Netivudine
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MedKoo CAT#: 584840

CAS#: 84558-93-0

Description: Netivudine is an inhibitor of varicella zoster virus.


Price and Availability

Size Price Shipping out time Quantity
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Pricing updated 2020-10-29. Prices are subject to change without notice.

Netivudine 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#: 584840
Name: Netivudine
CAS#: 84558-93-0
Chemical Formula: C12H14N2O6
Exact Mass: 282.0852
Molecular Weight: 282.252
Elemental Analysis: C, 51.07; H, 5.00; N, 9.93; O, 34.01


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


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:
>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


References

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.