Cyclic-HPMPC | CAS# 127757-45-3 | Prodrug for HPMPC

MedKoo Cat#: 412850 | Name: Cyclic-HPMPC

Description:

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

Cyclic-HPMPC is a prodrug for HPMPC.

Chemical Structure

Cyclic-HPMPC

CAS#127757-45-3

Theoretical Analysis

MedKoo Cat#: 412850

Name: Cyclic-HPMPC

CAS#: 127757-45-3

Chemical Formula: C8H12N3O5P

Exact Mass: 261.0515

Molecular Weight: 261.17

Elemental Analysis: C, 36.79; H, 4.63; N, 16.09; O, 30.63; P, 11.86

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 #

No Data

Synonym

Cyclic-HPMPC; GS930; GS-930; GS 930

IUPAC/Chemical Name

2(1H)-Pyrimidinone, 4-amino-1-((2-hydroxy-1,4,2-dioxaphosphorinan-5-yl)methyl)-, P-oxide, (S)-

InChi Key

YXQUGSXUDFTPLL-LURJTMIESA-N

InChi Code

InChI=1S/C8H12N3O5P/c9-7-1-2-11(8(12)10-7)3-6-4-16-17(13,14)5-15-6/h1-2,6H,3-5H2,(H,13,14)(H2,9,10,12)/t6-/m0/s1

SMILES Code

O=C1N=C(N)C=CN1C[C@@H]2OCP(OC2)(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

>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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 261.17 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

1: Cundy KC, Bidgood AM, Lynch G, Shaw JP, Griffin L, Lee WA. Pharmacokinetics, bioavailability, metabolism, and tissue distribution of cidofovir (HPMPC) and cyclic HPMPC in rats. Drug Metab Dispos. 1996 Jul;24(7):745-52. PMID: 8818571. 2: Smee DF, Bailey KW, Sidwell RW. Comparative effects of cidofovir and cyclic HPMPC on lethal cowpox and vaccinia virus respiratory infections in mice. Chemotherapy. 2003 Jun;49(3):126-31. doi: 10.1159/000070618. PMID: 12815205. 3: Oliyai R, Shaw JP, Sueoka-Lennen CM, Cundy KC, Arimilli MN, Jones RJ, Lee WA. Aryl ester prodrugs of cyclic HPMPC. I: Physicochemical characterization and in vitro biological stability. Pharm Res. 1999 Nov;16(11):1687-93. doi: 10.1023/a:1018945713623. PMID: 10571273. 4: Oliyai R, Arimilli MN, Jones RJ, Lee WA. Pharmacokinetics of salicylate ester prodrugs of cyclic HPMPC in dogs. Nucleosides Nucleotides Nucleic Acids. 2001 Apr-Jul;20(4-7):1411-4. doi: 10.1081/NCN-100002566. PMID: 11563033. 5: Cundy KC, Lynch G, Shaw JP, Hitchcock MJ, Lee WA. Distribution and metabolism of intravitreal cidofovir and cyclic HPMPC in rabbits. Curr Eye Res. 1996 May;15(5):569-76. doi: 10.3109/02713689609000768. PMID: 8670758. 6: Cundy KC, Barditch-Crovo P, Petty BG, Ruby A, Redpath M, Jaffe HS, Lietman PS. Clinical pharmacokinetics of 1-[((S)-2-hydroxy-2-oxo-1,4,2-dioxaphosphorinan-5-yl)methyl]cytosine in human immunodeficiency virus-infected patients. Antimicrob Agents Chemother. 1999 Feb;43(2):271-7. doi: 10.1128/AAC.43.2.271. PMID: 9925517; PMCID: PMC89062. 7: Peterson LW, Sala-Rabanal M, Krylov IS, Serpi M, Kashemirov BA, McKenna CE. Serine side chain-linked peptidomimetic conjugates of cyclic HPMPC and HPMPA: synthesis and interaction with hPEPT1. Mol Pharm. 2010 Dec 6;7(6):2349-61. doi: 10.1021/mp100186b. Epub 2010 Oct 7. PMID: 20929265; PMCID: PMC3205993. 8: Banker AS, De Clercq E, Taskintuna I, Keefe KS, Bergeron-Lynn G, Freeman WR. Influence of intravitreal injections of HPMPC and related nucleoside analogues on intraocular pressure in guinea pig eyes. Invest Ophthalmol Vis Sci. 1998 Jun;39(7):1233-42. PMID: 9620084. 9: Coen N, Duraffour S, Naesens L, Krecmerová M, Van den Oord J, Snoeck R, Andrei G. Evaluation of novel acyclic nucleoside phosphonates against human and animal gammaherpesviruses revealed an altered metabolism of cyclic prodrugs upon Epstein-Barr virus reactivation in P3HR-1 cells. J Virol. 2013 Nov;87(22):12422-32. doi: 10.1128/JVI.02231-13. Epub 2013 Sep 11. PMID: 24027315; PMCID: PMC3807898. 10: Bravo FJ, Cardin RD, Bernstein DI. Effect of maternal treatment with cyclic HPMPC in the guinea pig model of congenital cytomegalovirus infection. J Infect Dis. 2006 Feb 15;193(4):591-7. doi: 10.1086/499603. Epub 2006 Jan 13. PMID: 16425139.