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GSK1349572

GSK1349572 structure

CAS No:
1051375-16-6
Formula:
C20H19F2N3O5
Chemical Name:
GSK1349572
Synonyms:
Dolutegravir API;Dolutegravir (GSK1349572);2H-Pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-9-carboxamide, N-[(2,4-difluorophenyl)methyl]-3,4,6,8,12,12a-hexahydro-7-hydroxy-4-methyl-6,8-dioxo-, (4R,12aS)-;(4R,12aS)-N-[(2,4-Difluorophenyl)methyl]-3,4,6,8,12,12a-hexahydro-7-hydroxy-4-methyl-6,8-dioxo-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-9-carboxamide Dolutegravir (GSK1349572);GSK1349572, S-349572, GSK572;(4R,12aS)-N-(2,4-Difluorobenzyl)-7-hydroxy-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-9-carboxamide;Dolutegravir, >=98%;Dolutegravir free acid
Categories:
Biochemical Engineering > Inhibitors

Description

Dolutegravir is a second-generation HIV integrase strand transfer inhibitor (INSTI) with an IC50 of 2.7 nM.

In August 2013, the US FDA approved dolutegravir (also referred to as S/GSK1349572) for the treatment of HIV-1 infection in adults and children ages 12 years and older in combination with other antiretroviral drugs. Dolutegravir was approved in Canada in November 2013. HIV/AIDS remains a global epidemic with 35 million people infected, including 2.3 million new infections as of 2012. Dolutegravir joins raltegravir and elvitegravir (this chapter of ARMC) as the latest of three FDA-approved HIV integrase strand transfer inhibitors (INSTIs). Dolutegravir was discovered by rational design from a literature diketo acid HIV integrase inhibitor utilizing X-ray coordinates to predict ideal bond angles between the diketone and distal benzyl group. In dolutegravir, the monocyclic component of the reported inhibitor was replaced with the tricyclic carbamoyl pyridone moiety. The researchers postulated that the appropriate arrangement of three oxygens would permit chelation with two magnesium ions in the binding site thus affording improved potency. Ultimately, this arrangement along with further modifications afforded dolutegravir, a potent inhibitor of HIV integrase (IC50=1.7 nM).

White Solid

ChEBI: A monocarboxylic acid amide obtained by formal condensation of the carboxy group of (4R,12aS)-7-hydroxy-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]ox zine-9-carboxylic acid with the amino group of 2,4-difluorobenzylamine. Used (as its sodium salt) for treatment of HIV-1.

GSK1349572 Basic Attributes

Molecular Weight：

419.38

Exact Mass：

419.38

Color/Form：

White to Pale Beige

Characteristics

PSA：

99.2

XLogP3：

2.4

Appearance：

White to Pale Yellow Solid

Density：

1.53

Melting Point：

187-189°C

Boiling Point：

669.0±55.0 °C(Predicted)

Flash Point：

358.4±31.5 °C

Refractive Index：

1.650

Water Solubility：

In water, 95 mg/L at 25 deg C (est)

Storage Conditions：

Store at 25 deg C (77 deg F); excursions permitted 15 deg to 30 deg C (59 deg to 86 deg F)

Vapor Pressure：

1.39X10-17 mm Hg at 25 deg C (est)

PKA：

4.50±1.00(Predicted)

Critical Temperature & Pressure：

Refrigerator

Safety Information

wgk germany：

WGK 3

Precautionary statement(s)：

P273, P391, P501

Hazard Statements：

H400

GSK1349572 Use and Manufacturing

Dolutegravir is a second generation HIV-1 integrase strand transfer inhibitor. Dolutegravir is currently in Phase III clinical trials for the treatment of HIV infection. Dolutegravir has been shown to potently inhibit HIV replication in cells such as peripheral blood mononuclear cells (PBMCs), MT-4 cells and CIP4 cells infected with a self-inactivating PHIV lentiviral vector.

Dolutegravir (GSK1349572) is a HIV integrase inhibitor with an IC50 of 2.7 nM and is moderately effective against the significant mutants Y143R, Q148K, N155H, and G140S/Q148H against Raltegravir.

Drug Function and Efficacy

Inhibits HIV integrase by binding to the integrase active site and blocking the strand transfer step of reverse transcribed deoxyribonucleic acid (DNA) integration, a key step in the HIV replication cycle

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Dotiabalamil tablets
Ingredients	This product is a compound preparation. Each tablet contains 50 mg of dolutegravir sodium (calculated as dolutegravir), 600 mg of abacavir sulfate (calculated as abacavir) and 300 mg of lamivudine.
Indication	This product contains dolutegravir, abacavir, and lamivudine, so the interactions found when these drugs are used alone are related to this product. No clinically significant drug interactions are expected between dolutegravir, abacavir, and lamivudine.
Specifications	50mg/600mg/300mg x 30 tablets

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