Tenofovir Alafenamide FumarateCAS# 379270-38-9 |
Quality Control & MSDS
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| Cas No. | 379270-38-9 | SDF | Download SDF |
| PubChem ID | 68516365 | Appearance | Powder |
| Formula | C25H33N6O9P | M.Wt | 592.54 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Synonyms | GS-7340 fumarate | ||
| Solubility | DMSO : ≥ 36 mg/mL (60.76 mM) H2O : ≥ 25 mg/mL (42.19 mM) *"≥" means soluble, but saturation unknown. | ||
| Chemical Name | (E)-but-2-enedioic acid;propan-2-yl (2S)-2-[[[(2R)-1-(6-aminopurin-9-yl)propan-2-yl]oxymethyl-phenoxyphosphoryl]amino]propanoate | ||
| SMILES | CC(C)OC(=O)C(C)NP(=O)(COC(C)CN1C=NC2=C1N=CN=C2N)OC3=CC=CC=C3.C(=CC(=O)O)C(=O)O | ||
| Standard InChIKey | MEJAFWXKUKMUIR-FHPNUNMMSA-N | ||
| Standard InChI | InChI=1S/C21H29N6O5P.C4H4O4/c1-14(2)31-21(28)16(4)26-33(29,32-17-8-6-5-7-9-17)13-30-15(3)10-27-12-25-18-19(22)23-11-24-20(18)27;5-3(6)1-2-4(7)8/h5-9,11-12,14-16H,10,13H2,1-4H3,(H,26,29)(H2,22,23,24);1-2H,(H,5,6)(H,7,8)/b;2-1+/t15-,16+,33+;/m1./s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | GS-7340(Tenofovir alafenamide) is a prodrug of tenofovir (TFV) that more efficiently delivers TFV into lymphoid cells and tissues than TFV disoproxil fumarate.
IC50 value:
Target: NRTI; HIV reverse transcriptase inhibitor
GS-7340 reduces first-pass clearance to be an effective oral prodrug, its permeability and stability were characterized in vitro and detailed pharmacokinetic studies were completed in dogs. GS-7340 showed concentration-dependent permeability through monolayers of caco-2 cells and dose-dependent oral bioavailability in dogs, increasing from 1.7% at 2 mg/kg to 24.7% at 20 mg/kg, suggesting saturable intestinal efflux transport [1]. Significant reductions in plasma HIV-1 RNA from baseline to day 11 were observed for all TAF dose groups compared with placebo (P < 0.01), with a median decrease of 1.08-1.73 log10 copies per milliliter, including a dose-response relationship for viral load decrease up to 25 mg [2]. References: | |||||
Tenofovir Alafenamide Fumarate Dilution Calculator
Tenofovir Alafenamide Fumarate Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 1.6876 mL | 8.4382 mL | 16.8765 mL | 33.753 mL | 42.1912 mL |
| 5 mM | 0.3375 mL | 1.6876 mL | 3.3753 mL | 6.7506 mL | 8.4382 mL |
| 10 mM | 0.1688 mL | 0.8438 mL | 1.6876 mL | 3.3753 mL | 4.2191 mL |
| 50 mM | 0.0338 mL | 0.1688 mL | 0.3375 mL | 0.6751 mL | 0.8438 mL |
| 100 mM | 0.0169 mL | 0.0844 mL | 0.1688 mL | 0.3375 mL | 0.4219 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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GS-7340(Tenofovir alafenamide) is a prodrug of tenofovir (TFV) that more efficiently delivers TFV into lymphoid cells and tissues than TFV disoproxil fumarate.
GS7340 (Tenofovir Alafenamide, TAF) is a novel oral prodrug of Tenofovir with improved antiviral activity [1].
Tenofovir (TFV) is an HIV-1 nucleotide reverse transcriptase (RT) inhibitor for the treatment of HIV infections [1].
GS7340 (Tenofovir Alafenamide, TAF) is a novel oral prodrug of Tenofovir. In peripheral blood mononuclear cells, TAF is mostly converted to TFV and achieved higher tenofovir diphosphate (TFV-DP) levels, compared with TDF. In MT-2 and MT-4 cells infected with HIV-1IIIB, TAF exhibited anti-HIV-1 activity with EC50 values of 5 nM, while with CC50 (50% cell death) values of 42 and 4.7 nM, respectively. In the 29 primary HIV-1 isolates tested in PBMCs, EC50 values of TAF ranged from 0.10 to 12.0 nM with mean EC50 of 3.5 nM. For the HIV-2 isolates, the mean EC50 value was 1.8 nM. In MT-2 cells, TAF maintained its antiviral activity after HS (human serum) pretreatment, suggesting its plasma stability. TAF is a potent inhibitor of immunodeficiency viruses, such as HIV and SIV, and a weak inhibitor of HSV-2 [1]. In HIV-1 isolates with NRTI resistance amino acid substitutions, TAF exhibited reduced activity [2]. In primary human hepatocytes, TAF resulted in high levels of tenofovir diphosphate (TFV-DP), which exhibited half-life of >24 h [3].
In dogs, TAF orally administration for 7 days increased the levels of TFV-DP in dog livers for the treatment of HBV infection [3].
References:
[1]. Callebaut C, Stepan G, Tian Y, et al. In Vitro Virology Profile of Tenofovir Alafenamide, a Novel Oral Prodrug of Tenofovir with Improved Antiviral Activity Compared to That of Tenofovir Disoproxil Fumarate. Antimicrob Agents Chemother, 2015, 59(10): 5909-5916.
[2]. Margot NA, Johnson A, Miller MD, et al. Characterization of HIV-1 Resistance to Tenofovir Alafenamide In Vitro. Antimicrob Agents Chemother, 2015, 59(10): 5917-5924.
[3]. Murakami E, Wang T, Park Y, et al. Implications of efficient hepatic delivery by tenofovir alafenamide (GS-7340) for hepatitis B virus therapy. Antimicrob Agents Chemother, 2015, 59(6): 3563-3569.
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Evaluation of oral tenofovir disoproxil fumarate and topical tenofovir GS-7340 to protect infant macaques against repeated oral challenges with virulent simian immunodeficiency virus.[Pubmed:16810108]
J Acquir Immune Defic Syndr. 2006 Sep;43(1):6-14.
Simian immunodeficiency virus (SIV) infection of infant macaques is a useful animal model of pediatric HIV infection to evaluate the potential of chemoprophylactic regimens to reduce mother-to-infant transmission of HIV. Previous studies have demonstrated that short-term subcutaneous administration of the reverse transcriptase inhibitor tenofovir was highly effective in protecting newborn macaques against infection after a single high-dose oral inoculation with virulent SIVmac251. In the current study, we mimicked HIV transmission through breast-feeding by repeatedly feeding infant macaques low doses of SIVmac251. Topical administration of a low dose of the second-generation tenofovir prodrug GS-7340 did not have detectable prophylactic efficacy. Oral administration of tenofovir disoproxil fumarate (DF; 10 mg/kg SID) lowered the infection rate at birth, but had lower efficacy against virus infection at 4 weeks of age, most likely because drug levels became suboptimal relative to those obtained with the current tenofovir DF regimen in humans. These prophylactic results further underscore the relevance of the current tenofovir DF prevention trials in pediatric and adult populations.
