Netivudine | CAS#84558-93-0 | antiviral

MedKoo Cat#: 584840 | Name: Netivudine

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Description:

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

Netivudine is an inhibitor of varicella zoster virus.

Chemical Structure

Netivudine

CAS#84558-93-0

Theoretical Analysis

MedKoo Cat#: 584840

Name: Netivudine

CAS#: 84558-93-0

Chemical Formula: C12H14N2O6

Exact Mass: 282.0852

Molecular Weight: 282.25

Elemental Analysis: C, 51.07; H, 5.00; N, 9.93; O, 34.01

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Related CAS #

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Synonym

Netivudine; 882C87; BW882C87; BW-882C87; BW 882C87; DRG 0179; DRG-0179; DRG0179;

IUPAC/Chemical Name

2,4(1H,3H)-Pyrimidinedione, 1-beta-D-arabinofuranosyl-5-(1-propynyl)-

InChi Key

QLOCVMVCRJOTTM-SDNRWEOFSA-N

InChi Code

InChI=1S/C12H14N2O6/c1-2-3-6-4-14(12(19)13-10(6)18)11-9(17)8(16)7(5-15)20-11/h4,7-9,11,15-17H,5H2,1H3,(H,13,18,19)/t7-,8-,9+,11-/m1/s1

SMILES Code

O=C1NC(C(C#CC)=CN1[C@H]2[C@H]([C@@H]([C@@H](CO)O2)O)O)=O

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

>3 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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Netivudine is a nucleoside analogue with potent anti-varicella zoster virus activity.

In vitro activity:

TBD

In vivo activity:

TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 282.25 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

Formulation protocol:

TBD

In vitro protocol:

TBD

In vivo protocol:

TBD

1: Söltz-Szöts J, Tyring S, Andersen PL, Lucht RF, McKendrick MW, Diaz Perez JL, Shukla S, Fiddian AP. A randomized controlled trial of acyclovir versus netivudine for treatment of herpes zoster. International Zoster Study Group. J Antimicrob Chemother. 1998 May;41(5):549-56. PubMed PMID: 9630408. 2: Peck R, Wiggs R, Callaghan J, Wootton R, Crome P, Fraser I, Frick L, Posner J. Inhibition of dihydropyrimidine dehydrogenase by 5-propynyluracil, a metabolite of the anti-varicella zoster virus agent netivudine. Clin Pharmacol Ther. 1996 Jan;59(1):22-31. PubMed PMID: 8549030. 3: McGuigan C, Perry A, Yarnold CJ, Sutton PW, Lowe D, Miller W, Rahim SG, Slater MJ. Synthesis and evaluation of some masked phosphate esters of the anti-herpesvirus drug 882C (netivudine) as potential antiviral agents. Antivir Chem Chemother. 1998 May;9(3):233-43. PubMed PMID: 9875402. 4: Fillastre JP, Godin M, Legallicier B, Chretien P, Bidault R, Gillotin C, Wooton R, Posner J, Peck RW. Pharmacokinetics of netivudine, a potent anti-varicella zoster virus drug, in patients with renal impairment. J Antimicrob Chemother. 1996 May;37(5):965-74. PubMed PMID: 8737146. 5: Le Roy F, Godin M, Legallicler B, Fillastre JP, Bidault R, Posner J, Peck RW. Pharmacokinetics of netivudine in haemodialysis patients. J Antimicrob Chemother. 1996 Nov;38(5):913-5. PubMed PMID: 8961067. 6: Peck RW, Crome P, Wood MJ, McKendrick MW, Bannister B, Mandal BK, Crooks RJ. Multiple dose netivudine, a potent anti-varicella zoster virus agent, in healthy elderly volunteers and patients with shingles. J Antimicrob Chemother. 1996 Mar;37(3):583-97. PubMed PMID: 9182115. 7: Snoeck R, Andrei G, De Clercq E. Current pharmacological approaches to the therapy of varicella zoster virus infections: a guide to treatment. Drugs. 1999 Feb;57(2):187-206. Review. PubMed PMID: 10188760. 8: Purifoy DJ, Beauchamp LM, de Miranda P, Ertl P, Lacey S, Roberts G, Rahim SG, Darby G, Krenitsky TA, Powell KL. Review of research leading to new anti-herpesvirus agents in clinical development: valaciclovir hydrochloride (256U, the L-valyl ester of acyclovir) and 882C, a specific agent for varicella zoster virus. J Med Virol. 1993;Suppl 1:139-45. Review. PubMed PMID: 8245881. 9: Wood MJ, McKendrick MW, Bannister B, Mandal BK, Peck RW, Crooks RJ. Preliminary pharmacokinetics and safety of 882C87 in patients with herpes zoster. J Med Virol. 1993;Suppl 1:154-7. PubMed PMID: 8245884. 10: Buick AR, Sheung CT. Determination of 1-(beta-D-arabinofuranosyl)-5-(1-propynyl)-uracil and a metabolite, 5-propynyluracil, in plasma using ASTED (automated sequential trace enrichment of dialysates) combined, on-line, with high-performance liquid chromatography. J Chromatogr. 1993 Jul 23;617(1):65-70. PubMed PMID: 8376539. 11: Darby G. Acyclovir--and beyond. J Int Med Res. 1994;22 Suppl 1:33A-42A. Review. PubMed PMID: 8063023. 12: Fiddian AP. Antiviral drugs in development for herpes zoster. Scand J Infect Dis Suppl. 1996;100:51-4. Review. PubMed PMID: 9163026. 13: Nikkels AF, Piérard GE. Recognition and treatment of shingles. Drugs. 1994 Oct;48(4):528-48. Review. PubMed PMID: 7528128. 14: Wareham D. Postherpetic neuralgia. Clin Evid. 2005 Dec;(14):1017-25. Review. PubMed PMID: 16620445. 15: Wareham D. Postherpetic neuralgia. Clin Evid. 2004 Dec;(12):1182-93. Review. Update in: Clin Evid. 2005 Dec;(14):1017-25. PubMed PMID: 15865712. 16: Easterbrook P, Wood MJ. Successors to acyclovir. J Antimicrob Chemother. 1994 Sep;34(3):307-11. Review. PubMed PMID: 7829405. 17: Cooper JD, Sheung CT, Buick AR. Automated sequential trace enrichment of dialysates combined with high-performance liquid chromatography and automated heart-cutting for the determination of the nucleoside 1-(beta-D-arabinofuranosyl)-5-(1-propynyl)uracil and its metabolite 5-propynyluracil in urine. J Chromatogr. 1994 Jan 14;652(1):15-21. PubMed PMID: 8014223. 18: Peck RW, Wootton R, Lee DR, Jackson SH, Posner J. The bioavailability and disposition of 1-(beta-D-arabinofuranosyl)-5-(1-propynyl)uracil (882C87), a potent, new anti-varicella zoster virus agent. Br J Clin Pharmacol. 1995 Feb;39(2):143-9. PubMed PMID: 7742152; PubMed Central PMCID: PMC1364951. 19: Peck RW, Weatherley BC, Wootton R, Crome P, Holdich TA, Posner J. Pharmacokinetics and tolerability of single oral doses of 882C87, a potent, new anti-varicella-zoster virus agent, in healthy volunteers. Antimicrob Agents Chemother. 1995 Jan;39(1):20-7. PubMed PMID: 7695306; PubMed Central PMCID: PMC162478. 20: Lacey SF, Suzutani T, Powell KL, Purifoy DJ, Honess RW. Analysis of mutations in the thymidine kinase genes of drug-resistant varicella-zoster virus populations using the polymerase chain reaction. J Gen Virol. 1991 Mar;72 ( Pt 3):623-30. PubMed PMID: 1848597.