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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H18F3N3O5
Molecular Weight 449.3799
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BICTEGRAVIR

SMILES

OC1=C2N(C[C@H]3O[C@@H]4CC[C@@H](C4)N3C2=O)C=C(C(=O)NCC5=C(F)C=C(F)C=C5F)C1=O

InChI

InChIKey=SOLUWJRYJLAZCX-LYOVBCGYSA-N
InChI=1S/C21H18F3N3O5/c22-9-3-14(23)12(15(24)4-9)6-25-20(30)13-7-26-8-16-27(10-1-2-11(5-10)32-16)21(31)17(26)19(29)18(13)28/h3-4,7,10-11,16,29H,1-2,5-6,8H2,(H,25,30)/t10-,11+,16+/m0/s1

HIDE SMILES / InChI

Molecular Formula C21H18F3N3O5
Molecular Weight 449.3799
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Bictegravir is a component of the fixed-dose combination product bictegravir/emtricitabine/tenofovir alafenamide (BIKTARVY®), which received marketing approval for the treatment of human immunodeficiency virus (HIV) infection by the U.S. Food and Drug Administration in February 2018. Bictegravir inhibits the strand transfer activity of HIV-1 integrase, an HIV-1 encoded enzyme that is required for viral replication. Inhibition of integrase prevents the integration of linear HIV-1 DNA into host genomic DNA, blocking the formation of the HIV-1 provirus and propagation of the virus.

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
7.5 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
BIKTARVY
PubMed

PubMed

TitleDatePubMed
Antiviral Activity of Bictegravir (GS-9883), a Novel Potent HIV-1 Integrase Strand Transfer Inhibitor with an Improved Resistance Profile.
2016 Dec
Bictegravir: First Global Approval.
2018 Apr
Patents

Patents

Sample Use Guides

In Vivo Use Guide
BIKTARVY® is a three-drug fixed dose combination product containing 50 mg of bictegravir, 200 mg of emtricitabine, and 25 mg of tenofovir alafenamide. The recommended dosage of BIKTARVY is one tablet taken orally once daily with or without food.
Route of Administration: Oral
In Vitro Use Guide
The antiviral activity of bictegravir (BIC) against laboratory and clinical isolates of HIV-1 was assessed in lymphoblastoid cell lines, PBMCs, primary monocyte/macrophage cells, and CD4+ T-lymphocytes. In MT-4 cells (human lymphoblastoid T-cell line) acutely infected with HIV-1 IIIB, the mean 50% effective concentration (EC50) was 2.4+/-0.4 nM, and the protein-adjusted EC95 value was 361 nM (0.162 micrograms per mL). BIC displayed antiviral activity in activated PBMCs against clinical isolates of HIV-1 representing groups M, N, and O, including subtypes A, B, C, D, E, F, and G, with a median EC50 value of 0.55 nM (range <0.05 to 1.71 nM). The EC50 value against a single HIV-2 isolate was 1.1 nM.
Substance Class Chemical
Created
by admin
on Mon Oct 21 19:50:56 UTC 2019
Edited
by admin
on Mon Oct 21 19:50:56 UTC 2019
Record UNII
8GB79LOJ07
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BICTEGRAVIR
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
BIKTARVY COMPONENT BICTEGRAVIR
Brand Name English
BICTEGRAVIR [INN]
Common Name English
BICTEGRAVIR [USAN]
Common Name English
GS-9883
Code English
GS-9883-01
Code English
2,5-METHANOPYRIDO(1',2':4,5)PYRAZINO(2,1-B)(1,3)OXAZEPINE-10-CARBOXAMIDE, 2,3,4,5,7,9,13,13A-OCTAHYDRO-8-HYDROXY-7,9-DIOXO-N-((2,4,6-TRIFLUOROPHENYL)METHYL)-, (2R,5S,13AR)-
Systematic Name English
BICTEGRAVIR [WHO-DD]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 559316
Created by admin on Mon Oct 21 19:50:57 UTC 2019 , Edited by admin on Mon Oct 21 19:50:57 UTC 2019
WHO-ATC J05AR20
Created by admin on Mon Oct 21 19:50:57 UTC 2019 , Edited by admin on Mon Oct 21 19:50:57 UTC 2019
Code System Code Type Description
PUBCHEM
90311989
Created by admin on Mon Oct 21 19:50:57 UTC 2019 , Edited by admin on Mon Oct 21 19:50:57 UTC 2019
PRIMARY
INN
10133
Created by admin on Mon Oct 21 19:50:57 UTC 2019 , Edited by admin on Mon Oct 21 19:50:57 UTC 2019
PRIMARY
EVMPD
SUB182699
Created by admin on Mon Oct 21 19:50:57 UTC 2019 , Edited by admin on Mon Oct 21 19:50:57 UTC 2019
PRIMARY
CAS
1611493-60-7
Created by admin on Mon Oct 21 19:50:57 UTC 2019 , Edited by admin on Mon Oct 21 19:50:57 UTC 2019
PRIMARY
Related Record Type Details
TRANSPORTER -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
Coadministration of BIC (given without F/TAF) with rifampin decreased the mean BIC Cmax and AUC by 28% and 75%, respectively.
TRANSPORTER -> SUBSTRATE
TARGET -> INHIBITOR
INHIBITOR
IC50
TRANSPORTER -> INHIBITOR
Co€?administration of BIKTARVY with dofetilide may increase dofetilide plasma concentrations which can lead to serious and/or life threatening events.
IC50
BINDER->LIGAND
TARGET ORGANISM->INHIBITOR
METABOLIC ENZYME -> SUBSTRATE
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
Co€?administration of BIKTARVY with dofetilide may increase dofetilide plasma concentrations which can lead to serious and/or life threatening events.
CLINICALLY SIGNIFICANT
IC50
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
Cmax PHARMACOKINETIC ROUTE OF ADMINSTRATION
PHARMACOKINETIC
DOSE
PHARMACOKINETIC