Racivir

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

MedKoo CAT#: 328092

CAS#: 143491-54-7

Description: Racivir, also known as PSI-5004; (±)-FTC; RCV, 524W91, is a reverse transcriptase inhibitor potentially for the treatment of HIV infection. 524W91 was anabolized to the active 5'-triphosphate in these cells. HBV replication was equally inhibited in cultures incubated with 524W91 when the drug was added 24 h preinfection, at infection, or 24 h postinfection. 524W91 inhibited HBV replication by 50% at less than 20 nM in human hepatocytes.


Price and Availability

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Racivir is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 328092
Name: Racivir
CAS#: 143491-54-7
Chemical Formula: C8H10FN3O3S
Exact Mass: 247.0427
Molecular Weight: 247.2444
Elemental Analysis: C, 38.86; H, 4.08; F, 7.68; N, 17.00; O, 19.41; S, 12.97


Synonym: Racivir; PSI-5004; PSI5004; PSI5004; (±)-FTC; RCV; 24W91; BW 524W91.

IUPAC/Chemical Name: 4-amino-5-fluoro-1-((2S,5R)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one

SMILES Code: O=C1N=C(N)C(F)=CN1[C@H]2CS[C@@H](CO)O2


Technical Data

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).

Harmonized System Code:
293490


References

1: Amancha PK, Hong JJ, Rogers K, Ansari AA, Villinger F. In vivo blockade of the programmed cell death-1 pathway using soluble recombinant PD-1-Fc enhances CD4+ and CD8+ T cell responses but has limited clinical benefit. J Immunol. 2013 Dec 15;191(12):6060-70. doi: 10.4049/jimmunol.1302044. PubMed PMID: 24227774; PubMed Central PMCID: PMC3858463.

2: Ghosh RK, Ghosh SM, Chawla S. Recent advances in antiretroviral drugs. Expert Opin Pharmacother. 2011 Jan;12(1):31-46. doi: 10.1517/14656566.2010.509345. Review. PubMed PMID: 20698725.

3: Kohler JJ, Hosseini SH, Cucoranu I, Zhelyabovska O, Green E, Ivey K, Abuin A, Fields E, Hoying A, Russ R, Santoianni R, Raper CM, Yang Q, Lavie A, Lewis W. Transgenic cardiac-targeted overexpression of human thymidylate kinase. Lab Invest. 2010 Mar;90(3):383-90. doi: 10.1038/labinvest.2009.146. PubMed PMID: 20065942; PubMed Central PMCID: PMC2829097.

4: Verhoeven D, Sankaran S, Dandekar S. Simian immunodeficiency virus infection induces severe loss of intestinal central memory T cells which impairs CD4+ T-cell restoration during antiretroviral therapy. J Med Primatol. 2007 Aug;36(4-5):219-27. PubMed PMID: 17669210.

5: Waters L, Nelson MR. New drugs. HIV Med. 2005 Jul;6(4):225-31. Review. PubMed PMID: 16011526.

6: Herzmann C, Arastèh K, Murphy RL, Schulbin H, Kreckel P, Drauz D, Schinazi RF, Beard A, Cartee L, Otto MJ. Safety, pharmacokinetics, and efficacy of (+/-)-beta-2',3'-dideoxy-5-fluoro-3'-thiacytidine with efavirenz and stavudine in antiretroviral-naïve human immunodeficiency virus-infected patients. Antimicrob Agents Chemother. 2005 Jul;49(7):2828-33. PubMed PMID: 15980356; PubMed Central PMCID: PMC1168662.

7: Hurwitz SJ, Otto MJ, Schinazi RF. Comparative pharmacokinetics of Racivir, (+/-)-beta-2',3'-dideoxy-5-fluoro-3'-thiacytidine in rats, rabbits, dogs, monkeys and HIV-infected humans. Antivir Chem Chemother. 2005;16(2):117-27. PubMed PMID: 15889534.

8: Carruth LM, Zink MC, Tarwater PM, Miller MD, Li M, Queen LA, Mankowski JL, Shen A, Siliciano RF, Clements JE. SIV-specific T lymphocyte responses in PBMC and lymphoid tissues of SIV-infected pigtailed macaques during suppressive combination antiretroviral therapy. J Med Primatol. 2005 Jun;34(3):109-21. PubMed PMID: 15860119.

9: 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.

10: Ono SK, Kato N, Shiratori Y, Kato J, Goto T, Schinazi RF, Carrilho FJ, Omata M. The polymerase L528M mutation cooperates with nucleotide binding-site mutations, increasing hepatitis B virus replication and drug resistance. J Clin Invest. 2001 Feb;107(4):449-55. PubMed PMID: 11181644; PubMed Central PMCID: PMC199250.

11: Chan HL, Leung NW, Lau TC, Wong ML, Sung JJ. Comparison of three different sensitive assays for hepatitis B virus DNA in monitoring of responses to antiviral therapy. J Clin Microbiol. 2000 Sep;38(9):3205-8. PubMed PMID: 10970358; PubMed Central PMCID: PMC87356.

12: Feng JY, Shi J, Schinazi RF, Anderson KS. Mechanistic studies show that (-)-FTC-TP is a better inhibitor of HIV-1 reverse transcriptase than 3TC-TP. FASEB J. 1999 Sep;13(12):1511-7. PubMed PMID: 10463941.

13: Moraleda G, Saputelli J, Aldrich CE, Averett D, Condreay L, Mason WS. Lack of effect of antiviral therapy in nondividing hepatocyte cultures on the closed circular DNA of woodchuck hepatitis virus. J Virol. 1997 Dec;71(12):9392-9. PubMed PMID: 9371599; PubMed Central PMCID: PMC230243.

14: Cullen JM, Smith SL, Davis MG, Dunn SE, Botteron C, Cecchi A, Linsey D, Linzey D, Frick L, Paff MT, Goulding A, Biron K. In vivo antiviral activity and pharmacokinetics of (-)-cis-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine in woodchuck hepatitis virus-infected woodchucks. Antimicrob Agents Chemother. 1997 Oct;41(10):2076-82. PubMed PMID: 9333028; PubMed Central PMCID: PMC164073.

15: Smith RA, Remington KM, Lloyd RM Jr, Schinazi RF, North TW. A novel Met-to-Thr mutation in the YMDD motif of reverse transcriptase from feline immunodeficiency virus confers resistance to oxathiolane nucleosides. J Virol. 1997 Mar;71(3):2357-62. PubMed PMID: 9032372; PubMed Central PMCID: PMC191345.

16: Davis MG, Wilson JE, VanDraanen NA, Miller WH, Freeman GA, Daluge SM, Boyd FL, Aulabaugh AE, Painter GR, Boone LR. DNA polymerase activity of hepatitis B virus particles: differential inhibition by L-enantiomers of nucleotide analogs. Antiviral Res. 1996 May;30(2-3):133-45. PubMed PMID: 8783805.

17: Shockcor JP, Wurm RM, Frick LW, Sanderson PN, Farrant RD, Sweatman BC, Lindon JC. Hplc-nmr identification of the human urinary metabolites of (-)-cis-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl] cytosine, a nucleoside analogue active against human immunodeficiency virus (HIV). Xenobiotica. 1996 Feb;26(2):189-99. PubMed PMID: 8868002.

18: Condreay LD, Condreay JP, Jansen RW, Paff MT, Averett DR. (-)-cis-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine (524W91) inhibits hepatitis B virus replication in primary human hepatocytes. Antimicrob Agents Chemother. 1996 Feb;40(2):520-3. PubMed PMID: 8834915; PubMed Central PMCID: PMC163151.

19: Fourel I, Cullen JM, Saputelli J, Aldrich CE, Schaffer P, Averett DR, Pugh J, Mason WS. Evidence that hepatocyte turnover is required for rapid clearance of duck hepatitis B virus during antiviral therapy of chronically infected ducks. J Virol. 1994 Dec;68(12):8321-30. PubMed PMID: 7966625; PubMed Central PMCID: PMC237301.

20: Frick LW, Lambe CU, St John L, Taylor LC, Nelson DJ. Pharmacokinetics, oral bioavailability, and metabolism in mice and cynomolgus monkeys of (2'R,5'S-)-cis-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl] cytosine, an agent active against human immunodeficiency virus and human hepatitis B virus. Antimicrob Agents Chemother. 1994 Dec;38(12):2722-9. PubMed PMID: 7695253; PubMed Central PMCID: PMC188276.