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Wed Apr 02 10:00:32 GMT 2025
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| Record UNII |
4GDQ854U53
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Validated (UNII)
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WHO-VATC |
QJ05AX11
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WHO-VATC |
QJ05AR09
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WHO-ATC |
J05AR09
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J05AX11
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J05AR18
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N0000175887
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C281
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LIVERTOX |
NBK547911
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EMA ASSESSMENT REPORTS |
GENVOYA (AUTHORIZED: HIV INFECTIONS)
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EMA ASSESSMENT REPORTS |
VITEKTA (AUTHORIZED: HIV INFECTIONS)
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SS-98
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Elvitegravir
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N0000185507
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5277135
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m4880
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Elvitegravir
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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TARGET -> INHIBITOR |
INHIBITOR
IC50
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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METABOLITE LESS ACTIVE -> PARENT |
produced by uridine diphosphate glucuronoslytransferase UGT 1A1/3
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METABOLITE LESS ACTIVE -> PARENT |
Elvitegravir is also metabolized via CYP3A to hydroxy-EVG [metabolite M1]
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |
