Abacavir
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MedKoo CAT#: 317150

CAS#: 136470-78-5 (free base)

Description: Abacavir (ABC) is an antiretroviral medication used to prevent and treat HIV/AIDS. It is of the nucleoside analog reverse transcriptase inhibitor (NRTI) type. Viral strains that are resistant to zidovudine (AZT) or lamivudine (3TC) are generally, but not always, sensitive to abacavir. It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system. It is available under the trade name Ziagen and in the combination formulations abacavir/lamivudine/zidovudine, abacavir/dolutegravir/lamivudine, abacavir/lamivudine.


Chemical Structure

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Abacavir
CAS# 136470-78-5 (free base)

Theoretical Analysis

MedKoo Cat#: 317150
Name: Abacavir
CAS#: 136470-78-5 (free base)
Chemical Formula: C14H18N6O
Exact Mass: 286.15421
Molecular Weight: 286.34
Elemental Analysis: C, 58.73; H, 6.34; N, 29.35; O, 5.59

Price and Availability

Size Price Availability Quantity
200.0mg USD 100.0 Same Day
1.0g USD 310.0 2 Weeks
2.0g USD 480.0 2 Weeks
5.0g USD 750.0 2 Weeks
10.0g USD 1250.0 2 Weeks
20.0g USD 2050.0 2 Weeks
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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 (caeboxylate)    

Synonym: ABC, Ziagen; Epzicom; Abacavir.

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

InChi Key: MCGSCOLBFJQGHM-SCZZXKLOSA-N

InChi Code: InChI=1S/C14H18N6O/c15-14-18-12(17-9-2-3-9)11-13(19-14)20(7-16-11)10-4-1-8(5-10)6-21/h1,4,7-10,21H,2-3,5-6H2,(H3,15,17,18,19)/t8-,10+/m1/s1

SMILES Code: NC1=NC2=C(N=CN2[C@@H]2C[C@H](CO)C=C2)C(NC2CC2)=N1

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, not in water

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: 2933.99.7500

Product Data:

Certificate of Analysis:

Safety Data Sheet (SDS):

Biological target: Abacavir is a potent nucleoside analog reverse-transcriptase inhibitor (NRTI).
In vitro activity: The cytotoxic effects of six NRTIs (ddI, d4T, 3TC, AZT, TDF, and ABC) were examined, all of which are current therapeutic agents for HIV-1, on ATL cell lines [ED-40515(−), ED-40515(+), SYK-11L(+), and ATL-43T] and on HTLV-1–infected cell lines (MT-2 and Hut-102). Strikingly, the clinically relevant concentration of ABC was highly toxic to all ATL- and HTLV-1–infected cell lines but not to non–HTLV-1–infected cell lines (Jurkat, H9, and SU-DHL-6) (Fig. 1, A and B, fig. S1, and table S1). Therefore, it is concluded that ABC potently and selectively kills HTLV-1–infected cells, including ATL cells, in vitro. Next, the effect of ABC on cell cycle and apoptosis in ATL cells was examined. ABC induced S/G2-phase arrest and apoptosis in ED-40515(−) cells, but not in Jurkat cells (Fig. 2, A to C, and fig. S3). This finding suggests that ABC may cause DNA damage by prematurely terminating the replication of host chromosomal DNA, thereby activating the DNA damage checkpoint to induce transient S/G2-phase arrest and apoptosis. Sci Adv. 2015 Apr; 1(3): e1400203. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4640626/
In vivo activity: Since NRTIs exhibit tissue-specific inhibition of mitochondrial DNA (mtDNA) synthesis, the ability of ABC (Abacavir) to inhibit mtDNA synthesis in vivo was evaluated. Inbred wild-type (WT) and transgenic mice (TG) treated with ABC (3.125 mg/d p. o., 35 days) were used to define mitochondrial oxidative stress and cardiac function. Cardiac function was assessed for each group of mice. LV (left ventrical) mass and LVEDD (left ventricle end-diastolic dimension) were derived from direct echocardiographic measurements of cavity and wall thickness in each mouse to define effects of ABC and/or genetic manipulation on LV. Results showed LV mass was unchanged in all vehicle-treated TGs (including MSB, MnSOD OX, SOD2+/− KO, MCAT, and ALDH2 KO) compared to vehicle-treated WTs (Fig. 2a). Similarly, ABC had no effect on LV mass in the MnSOD OX and MCAT TGs, as expected (Fig. 2a). Surprisingly, SOD2+/− KOs were also found to have no change in LV mass following ABC, further supporting the hypothesis that oxidative stress is not associated with ABC treatment (Fig. 2a). In contrast, SOD2+/− KO previously was shown to have increased LV mass following AZT treatment for 5 weeks [3]. Any potential changes in LV mass due to the absence of ALDH2 activity was also disproven with results here that showed no change in ALDH2 KOs treated with ABC compared to WTs (Fig. 2a). LVEDD also remained unchanged (with or without ABC treatment) in WTs and all TGs, even SOD2+/− KO and ALDH2 KO (Fig. 2b). These results further support the conclusion that ABC treatment for 5 weeks has no detectable cardiotoxicity and suggests that oxidative stress is not associated with ABC treatment. Cardiovasc Toxicol. Author manuscript; available in PMC 2020 Nov 30. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7704124/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 79.0 274.15

Preparing Stock Solutions

The following data is based on the product molecular weight 286.34 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: 1. Tada K, Kobayashi M, Takiuchi Y, Iwai F, Sakamoto T, Nagata K, Shinohara M, Io K, Shirakawa K, Hishizawa M, Shindo K, Kadowaki N, Hirota K, Yamamoto J, Iwai S, Sasanuma H, Takeda S, Takaori-Kondo A. Abacavir, an anti-HIV-1 drug, targets TDP1deficient adult T cell leukemia. Sci Adv. 2015 Apr 24;1(3):e1400203. doi: 10.1126/sciadv.1400203. PMID: 26601161; PMCID: PMC4640626. 2. 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. 3. Kohler JJ, Hosseini SH, Green E, Fields E, Abuin A, Ludaway T, Russ R, Lewis W. Absence of mitochondrial toxicity in hearts of transgenic mice treated with abacavir. Cardiovasc Toxicol. 2010 Jun;10(2):146-51. doi: 10.1007/s12012-010-9070-2. PMID: 20379802; PMCID: PMC7704124 4. . Cardone M, Garcia K, Tilahun ME, Boyd LF, Gebreyohannes S, Yano M, Roderiquez G, Akue AD, Juengst L, Mattson E, Ananthula S, Natarajan K, Puig M, Margulies DH, Norcross MA. A transgenic mouse model for HLA-B*57:01-linked abacavir drug tolerance and reactivity. J Clin Invest. 2018 Jul 2;128(7):2819-2832. doi: 10.1172/JCI99321. Epub 2018 May 21. PMID: 29782330; PMCID: PMC6025983
In vitro protocol: 1. Tada K, Kobayashi M, Takiuchi Y, Iwai F, Sakamoto T, Nagata K, Shinohara M, Io K, Shirakawa K, Hishizawa M, Shindo K, Kadowaki N, Hirota K, Yamamoto J, Iwai S, Sasanuma H, Takeda S, Takaori-Kondo A. Abacavir, an anti-HIV-1 drug, targets TDP1deficient adult T cell leukemia. Sci Adv. 2015 Apr 24;1(3):e1400203. doi: 10.1126/sciadv.1400203. PMID: 26601161; PMCID: PMC4640626. 2. 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.Kohler JJ, Hosseini SH, Green E, Fields E, Abuin A, Ludaway T, Russ R, Lewis W. Absence of mitochondrial toxicity in hearts of transgenic mice treated with abacavir. Cardiovasc Toxicol. 2010 Jun;10(2):146-51. doi: 10.1007/s12012-010-9070-2. PMID: 20379802; PMCID: PMC7704124 2. Cardone M, Garcia K, Tilahun ME, Boyd LF, Gebreyohannes S, Yano M, Roderiquez G, Akue AD, Juengst L, Mattson E, Ananthula S, Natarajan K, Puig M, Margulies DH, Norcross MA. A transgenic mouse model for HLA-B*57:01-linked abacavir drug tolerance and reactivity. J Clin Invest. 2018 Jul 2;128(7):2819-2832. doi: 10.1172/JCI99321. Epub 2018 May 21. PMID: 29782330; PMCID: PMC6025983

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1: Fantauzzi A, Floridia M, Falasca F, Spanedda P, Turriziani O, Vullo V, Mezzaroma I. Backbone switch to abacavir/lamivudine fixed-dose combination: implications for antiretroviral therapy optimization. New Microbiol. 2015 Oct 20;38(4). [Epub ahead of print] PubMed PMID: 26485011.

2: Mulenga V, Musiime V, Kekitiinwa A, Cook AD, Abongomera G, Kenny J, Chabala C, Mirembe G, Asiimwe A, Owen-Powell E, Burger D, McIlleron H, Klein N, Chintu C, Thomason MJ, Kityo C, Walker AS, Gibb DM; CHAPAS-3 trial team. Abacavir, zidovudine, or stavudine as paediatric tablets for African HIV-infected children (CHAPAS-3): an open-label, parallel-group, randomised controlled trial. Lancet Infect Dis. 2015 Oct 5. pii: S1473-3099(15)00319-9. doi: 10.1016/S1473-3099(15)00319-9. [Epub ahead of print] PubMed PMID: 26481928.

3: Naisbitt DJ, Yang EL, Alhaidari M, Berry NG, Lawrenson AS, Farrell J, Martin P, Strebel K, Owen A, Pye M, French N, Clarke SE, O'Neill PM, Park BK. Towards depersonalized abacavir therapy: chemical modification eliminates HLA-B*57 : 01-restricted CD8+ T-cell activation. AIDS. 2015 Sep 13. [Epub ahead of print] PubMed PMID: 26372480.

4: Wilson B, Paladugu L, Priyadarshini SR, Jenita JJ. Development of albumin-based nanoparticles for the delivery of abacavir. Int J Biol Macromol. 2015 Sep 10;81:763-767. doi: 10.1016/j.ijbiomac.2015.09.015. [Epub ahead of print] PubMed PMID: 26365020.

5: Tebas P, Kumar P, Hicks C, Granier C, Wynne B, Min S, Pappa K. Greater change in bone turnover markers for efavirenz/emtricitabine/tenofovir disoproxil fumarate versus dolutegravir + abacavir/lamivudine in antiretroviral therapy-naive adults over 144 weeks. AIDS. 2015 Sep 9. [Epub ahead of print] PubMed PMID: 26355674.

6: Walmsley S, Baumgarten A, Berenguer J, Felizarta F, Florence E, Khuong-Josses MA, Kilby JM, Lutz T, Podzamczer D, Portilla J, Roth N, Wong D, Granier C, Wynne B, Pappa K. Dolutegravir Plus Abacavir/Lamivudine for the Treatment of HIV-1 Infection in Antiretroviral Therapy-Naive Patients: Week 96 and Week 144 Results from the SINGLE Randomized Clinical Trial. J Acquir Immune Defic Syndr. 2015 Aug 7. [Epub ahead of print] PubMed PMID: 26262777.

7: Gao S, Zhu S, Huang R, Lu Y, Zheng G. Efficient synthesis of the intermediate of abacavir and carbovir using a novel (+)-γ-lactamase as a catalyst. Bioorg Med Chem Lett. 2015 Sep 15;25(18):3878-81. doi: 10.1016/j.bmcl.2015.07.054. Epub 2015 Jul 26. PubMed PMID: 26235952.

8: Wohl DA, Bhatti L, Small CB, Edelstein H, Zhao HH, Margolis DA, DeJesus E, Weinberg WG, Ross LL, Shaefer MS. The ASSURE study: HIV-1 suppression is maintained with bone and renal biomarker improvement 48 weeks after ritonavir discontinuation and randomized switch to abacavir/lamivudine + atazanavir. HIV Med. 2015 Jul 14. doi: 10.1111/hiv.12281. [Epub ahead of print] PubMed PMID: 26176344.

9: Neumanova Z, Cerveny L, Greenwood SL, Ceckova M, Staud F. Effect of drug efflux transporters on placental transport of antiretroviral agent abacavir. Reprod Toxicol. 2015 Nov;57:176-82. doi: 10.1016/j.reprotox.2015.07.070. Epub 2015 Jul 10. PubMed PMID: 26169552.

10: Young B, Squires KE, Tashima K, Henry K, Schneider S, LaMarca A, Zhao HH, Ross LL, Shaefer MS. Estimated glomerular filtration rates through 144 weeks on therapy in HIV-1-infected subjects receiving atazanavir/ritonavir and abacavir/lamivudine or simplified to unboosted atazanavir/abacavir/lamivudine. HIV Clin Trials. 2015 Aug;16(4):125-9. doi: 10.1179/1528433614Z.0000000017. Epub 2015 Jul 2. PubMed PMID: 26133089.

Abacavir

200.0mg / USD 100.0