Dolutegravir sodium

Dolutegravir sodium Struktur
1051375-19-9
CAS-Nr.
1051375-19-9
Englisch Name:
Dolutegravir sodium
Synonyma:
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
Summenformel:
C20H20F2N3NaO5
Molgewicht:
443.38
MOL-Datei:
1051375-19-9.mol

Dolutegravir sodium Eigenschaften

Schmelzpunkt:
>300oC
storage temp. 
Hygroscopic, -20°C Freezer, Under inert atmosphere
Löslichkeit
DMSO (Slightly, Heated), Methanol (Slightly, Heated)
Aggregatzustand
Solid
Farbe
White to Green
Stabilität:
Hygroscopic
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
Bildanzeige (GHS) GHS hazard pictograms
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H400 Sehr giftig für Wasserorganismen. Kurzfristig (akut) gewässergefährdend Kategorie 1 Warnung P273, P391, P501
H410 Sehr giftig für Wasserorganismen mit langfristiger Wirkung. Langfristig (chronisch) gewässergefährdend Kategorie 1 Warnung P273, P391, P501
Sicherheit
P273 Freisetzung in die Umwelt vermeiden.
P391 Verschüttete Mengen aufnehmen.
P501 Inhalt/Behälter ... (Entsorgungsvorschriften vom Hersteller anzugeben) zuführen.

Dolutegravir sodium Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung

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.

Verwenden

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-).

Nebenwirkungen

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

Synthese

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

Dolutegravir sodium Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Dolutegravir sodium Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global( 224)Lieferanten
Firmenname Telefon E-Mail Land Produktkatalog Edge Rate
Henan Fengda Chemical Co., Ltd
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Capot Chemical Co.,Ltd.
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sales@capotchem.com China 29797 60
Shanghai Daken Advanced Materials Co.,Ltd
+86-371-66670886
info@dakenam.com China 14936 58
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512
info@tianfuchem.com China 21700 55
career henan chemical co
+86-0371-86658258
sales@coreychem.com China 29914 58
Hubei Jusheng Technology Co.,Ltd.
18871490254
linda@hubeijusheng.com CHINA 28180 58
BOC Sciences
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inquiry@bocsci.com United States 19553 58
Beijing Yibai Biotechnology Co., Ltd
0086-182-6772-3597
sales04@yibaibiotech.com CHINA 419 58
Chongqing Chemdad Co., Ltd
+86-023-61398051 +8613650506873
sales@chemdad.com China 39916 58
Shaanxi Dideu Medichem Co. Ltd
+86-29-87569266 15319487004
1015@dideu.com China 2263 58

  • 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
  • 1051375-19-9
  • C20H18F2N3NaO5
  • C20H18F2N3O5Na
  • C20H19F2N3NaO5
  • Inhibitors
  • HIV-1 integrase inhibitor
  • 1051375-19-9
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