Acyclovir monophosphate

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

MedKoo CAT#: 317158

CAS#: 66341-16-0

Description: Acyclovir monophosphate is the monophosphate ester of Acyclovir. Acyclovir is an antiviral agent with activity against herpes simplex virus types 1 and 2 (HSV-1 and HSV-2) and varicella zoster virus. Acyclovir is converted by a herpesvirus enzyme into acyclovir triphosphate that inhibits the synthesis of deoxyribonucleic acid (DNA) molecules in the virally infected cells, thereby inhibiting viral replication. It induces apoptosis in cells transfected with HSV-TK (suicidal gene therapy).


Chemical Structure

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Acyclovir monophosphate
CAS# 66341-16-0

Theoretical Analysis

MedKoo Cat#: 317158
Name: Acyclovir monophosphate
CAS#: 66341-16-0
Chemical Formula: C8H12N5O6
Exact Mass: 305.0525
Molecular Weight: 305.1868
Elemental Analysis: C, 31.48; H, 3.96; N, 22.95; O, 31.45; P, 10.15

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Pricing updated 2021-02-28. Prices are subject to change without notice.

Acyclovir monophosphate, purity > 98%, is out of stock. Price will be listed after it is in stock.

Synonym: Acyclovir monophosphate; Acyclo-GMP.

IUPAC/Chemical Name: 6H-Purin-6-one, 2-amino-1,9-dihydro-9-((2-(phosphonooxy)ethoxy)methyl)-

InChi Key: KUOAJOVOKFATQE-UHFFFAOYSA-N

InChi Code: InChI=1S/C8H12N5O6P/c9-8-11-6-5(7(14)12-8)10-3-13(6)4-18-1-2-19-20(15,16)17/h3H,1-2,4H2,(H2,15,16,17)(H3,9,11,12,14)

SMILES Code: O=C1NC(N)=NC2=C1N=CN2COCCOP(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, not in water

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

Handling Instructions:

Preparing Stock Solutions

The following data is based on the product molecular weight 305.1868 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.

Select a batch to recalculate based on the batch molecular weight:
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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1: Yao J, Zhang Y, Ramishetti S, Wang Y, Huang L. Turning an antiviral into an anticancer drug: nanoparticle delivery of acyclovir monophosphate. J Control Release. 2013 Sep 28;170(3):414-20. doi: 10.1016/j.jconrel.2013.06.009. Epub 2013 Jun 18. PubMed PMID: 23791977; PubMed Central PMCID: PMC3742590.

2: Ensign LM, Tang BC, Wang YY, Tse TA, Hoen T, Cone R, Hanes J. Mucus-penetrating nanoparticles for vaginal drug delivery protect against herpes simplex virus. Sci Transl Med. 2012 Jun 13;4(138):138ra79. doi: 10.1126/scitranslmed.3003453. PubMed PMID: 22700955; PubMed Central PMCID: PMC3817739.

3: Zahn KE, Tchesnokov EP, Götte M, Doublié S. Phosphonoformic acid inhibits viral replication by trapping the closed form of the DNA polymerase. J Biol Chem. 2011 Jul 15;286(28):25246-55. doi: 10.1074/jbc.M111.248864. Epub 2011 May 12. PubMed PMID: 21566148; PubMed Central PMCID: PMC3137095.

4: McMahon MA, Parsons TL, Shen L, Siliciano JD, Siliciano RF. Consistent inhibition of HIV-1 replication in CD4+ T cells by acyclovir without detection of human herpesviruses. J Virol. 2011 May;85(9):4618-22. doi: 10.1128/JVI.02423-10. Epub 2011 Feb 16. PubMed PMID: 21325417; PubMed Central PMCID: PMC3126274.

5: Skoblov YS, Karpenko IL, Jasko MV, Kukhanova MK, Andronova VL, Galegov GA, Sidorov GV, Myasoedov NF. Cell metabolism of acyclovir phosphonate derivatives and antiherpesvirus activity of their combinations with alpha2-interferon. Chem Biol Drug Des. 2007 Jun;69(6):429-34. PubMed PMID: 17581237.

6: Hostetler KY, Beadle JR, Hornbuckle WE, Bellezza CA, Tochkov IA, Cote PJ, Gerin JL, Korba BE, Tennant BC. Antiviral activities of oral 1-O-hexadecylpropanediol-3-phosphoacyclovir and acyclovir in woodchucks with chronic woodchuck hepatitis virus infection. Antimicrob Agents Chemother. 2000 Jul;44(7):1964-9. PubMed PMID: 10858362; PubMed Central PMCID: PMC89993.

7: Kern ER, Palmer J, Szczech G, Painter G, Hostetler KY. Efficacy of topical acyclovir monophosphate, acyclovir, or penciclovir in orofacial HSV-1 infections of mice and genital HSV-2 infections of guinea pigs. Nucleosides Nucleotides Nucleic Acids. 2000 Jan-Feb;19(1-2):501-13. PubMed PMID: 10772730.

8: Yedidag EN, Koffron AJ, Mueller KH, Kaplan B, Kaufman DB, Fryer JP, Stuart FP, Abecassis M. Acyclovir triphosphate inhibits the diagnostic polymerase chain reaction for cytomegalovirus. Transplantation. 1996 Jul 27;62(2):238-42. PubMed PMID: 8755822.

9: Pottage JC Jr, Kessler HA. Herpes simplex virus resistance to acyclovir: clinical relevance. Infect Agents Dis. 1995 Sep;4(3):115-24. Review. PubMed PMID: 8548189.

10: Hostetler KY, Parker S, Sridhar CN, Martin MJ, Li JL, Stuhmiller LM, van Wijk GM, van den Bosch H, Gardner MF, Aldern KA, et al. Acyclovir diphosphate dimyristoylglycerol: a phospholipid prodrug with activity against acyclovir-resistant herpes simplex virus. Proc Natl Acad Sci U S A. 1993 Dec 15;90(24):11835-9. PubMed PMID: 8265634; PubMed Central PMCID: PMC48079.

11: Ponzetto A, Fiume L, Forzani B, Song SY, Busi C, Mattioli A, Spinelli C, Marinelli M, Smedile A, Chiaberge E, et al. Adenine arabinoside monophosphate and acyclovir monophosphate coupled to lactosaminated albumin reduce woodchuck hepatitis virus viremia at doses lower than do the unconjugated drugs. Hepatology. 1991 Jul;14(1):16-24. PubMed PMID: 1712338.

12: Reardon JE. Herpes simplex virus type 1 DNA polymerase. Mechanism-based affinity chromatography. J Biol Chem. 1990 May 5;265(13):7112-5. PubMed PMID: 2158986.

13: Rathschuler F, Lai S, Ghiglione D, Rossi P, Ciurlo G. A new therapeutical approach to central serous retinopathy, a hypothesis. Int Ophthalmol. 1990 Mar;14(2):125-9. PubMed PMID: 2338384.

14: Reardon JE. Herpes simplex virus type 1 and human DNA polymerase interactions with 2'-deoxyguanosine 5'-triphosphate analogues. Kinetics of incorporation into DNA and induction of inhibition. J Biol Chem. 1989 Nov 15;264(32):19039-44. PubMed PMID: 2553730.

15: Reardon JE, Spector T. Herpes simplex virus type 1 DNA polymerase. Mechanism of inhibition by acyclovir triphosphate. J Biol Chem. 1989 May 5;264(13):7405-11. PubMed PMID: 2540193.

16: Fiume L, Busi C, Mattioli A, Spinelli C, Spinosa G, Bongini A. A conjugate of acyclovir monophosphate with lactosaminated albumin releases the phosphorylated drug in liver cells. Naturwissenschaften. 1989 Feb;76(2):74-6. PubMed PMID: 2725686.

17: King DH. History, pharmacokinetics, and pharmacology of acyclovir. J Am Acad Dermatol. 1988 Jan;18(1 Pt 2):176-9. PubMed PMID: 2828440.

18: Fiume L, Bassi B, Busi C, Mattioli A, Spinosa G, Faulstich H. Galactosylated poly(L-lysine) as a hepatotropic carrier of 9-beta-D-arabinofuranosyladenine 5'-monophosphate. FEBS Lett. 1986 Jul 28;203(2):203-6. PubMed PMID: 2426140.

19: Labenz J, Müller WE, Falke D. Inhibition of the herpes simplex virus-coded thymidine kinase-complex by 9-beta-D-arabinofuranosyladenine 5'-monophosphate (ara-AMP) and 9-(2-hydroxyethoxymethyl)guanine-monophosphate (acyclo-GMP). Arch Virol. 1984;81(3-4):205-12. PubMed PMID: 6206825.

20: Tuttle JV, Krenitsky TA, Elion GB. Effects of acyclovir and its metabolites on hypoxanthine-guanine phosphoribosyltransferase. Biochem Pharmacol. 1983 Oct 15;32(20):3011-5. PubMed PMID: 6639669.