Abacavir sulfate
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MedKoo CAT#: 562587

CAS#: 188062-50-2 (sulfate)

Description: Abacavir sulfate is a nucleoside reverse transcriptase inhibitor analog of guanosine. It acts by decreasing HIV viral loads, retarding or preventing the damage to the immune system, and reducing the risk of developing AIDS.

Chemical Structure

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Abacavir sulfate
CAS# 188062-50-2 (sulfate)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 562587
Name: Abacavir sulfate
CAS#: 188062-50-2 (sulfate)
Chemical Formula: C28H38N12O6S
Exact Mass: 0.00
Molecular Weight: 670.750
Elemental Analysis: C, 50.14; H, 5.71; N, 25.06; O, 14.31; S, 4.78

Price and Availability

Size Price Availability Quantity
100mg USD 90 Ready to ship
500mg USD 150 Ready to ship
1g USD 225 Ready to ship
2g USD 350 Ready to ship
5g USD 550 Ready to ship
10g USD 850 Ready to ship
25g USD 1450 Ready to ship
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Related CAS #: 136470-78-5 (free base)   136777-48-5 (HCl)   168146-84-7 (succinate)   188062-50-2 (sulfate)   1446418-48-9 (hydroxyacetate)   384380-52-3 (carboxylate)  

Synonym: Abacavir sulfate; Abacavir sulfate salt; Abacavir hemisulfate; 1592U89; 1592U89 sulfate;

IUPAC/Chemical Name: [(1S,4R)-4-[2-amino-6-(cyclopropylamino)purin-9-yl]cyclopent-2-en-1-yl]methanol, sulfuric acid (2:1)

InChi Key: WMHSRBZIJNQHKT-FFKFEZPRSA-N

InChi Code: 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

SMILES Code: OC[C@@H]1C=C[C@H](N2C=NC3=C(NC4CC4)N=C(N)N=C23)C1.OC[C@@H]5C=C[C@H](N6C=NC7=C(NC8CC8)N=C(N)N=C67)C5.O=S(O)(O)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO and PBS

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target: Abacavir (1592U89) is a commonly used nucleoside analogue with potent antiviral activity against HIV-1.
In vitro activity: In vitro culture of PBMC with abacavir results in the outgrowth of abacavir-reacting CD8+ T cells, which release IFNγ and are cytotoxic. How this immune response is induced and what is recognized by these T cells is still a matter of debate. The conditions required to develop an abacavir-dependent T cell response in vitro is analyzed. The abacavir reactivity was independent of co-stimulatory signals, as neither DC maturation nor release of inflammatory cytokines were observed upon abacavir exposure. Abacavir induced T cells arose in the absence of professional APC and stemmed from naïve and memory compartments. These features are reminiscent of allo-reactivity. Screening for allo-reactivity revealed that about 5% of generated T cell clones (n = 136) from three donors were allo-reactive exclusively to the related HLA-B*58∶01. The addition of peptides which can bind to the HLA-B*57∶01-abacavir complex and to HLA-B*58∶01 during the induction phase increased the proportion of HLA-B*58∶01 allo-reactive T cell clones from 5% to 42%. In conclusion, abacavir can alter the HLA-B*57∶01-peptide complex in a way that mimics an allo-allele ('altered self-allele') and create the potential for robust T cell responses. Reference: PLoS One. 2014 Apr 21;9(4):e95339. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/24751900/
In vivo activity: Pretreatment with ABC intrascrotally (at doses of 2.5, 5, and 7.5 μg/mL) or orally (dose range, 100–200 mg/kg) neither altered blood flow (measured as the vascular wall shear rate) nor resulted in the formation of thrombi (measured as the time to occlusion; data not shown). Likewise, in the absence of any pretreatment, superfusion with 25 or 50 mM of ferric chloride did not affect the aforementioned parameters. However, when the concentration of ferric chloride in the superfusion was augmented to 75 mM, there was a rapid formation of thrombi and a subsequent reduction in wall shear rate characteristic of a cessation of blood flow (Supplementary Figure 1). Likewise, the arterioles became occluded when the 25 mM concentration of ferric chloride was perfused over the cremaster of animals intrascrotally pretreated with ABC. This occlusion developed more rapidly as the dose of ABC increased (Figure 1A and 1B) and was accompanied by a parallel dose-dependent reduction in the arterial wall shear rate (Figure 1D). The oral administration of ABC (mean plasma concentration [±SEM], 5.3 ± 0.8 and 16.2 ± 1.9 µg/mL following 100 and 200 mg/kg, respectively) reproduced the effects of locally administered ABC (Figure 1B). Superfusion with 25 mM of ferric chloride had no effects in mice pretreated intrascrotally with one of the other NRTIs analyzed (TDF, ddI, FTC, or 3TC), even at concentrations (7.5 µg/mL) substantially higher than those considered clinically appropriate (Figure 1C). In contrast, in animals pretreated with a clinical concentration of diclofenac or rofecoxib—2 well-known vascular injurious agents—25 mM of ferric chloride led to the formation of arterial thrombi in a similar way to that produced by the 2 highest doses of ABC evaluated (Figure 2A). Reference: J Infect Dis. 2018 Jun 20;218(2):228-233. https://academic.oup.com/jid/article-lookup/doi/10.1093/infdis/jiy001

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 0.2 0.22

Preparing Stock Solutions

The following data is based on the product molecular weight 670.75 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol: 1. Adam J, Wuillemin N, Watkins S, Jamin H, Eriksson KK, Villiger P, Fontana S, Pichler WJ, Yerly D. Abacavir induced T cell reactivity from drug naïve individuals shares features of allo-immune responses. PLoS One. 2014 Apr 21;9(4):e95339. doi: 10.1371/journal.pone.0095339. PMID: 24751900; PMCID: PMC3994040.
In vivo protocol: 1. Collado-Diaz V, Andujar I, Sanchez-Lopez A, Orden S, Blanch-Ruiz MA, Martinez-Cuesta MA, Blas-García A, Esplugues JV, Álvarez Á. Abacavir Induces Arterial Thrombosis in a Murine Model. J Infect Dis. 2018 Jun 20;218(2):228-233. doi: 10.1093/infdis/jiy001. PMID: 29346575.

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3: Gerogianni K, Tsezou A, Dimas K. Drug-Induced Skin Adverse Reactions: The Role of Pharmacogenomics in Their Prevention. Mol Diagn Ther. 2018 Mar 21. doi: 10.1007/s40291-018-0330-3. [Epub ahead of print] Review. PubMed PMID: 29564734.

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7: Clare KE, Miller MH, Dillon JF. Genetic Factors Influencing Drug-Induced Liver Injury: Do They Have a Role in Prevention and Diagnosis? Curr Hepatol Rep. 2017;16(3):258-264. doi: 10.1007/s11901-017-0363-9. Epub 2017 Aug 7. Review. PubMed PMID: 28856081; PubMed Central PMCID: PMC5556130.

8: Somogyi AA, Phillips E. Genomic testing as a tool to optimise drug therapy. Aust Prescr. 2017 Jun;40(3):101-104. doi: 10.18773/austprescr.2017.027. Epub 2017 Jun 1. Review. PubMed PMID: 28798515; PubMed Central PMCID: PMC5478394.

9: Illing PT, Purcell AW, McCluskey J. The role of HLA genes in pharmacogenomics: unravelling HLA associated adverse drug reactions. Immunogenetics. 2017 Aug;69(8-9):617-630. doi: 10.1007/s00251-017-1007-5. Epub 2017 Jul 10. Review. PubMed PMID: 28695285.

10: Mallolas J. Darunavir Stands Up as Preferred HIV Protease Inhibitor. AIDS Rev. 2017 Apr - Jun;19(2):105-112. Review. PubMed PMID: 28664942.

11: Alvarez A, Orden S, Andújar I, Collado-Diaz V, Núñez-Delgado S, Galindo MJ, Estrada V, Apostolova N, Esplugues JV. Cardiovascular toxicity of abacavir: a clinical controversy in need of a pharmacological explanation. AIDS. 2017 Aug 24;31(13):1781-1795. doi: 10.1097/QAD.0000000000001547. Review. PubMed PMID: 28537935.

12: Cahn P. Candidates for inclusion in a universal antiretroviral regimen: dolutegravir. Curr Opin HIV AIDS. 2017 Jul;12(4):318-323. doi: 10.1097/COH.0000000000000388. Review. PubMed PMID: 28520610.

13: Garon SL, Pavlos RK, White KD, Brown NJ, Stone CA Jr, Phillips EJ. Pharmacogenomics of off-target adverse drug reactions. Br J Clin Pharmacol. 2017 Sep;83(9):1896-1911. doi: 10.1111/bcp.13294. Epub 2017 Apr 27. Review. PubMed PMID: 28345177; PubMed Central PMCID: PMC5555876.

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17: Institute for Quality and Efficiency in Health Care. Dolutegravir / Abacavir / Lamivudine -- Benefit Assessment According to §35a Social Code Book V [Internet]. Cologne, Germany: Institute for Quality and Efficiency in Health Care (IQWiG); 2014 Dec 18. Available from http://www.ncbi.nlm.nih.gov/books/NBK385734/ PubMed PMID: 27905804.

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