Abacavir sulfate

Abacavir sulfate Struktur
188062-50-2
CAS-Nr.
188062-50-2
Englisch Name:
Abacavir sulfate
Synonyma:
ABACAVIR SULPHATE;ZIAGEN;DRG 0257;Hsdb 7154;ABC sulfate;1592U89 sulfate;Unii-J220T4J9Q2;bacavir sulfate;ABACAVIR SULFATE;Abacavir Hemisulfate
CBNumber:
CB8425548
Summenformel:
C14H20N6O5S
Molgewicht:
384.41
MOL-Datei:
188062-50-2.mol

Abacavir sulfate 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
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
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)
Bildanzeige (GHS) GHS hazard pictogramsGHS hazard pictograms
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H317 Kann allergische Hautreaktionen verursachen. Sensibilisierung der Haut Kategorie 1A Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H319 Verursacht schwere Augenreizung. Schwere Augenreizung Kategorie 2 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P280, P305+P351+P338,P337+P313P
H341 Kann vermutlich genetische Defekte verursachen. Keimzellmutagenität Kategorie 2 Warnung P201,P202, P281, P308+P313, P405,P501
H351 Kann vermutlich Krebs verursachen. Karzinogenität Kategorie 2 Warnung P201, P202, P281, P308+P313, P405,P501
H361 Kann vermutlich die Fruchtbarkeit beeinträchtigen oder das Kind im Mutterleib schädigen. Reproduktionstoxizität Kategorie 2 Warnung P201, P202, P281, P308+P313, P405,P501
Sicherheit
P201 Vor Gebrauch besondere Anweisungen einholen.
P202 Vor Gebrauch alle Sicherheitshinweise lesen und verstehen.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P302+P352 BEI BERÜHRUNG MIT DER HAUT: Mit viel Wasser/... (Hersteller kann, falls zweckmäßig, ein Reinigungsmittel angeben oder, wenn Wasser eindeutig ungeeignet ist, ein alternatives Mittel empfehlen) waschen.
P305+P351+P338 BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.
P308+P313 BEI Exposition oder falls betroffen: Ärztlichen Rat einholen/ärztliche Hilfe hinzuziehen.

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).

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.

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.

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.

Abacavir sulfate Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Abacavir sulfate Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global( 377)Lieferanten
Firmenname Telefon E-Mail Land Produktkatalog Edge Rate
Sinoway Industrial co., ltd.
0592-5800732; +8613806035118
xie@china-sinoway.com China 992 58
Henan Bao Enluo International TradeCo.,LTD
+86-17331933971 +86-17331933971
deasea125996@gmail.com China 2503 58
Henan Fengda Chemical Co., Ltd
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Henan Tianfu Chemical Co.,Ltd.
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info@tianfuchem.com China 21689 55
Hubei XinRunde Chemical Co., Ltd.
+8615102730682
bruce@xrdchem.cn CHINA 566 55
career henan chemical co
+86-0371-86658258
sales@coreychem.com China 29914 58
Shaanxi Yikanglong Biotechnology Co., Ltd.
17791478691
yklbiotech@163.com CHINA 296 58
SHANDONG ZHI SHANG CHEMICAL CO.LTD
+86 18953170293
sales@sdzschem.com China 2931 58
HubeiwidelychemicaltechnologyCo.,Ltd
18627774460
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Chongqing Chemdad Co., Ltd
+86-023-61398051 +8613650506873
sales@chemdad.com China 39916 58

188062-50-2()Verwandte Suche:


  • (1S,4R)-4-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cycpentene-1-methanol Sulfate
  • Hsdb 7154
  • ABACAVIR SULFATE
  • (1S,4R)-4-[2-AMINO-6-(CYCLOPROPYLAMINO)-9H-PURIN-9-YL]-2-CYCLOPENTENE-1-METHANOL, SULFATE
  • Ziagen, (1S,4R)-4-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cycpentene-1-methanol, Sulfate,
  • 1592U89 sulfate
  • 2-Cyclopentene-1-methanol, 4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-, (1S,4R)-, sulfate (2:1) (salt)
  • 2-Cyclopentene-1-methanol, 4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-, (1S-cis)-, sulfate (2:1) (salt)
  • ABC sulfate
  • DRG 0257
  • (1S,4R)-4-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol
  • Unii-J220T4J9Q2
  • Abacavir Sulfate (200 mg)
  • Abacavir Sulfate Racemic (20 mg) (4-[2-amino-6-(cyclopropylamino)-9H-purin-9yl]-2-cyclopentene-1-methanol sulfate (2:1))
  • Abacavir Sulfate RaceMic
  • 2-Cyclopentene-1-methanol, 4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-, (1S,4R)-, sulfate (2:1)
  • Abacavir Hemisulfate
  • Abacavir for system suitability
  • Abacavir for peak identification
  • Abacavir Impurity (3-Hydroxy Abacavir)
  • ((1S,4R)-4-(2-Amino-6-(cyclopropylamino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hemisulfate
  • (1S,4R)-4-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol hemisulfate
  • bacavir sulfate
  • Abacavir sulfate CRS
  • Abacavir for peak identification CRS
  • Abacavir for system suitability CRS
  • Abacavir Sulphate IP/usp
  • Abacavir Sulfate (2:1)
  • Abacavir sulfate USP/EP/BP
  • Abacavir sulfate (ABC)
  • Abacavir SulfateQ: What is Abacavir Sulfate Q: What is the CAS Number of Abacavir Sulfate Q: What is the storage condition of Abacavir Sulfate Q: What are the applications of Abacavir Sulfate
  • Abacavir for peak identification (Y0001552)
  • Abacavir for system suitability (Y0001551)
  • Abacavir Sulfate Racemic (4-[2-amino-6-(cyclopropylamino)-9H-purin-9yl]-2-cyclopentene-1-methanol s (1000419)
  • Abacavir Sulfate (1000408)
  • ZIAGEN
  • ABACAVIR SULPHATE
  • Abacavir sulfate salt
  • ((1S,4R)-4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol sulfate
  • 3-O-Desacyl-4′-MonophosphorylLipidA
  • 188062-50-2
  • 2C14H18N6OH2O4S
  • C14H18N6O12H2O4S
  • C14H18N6OH2SO4
  • C28H38N12O6S
  • API
  • ZIAGEN
  • Abacavir
  • Bases & Related Reagents
  • Inhibitors
  • Intermediates & Fine Chemicals
  • Nucleotides
  • Pharmaceuticals
  • Antiviral Agents
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