Skip to Content
Merck
All Photos(2)

Documents

SML0089

Sigma-Aldrich

Abacavir sulfate

≥98% (HPLC)

Synonym(s):

(1S,4R)-4-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol sulfate, ABC, Abacavir Hemisulfate

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Empirical Formula (Hill Notation):
C14H18N6O · 0.5 H2SO4
CAS Number:
188062-50-2
Molecular Weight:
335.37
MDL number:
MFCD04112763
UNSPSC Code:
12352200
PubChem Substance ID:
329825149
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -30 to -40°, c = 0.5 in methanol

color

white to tan

solubility

H2O: ≥17 mg/mL

originator

GlaxoSmithKline

storage temp.

2-8°C

SMILES string

OS(O)(=O)=O.Nc1nc(NC2CC2)c3ncn([C@@H]4C[C@H](CO)C=C4)c3n1.Nc5nc(NC6CC6)c7ncn([C@@H]8C[C@H](CO)C=C8)c7n5

InChI

1S/2C14H18N6O.H2O4S/c2*15-14-18-12(17-9-2-3-9)11-13(19-14)20(7-16-11)10-4-1-8(5-10)6-21;1-5(2,3)4/h2*1,4,7-10,21H,2-3,5-6H2,(H3,15,17,18,19);(H2,1,2,3,4)/t2*8-,10+;/m11./s1

InChI key

WMHSRBZIJNQHKT-FFKFEZPRSA-N

General description

Abacavir exhibits antiviral activity. It is associated with myocardial infarction and fatal hypersensitivity reaction (HSR).

Application

Abacavir sulfate has been used as a compound to validate the P19C5 gastrulation in mouse. It has also been used to induces chromosomal double-strand breaks (DSBs) and kills adult T cell leukemia (ATL) cells.
Abacavir sulfate has been used in the cytotoxicity to test its tumour promoting activity U937 cells.

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).
Abacavir sulfate is a Nucleoside analog reverse transcriptase inhibitor (NRTI); guanosine analog used to treat HIV and AIDS.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by GlaxoSmithKline. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H317,H319,H341,H351,H361

Hazard Classifications

Carc. 2 - Eye Irrit. 2 - Muta. 2 - Repr. 2 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Hypersensitivity reaction associated with abacavir therapy in an Indian HIV patient-A case report
Janardhanan M, et al.
Journal of Clinical and Diagnostic Research : JCDR, 8(9), HD01-HD01 (2014)
Tumour Promoting Potentials of HAART backbone (NNRTIs and NRTIs) leading to increase cancer risk among AIDs patients
Aisha Z
Microbioz Journals,Journal of Microbiology and Biomedical Research, 4(3), e1400203-e1400203 (2018)
Abacavir, an anti-HIV-1 drug, targets TDP1-deficient adult T cell leukemia
Tada K, et al.
Science advances, 1(3), e1400203-e1400203 (2015)
Boe-Hyun Kim et al.
Viruses, 16(5) (2024-05-25)
EcoHIV is a chimeric HIV that replicates in mice in CD4+ T cells, macrophages, and microglia (but not in neurons), causing lasting neurocognitive impairment resembling neurocognitive disease in people living with HIV. The present study was designed to develop EcoHIV-susceptible
Steady-state pharmacokinetics of abacavir in plasma and intracellular carbovir triphosphate following administration of abacavir at 600 milligrams once daily and 300 milligrams twice daily in human immunodeficiency virus-infected subjects
Moyle G, et al.
Antimicrobial agents and chemotherapy, 53(4), 1532-1538 (2009)
View All Related Papers

Articles

Bioactive Molecules for Immunology Research

Bioactive small molecules for immune system signaling target identification/validation and antibiotics, antivirals, and antifungals offered.

Bioactive Molecules for Immunology Research

Bioactive small molecules for immune system signaling target identification/validation and antibiotics, antivirals, and antifungals offered.

Bioactive Molecules for Immunology Research

Bioactive small molecules for immune system signaling target identification/validation and antibiotics, antivirals, and antifungals offered.

Bioactive Molecules for Immunology Research

Bioactive small molecules for immune system signaling target identification/validation and antibiotics, antivirals, and antifungals offered.

See All

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service