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MedKoo Cat#: 562587 | Name: Abacavir sulfate
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Abacavir sulfate
Abacavir sulfate
CAS#188062-50-2 (sulfate)

Theoretical Analysis

MedKoo Cat#: 562587

Name: Abacavir sulfate

CAS#: 188062-50-2 (sulfate)

Chemical Formula: C28H38N12O6S

Exact Mass: 0.0000

Molecular Weight: 670.75

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 90.00 Ready to ship
500mg USD 150.00 Ready to ship
1g USD 225.00 Ready to ship
2g USD 350.00 Ready to ship
5g USD 550.00 Ready to ship
10g USD 850.00 Ready to ship
25g USD 1,450.00 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
Solvent mg/mL mM
Solubility
DMSO 0.2 0.22
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.
1: Dean L. Abacavir Therapy and HLA-B*57:01 Genotype. 2015 Sep 1 [updated 2018 Apr 18]. In: Pratt V, McLeod H, Dean L, Malheiro A, Rubinstein W, editors. Medical Genetics Summaries [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2012-. Available from http://www.ncbi.nlm.nih.gov/books/NBK315783/ PubMed PMID: 28520363. 2: McLaughlin MM, Guerrero AJ, Merker A. Renal effects of non-tenofovir antiretroviral therapy in patients living with HIV. Drugs Context. 2018 Mar 21;7:212519. doi: 10.7573/dic.212519. eCollection 2018. Review. PubMed PMID: 29623097; PubMed Central PMCID: PMC5866095. 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. 4: Fan WL, Shiao MS, Hui RC, Su SC, Wang CW, Chang YC, Chung WH. HLA Association with Drug-Induced Adverse Reactions. J Immunol Res. 2017;2017:3186328. doi: 10.1155/2017/3186328. Epub 2017 Nov 23. Review. PubMed PMID: 29333460; PubMed Central PMCID: PMC5733150. 5: Redwood AJ, Pavlos RK, White KD, Phillips EJ. HLAs: Key regulators of T-cell-mediated drug hypersensitivity. HLA. 2018 Jan;91(1):3-16. doi: 10.1111/tan.13183. Review. PubMed PMID: 29171940; PubMed Central PMCID: PMC5743596. 6: McCoy C, Badowski M, Sherman E, Crutchley R, Smith E, Chastain DB; Society of Infectious Diseases Pharmacists. Strength in Amalgamation: Newer Combination Agents for HIV and Implications for Practice. Pharmacotherapy. 2018 Jan;38(1):86-107. doi: 10.1002/phar.2055. Epub 2017 Dec 11. Review. PubMed PMID: 29105160. 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. 14: Fricke-Galindo I, LLerena A, López-López M. An update on HLA alleles associated with adverse drug reactions. Drug Metab Pers Ther. 2017 May 24;32(2):73-87. doi: 10.1515/dmpt-2016-0025. Review. PubMed PMID: 28315856. 15: Negrini S, Becquemont L. Pharmacogenetics of hypersensitivity drug reactions. Therapie. 2017 Apr;72(2):231-243. doi: 10.1016/j.therap.2016.12.009. Epub 2017 Jan 3. Review. PubMed PMID: 28162244. 16: Usui T, Naisbitt DJ. Human leukocyte antigen and idiosyncratic adverse drug reactions. Drug Metab Pharmacokinet. 2017 Feb;32(1):21-30. doi: 10.1016/j.dmpk.2016.11.003. Epub 2016 Nov 18. Review. PubMed PMID: 28017537. 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. 18: Institute for Quality and Efficiency in Health Care. Rilpivirine -- Benefit Assessment According to §35a Social Code Book V [Internet]. Cologne, Germany: Institute for Quality and Efficiency in Health Care (IQWiG); 2012 Apr 12. Available from http://www.ncbi.nlm.nih.gov/books/NBK385641/ PubMed PMID: 27905736. 19: Su SC, Hung SI, Fan WL, Dao RL, Chung WH. Severe Cutaneous Adverse Reactions: The Pharmacogenomics from Research to Clinical Implementation. Int J Mol Sci. 2016 Nov 15;17(11). pii: E1890. Review. PubMed PMID: 27854302; PubMed Central PMCID: PMC5133889. 20: Illing PT, Mifsud NA, Purcell AW. Allotype specific interactions of drugs and HLA molecules in hypersensitivity reactions. Curr Opin Immunol. 2016 Oct;42:31-40. doi: 10.1016/j.coi.2016.05.003. Epub 2016 Jun 2. Review. PubMed PMID: 27261882.