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Abacavir sulfate

Product Name
Abacavir sulfate
CAS No.
188062-50-2
Chemical Name
Abacavir sulfate
Synonyms
ABACAVIR SULPHATE;ZIAGEN;DRG 0257;Hsdb 7154;ABC sulfate;1592U89 sulfate;Unii-J220T4J9Q2;bacavir sulfate;ABACAVIR SULFATE;Abacavir Hemisulfate
CBNumber
CB8425548
Molecular Formula
C14H20N6O5S
Formula Weight
384.41
MOL File
188062-50-2.mol
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Abacavir sulfate Property

Melting point:
222-225°C
storage temp. 
2-8°C
solubility 
H2O: ≥17mg/mL
form 
powder
color 
white to tan
optical activity
[α]/D -30 to -40°, c = 0.5 in methanol
Water Solubility 
1.68ug/L(32 ºC)
BCS Class
3
CAS DataBase Reference
188062-50-2(CAS DataBase Reference)
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Safety

Hazard Codes 
Xn
Risk Statements 
63-40
Safety Statements 
36/37
WGK Germany 
3
HS Code 
2933595960
Hazardous Substances Data
188062-50-2(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H317May cause an allergic skin reaction

H319Causes serious eye irritation

H341Suspected of causing genetic defects

H351Suspected of causing cancer

H361Suspected of damaging fertility or the unborn child

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PHR1256
Product name
Abacavir sulfate
Packaging
500mg
Price
$253
Updated
2024/03/01
Sigma-Aldrich
Product number
1000408
Product name
Abacavir sulfate
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$393
Updated
2024/03/01
Sigma-Aldrich
Product number
Y0001561
Product name
Abacavir sulfate
Purity
European Pharmacopoeia (EP) Reference Standard
Packaging
y0001561
Price
$223
Updated
2024/03/01
Sigma-Aldrich
Product number
Y0001552
Product name
Abacavir for peak identification
Purity
European Pharmacopoeia (EP) Reference Standard
Packaging
y0001552
Price
$220
Updated
2024/03/01
Sigma-Aldrich
Product number
SML0089
Product name
Abacavir sulfate
Purity
≥98% (HPLC)
Packaging
10mg
Price
$114
Updated
2024/03/01
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Abacavir sulfate Chemical Properties,Usage,Production

Description

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.

Chemical Properties

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)

Uses

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.

brand name

Ziagen (GlaxoSmithKline).

Therapeutic Function

Antiviral

General Description

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).

Side effects

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).

Synthesis

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.

storage

Store at +4°C

Abacavir sulfate Preparation Products And Raw materials

Raw materials

Preparation Products

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Abacavir sulfate Suppliers

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View Lastest Price from Abacavir sulfate manufacturers

Sinoway Industrial co., ltd.
Product
Abacavir Sulfate 188062-50-2
Price
US $0.00-0.00/Kg/Bag
Min. Order
1Kg/Bag
Purity
98% up
Supply Ability
20 tons
Release date
2024-06-27
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Abacavir sulfate 188062-50-2
Price
US $0.00-0.00/Kg/Drum
Min. Order
1KG
Purity
97%-102%; USP
Supply Ability
500KGS
Release date
2021-09-10
Shaanxi Dideu New Materials Co. Ltd
Product
Abacavir sulfate 188062-50-2
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
100000KGS
Release date
2024-11-13

188062-50-2, Abacavir sulfateRelated Search:

Aluminum sulfate Zinc sulfate heptahydrate Dimethyl sulfate Glycine Barium sulfate Lithium diisopropylamide 6-Aminocaproic acid Magnesium sulfate heptahydrate Ammonium sulfate 4-Methylaminophenol sulfate Copper(II) sulfate Tris(hydroxymethyl)aminomethane Sodium sulfate ALTRENOGEST Sodium thiosulfate calcium sulfate D-Glucosamine sulfate Ferrous sulfate heptahydrate

  • (1S,4R)-4-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cycpentene-1-methanol Sulfate
  • Hsdb 7154
  • ZIAGEN
  • ABACAVIR SULPHATE
  • 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
  • ((1S,4R)-4-(2-Amino-6-(cyclopropylamino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hemisulfate
  • 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]-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 for peak identification (Y0001552)
  • Abacavir for system suitability (Y0001551)
  • 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 Sulfate (1000408)
  • Abacavir Sulfate Racemic (4-[2-amino-6-(cyclopropylamino)-9H-purin-9yl]-2-cyclopentene-1-methanol s (1000419)
  • ((1S,4R)-4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol sulfate
  • 3-O-Desacyl-4′-MonophosphorylLipidA
  • Abacavir Hemisulfate|||1592U89|||ABC sulfate|||Ziagen
  • Abacavelli sulfonamides
  • 188062-50-2
  • 2C14H18N6OH2O4S
  • C14H18N6O12H2O4S
  • C14H18N6OH2SO4
  • C28H38N12O6S
  • API
  • ZIAGEN
  • Abacavir
  • Bases & Related Reagents
  • Inhibitors
  • Intermediates & Fine Chemicals
  • Nucleotides
  • Pharmaceuticals
  • Antiviral Agents