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MedKoo Cat#: 530136 | Name: Amdoxovir

Description:

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

A reverse transcriptase inhibitor potentially for the treatment of HIV infection. In vitro studies have shown that amdoxovir may be an effective option for treating people for whom the NRTIs(nucleoside reverse transcriptase inhibitors) lamivudine, emtricitabine, zidovudine, and stavudine are not working. In one such study, Amdoxovir was shown to act synergistically with zidovudine in vitro and the combination prevents or delays the selection of thymidine analogue and K65R mutations.

Chemical Structure

Amdoxovir
Amdoxovir
CAS#145514-04-1

Theoretical Analysis

MedKoo Cat#: 530136

Name: Amdoxovir

CAS#: 145514-04-1

Chemical Formula: C9H12N6O3

Exact Mass: 252.1000

Molecular Weight: 252.23

Elemental Analysis: C, 42.86; H, 4.80; N, 33.32; O, 19.03

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
AMDX; DAPD
IUPAC/Chemical Name
((2R,4R)-4-(2,6-diamino-9H-purin-9-yl)-1,3-dioxolan-2-yl)methanol
InChi Key
RLAHNGKRJJEIJL-RFZPGFLSSA-N
InChi Code
InChI=1S/C9H12N6O3/c10-7-6-8(14-9(11)13-7)15(3-12-6)4-2-17-5(1-16)18-4/h3-5,16H,1-2H2,(H4,10,11,13,14)/t4-,5-/m1/s1
SMILES Code
OC[C@@H]1OC[C@H](N2C=NC3=C(N)N=C(N)N=C23)O1
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
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

Preparing Stock Solutions

The following data is based on the product molecular weight 252.23 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
1: Murphy RL, Kivel NM, Zala C, Ochoa C, Tharnish P, Mathew J, Pascual ML, Schinazi RF. Antiviral activity and tolerability of amdoxovir with zidovudine in a randomized double-blind placebo-controlled study in HIV-1-infected individuals. Antivir Ther. 2010;15(2):185-92. doi: 10.3851/IMP1514. PubMed PMID: 20386073. 2: Fromentin E, Asif G, Obikhod A, Hurwitz SJ, Schinazi RF. Simultaneous quantification of 9-(beta-D-1,3-dioxolan-4-yl)guanine, Amdoxovir and Zidovudine in human plasma by liquid chromatography-tandem mass spectrometric assay. J Chromatogr B Analyt Technol Biomed Life Sci. 2009 Nov 1;877(29):3482-8. doi: 10.1016/j.jchromb.2009.08.030. PubMed PMID: 19740712; PubMed Central PMCID: PMC2769996. 3: Hurwitz SJ, Asif G, Fromentin E, Tharnish PM, Schinazi RF. Lack of pharmacokinetic interaction between amdoxovir and reduced- and standard-dose zidovudine in HIV-1-infected individuals. Antimicrob Agents Chemother. 2010 Mar;54(3):1248-55. doi: 10.1128/AAC.01209-09. PubMed PMID: 20038617; PubMed Central PMCID: PMC2826005. 4: Borroto-Esoda K, Myrick F, Feng J, Jeffrey J, Furman P. In vitro combination of amdoxovir and the inosine monophosphate dehydrogenase inhibitors mycophenolic acid and ribavirin demonstrates potent activity against wild-type and drug-resistant variants of human immunodeficiency virus type 1. Antimicrob Agents Chemother. 2004 Nov;48(11):4387-94. PubMed PMID: 15504868; PubMed Central PMCID: PMC525453. 5: Narayanasamy J, Pullagurla MR, Sharon A, Wang J, Schinazi RF, Chu CK. Synthesis and anti-HIV activity of (-)-beta-D-(2R,4R)-1,3-dioxolane-2,6-diamino purine (DAPD) (amdoxovir) and (-)-beta-D-(2R,4R)-1,3-dioxolane guanosine (DXG) prodrugs. Antiviral Res. 2007 Sep;75(3):198-209. PubMed PMID: 17532483; PubMed Central PMCID: PMC2025703. 6: Zhou L, Coats SJ, Zhang H, Junxing S, Bobeck DR, Schinazi RF. Scaleable processes for the synthesis of (-)-β-D-2,6-diaminopurine dioxolane (Amdoxovir, DAPD) and (-)-β-D-2-aminopurine dioxolane (APD). Tetrahedron. 2012 Jul 22;68(29):5738-5743. PubMed PMID: 23162170; PubMed Central PMCID: PMC3496293. 7: Gripshover BM, Ribaudo H, Santana J, Gerber JG, Campbell TB, Hogg E, Jarocki B, Hammer SM, Kuritzkes DR; A5118 Team.. Amdoxovir versus placebo with enfuvirtide plus optimized background therapy for HIV-1-infected subjects failing current therapy (AACTG A5118). Antivir Ther. 2006;11(5):619-23. PubMed PMID: 16964830. 8: Thompson MA, Kessler HA, Eron JJ Jr, Jacobson JM, Adda N, Shen G, Zong J, Harris J, Moxham C, Rousseau FS; DAPD-101 Study Group.. Short-term safety and pharmacodynamics of amdoxovir in HIV-infected patients. AIDS. 2005 Oct 14;19(15):1607-15. PubMed PMID: 16184030. 9: Feng JY, Parker WB, Krajewski ML, Deville-Bonne D, Veron M, Krishnan P, Cheng YC, Borroto-Esoda K. Anabolism of amdoxovir: phosphorylation of dioxolane guanosine and its 5'-phosphates by mammalian phosphotransferases. Biochem Pharmacol. 2004 Nov 1;68(9):1879-88. PubMed PMID: 15450953. 10: Margolis DM, Mukherjee AL, Fletcher CV, Hogg E, Ogata-Arakaki D, Petersen T, Rusin D, Martinez A, Mellors JW. The use of beta-D-2,6-diaminopurine dioxolane with or without mycophenolate mofetil in drug-resistant HIV infection. AIDS. 2007 Oct 1;21(15):2025-32. PubMed PMID: 17885292. 11: Otto MJ. New nucleoside reverse transcriptase inhibitors for the treatment of HIV infections. Curr Opin Pharmacol. 2004 Oct;4(5):431-6. Review. PubMed PMID: 15351346. 12: Kewn S, Wang LH, Hoggard PG, Rousseau F, Hart R, MacNeela JP, Khoo SH, Back DJ. Enzymatic assay for measurement of intracellular DXG triphosphate concentrations in peripheral blood mononuclear cells from human immunodeficiency virus type 1-infected patients. Antimicrob Agents Chemother. 2003 Jan;47(1):255-61. PubMed PMID: 12499199; PubMed Central PMCID: PMC149017. 13: Seignères B, Martin P, Werle B, Schorr O, Jamard C, Rimsky L, Trépo C, Zoulim F. Effects of pyrimidine and purine analog combinations in the duck hepatitis B virus infection model. Antimicrob Agents Chemother. 2003 Jun;47(6):1842-52. PubMed PMID: 12760857; PubMed Central PMCID: PMC155836. 14: Jeffrey JL, Feng JY, Qi CC, Anderson KS, Furman PA. Dioxolane guanosine 5'-triphosphate, an alternative substrate inhibitor of wild-type and mutant HIV-1 reverse transcriptase. Steady state and pre-steady state kinetic analyses. J Biol Chem. 2003 May 23;278(21):18971-9. PubMed PMID: 12651859. 15: Mewshaw JP, Myrick FT, Wakefield DA, Hooper BJ, Harris JL, McCreedy B, Borroto-Esoda K. Dioxolane guanosine, the active form of the prodrug diaminopurine dioxolane, is a potent inhibitor of drug-resistant HIV-1 isolates from patients for whom standard nucleoside therapy fails. J Acquir Immune Defic Syndr. 2002 Jan 1;29(1):11-20. PubMed PMID: 11782585. 16: North TW, Villalobos A, Hurwitz SJ, Deere JD, Higgins J, Chatterjee P, Tao S, Kauffman RC, Luciw PA, Kohler JJ, Schinazi RF. Enhanced antiretroviral therapy in rhesus macaques improves RT-SHIV viral decay kinetics. Antimicrob Agents Chemother. 2014 Jul;58(7):3927-33. doi: 10.1128/AAC.02522-14. PubMed PMID: 24777106; PubMed Central PMCID: PMC4068512. 17: Schwartz AM, McCrackin MA, Schinazi RF, Hill PB, Vahlenkamp TW, Tompkins MB, Hartmann K. Antiviral efficacy of nine nucleoside reverse transcriptase inhibitors against feline immunodeficiency virus in feline peripheral blood mononuclear cells. Am J Vet Res. 2014 Mar;75(3):273-81. doi: 10.2460/ajvr.75.3.273. PubMed PMID: 24564313. 18: Kauffman RC, Villalobos A, Bowen JH, Adamson L, Schinazi RF. Residual viremia in an RT-SHIV rhesus macaque HAART model marked by the presence of a predominant plasma clone and a lack of viral evolution. PLoS One. 2014 Feb 5;9(2):e88258. doi: 10.1371/journal.pone.0088258. PubMed PMID: 24505452; PubMed Central PMCID: PMC3914964. 19: Liu K, Xie L. [Advances in the study of nucleoside antiviral drugs]. Yao Xue Xue Bao. 2006 Aug;41(8):689-93. Review. Chinese. PubMed PMID: 17039770. 20: Schinazi RF, Massud I, Rapp KL, Cristiano M, Detorio MA, Stanton RA, Bennett MA, Kierlin-Duncan M, Lennerstrand J, Nettles JH. Selection and characterization of HIV-1 with a novel S68 deletion in reverse transcriptase. Antimicrob Agents Chemother. 2011 May;55(5):2054-60. doi: 10.1128/AAC.01700-10. PubMed PMID: 21357304; PubMed Central PMCID: PMC3088218.

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