Identification

Name
Elvitegravir
Accession Number
DB09101
Type
Small Molecule
Groups
Approved
Description

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.

It was developed by the pharmaceutical company Gilead Sciences, which licensed EVG from Japan Tobacco in March 2008. The drug gained approval by the U.S. Food and Drug Administration on August 27, 2012 for use in adult patients starting HIV treatment for the first time as part of the fixed dose combination known as Stribild. On September 24, 2014 the FDA approved Elvitegravir (tradename Vitekta) as a single pill formulation.

Structure
Thumb
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
  • EVG
External IDs
GS 9137 / GS-9137 / GS9137 / JTK 303 / JTK-303 / JTK303
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
VitektaTablet, film coated85 mg/1OralGilead Sciences2014-09-242017-03-11Us
VitektaTablet, film coated150 mgOralGilead Sciences2013-11-13Not applicableEu
VitektaTablet, film coated150 mg/1OralGilead Sciences2014-09-242017-03-11Us
VitektaTablet85 mgOralGilead Sciences2015-04-212017-01-09Canada
VitektaTablet, film coated85 mgOralGilead Sciences2013-11-13Not applicableEu
VitektaTablet150 mgOralGilead Sciences2015-04-212017-01-09Canada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
GenvoyaElvitegravir (150 mg) + Cobicistat (150 mg) + Emtricitabine (200 mg) + Tenofovir alafenamide (10 mg)Tablet, film coatedOralGilead Sciences2015-11-19Not applicableEu
GenvoyaElvitegravir (150 mg/1) + Cobicistat (150 mg/1) + Emtricitabine (200 mg/1) + Tenofovir alafenamide fumarate (10 mg/1)TabletOralGilead Sciences2015-11-05Not applicableUs
GenvoyaElvitegravir (150 mg/1) + Cobicistat (150 mg/1) + Emtricitabine (200 mg/1) + Tenofovir alafenamide (10 mg/1)TabletOralRemedy Repack2017-06-06Not applicableUs
GenvoyaElvitegravir (150 mg/1) + Cobicistat (150 mg/1) + Emtricitabine (200 mg/1) + Tenofovir alafenamide (10 mg/1)TabletOralA S Medication Solutions2015-11-052017-06-20Us
GenvoyaElvitegravir (150 mg) + Cobicistat (150 mg) + Emtricitabine (200 mg) + Tenofovir alafenamide (10 mg)Tablet, film coatedOralGilead Sciences2015-11-19Not applicableEu
GenvoyaElvitegravir (150 mg) + Cobicistat (150 mg) + Emtricitabine (200 mg) + Tenofovir alafenamide (10 mg)TabletOralGilead Sciences2016-02-03Not applicableCanada
StribildElvitegravir (150 mg/1) + Cobicistat (150 mg/1) + Emtricitabine (200 mg/1) + Tenofovir disoproxil fumarate (300 mg/1)Tablet, film coatedOralState of Florida DOH Central Pharmacy2014-01-01Not applicableUs
StribildElvitegravir (150 mg/1) + Cobicistat (150 mg/1) + Emtricitabine (200 mg/1) + Tenofovir disoproxil fumarate (300 mg/1)Tablet, film coatedOralA S Medication Solutions2012-08-272017-06-20Us
StribildElvitegravir (150 mg) + Cobicistat (150 mg) + Emtricitabine (200 mg) + Tenofovir disoproxil fumarate (300 mg)TabletOralGilead Sciences2012-12-20Not applicableCanada
StribildElvitegravir (150 mg/1) + Cobicistat (150 mg/1) + Emtricitabine (200 mg/1) + Tenofovir disoproxil fumarate (300 mg/1)Tablet, film coatedOralRemedy Repack2017-08-16Not applicableUs
Categories
UNII
4GDQ854U53
CAS number
697761-98-1
Weight
Average: 447.884
Monoisotopic: 447.124878763
Chemical Formula
C23H23ClFNO5
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][[email protected]@](CO)(C(C)C)N1C=C(C(O)=O)C(=O)C2=C1C=C(OC)C(CC1=C(F)C(Cl)=CC=C1)=C2

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.

Structured Indications
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.

TargetActionsOrganism
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
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.

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AlgeldrateThe serum concentration of Elvitegravir can be decreased when it is combined with Algeldrate.Experimental
AlmagateThe serum concentration of Elvitegravir can be decreased when it is combined with Almagate.Experimental
AlmasilateThe serum concentration of Elvitegravir can be decreased when it is combined with Almasilate.Experimental
AloglutamolThe serum concentration of Elvitegravir can be decreased when it is combined with Aloglutamol.Experimental
AluminiumThe serum concentration of Elvitegravir can be decreased when it is combined with Aluminium.Approved
Aluminium acetoacetateThe serum concentration of Elvitegravir can be decreased when it is combined with Aluminium acetoacetate.Experimental
Aluminium glycinateThe serum concentration of Elvitegravir can be decreased when it is combined with Aluminium glycinate.Experimental
Aluminum hydroxideThe serum concentration of Elvitegravir can be decreased when it is combined with Aluminum hydroxide.Approved
AmiodaroneThe metabolism of Elvitegravir can be decreased when combined with Amiodarone.Approved, Investigational
AprepitantThe serum concentration of Elvitegravir can be increased when it is combined with Aprepitant.Approved, Investigational
AtazanavirThe serum concentration of Elvitegravir can be increased when it is combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Elvitegravir can be decreased when combined with Atomoxetine.Approved
Bismuth SubcitrateThe serum concentration of Elvitegravir can be decreased when it is combined with Bismuth Subcitrate.Approved
Bismuth subnitrateThe serum concentration of Elvitegravir can be decreased when it is combined with Bismuth subnitrate.Experimental
BoceprevirThe metabolism of Elvitegravir can be decreased when combined with Boceprevir.Withdrawn
BortezomibThe metabolism of Elvitegravir can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Elvitegravir can be decreased when it is combined with Bosentan.Approved, Investigational
Calcium CarbonateThe serum concentration of Elvitegravir can be decreased when it is combined with Calcium Carbonate.Approved
Calcium silicateThe serum concentration of Elvitegravir can be decreased when it is combined with Calcium silicate.Experimental
CarbamazepineThe serum concentration of Elvitegravir can be decreased when it is combined with Carbamazepine.Approved, Investigational
CeritinibThe serum concentration of Elvitegravir can be increased when it is combined with Ceritinib.Approved
ChlorotrianiseneThe serum concentration of Chlorotrianisene can be decreased when it is combined with Elvitegravir.Withdrawn
ClarithromycinThe metabolism of Elvitegravir can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Elvitegravir can be decreased when combined with Clemastine.Approved
ClotrimazoleThe metabolism of Elvitegravir can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe metabolism of Elvitegravir can be decreased when combined with Cobicistat.Approved
ConivaptanThe serum concentration of Elvitegravir can be increased when it is combined with Conivaptan.Approved, Investigational
Conjugated estrogensThe serum concentration of Conjugated estrogens can be decreased when it is combined with Elvitegravir.Approved
CrizotinibThe metabolism of Elvitegravir can be decreased when combined with Crizotinib.Approved
CyclosporineThe metabolism of Elvitegravir can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
DabrafenibThe serum concentration of Elvitegravir can be decreased when it is combined with Dabrafenib.Approved
DarunavirThe serum concentration of Elvitegravir can be increased when it is combined with Darunavir.Approved
DasatinibThe serum concentration of Elvitegravir can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Elvitegravir can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Elvitegravir can be decreased when combined with Delavirdine.Approved
DexamethasoneThe serum concentration of Elvitegravir can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DienestrolThe serum concentration of Dienestrol can be decreased when it is combined with Elvitegravir.Approved
DiethylstilbestrolThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Elvitegravir.Approved
DihydroergotamineThe metabolism of Elvitegravir can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Elvitegravir can be decreased when combined with Diltiazem.Approved
DoxycyclineThe metabolism of Elvitegravir can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Elvitegravir can be decreased when combined with Dronedarone.Approved
EfavirenzThe serum concentration of Elvitegravir can be decreased when it is combined with Efavirenz.Approved, Investigational
EnzalutamideThe serum concentration of Elvitegravir can be decreased when it is combined with Enzalutamide.Approved
ErythromycinThe metabolism of Elvitegravir can be decreased when combined with Erythromycin.Approved, Vet Approved
EstradiolThe serum concentration of Estradiol can be decreased when it is combined with Elvitegravir.Approved, Investigational, Vet Approved
EstramustineThe serum concentration of Estramustine can be decreased when it is combined with Elvitegravir.Approved
Estrogens, esterifiedThe serum concentration of Estrogens, esterified can be decreased when it is combined with Elvitegravir.Approved
Estrone sulfateThe serum concentration of Estrone sulfate can be decreased when it is combined with Elvitegravir.Approved
Ethinyl EstradiolThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Elvitegravir.Approved
FluconazoleThe metabolism of Elvitegravir can be decreased when combined with Fluconazole.Approved
FluvoxamineThe metabolism of Elvitegravir can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Elvitegravir can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Elvitegravir can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe serum concentration of Elvitegravir can be decreased when it is combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Elvitegravir can be increased when it is combined with Fusidic Acid.Approved
HexestrolThe serum concentration of Hexestrol can be decreased when it is combined with Elvitegravir.Withdrawn
HydrotalciteThe serum concentration of Elvitegravir can be decreased when it is combined with Hydrotalcite.Experimental
IdelalisibThe serum concentration of Elvitegravir can be increased when it is combined with Idelalisib.Approved
ImatinibThe metabolism of Elvitegravir can be decreased when combined with Imatinib.Approved
IndinavirThe metabolism of Elvitegravir can be decreased when combined with Indinavir.Approved
IsavuconazoniumThe metabolism of Elvitegravir can be decreased when combined with Isavuconazonium.Approved, Investigational
IsradipineThe metabolism of Elvitegravir can be decreased when combined with Isradipine.Approved
ItraconazoleThe serum concentration of Elvitegravir can be increased when it is combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Elvitegravir can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe serum concentration of Elvitegravir can be increased when it is combined with Ketoconazole.Approved, Investigational
LopinavirThe serum concentration of Elvitegravir can be increased when it is combined with Lopinavir.Approved
LovastatinThe metabolism of Elvitegravir can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Elvitegravir can be increased when it is combined with Luliconazole.Approved
LumacaftorThe metabolism of Elvitegravir can be increased when combined with Lumacaftor.Approved
MagaldrateThe serum concentration of Elvitegravir can be decreased when it is combined with Magaldrate.Withdrawn
Magnesium HydroxideThe serum concentration of Elvitegravir can be decreased when it is combined with Magnesium Hydroxide.Approved
Magnesium oxideThe serum concentration of Elvitegravir can be decreased when it is combined with Magnesium oxide.Approved
Magnesium peroxideThe serum concentration of Elvitegravir can be decreased when it is combined with Magnesium peroxide.Experimental
Magnesium silicateThe serum concentration of Elvitegravir can be decreased when it is combined with Magnesium silicate.Experimental
Magnesium TrisilicateThe serum concentration of Elvitegravir can be decreased when it is combined with Magnesium Trisilicate.Approved
MestranolThe serum concentration of Mestranol can be decreased when it is combined with Elvitegravir.Approved
MethallenestrilThe serum concentration of Methallenestril can be decreased when it is combined with Elvitegravir.Experimental
MifepristoneThe serum concentration of Elvitegravir can be increased when it is combined with Mifepristone.Approved, Investigational
MitotaneThe serum concentration of Elvitegravir can be decreased when it is combined with Mitotane.Approved
NefazodoneThe metabolism of Elvitegravir can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Elvitegravir can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Elvitegravir can be increased when it is combined with Netupitant.Approved
NevirapineThe serum concentration of Elvitegravir can be decreased when it is combined with Nevirapine.Approved
NilotinibThe metabolism of Elvitegravir can be decreased when combined with Nilotinib.Approved, Investigational
OlaparibThe metabolism of Elvitegravir can be decreased when combined with Olaparib.Approved
OsimertinibThe serum concentration of Elvitegravir can be increased when it is combined with Osimertinib.Approved
OxcarbazepineThe serum concentration of Elvitegravir can be decreased when it is combined with Oxcarbazepine.Approved
PalbociclibThe serum concentration of Elvitegravir can be increased when it is combined with Palbociclib.Approved
PentobarbitalThe metabolism of Elvitegravir can be increased when combined with Pentobarbital.Approved, Vet Approved
PhenobarbitalThe serum concentration of Elvitegravir can be decreased when it is combined with Phenobarbital.Approved
PhenytoinThe serum concentration of Elvitegravir can be decreased when it is combined with Phenytoin.Approved, Vet Approved
PosaconazoleThe metabolism of Elvitegravir can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PrimidoneThe metabolism of Elvitegravir can be increased when combined with Primidone.Approved, Vet Approved
RanolazineThe metabolism of Elvitegravir can be decreased when combined with Ranolazine.Approved, Investigational
RifabutinThe serum concentration of the active metabolites of Rifabutin can be increased when Rifabutin is used in combination with Elvitegravir.Approved
RifampicinThe serum concentration of Elvitegravir can be decreased when it is combined with Rifampicin.Approved
RifapentineThe serum concentration of Elvitegravir can be decreased when it is combined with Rifapentine.Approved
RitonavirThe metabolism of Elvitegravir can be decreased when combined with Ritonavir.Approved, Investigational
SaquinavirThe metabolism of Elvitegravir can be decreased when combined with Saquinavir.Approved, Investigational
SildenafilThe metabolism of Elvitegravir can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Elvitegravir can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Elvitegravir can be increased when it is combined with Simeprevir.Approved
St. John's WortThe serum concentration of Elvitegravir can be decreased when it is combined with St. John&#39;s Wort.Nutraceutical
StiripentolThe serum concentration of Elvitegravir can be increased when it is combined with Stiripentol.Approved
SulfisoxazoleThe metabolism of Elvitegravir can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
Synthetic Conjugated Estrogens, AThe serum concentration of Synthetic Conjugated Estrogens, A can be decreased when it is combined with Elvitegravir.Approved
TelaprevirThe metabolism of Elvitegravir can be decreased when combined with Telaprevir.Withdrawn
TelithromycinThe metabolism of Elvitegravir can be decreased when combined with Telithromycin.Approved
TiclopidineThe metabolism of Elvitegravir can be decreased when combined with Ticlopidine.Approved
TocilizumabThe serum concentration of Elvitegravir can be decreased when it is combined with Tocilizumab.Approved
VenlafaxineThe metabolism of Elvitegravir can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Elvitegravir can be decreased when combined with Verapamil.Approved
VoriconazoleThe serum concentration of Elvitegravir can be increased when it is combined with Voriconazole.Approved, Investigational
WarfarinThe serum concentration of Warfarin can be decreased when it is combined with Elvitegravir.Approved
ZiprasidoneThe metabolism of Elvitegravir can be decreased when combined with Ziprasidone.Approved
Food Interactions
Not Available

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. [PubMed:15729361]
  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. [PubMed:20040702]
  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. [PubMed:10649997]
  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. [PubMed:21044030]
  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. [PubMed:21505303]
  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. [PubMed:22347806]
  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. [PubMed:22321026]
  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. [PubMed:22789987]
  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. [PubMed:23028968]
External Links
PubChem Compound
5277135
PubChem Substance
310265026
ChemSpider
4441060
BindingDB
50183273
ChEBI
72289
ChEMBL
CHEMBL204656
HET
ELV
RxList
RxList Drug Page
Wikipedia
Elvitegravir
ATC Codes
J05AR18 — Emtricitabine, tenofovir alafenamide, elvitegravir and cobicistatJ05AR09 — Emtricitabine, tenofovir disoproxil, elvitegravir and cobicistatJ05AX11 — Elvitegravir
AHFS Codes
  • 08:18.08.12 — HIV Integrase Inhibitors
  • 08:18.08.20 — Nucleoside and Nucleotide Reverse Transcriptase Inhibitors
  • 92:92.00 — Other Miscellaneous Therapeutic Agents
PDB Entries
3l2u / 3l2w
FDA label
Download (435 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableHuman Immunodeficiency Virus (HIV)2
1CompletedOtherHIV-DDI1
1CompletedTreatmentInsulin Resistance1
1RecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections1
1RecruitingTreatmentInsulin Resistance1
2CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections1
2Not Yet RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2, 3Active Not RecruitingTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections2
2, 3Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV)1
2, 3RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
3Active Not RecruitingTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
3Active Not RecruitingTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections1
3Active Not RecruitingTreatmentHepatitis C, Chronic / Human Immunodeficiency Virus (HIV)1
3Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV)1
3Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections4
3Active Not RecruitingTreatmentInfection, Human Immunodeficiency Virus I4
3CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections4
3CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections / Human Immunodeficiency Virus Type 1 (HIV-1)1
3CompletedTreatmentHBV / Human Immunodeficiency Virus (HIV)1
3CompletedTreatmentHCV Infections / Infection, Human Immunodeficiency Virus I1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections2
3Not Yet RecruitingTreatmentHIV Risk1
3RecruitingTreatmentInfection, Human Immunodeficiency Virus I1
4CompletedHealth Services ResearchHuman Immunodeficiency Virus (HIV)1
4CompletedPreventionHuman Immunodeficiency Virus (HIV)2
4CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) / Sleep disorders and disturbances1
4CompletedTreatmentHepatitis C Infection / Human Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentInfection, Human Immunodeficiency Virus I1
4RecruitingSupportive CareHuman Immunodeficiency Virus (HIV)1
4RecruitingTreatmentAntiretroviral Therapy Intolerance / Patients Compliance1
4RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedBasic ScienceHuman Immunodeficiency Virus (HIV)1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV)1
Not AvailableRecruitingNot AvailableHuman Immunodeficiency Virus (HIV)1
Not AvailableRecruitingNot AvailableHuman Immunodeficiency Virus (HIV) / Illicit Drug User1
Not AvailableRecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
TabletOral
Tablet, film coatedOral
TabletOral150 mg
TabletOral85 mg
Tablet, film coatedOral150 mg
Tablet, film coatedOral150 mg/1
Tablet, film coatedOral85 mg/1
Tablet, film coatedOral85 mg
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US7800788No2002-02-022022-02-02Us
US5914331Yes1998-01-022018-01-02Us
US6043230Yes1998-01-252018-01-25Us
US5814639Yes1997-03-292017-03-29Us
US6642245Yes2001-05-042021-05-04Us
US6703396Yes2001-09-092021-09-09Us
US5922695Yes1998-01-252018-01-25Us
US5935946Yes1998-01-252018-01-25Us
US5977089Yes1998-01-252018-01-25Us
US8592397No2004-01-132024-01-13Us
US8716264No2004-01-132024-01-13Us
US8148374No2009-09-032029-09-03Us
US7635704No2006-10-262026-10-26Us
US7176220No2003-11-202023-11-20Us
US8981103No2006-10-262026-10-26Us
US8633219No2010-04-242030-04-24Us
US9296769No2012-08-152032-08-15Us
US7803788No2002-02-022022-02-02Us
US8754065No2012-08-152032-08-15Us
US7390791No2002-05-072022-05-07Us
US9457036No2004-01-132024-01-13Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubility<0.3 mcg/mLNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00652 mg/mLALOGPS
logP3.66ALOGPS
logP4.67ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)6.16ChemAxon
pKa (Strongest Basic)-0.53ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area87.07 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity116.26 m3·mol-1ChemAxon
Polarizability44.8 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0002-0004900000-925d782802c34a81f43a

Taxonomy

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
show 11 more
Substituents
Quinoline-3-carboxylic acid / Dihydroquinolone / Dihydroquinoline / Pyridine carboxylic acid / Pyridine carboxylic acid or derivatives / Anisole / Alkyl aryl ether / Halobenzene / Fluorobenzene / Chlorobenzene
show 26 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organofluorine compound, aromatic ether, monochlorobenzenes, quinolone, quinolinemonocarboxylic acid (CHEBI:72289)

Targets

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

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
2. UDP-glucuronosyltransferase 1A1
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate

Drug created on September 16, 2015 15:56 / Updated on October 21, 2017 19:33