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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

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About This Item

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

Quality Level

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

signalword

Warning

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk_germany

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’.

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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)
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)
Abacavir use and risk for myocardial infarction and cardiovascular events: pooled analysis of data from clinical trials
Nan C, et al.
Open forum infectious diseases, 5(5), ofy086-ofy086 (2018)
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)
Abacavir, an anti-HIV-1 drug, targets TDP1-deficient adult T cell leukemia
Tada K, et al.
Science advances, 1(3), e1400203-e1400203 (2015)

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