MedKoo Cat#: 597078 | Name: Clevudine triphosphate

Description:

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

Clevudine triphosphate is a TTP analog that is able to inhibit protein priming independently of the deoxynucleoside triphosphate (dNTP) substrate and without being incorporated into DNA.

Chemical Structure

Clevudine triphosphate
Clevudine triphosphate
CAS#174625-00-4

Theoretical Analysis

MedKoo Cat#: 597078

Name: Clevudine triphosphate

CAS#: 174625-00-4

Chemical Formula: C10H16FN2O14P3

Exact Mass: 499.9798

Molecular Weight: 500.15

Elemental Analysis: C, 24.01; H, 3.22; F, 3.80; N, 5.60; O, 44.78; P, 18.58

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
Clevudine triphosphate; L-FMAU-TP;
IUPAC/Chemical Name
((2S,3S,4R,5S)-4-fluoro-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl tetrahydrogen triphosphate
InChi Key
RUKRVHYQIIURNV-XQXXSGGOSA-N
InChi Code
InChI=1S/C10H16FN2O14P3/c1-4-2-13(10(16)12-8(4)15)9-6(11)7(14)5(25-9)3-24-29(20,21)27-30(22,23)26-28(17,18)19/h2,5-7,9,14H,3H2,1H3,(H,20,21)(H,22,23)(H,12,15,16)(H2,17,18,19)/t5-,6+,7-,9-/m0/s1
SMILES Code
CC1=CN(C(=O)NC1=O)[C@@H]2[C@@H]([C@H]([C@@H](O2)COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O)F
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 500.15 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
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Clevudine is efficiently phosphorylated to the active triphosphate form in primary human hepatocytes. Antivir Ther. 2008;13(2):263-9. PubMed PMID: 18505177. 5: Nishii R, Volgin AY, Mawlawi O, Mukhopadhyay U, Pal A, Bornmann W, Gelovani JG, Alauddin MM. Evaluation of 2'-deoxy-2'-[18F]fluoro-5-methyl-1-beta-L: -arabinofuranosyluracil ([18F]-L: -FMAU) as a PET imaging agent for cellular proliferation: comparison with [18F]-D: -FMAU and [18F]FLT. Eur J Nucl Med Mol Imaging. 2008 May;35(5):990-8. Epub 2007 Dec 4. PubMed PMID: 18057932. 6: Korba BE, Furman PA, Otto MJ. Clevudine: a potent inhibitor of hepatitis B virus in vitro and in vivo. Expert Rev Anti Infect Ther. 2006 Aug;4(4):549-61. Review. PubMed PMID: 17009935. 7: Lee J, Yoo BC, Lee HS, Yoo HW, Yoo HH, Kang MJ, Kim DH. Rapid quantitative determination of L-FMAU-TP from human peripheral-blood mononuclear cells of hepatitis B virus-infected patients treated with L-FMAU by ion-pairing, reverse-phase, liquid chromatography/electrospray tandem mass spectrometry. Ther Drug Monit. 2006 Feb;28(1):131-7. PubMed PMID: 16418707. 8: Hu R, Li L, Degrève B, Dutschman GE, Lam W, Cheng YC. Behavior of thymidylate kinase toward monophosphate metabolites and its role in the metabolism of 1-(2'-deoxy-2'-fluoro-beta-L-arabinofuranosyl)-5-methyluracil (Clevudine) and 2',3'-didehydro-2',3'-dideoxythymidine in cells. Antimicrob Agents Chemother. 2005 May;49(5):2044-9. PubMed PMID: 15855530; PubMed Central PMCID: PMC1087619. 9: 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. 10: Seignères B, Pichoud C, Martin P, Furman P, Trépo C, Zoulim F. Inhibitory activity of dioxolane purine analogs on wild-type and lamivudine-resistant mutants of hepadnaviruses. Hepatology. 2002 Sep;36(3):710-22. PubMed PMID: 12198665. 11: Kocic I. Clevudine University of Georgia/Abbott/Bukwang/Triangle/Yale University. Curr Opin Investig Drugs. 2000 Nov;1(3):308-13. Review. PubMed PMID: 11249713. 12: Chu CK, Boudinot FD, Peek SF, Hong JH, Choi Y, Korba BE, Gerin JL, Cote PJ, Tennant BC, Cheng YC. Preclinical investigation of L-FMAU as an anti-hepatitis B virus agent. Antivir Ther. 1998;3(Suppl 3):113-21. Review. PubMed PMID: 10726061. 13: Liu SH, Grove KL, Cheng YC. Unique metabolism of a novel antiviral L-nucleoside analog, 2'-fluoro-5-methyl-beta-L-arabinofuranosyluracil: a substrate for both thymidine kinase and deoxycytidine kinase. Antimicrob Agents Chemother. 1998 Apr;42(4):833-9. PubMed PMID: 9559792; PubMed Central PMCID: PMC105551. 14: Aguesse-Germon S, Liu SH, Chevallier M, Pichoud C, Jamard C, Borel C, Chu CK, Trépo C, Cheng YC, Zoulim F. Inhibitory effect of 2'-fluoro-5-methyl-beta-L-arabinofuranosyl-uracil on duck hepatitis B virus replication. Antimicrob Agents Chemother. 1998 Feb;42(2):369-76. PubMed PMID: 9527788; PubMed Central PMCID: PMC105416. 15: Yao GQ, Liu SH, Chou E, Kukhanova M, Chu CK, Cheng YC. Inhibition of Epstein-Barr virus replication by a novel L-nucleoside, 2'-fluoro-5-methyl-beta-L-arabinofuranosyluracil. Biochem Pharmacol. 1996 Apr 12;51(7):941-7. PubMed PMID: 8651944. 16: Balakrishna Pai S, Liu SH, Zhu YL, Chu CK, Cheng YC. Inhibition of hepatitis B virus by a novel L-nucleoside, 2'-fluoro-5-methyl-beta-L-arabinofuranosyl uracil. Antimicrob Agents Chemother. 1996 Feb;40(2):380-6. PubMed PMID: 8834884; PubMed Central PMCID: PMC163120. 17: Cui L, Yoon S, Schinazi RF, Sommadossi JP. Cellular and molecular events leading to mitochondrial toxicity of 1-(2-deoxy-2-fluoro-1-beta-D-arabinofuranosyl)-5-iodouracil in human liver cells. J Clin Invest. 1995 Feb;95(2):555-63. PubMed PMID: 7860738; PubMed Central PMCID: PMC295512. 18: Mar EC, Chiou JF, Cheng YC, Huang ES. Human cytomegalovirus-induced DNA polymerase and its interaction with the triphosphates of 1-(2'-deoxy-2'-fluoro-beta-D-arabinofuranosyl)-5-methyluracil, -5-iodocytosine, and -5-methylcytosine. J Virol. 1985 Dec;56(3):846-51. PubMed PMID: 2999440; PubMed Central PMCID: PMC252656. 19: Coen DM, Fleming HE Jr, Leslie LK, Retondo MJ. Sensitivity of arabinosyladenine-resistant mutants of herpes simplex virus to other antiviral drugs and mapping of drug hypersensitivity mutations to the DNA polymerase locus. J Virol. 1985 Feb;53(2):477-88. PubMed PMID: 2982032; PubMed Central PMCID: PMC254660.