(S)-HPMPA | CAS#92999-29-6 | antiviral

MedKoo Cat#: 130186 | Name: (S)-HPMPA

Description:

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

(S)-HPMPA is a potent antiviral. In one study, (S)-HPMPA that was administered orally was found to be ineffective in treating murine CMV.

Chemical Structure

(S)-HPMPA

CAS#92999-29-6

Theoretical Analysis

MedKoo Cat#: 130186

Name: (S)-HPMPA

CAS#: 92999-29-6

Chemical Formula: C9H14N5O5P

Exact Mass: 303.0733

Molecular Weight: 303.21

Elemental Analysis: C, 35.65; H, 4.65; N, 23.10; O, 26.38; P, 10.22

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.

Bulk Inquiry

Related CAS #

No Data

Synonym

(S)-HPMPA; HPMPA; (S) HPMPA

IUPAC/Chemical Name

(S)-(((1-(6-amino-9H-purin-9-yl)-3-hydroxypropan-2-yl)oxy)methyl)phosphonic acid

InChi Key

FRPXSOOHWNMLPH-LURJTMIESA-N

InChi Code

InChI=1S/C9H14N5O5P/c10-8-7-9(12-3-11-8)14(4-13-7)1-6(2-15)19-5-20(16,17)18/h3-4,6,15H,1-2,5H2,(H2,10,11,12)(H2,16,17,18)/t6-/m0/s1

SMILES Code

OP(CO[C@H](CO)CN1C=NC2=C(N)N=CN=C12)(O)=O

Appearance

To be determined

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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 303.21 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. Kumar RK, Sanghvi YS, Reddy PY, Banerjee S. An Improved Scalable Synthesis of the Potent Antiviral (S)-HPMPA. Curr Protoc. 2022 Nov;2(11):e602. doi: 10.1002/cpz1.602. PMID: 36440983. 2. Quenelle DC, Collins DJ, Pettway LR, Hartline CB, Beadle JR, Wan WB, Hostetler KY, Kern ER. Effect of oral treatment with (S)-HPMPA, HDP-(S)-HPMPA or ODE-(S)-HPMPA on replication of murine cytomegalovirus (MCMV) or human cytomegalovirus (HCMV) in animal models. Antiviral Res. 2008 Aug;79(2):133-5. doi: 10.1016/j.antiviral.2008.01.155. Epub 2008 Feb 22. PMID: 18336926; PMCID: PMC2650230. 3. Quenelle DC, Collins DJ, Herrod BP, Keith KA, Trahan J, Beadle JR, Hostetler KY, Kern ER. Effect of oral treatment with hexadecyloxypropyl-[(S)-9-(3-hydroxy-2- phosphonylmethoxypropyl)adenine] [(S)-HPMPA] or octadecyloxyethyl-(S)-HPMPA on cowpox or vaccinia virus infections in mice. Antimicrob Agents Chemother. 2007 Nov;51(11):3940-7. doi: 10.1128/AAC.00184-07. Epub 2007 Sep 10. PMID: 17846137; PMCID: PMC2151427. 4. Beadle JR. Synthesis of cidofovir and (S)-HPMPA ether lipid prodrugs. Curr Protoc Nucleic Acid Chem. 2007 Jun;Chapter 15:Unit 15.2. doi: 10.1002/0471142700.nc1502s29. PMID: 18428972. 5. Gordon YJ, Romanowski E, Araullo-Cruz T, Seaberg L, Erzurum S, Tolman R, De Clercq E. Inhibitory effect of (S)-HPMPC, (S)-HPMPA, and 2'-nor-cyclic GMP on clinical ocular adenoviral isolates is serotype-dependent in vitro. Antiviral Res. 1991 Jul;16(1):11-6. doi: 10.1016/0166-3542(91)90054-u. PMID: 1776874. 6. Kaminsky R, Schmid C, Grether Y, Holý A, DeClercq E, Naesens L, Brun R. (S)-9-(3-hydroxy-2-phosphonylmethoxypropyl)adenine [(S)-HPMPA]: a purine analogue with trypanocidal activity in vitro and in vivo. Trop Med Int Health. 1996 Apr;1(2):255-63. doi: 10.1111/j.1365-3156.1996.tb00036.x. PMID: 8665394. 7. Zakharova VM, Serpi M, Krylov IS, Peterson LW, Breitenbach JM, Borysko KZ, Drach JC, Collins M, Hilfinger JM, Kashemirov BA, McKenna CE. Tyrosine-based 1-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]cytosine and -adenine ((S)-HPMPC and (S)-HPMPA) prodrugs: synthesis, stability, antiviral activity, and in vivo transport studies. J Med Chem. 2011 Aug 25;54(16):5680-93. doi: 10.1021/jm2001426. Epub 2011 Aug 3. PMID: 21812420; PMCID: PMC3166236. 8. Maudgal PC, De Clercq E, Huyghe P. Efficacy of (S)-HPMPA against thymidine kinase-deficient herpes simplex virus-keratitis. Invest Ophthalmol Vis Sci. 1987 Feb;28(2):243-8. PMID: 8591903. 9. Kaminsky R, Nickel B, Holý A. Arrest of Trypanosoma brucei rhodesiense and T. brucei brucei in the S-phase of the cell cycle by (S)-9-(3-hydroxy-2-phosphonylmethoxypropyl)adenine ((S)-HPMPA). Mol Biochem Parasitol. 1998 May 15;93(1):91-100. doi: 10.1016/s0166-6851(98)00023-1. PMID: 9662031. 10. Dal Pozzo F, Andrei G, Lebeau I, Beadle JR, Hostetler KY, De Clercq E, Snoeck R. In vitro evaluation of the anti-orf virus activity of alkoxyalkyl esters of CDV, cCDV and (S)-HPMPA. Antiviral Res. 2007 Jul;75(1):52-7. doi: 10.1016/j.antiviral.2006.11.010. Epub 2006 Dec 13. PMID: 17184854.