1611493-60-7

Basic information

• Product Name: Bictegravir
• Synonyms: Bictegravir;GS-9883;(2R,5S,13aR)-2,3,4,5,7,9,13,13a-Octahydro-8-hydroxy-7,9-dioxo-N-[(2,4,6-trifluorophenyl)methyl]-2,5-methanopyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazepine-10-carboxamide
• CAS NO: 1611493-60-7
• Molecular Formula: C₂₁H₁₈F₃N₃O₅
• Molecular Weight: 449.38
• EINECS: -0
• Product Categories: Pharmaceutical
• Mol File: 1611493-60-7.mol

Chemical Properties

• Boiling Point: 682.5±55.0 °C(Predicted)
• Appearance: /
• Density: 1.62±0.1 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.50±1.00(Predicted)
• CAS DataBase Reference: Bictegravir(CAS DataBase Reference)
• NIST Chemistry Reference: Bictegravir(1611493-60-7)
• EPA Substance Registry System: Bictegravir(1611493-60-7)

Safety Data

• Hazardous Substances Data: 1611493-60-7(Hazardous Substances Data)

Usage

Uses

Used in HIV Treatment:
Bictegravir is used as an antiretroviral agent for the treatment of HIV-1 infection. It is administered in combination with other antiretroviral agents, such as tenofovir and emtricitabine, to enhance the therapeutic effect and manage the infection more effectively.
Used in HIV-1 Monotherapy:
Bictegravir is approved for HIV-1 monotherapy combined with two other antiretrovirals in a single tablet. This combination therapy is particularly useful for patients who are not previously treated with antiretroviral therapy or those who are virologically suppressed (HIV-1 RNA <50 c/mL) on a regular antiretroviral regimen for a minimum of three months without a history of treatment failure and no known factors associated with resistance to the individual components of the medication.
Used in Clinical Trials:
Bictegravir has been used in trials studying the treatment of HIV-1 and HIV-2 infection. These trials aim to evaluate the safety, efficacy, and potential benefits of Bictegravir in managing and treating HIV infections, further expanding its applications in the field of HIV treatment.

Mechanism of action

This single dose medication inhibits the strand transfer of viral DNA into the human genome, preventing HIV-1 virus replication and propagation 2. In vitro, bictegravir has shown powerful antiviral activity against HIV-2 and various subtypes of HIV-1. It has shown synergistic effects when combined with other ARVs, including tenofovir alafenamide (TAF), emtricitabine (FTC), and darunavir (DRV) Label. The three components of the first USA approved medication ( trade name: Biktarvy ) are as follows: Bictegravir: integrase strand transfer inhibitor; INSTI), an HIV-1 encoded enzyme necessary for viral replication. Inhibition of the integrase enzyme prevents the integration of HIV-1 into host DNA, blocking the conversion of the HIV-1 provirus and progression of the virus. Emtricitabine: FTC, is phosphorylated by cellular enzymes to form emtricitabine 5'-triphosphate. Emtricitabine is phosphorylated to form emtricitabine 5'-triphosphate intracellularly. This metabolite inhibits the activity of human immunodeficiency virus (HIV) reverse transcriptase by competing with the substrate deoxycytidine 5'-triphosphate and by incorporating itself into viral DNA preventing DNA chain elongation. Tenofovir Alafenamide: TAF is a phosphonamidate prodrug of tenofovir (2′-deoxyadenosine monophosphate analog). Plasma exposure to TAF leads to leakage into cells and then TAF is intracellularly converted to tenofovir by hydrolysis by cathepsin. Tenofovir is subsequently phosphorylated by cellular kinases to the metabolite tenofovir diphosphate, which is the active form of the drug. Tenofovir diphosphate inhibits HIV-1 replication by incorporating into viral DNA by the HIV reverse transcriptase, resulting in DNA chain-termination. Tenofovir diphosphate also weakly inhibits mammalian DNA polymerases.

Pharmacokinetics

Bictegravir is an HIV-1 integrase strand transfer inhibitor (INSTI). Bictegravir (BIC) inhibits HIV-1 virus replication into the human genome. It can be taken once daily without additional dosing. Bictegravir (BIC) inhibits strand transfer of viral DNA into the host genome and thereby prevents HIV-1 replication.

Upstream product

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• 1335210-23-5 1-[2,2-bis(methyloxy)ethyl]-5-(methyloxy)-6-[(methyloxy)carbonyl]-4-oxo-1,4-dihydro-3-pyridinecarboxylic acid 
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• 1616340-94-3 (2R,5S,13aR)-8-methoxy-7,9-dioxo-N-[(2,4,6-trifluorophenyl)methyl]-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido[1‘,2’:4,5]pyrazino[2,1-b][1,3]oxazepine-10-carboxamide 
• 1616342-45-0 (2R,5S,13aR)-8-methoxy-7,9-dioxo-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazepine-10-carboxylic acid 

Relevant articles and documents

Process for Preparation of Intermediates Used for the Synthesis of HIV Integrase Inhibitor

Provided herein is a process for the intermediates used for preparation of HIV Integrase Inhibitor such as Bictegravir, Dolutegravir, Cabotegravir or their pharmaceutically acceptable salts.

PROCESS FOR THE PREPARATION OF SODIUM (2R,5S,13AR)-7,9-DIOXO-10-((2,4,6-TRIFLUOROBENZYL)CARBAMOYL)-2,3,4,5,7,9,13,13A-OCTAHYDRO-2,5-METHANOPYRIDO[1', 2':4,5]PYRAZINO[2,1-B] [1,3] OXAZEPIN-8-OLATE AND ITS POLYMORPHIC FORM

The present invention relates to process for the preparation of sodium (2R,5S,13aR)-7,9-dioxo-10-((2,4,6-trifluorobenzyl)carbamoyl)-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido [1',2':4,5] pyrazino[2,1-b] [1,3] oxazepin-8-olate of Formula-I and its poly

PROCESS AND POLYMORPHIC FORMS OF BICTEGRAVIR AND ITS PHARMACEUTICALLY ACCEPTABLE SALTS OR CO-CRYSTALS THEREOF

The present invention generally relates to polymorphic forms of bictegravir, its salts, co-crystals, solvates or hydrates thereof and process for the preparation of the same and also relates to pharmaceutical compositions containing the same. The present

CONTINUES FLOW PROCESS FOR THE PREPARATION OF ACTIVE PHARMACEUTICAL INGREDIENTS - POLYCYCLIC CARBAMOYL PYRIDONE DERIVATIVES AND INTERMEDIATES THEREOF

The present invention discloses continues flow process for the preparation of polycyclic carbamoyl pyridone derivatives and intermediates thereof. In particular, the present invention discloses a process for the preparation of intermediate. Formule (V).

PROCESS FOR THE PREPARATION OF BICTEGRAVIR AND INTERMEDIATE THEREOF

The present invention provides processes and intermediates for the synthesis of bictegravir and its pharmaceutical salt.

CRYSTALLINE FORMS OF (2R,5S,13AR)-8-HYDROXY-7,9-DIOXO-N-(2,4,6-TRIFLUOROBENZYL)-2,3,4,5,7,9,13,13A-OCTAHYDRO-2,5-METHANOPYRIDO[1',2':4,5]PYRAZINO[2,1-B][1,3]OXAZEPINE-10-CARBOXAMIDE

The present invention relates to crystalline forms and co-crystals of (2R,5S,13aR)-8-hydroxy-7,9-dioxo-N-(2,4,6-trifluorobenzyl)-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido[1′,2′:4,5]pyrazino[2,1-b][1,3]oxazepine-10-carboxamide, the pharmaceutical form

POLYCYCLIC-CARBAMOYLPYRIDONE COMPOUNDS AND THEIR PHARMACEUTICAL USE

Compounds for use in the treatment of human immunodeficiency virus (HIV) infection are disclosed. The compounds have the following Formula (I): including stereoisomers and pharmaceutically acceptable salts thereof, wherein R1, X, W, Y1, Y2, Ζ1 and Z4 are as defined herein. Methods associated with preparation and use of such compounds, as well as pharmaceutical compositions comprising such compounds, are also disclosed.