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ChemicalBook >> CAS DataBase List >>Dolutegravir sodium

Dolutegravir sodium

CAS No.
1051375-19-9
Chemical Name:
Dolutegravir sodium
Synonyms
DOLUTEGRAVIR SODIUM;Dolutegravi Sodium;Dolutegravir sodiuM salt;GSK1349572 sodiuM salt USP/EP/BP;Sodium (4R,12aS)-9-((2,4-difluorobenzyl)carbamoyl)-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazin-7-olate;158439;GSK 1349572A;Dulutevir sodium;Dulutewei sodium salt;GSK1349572 sodiuM salt
CBNumber:
CB52646573
Molecular Formula:
C20H20F2N3NaO5
Molecular Weight:
443.38
MDL Number:
MFCD28405599
MOL File:
1051375-19-9.mol
Last updated:2024-11-19 15:53:33

Dolutegravir sodium Properties

Melting point >300oC
storage temp. Hygroscopic, -20°C Freezer, Under inert atmosphere
solubility DMSO (Slightly, Heated), Methanol (Slightly, Heated)
form Solid
color White to Green
Stability Hygroscopic
InChIKey FWLDGCYHMZPGGI-SBBUJZKLNA-N
SMILES O=C1N2[C@@H](CCO[C@@]2([H])CN2C=C(C(=O)NCC3C=CC(F)=CC=3F)C(=O)C(O)=C12)C.[NaH] |&1:3,7,r|
FDA UNII 1Q1V9V5WYQ

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS09
Signal word  Warning
Hazard statements  H400-H410
Precautionary statements  P273-P391-P501-P273-P391-P501

Dolutegravir sodium price

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
TRC D528805 DolutegravirSodiumSalt 1051375-19-9 25mg $335 2021-12-16 Buy
Usbiological 447645 Dolutegravir Sodium Salt 1051375-19-9 2mg $446 2021-12-16 Buy
ApexBio Technology B5856 GSK1349572sodiuMsalt 1051375-19-9 50mg $585 2021-12-16 Buy
ChemScene CS-3496 Dolutegravirsodium 99.96% 1051375-19-9 2mg $97 2021-12-16 Buy
ApexBio Technology B5856 GSK1349572sodiuMsalt 1051375-19-9 5mg $110 2021-12-16 Buy
Product number Packaging Price Buy
D528805 25mg $335 Buy
447645 2mg $446 Buy
B5856 50mg $585 Buy
CS-3496 2mg $97 Buy
B5856 5mg $110 Buy

Dolutegravir sodium Chemical Properties,Uses,Production

Description

Dolutegravir, also known as DTG or dolutegravir sodium, is an antiretroviral therapy drug used to treat HIV infection. It belongs to the Integrase Strand Transfer inhibitor (INSTi) class of drugs and was fast-tracked by the FDA in February 2012. GlaxoSmithKline developed and markets dolutegravir sodium (Tivicay), which received FDA approval in August 2013 as a novel integrase inhibitor for HIV treatment, including adults undergoing their first treatment as well as those who have been treated with other integrase transfer strand inhibiting agents.

Uses

Dolutegravir, a second-generation HIV-1 integrase strand transfer inhibitor, is commonly used along with other medications to manage HIV infection. Its potency in inhibiting HIV replication has been demonstrated in various cell types infected with a self-inactivating PHIV lentiviral vector, including peripheral blood mononuclear cells (PBMCs), MT-4 cells, and CIP4 cells.

Definition

ChEBI: Dolutegravir sodium is an organic sodium salt that is the monosodium salt of dolutegravir. Used for treatment of HIV-1. It has a role as a HIV-1 integrase inhibitor. It contains a dolutegravir(1-).

Side effects

Dolutegravir, an HIV medication, can lead to a variety of side effects. While some can be serious, many, such as nausea or sporadic dizziness, can be effectively managed. Dolutegravir may also cause alterations in your immune system, resulting in a condition known as immune reconstitution inflammatory syndrome (IRIS).
clinicalinfo.hiv.gov/en/drugs/dolutegravir/patient

Synthesis

The most likely process-scale synthesis of dolutegravir sodium, began with benzyl protection and alkylation of pyrone 46 with benzaldehyde, yielding alcohol 47 in 74% over 2 steps. Alcohol mesylation and in situ elimination provided the styrenyl olefin 48 in 94% yield, which further underwent an oxidative cleavage of the olefin to generate 49 by sequential addition of RuCl3/NaIO4 and NaClO2 (56% overall yield). Treatment of pyranone 49 with 3-amino-propane-2-diol (50) in ethanol at elevated temperatures delivered the corresponding pyridinone in 83% yield, and this was followed by esterification and sodium periodate-mediated diol cleavage to furnish intermediate 51 in 71% overall yield across the two-step sequence. l Next, the key ring-forming step in the synthesis of dolutegravir sodium consisted of cyclization of 51 with (R)-3- amino-butan-1-ol, a process which relies on substrate control to provide the desired tricyclic carbamoylpyridone system 52 in high stereoselectivity (20/1 in favor of the desired isomer).51 Previously, cyclization of systems such as 51 with unsubstituted amino alcohols were found to yield a mixture of diastereomeric products, therefore indicating the pivotal role of the chiral amino alcohol in influencing stereochemical bias during the overall cyclization step. In practice, reaction of 51 with (R)-3-amino-butan-1-ol at 90 ?? led to isolation of a single cyclization product 52, after recrystallization from EtOAc. From 52, N-bromosuccinimide (NBS) bromination and subsequent treatment with amine 53 under palladium-catalyzed amidocarbonylative conditions led to amide 54 in 75% yield over 2 steps. Finally, removal of the benzyl group and subsequent crystallization using sodium hydroxide in water and ethanol provided dolutegravir sodium (VII) in 99% yield.

Synthesis_1051375-19-9

in vitro

gsk1349572 is a two-metal-binding hiv integrase strand transfer inhibitor whose mechanism of action was established through resistance passage experiments, integrase enzyme assays, mechanistic cellular assays and activity against viral strains resistant to other classes of anti-hiv agents. in a variety of cellular antiviral assays, gsk1349572 inhibited hiv replication with subnanomolar or low-nanomolar potency and with a selectivity index of 9,400. the protein-adjusted half-maximal effective concentration extrapolated to 100% human serum was 38 nm [1].

References

[1] kobayashi m, yoshinaga t, seki t, wakasa-morimoto c, brown kw, ferris r, foster sa, hazen rj, miki s, suyama-kagitani a, kawauchi-miki s, taishi t, kawasuji t, johns ba, underwood mr, garvey ep, sato a, fujiwara t. in vitro antiretroviral properties of s/gsk1349572, a next-generation hiv integrase inhibitor. antimicrob agents chemother. 2011 feb;55(2):813-21.
[2] van lunzen j, maggiolo f, arribas jr, rakhmanova a, yeni p, young b, rockstroh jk, almond s, song i, brothers c, min s. once daily dolutegravir (s/gsk1349572) in combination therapy in antiretroviral-naive adults with hiv: planned interim 48 week results from spring-1, a dose-ranging, randomised, phase 2b trial. lancet infect dis. 2012 feb;12(2):111-8.

1206102-11-5
1051375-19-9
Synthesis of Dolutegravir sodium from (4R,12aS)-N-(2,4-difluorobenzyl)-7-benzylhydroxy-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
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View Lastest Price from Dolutegravir sodium manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Dolutegravir sodium pictures 2024-11-19 Dolutegravir sodium
1051375-19-9
US $31.00-72.00 / mg 99.74% 10g TargetMol Chemicals Inc.
Dolutegravir Sodium pictures 2024-11-18 Dolutegravir Sodium
1051375-19-9
US $0.00 / g 1g More Than 99% 50kg/Month BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.
Dolutegravir sodium pictures 2024-03-23 Dolutegravir sodium
1051375-19-9
US $6.00-0.50 / KG 1KG 99% g-kg-tons, free sample is available Henan Fengda Chemical Co., Ltd
  • Dolutegravir Sodium pictures
  • Dolutegravir Sodium
    1051375-19-9
  • US $0.00 / g
  • More Than 99%
  • BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.
GSK1349572 sodiuM salt GSK 1349572A Dolutegravir SodiuM ( API) Dolutegravir sodium(GSK1349572) (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 sodium salt (1:1) (4R,12AS)-N-(2,4-difluorobenzyl)-7-hydroxy-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyri 158439 Dolutegravir Sodium (GSK-1349572A) (4r,12as)-9-[(2,4-difluorophenyl)methylcarbamoyl]-4-methyl-6,8-dioxo-3,4,12,12a-tetrahydro-2h-pyrido[5,6]pyrazino[2,6-b][1,3]oxazin-7-olate DOLUTEGRAVIR SODIUM Dolutegravir sodiuM salt Dolutegravi Sodium Dulutewei sodium salt Sodium (4R,12aS)-9-((2,4-difluorobenzyl)carbamoyl)-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazin-7-olate GSK1349572 sodiuM salt USP/EP/BP Dulutevir sodium Sodium (4R,12aS)-9-((2,4-difluorobenzyl)carbamoyl)-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazin-7-olate GSK1349572|||GSK-1349572A Durutevir (sodium salt) 1051375-19-9 C20H18F2N3NaO5 C20H18F2N3O5Na C20H19F2N3NaO5 Inhibitors HIV-1 integrase inhibitor 1051375-19-9