Synonym
Fosamprenavir sodium; GW 433908A; VX175; VX-175; VX 175
IUPAC/Chemical Name
sodium (2R,3S)-1-((4-amino-N-isobutylphenyl)sulfonamido)-4-phenyl-3-(((((S)-tetrahydrofuran-3-yl)oxy)carbonyl)amino)butan-2-yl phosphate
InChi Key
FZMGUXZZROZJIT-KMIZVRHLSA-L
InChi Code
InChI=1S/C25H36N3O9PS.2Na/c1-18(2)15-28(39(33,34)22-10-8-20(26)9-11-22)16-24(37-38(30,31)32)23(14-19-6-4-3-5-7-19)27-25(29)36-21-12-13-35-17-21;;/h3-11,18,21,23-24H,12-17,26H2,1-2H3,(H,27,29)(H2,30,31,32);;/q;2*+1/p-2/t21-,23-,24+;;/m0../s1
SMILES Code
[Na+].[Na+].CC(C)CN(C[C@@H](OP(=O)([O-])[O-])[C@H](Cc1ccccc1)NC(=O)O[C@H]2CCOC2)S(=O)(=O)c3ccc(N)cc3
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
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
629.57
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.
| 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 |
1: Ross LL, Cotton MF, Cassim H, Voronin E, Givens N, Sievers J, Cheng KY; APV29005 & APV20002 Pediatric Study Groups. Treatment-Emergent Mutations and Resistance in HIV-Infected Children Treated with Fosamprenavir-Containing Antiretroviral Regimens. Open AIDS J. 2015 May 15;9:38-44. doi: 10.2174/1874613601509010038. eCollection 2015. PubMed PMID: 26157536; PubMed Central PMCID: PMC4484231.
2: Song I, Borland J, Chen S, Peppercorn A, Wajima T, Piscitelli SC. Effect of fosamprenavir-ritonavir on the pharmacokinetics of dolutegravir in healthy subjects. Antimicrob Agents Chemother. 2014 Nov;58(11):6696-700. doi: 10.1128/AAC.03282-14. Epub 2014 Aug 25. PubMed PMID: 25155604; PubMed Central PMCID: PMC4249430.
3: Barbour AM, Gibiansky L, Wire MB. Population pharmacokinetic modeling and simulation of amprenavir following fosamprenavir/ritonavir administration for dose optimization in HIV infected pediatric patients. J Clin Pharmacol. 2014 Feb;54(2):206-14. doi: 10.1002/jcph.205. Epub 2013 Nov 5. PubMed PMID: 25272370.
4: Wood R, Gathe JC, Givens N, Sedani S, Cheng K, Sievers J. Long-term safety study of fosamprenavir-containing regimens in HIV-1-infected patients. HIV Clin Trials. 2013 Sep-Oct;14(5):183-91. doi: 10.1310/hct1405-183. PubMed PMID: 24144895.
5: Torres HA, Arduino RC. Fosamprenavir calcium plus ritonavir for HIV infection. Expert Rev Anti Infect Ther. 2007 Jun;5(3):349-63. Review. PubMed PMID: 17547501.
