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MedKoo Cat#: 328002 | Name: Pradefovir

Description:

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

Pradefovir, also known as Remofovir, ICN-2001-3; MB-06866; MB-6866; ICN-20013, is a reverse transcriptase inhibitor potentially for treatment of chronic HBV infection. Pradefovir is also a liver-targeted prodrug of adefovir. After metabolic activation, Pradefovir was converted to PMEA (9-(2-phosphonylmethoxyethyl)adenine ) in human liver microsomes with a K(m) of 60 microM, a maximum rate of metabolism of 228 pmol/min/mg protein, and an intrinsic clearance of about 359 ml/min.

Chemical Structure

Pradefovir
Pradefovir
CAS#625095-60-5

Theoretical Analysis

MedKoo Cat#: 328002

Name: Pradefovir

CAS#: 625095-60-5

Chemical Formula: C17H19ClN5O4P

Exact Mass: 423.0863

Molecular Weight: 423.79

Elemental Analysis: C, 48.18; H, 4.52; Cl, 8.36; N, 16.53; O, 15.10; P, 7.31

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 #
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Synonym
Pradefovir; Remofovir; ICN-2001-3; MB-06866; MB-6866; ICN-20013; ICN2001-3; MB06866; MB6866; ICN20013.
IUPAC/Chemical Name
(2R,4S)-2-((2-(6-amino-9H-purin-9-yl)ethoxy)methyl)-4-(3-chlorophenyl)-1,3,2-dioxaphosphinane 2-oxide
InChi Key
GWNHAOBXDGOXRR-HJFSHJIFSA-N
InChi Code
InChI=1S/C17H19ClN5O4P/c18-13-3-1-2-12(8-13)14-4-6-26-28(24,27-14)11-25-7-5-23-10-22-15-16(19)20-9-21-17(15)23/h1-3,8-10,14H,4-7,11H2,(H2,19,20,21)/t14-,28+/m0/s1
SMILES Code
ClC1=CC([C@H]2O[P@](OCC2)(COCCN3C=NC4=C(N)N=CN=C34)=O)=CC=C1
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 423.79 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: Xiao Q, Wang D, Yang W, Chen L, Ding Y, Yang J. Simultaneous determination of pradefovir, PMEA and tenofovir in HBV patient serum using liquid chromatography-tandem mass spectrometry and application to phase 2 clinical trial. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 Jun 1;1022:133-40. doi: 10.1016/j.jchromb.2016.04.019. Epub 2016 Apr 11. PubMed PMID: 27089519. 2: Xiao Q, Yang W, Wang D, Chen L, Yuan L, Ding Y, Yang J. Factors limiting the extent of absolute bioavailability of pradefovir in rat. Xenobiotica. 2016 Oct;46(10):913-21. doi: 10.3109/00498254.2015.1133866. Epub 2016 Feb 5. PubMed PMID: 26846680. 3: Zhang Y, Shen L, Zhan Y, Xiao QQ, Yang J. Development and Validation of a Sensitive LC-MS-MS Method for the Determination of Adefovir in Human Serum and Urine: Application to a Clinical Pharmacokinetic Study. J Chromatogr Sci. 2016 Apr;54(4):507-15. doi: 10.1093/chromsci/bmv172. Epub 2015 Dec 10. PubMed PMID: 26657410; PubMed Central PMCID: PMC4885381. 4: Hynicka LM, Yunker N, Patel PH. A review of oral antiretroviral therapy for the treatment of chronic hepatitis B. Ann Pharmacother. 2010 Jul-Aug;44(7-8):1271-86. doi: 10.1345/aph.1M590. Epub 2010 Jun 29. Review. PubMed PMID: 20587747. 5: Tillmann HL. The treatment of chronic hepatitis B: Focus on adefovir-like antivirals. Ther Clin Risk Manag. 2008 Aug;4(4):797-802. PubMed PMID: 19209262; PubMed Central PMCID: PMC2621388. 6: Reddy KR, Matelich MC, Ugarkar BG, Gómez-Galeno JE, DaRe J, Ollis K, Sun Z, Craigo W, Colby TJ, Fujitaki JM, Boyer SH, van Poelje PD, Erion MD. Pradefovir: a prodrug that targets adefovir to the liver for the treatment of hepatitis B. J Med Chem. 2008 Feb 14;51(3):666-76. doi: 10.1021/jm7012216. Epub 2008 Jan 4. PubMed PMID: 18173234. 7: Tillmann HL. Pradefovir, a liver-targeted prodrug of adefovir against HBV infection. Curr Opin Investig Drugs. 2007 Aug;8(8):682-90. PubMed PMID: 17668370. 8: Lin CC, Fang C, Benetton S, Xu GF, Yeh LT. Metabolic activation of pradefovir by CYP3A4 and its potential as an inhibitor or inducer. Antimicrob Agents Chemother. 2006 Sep;50(9):2926-31. PubMed PMID: 16940083; PubMed Central PMCID: PMC1563525. 9: Erion MD, Bullough DA, Lin CC, Hong Z. HepDirect prodrugs for targeting nucleotide-based antiviral drugs to the liver. Curr Opin Investig Drugs. 2006 Feb;7(2):109-17. Review. PubMed PMID: 16499280. 10: Lin CC, Xu C, Teng A, Yeh LT, Peterson J. Pharmacokinetics of pradefovir and PMEA in healthy volunteers after oral dosing of pradefovir. J Clin Pharmacol. 2005 Nov;45(11):1250-8. PubMed PMID: 16239358. 11: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2005 Jul-Aug;27(6):411-61. PubMed PMID: 16179960. 12: Gish RG. Clinical trial results of new therapies for HBV: implications for treatment guidelines. Semin Liver Dis. 2005;25 Suppl 1:29-39. Review. PubMed PMID: 16103979. 13: Lin CC, Xu C, Zhu N, Lourenco D, Yeh LT. Single-dose pharmacokinetics and metabolism of [14C]remofovir in rats and cynomolgus monkeys. Antimicrob Agents Chemother. 2005 Mar;49(3):925-30. PubMed PMID: 15728885; PubMed Central PMCID: PMC549278. 14: Lin CC, Yeh LT, Vitarella D, Hong Z, Erion MD. Remofovir mesylate: a prodrug of PMEA with improved liver-targeting and safety in rats and monkeys. Antivir Chem Chemother. 2004 Nov;15(6):307-17. PubMed PMID: 15646644. 15: Erion MD, van Poelje PD, Mackenna DA, Colby TJ, Montag AC, Fujitaki JM, Linemeyer DL, Bullough DA. Liver-targeted drug delivery using HepDirect prodrugs. J Pharmacol Exp Ther. 2005 Feb;312(2):554-60. Epub 2004 Aug 31. PubMed PMID: 15340017.