Abacavir sulfate

Bezeichnung:Abacavir sulfate

CAS-Nr188062-50-2

Englisch Name:Abacavir sulfate

CBNumberCB8425548

SummenformelC14H20N6O5S

Molgewicht384.41

MOL-Datei188062-50-2.mol

Abacavir sulfate physikalisch-chemischer Eigenschaften

Schmelzpunkt	222-225°C
storage temp.	2-8°C
Löslichkeit	H2O: ≥17mg/mL
Aggregatzustand	powder
Farbe	white to tan
Optische Aktivität	[α]/D -30 to -40°, c = 0.5 in methanol
Wasserlöslichkeit	1.68ug/L(32 ºC)
BCS Class	3
CAS Datenbank	188062-50-2(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	63-40
S-Sätze:	36/37
WGK Germany	3
HS Code	2933595960
Giftige Stoffe Daten	188062-50-2(Hazardous Substances Data)

Gefahreninformationscode (GHS)

Abacavir sulfate Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
Abacavir sulfate was first launched as Ziagen in the US for the treatment of human immunodeficiency virus (HIV) infection, in combination with other antiretroviral drugs. Abacavir is a carbocyclic nucleoside reverse transcriptase inhibitor (nRTI); it is one of the most potent anti-HIV agents to date. In vitro, Abacavir is a potent and selective inhibitor of HIV-1 and HIV-2 replication. Resistance to Abacavir develops more slowly than for other anti-HIV agents. Abacavir is highly synergistic with protease inhibitors such as Amprenavir. In clinical trials for HIV infections in adults, it produced durable suppression in viral load. Combinations with different protease inhibitors such as Nelfinavir, Saquinavir or Indinavir markedly reduced plasma viral load to undetectable levels for at least 48 weeks, and significantly raised CD4+ cell counts in adults with HIV infection, especially nRTI-naive patients. Abacavir has a good oral availability and its penetration into CSF is much more significant than for other anti-HIV drugs. The two major metabolites identified in humans were the 5'-carboxylate and the 5'-glucuronide, mainly excreted via the renal route.
Chemische Eigenschaften
Abacavir sulfate is white to off-white crystalline powder and the solubility is pH dependent with minimal solubility at basic pH and increased solubility at acid. This active substance is slightly soluble in diethyl ether and ethanol. Abacavir exhibits stereoisomerism due to the presence of two chiral centres (1S,4R absolute configuration).
Originator
Glaxo Wellcome (UK)
Verwenden
Abacavir sulfate is a nucleoside reverse transcriptase inhibitor (NRTI) used for the treatment of HIV-1 infection and anti-AIDS drug. It has been used in the cytotoxicity to test its tumour promoting activity U937 cells.
Definition
ChEBI: Abacavir sulfate is an azaheterocycle sulfate salt that is the sulfate salt of the HIV-1 reverse transcriptase inhibitor abacavir. It is functionally related to an abacavir.
Trademarks
Ziagen (GlaxoSmithKline).
Therapeutic Function
Antiviral
Allgemeine Beschreibung
Abacavir sulfate belongs to the class of human immunodeficiency virus (HIV) medicines called nucleoside reverse transcriptase inhibitors, with antiretroviral activity against HIV.
Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.
Biochem/physiol Actions
Abacavir incorporated in the cells is converted to triphosphate containing guanine analog carbovir (CBV) and it favors the generation of higher double stranded breaks (DSBs).
Nebenwirkungen
Abacavir can cause serious, life-threatening side effects. These include allergic reactions, a buildup of lactic acid in the blood (lactic acidosis), and liver problems. People who take abacavir may have a serious allergic reaction (hypersensitivity reaction) that can cause death.
Common side effects of Ziagen include: trouble sleeping, loss of appetite, strange dreams, headache, ear pain, cold symptoms (stuffy nose, sneezing, sinus pain), or changes in the shape or location of body fat (especially in your arms, legs, face, neck, breasts, and trunk).
Synthese
Abacavir Sulfate can be prepared by an enantioselective synthesis involving palladium-catalyzed coupling of a chloropurine with a carbocyclic allylic diacetate.
Synthesis Step: Treatment of 2,5-diamino-4,6-dihydroxypyrimidine (I) with (chloromethylene)dimethylammonium chloride yielded the dichloropyrimidine with both amino groups derivatized as amidines. Partial hydrolysis with aqueous HCl in hot ethanol gave N-(2-amino-4,6-dichloro-pyrimidin-5-yl)-N,Ndimethylformamidene (II). Subseqent buffered hydrolysis at pH 3.2 yielded the (2-amino-4,6-dichloro-pyrimididin-5-ylamino)acetaldehyde (III). Condensation chloropyrimidine (III) with (1S,4R)-4-amino-2-cyclopentene-1- methanol (IV) in the presence of triethylamine and NaOH gave [2-amino-4- chloro-6-(4-hydroxymethyl-cyclopent-2-enylamino)pyrimidin-5-ylamino]- acetaldehyde (V). The correct enantiomer (IV) of racemic aminocyclopentene was obtained by resolution of diastereomeric salts with D-dibenzoyltartaric acid. Cyclization of (V) to the corresponding purine was accomplished with refluxing triethyl orthoformate or diethoxymethyl acetate to give nucleoside analogue [4-(2-amino-6-chloro-purin-9-yl)-cyclopent-2-enyl]methanol (VI). Displacement of chloride in the purine nucleus with cyclopropyl amine in refluxing butanol afforded abacavir. The structure of obtained compound was confirmed by 1H NMR method and elemental analysis.
In practice it is usually used as sulfate salt.
Solubility in organics
Soluble in water (77 mg/ml), DMSO (< 1 mg/ml at 25° C), ethanol (< 1 mg/ml at 25° C), and methanol.
Lager
Store at +4°C

Abacavir sulfate Upstream-Materialien And Downstream Produkte

Abacavir sulfate Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

188062-50-2, Abacavir sulfate Verwandte Suche:

Send Inquriy