Elvitegravir

Identification

Summary

Elvitegravir is an antiretroviral agent used in combination with other antiretrovirals for the treatment of HIV-1 infection in antiretroviral treatment-experienced adults.

Brand Names

Genvoya, Stribild

Generic Name

Elvitegravir

DrugBank Accession Number

DB09101

Background

Elvitegravir is a human immunodeficiency virus type 1 (HIV-1) integrase strand transfer inhibitor (INSTI) used 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. Although available as a single dose tablet, elvitegravir must be used in combination with an HIV protease inhibitor coadministered with ritonavir and another antiretroviral drug.

Elvitegravir was first licensed from Japan Tobacco in 2008 and developed by Gilead Sciences. It was FDA approved on August 27, 2012. On September 24, 2014, the FDA approved the single pill form of elvitegravir.

Type

Small Molecule

Groups

Approved

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Elvitegravir (DB09101)

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Weight

Average: 447.884
Monoisotopic: 447.124878763

Chemical Formula

C₂₃H₂₃ClFNO₅

Synonyms

• 6-(3-chloro-2-fluorobenzyl)-1-[(2S)-1-hydroxy-3-methylbutan-2-yl]-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• elvitégravir
• Elvitegravir
• EVG
• GS 9137

External IDs

• GS 9137
• GS-9137
• GS9137
• JTK 303
• JTK-303
• JTK303

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Pharmacology

Indication

Elvitegravir in combination with an HIV protease inhibitor coadministered with ritonavir and with other antiretroviral drug(s) is indicated for the treatment of HIV-1 infection in antiretroviral treatment-experienced adults.

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Treatment of	Hiv-1 infection		••••••••••••	•••••	•••••••••••••••••••••
Treatment of	Hiv-1 infection		••• •••••		•••••••••••••••

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Pharmacodynamics

Not Available

Mechanism of action

Elvitegravir is an HIV-1 integrase strand transfer inhibitor (INSTI). Integrase is an HIV-1 encoded enzyme that is required for viral replication. Inhibition of integrase prevents the integration of HIV-1 DNA into host genomic DNA, blocking the formation of the HIV-1 provirus and propagation of the viral infection. Elvitegravir does not inhibit human topoisomerases I or II.

Target	Actions	Organism
AIntegrase	inhibitor	Human immunodeficiency virus 1

Absorption

Following oral administration of elvitegravir and ritonavir with food, in HIV-1 infected subjects, peak elvitegravir plasma concentrations were observed approximately 4 hours post-dose.

Volume of distribution

Not Available

Protein binding

Elvitegravir is 98–99% bound to human plasma proteins

Metabolism

Elvitegravir undergoes primarily oxidative metabolism via CYP3A, and is secondarily glucuronidated via UGT1A1/3 enzymes. Metabolites are found in the plasma at very low concentrations, displayed considerably lower anti-HIV activity, and did not contribute to the overall antiviral activity of elvitegravir.

Route of elimination

Following oral administration of [14C]elvitegravir/ritonavir, 94.8% of the dose was recovered in feces, while 6.7% was recovered in urine as metabolites.

Half-life

The median terminal plasma half-life following administration of elvitegravir and ritonavir was approximately 8.7 hours.

Clearance

Not Available

Adverse Effects

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Toxicity

The most common adverse reactions reported for elvitegravir use during clinical trials include nausea, vomiting, and diarrhea. Less common side effects occurring in <2% of patients, include abdominal pain, dyspepsia, fatigue, insomnia, rash, depression, suicidal ideation, and suicidal attempt.

Pathways

Not Available

Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

Not Available

Interactions

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This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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1,2-Benzodiazepine	The metabolism of 1,2-Benzodiazepine can be decreased when combined with Elvitegravir.
Abametapir	The serum concentration of Elvitegravir can be increased when it is combined with Abametapir.
Abemaciclib	The metabolism of Abemaciclib can be decreased when combined with Elvitegravir.
Abiraterone	The metabolism of Abiraterone can be decreased when combined with Elvitegravir.
Acalabrutinib	The metabolism of Acalabrutinib can be decreased when combined with Elvitegravir.

Food Interactions

• Avoid St. John's Wort. This herb induces the CYP3A metabolism of elvitegravir. Therefore, it may reduce the serum concentration of elvitegravir and its effectiveness.
• Take separate from antacids. Take at least 2 hours before or after antacids.
• Take with food.

Products

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Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Vitekta	Tablet, film coated	85 mg	Oral	Gilead Sciences	2016-09-08	2017-05-29
Vitekta	Tablet, film coated	150 mg/1	Oral	Gilead Sciences	2014-09-24	2017-02-28
Vitekta	Tablet	150 mg	Oral	Gilead Sciences	2015-04-21	2017-01-09
Vitekta	Tablet, film coated	85 mg/1	Oral	Gilead Sciences	2014-09-24	2017-02-28
Vitekta	Tablet, film coated	150 mg	Oral	Gilead Sciences	2016-09-08	2017-05-29

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Genvoya	Elvitegravir (90 mg) + Cobicistat (90 mg) + Emtricitabine (120 mg) + Tenofovir alafenamide (6 mg)	Tablet, film coated	Oral	Gilead Sciences Ireland Uc	2023-11-20	Not applicable
Genvoya	Elvitegravir (150 mg) + Cobicistat (150 mg) + Emtricitabine (200 mg) + Tenofovir alafenamide (10 mg)	Tablet, film coated	Oral	Gilead Sciences Ireland Uc	2016-09-08	Not applicable
Genvoya	Elvitegravir (150 mg/1) + Cobicistat (150 mg/1) + Emtricitabine (200 mg/1) + Tenofovir alafenamide fumarate (10 mg/1)	Tablet	Oral	REMEDYREPACK INC.	2017-06-06	Not applicable
Genvoya	Elvitegravir (90 mg) + Cobicistat (90 mg) + Emtricitabine (120 mg) + Tenofovir alafenamide (6 mg)	Tablet, film coated	Oral	Gilead Sciences Ireland Uc	2023-11-20	Not applicable
Genvoya	Elvitegravir (150 mg) + Cobicistat (150 mg) + Emtricitabine (200 mg) + Tenofovir alafenamide fumarate (10 mg)	Tablet	Oral	Gilead Sciences	2016-02-03	Not applicable

Categories

ATC Codes

J05AJ02 — Elvitegravir

• J05AJ — Integrase inhibitors
• J05A — DIRECT ACTING ANTIVIRALS
• J05 — ANTIVIRALS FOR SYSTEMIC USE
• J — ANTIINFECTIVES FOR SYSTEMIC USE

J05AR09 — Emtricitabine, tenofovir disoproxil, elvitegravir and cobicistat

• J05AR — Antivirals for treatment of HIV infections, combinations
• J05A — DIRECT ACTING ANTIVIRALS
• J05 — ANTIVIRALS FOR SYSTEMIC USE
• J — ANTIINFECTIVES FOR SYSTEMIC USE

J05AR18 — Emtricitabine, tenofovir alafenamide, elvitegravir and cobicistat

• J05AR — Antivirals for treatment of HIV infections, combinations
• J05A — DIRECT ACTING ANTIVIRALS
• J05 — ANTIVIRALS FOR SYSTEMIC USE
• J — ANTIINFECTIVES FOR SYSTEMIC USE

Drug Categories

• Anti-HIV Agents
• Anti-Infective Agents
• Anti-Retroviral Agents
• Antiinfectives for Systemic Use
• Antiviral Agents
• Antivirals for Systemic Use
• Antivirals used in combination for the treatment of HIV infections
• Cytochrome P-450 CYP2C9 Inducers
• Cytochrome P-450 CYP3A Inhibitors
• Cytochrome P-450 CYP3A Substrates
• Cytochrome P-450 CYP3A4 Inhibitors
• Cytochrome P-450 CYP3A4 Inhibitors (strong)
• Cytochrome P-450 CYP3A4 Substrates
• Cytochrome P-450 Enzyme Inducers
• Cytochrome P-450 Enzyme Inhibitors
• Cytochrome P-450 Substrates
• Direct Acting Antivirals
• Enzyme Inhibitors
• Heterocyclic Compounds, Fused-Ring
• HIV Integrase
• HIV Integrase Inhibitors
• Human Immunodeficiency Virus Integrase Strand Transfer Inhibitor
• Integrase Inhibitors
• Quinolines
• UGT1A1 Substrates

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinoline carboxylic acids

Direct Parent

Quinoline carboxylic acids

Alternative Parents

Hydroquinolones / Hydroquinolines / Pyridinecarboxylic acids / Anisoles / Alkyl aryl ethers / Chlorobenzenes / Fluorobenzenes / Aryl chlorides / Aryl fluorides / Vinylogous amides / Heteroaromatic compounds / Azacyclic compounds / Carboxylic acids / Monocarboxylic acids and derivatives / Organochlorides / Organopnictogen compounds / Primary alcohols / Organofluorides / Organic oxides / Organonitrogen compounds / Hydrocarbon derivatives

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Substituents

Alcohol / Alkyl aryl ether / Anisole / Aromatic heteropolycyclic compound / Aryl chloride / Aryl fluoride / Aryl halide / Azacycle / Benzenoid / Carboxylic acid / Carboxylic acid derivative / Chlorobenzene / Dihydroquinoline / Dihydroquinolone / Ether / Fluorobenzene / Halobenzene / Heteroaromatic compound / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Monocyclic benzene moiety / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organochloride / Organofluoride / Organohalogen compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Primary alcohol / Pyridine / Pyridine carboxylic acid / Pyridine carboxylic acid or derivatives / Quinoline-3-carboxylic acid / Vinylogous amide

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Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organofluorine compound, aromatic ether, monochlorobenzenes, quinolone, quinolinemonocarboxylic acid (CHEBI:72289)

Affected organisms

Not Available

Chemical Identifiers

UNII

4GDQ854U53

CAS number

697761-98-1

InChI Key

JUZYLCPPVHEVSV-LJQANCHMSA-N

InChI

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

IUPAC Name

6-[(3-chloro-2-fluorophenyl)methyl]-1-[(2S)-1-hydroxy-3-methylbutan-2-yl]-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

SMILES

[H][C@@](CO)(C(C)C)N1C=C(C(O)=O)C(=O)C2=C1C=C(OC)C(CC1=C(F)C(Cl)=CC=C1)=C2

References

General References

1. Pommier Y, Johnson AA, Marchand C: Integrase inhibitors to treat HIV/AIDS. Nat Rev Drug Discov. 2005 Mar;4(3):236-48. [Article]
2. Schafer JJ, Squires KE: Integrase inhibitors: a novel class of antiretroviral agents. Ann Pharmacother. 2010 Jan;44(1):145-56. doi: 10.1345/aph.1M309. Epub 2009 Dec 29. [Article]
3. Hazuda DJ, Felock P, Witmer M, Wolfe A, Stillmock K, Grobler JA, Espeseth A, Gabryelski L, Schleif W, Blau C, Miller MD: Inhibitors of strand transfer that prevent integration and inhibit HIV-1 replication in cells. Science. 2000 Jan 28;287(5453):646-50. [Article]
4. Luo ZG, Tan JJ, Zeng Y, Wang CX, Hu LM: Development of integrase inhibitors of quinolone acid derivatives for treatment of AIDS: an overview. Mini Rev Med Chem. 2010 Oct;10(11):1046-57. [Article]
5. Metifiot M, Vandegraaff N, Maddali K, Naumova A, Zhang X, Rhodes D, Marchand C, Pommier Y: Elvitegravir overcomes resistance to raltegravir induced by integrase mutation Y143. AIDS. 2011 Jun 1;25(9):1175-8. doi: 10.1097/QAD.0b013e3283473599. [Article]
6. Lee JS, Calmy A, Andrieux-Meyer I, Ford N: Review of the safety, efficacy, and pharmacokinetics of elvitegravir with an emphasis on resource-limited settings. HIV AIDS (Auckl). 2012;4:5-15. doi: 10.2147/HIV.S20993. Epub 2012 Jan 12. [Article]
7. Wills T, Vega V: Elvitegravir: a once-daily inhibitor of HIV-1 integrase. Expert Opin Investig Drugs. 2012 Mar;21(3):395-401. doi: 10.1517/13543784.2012.658914. Epub 2012 Feb 10. [Article]
8. Adams JL, Greener BN, Kashuba AD: Pharmacology of HIV integrase inhibitors. Curr Opin HIV AIDS. 2012 Sep;7(5):390-400. doi: 10.1097/COH.0b013e328356e91c. [Article]
9. Smith RA, Raugi DN, Pan C, Coyne M, Hernandez A, Church B, Parker K, Mullins JI, Sow PS, Gottlieb GS: Three main mutational pathways in HIV-2 lead to high-level raltegravir and elvitegravir resistance: implications for emerging HIV-2 treatment regimens. PLoS One. 2012;7(9):e45372. doi: 10.1371/journal.pone.0045372. Epub 2012 Sep 18. [Article]
10. FDA Approved Drug Products: Stribild (elvitegravir, cobicistat, emtricitabine, tenofovir disoproxil fumarate) tablets for oral use [Link]

External Links

PubChem Compound

5277135

PubChem Substance

310265026

ChemSpider

4441060

BindingDB

50183273

RxNav

1306286

ChEBI

72289

ChEMBL

CHEMBL204656

ZINC

ZINC000013682481

PDBe Ligand

ELV

RxList

RxList Drug Page

Wikipedia

Elvitegravir

PDB Entries

3l2u / 3l2w

FDA label

Download (435 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Health Services Research	Human Immunodeficiency Virus (HIV) Infections	1
4	Completed	Other	Healthy Subjects (HS)	1
4	Completed	Other	Human Immunodeficiency Virus (HIV) Infections	1
4	Completed	Prevention	Human Immunodeficiency Virus (HIV) Infections	2
4	Completed	Treatment	2- HIV Infection	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Tablet	Oral
Tablet, coated	Oral
Tablet, film coated	Oral
Tablet, film coated	Oral	150 mg
Tablet	Oral	150 mg
Tablet	Oral	85 mg
Tablet, film coated	Oral	150 mg/1
Tablet, film coated	Oral	150 MG
Tablet, film coated	Oral	85 mg/1
Tablet, film coated	Oral	85 MG

Prices

Not Available

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US7800788	No	2010-09-21	2022-02-02
US5914331	Yes	1999-06-22	2018-01-02
US6043230	Yes	2000-03-28	2018-01-25
US5814639	Yes	1998-09-29	2017-03-29
US6642245	Yes	2003-11-04	2021-05-04
US6703396	Yes	2004-03-09	2021-09-09
US5922695	Yes	1999-07-13	2018-01-25
US5935946	Yes	1999-08-10	2018-01-25
US5977089	Yes	1999-11-02	2018-01-25
US8592397	No	2013-11-26	2024-01-13
US8716264	No	2014-05-06	2024-01-13
US8148374	Yes	2012-04-03	2030-03-03
US7635704	Yes	2009-12-22	2027-04-26
US7176220	Yes	2007-02-13	2027-02-27
US8981103	Yes	2015-03-17	2027-04-26
US8633219	Yes	2014-01-21	2030-10-24
US9296769	Yes	2016-03-29	2033-02-15
US7803788	No	2010-09-28	2022-02-02
US8754065	Yes	2014-06-17	2033-02-15
US7390791	Yes	2008-06-24	2025-10-17
US9457036	No	2016-10-04	2024-01-13
US9744181	No	2017-08-29	2024-01-13
US9891239	Yes	2018-02-13	2030-03-03
US10039718	Yes	2018-08-07	2033-04-06

Properties

State

Solid

Experimental Properties

Property	Value	Source
water solubility	<0.3 mcg/mL	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00652 mg/mL	ALOGPS
logP	3.66	ALOGPS
logP	4.67	Chemaxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	5.97	Chemaxon
pKa (Strongest Basic)	-0.53	Chemaxon
Physiological Charge	-1	Chemaxon
Hydrogen Acceptor Count	6	Chemaxon
Hydrogen Donor Count	2	Chemaxon
Polar Surface Area	87.07 Å2	Chemaxon
Rotatable Bond Count	7	Chemaxon
Refractivity	116.26 m3·mol-1	Chemaxon
Polarizability	44.8 Å3	Chemaxon
Number of Rings	3	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-00di-0900000000-6549521c2c4645bc9542
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0002-0004900000-925d782802c34a81f43a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-000t-0000900000-86e4fa34ed9d47868dfd
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0089-0009100000-e5b116ebd0c170901fd7
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-01qc-0102900000-143a1d63a82d13dd2056
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00si-1009100000-03eb8e1bca8903cde7f6
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-003v-0239300000-fbc3f223839b52c365d9
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-014i-0009000000-16b5e22a6ccd3cb16586
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	196.74272	predicted	DeepCCS 1.0 (2019)
[M+H]+	199.1383	predicted	DeepCCS 1.0 (2019)
[M+Na]+	205.10847	predicted	DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.

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Details1. Integrase

Kind

Protein

Organism

Human immunodeficiency virus 1

Pharmacological action

Yes

Actions

Inhibitor

General Function

Zinc ion binding

Specific Function

Not Available

Gene Name

pol

Uniprot ID

Q7ZJM1

Uniprot Name

Integrase

Molecular Weight

32226.645 Da

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Drug created at September 16, 2015 21:56 / Updated at February 20, 2024 23:54