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MedKoo Cat#: 414054 | Name: Eprociclovir potassium

Description:

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

Eprociclovir potassium is a new acyclovir analogue and a potent inhibitor of EHV1 replication and may have potential for the treatment and/or prophylaxis of infections with this virus. Eprociclovir possess potent anti-herpetic activity against most human herpesviruses. A-5021 proved to be about 15-fold more potent than acyclovir in inhibiting viral replication. Eprociclovir inhibits murine herpetic keratitis. A-5021 eyedrops, which are easily applied onto the affected cornea, ameliorated clinical scores and suppressed virus growth. Eprociclovir is a promising alternative treatment of herpetic keratitis.

Chemical Structure

Eprociclovir potassium
Eprociclovir potassium
CAS#19657-37-1 (potassium)

Theoretical Analysis

MedKoo Cat#: 414054

Name: Eprociclovir potassium

CAS#: 19657-37-1 (potassium)

Chemical Formula: C11H14KN5O3

Exact Mass:

Molecular Weight: 303.36

Elemental Analysis: C, 43.55; H, 4.65; K, 12.89; N, 23.09; O, 15.82

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 #
219657-36-0 (sodium) 219657-37-1 (potassium) 635678-85-2 (dihydrate) 145512-85-2 (free base)
Synonym
Eprociclovir potassium; Eprociclovir monopotassium
IUPAC/Chemical Name
6H-Purin-6-one, 2-amino-9-(((1S,2R)-1,2-bis(hydroxymethyl)cyclopropyl)methyl)-1,9-dihydro-, monopotassium salt
InChi Key
USCJSMITHWAFOD-BJUCTQDSSA-N
InChi Code
InChI=1S/C11H14N5O3.K/c12-10-14-8-7(9(19)15-10)13-5-16(8)3-11(4-18)1-6(11)2-17;/h5-6,18H,1-4H2,(H3,12,14,15,19);/q-1;+1/t6-,11-;/m0./s1
SMILES Code
O=C1NC(N)=NC2=C1N=CN2C[C@@]3(CO)[C@H](C[O-])C3.[K+]
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
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

Preparing Stock Solutions

The following data is based on the product molecular weight 303.36 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.

Recalculate based on batch purity %
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: Glorieux S, Vandekerckhove AP, Goris N, Yang XY, Steukers L, Van de Walle GR, Croubels S, Neyts J, Nauwynck HJ. Evaluation of the antiviral activity of (1'S,2'R)-9-[[1',2'-bis(hydroxymethyl)cycloprop-1'-yl]methyl]guanine (A-5021) against equine herpesvirus type 1 in cell monolayers and equine nasal mucosal explants. Antiviral Res. 2012 Feb;93(2):234-8. doi: 10.1016/j.antiviral.2011.11.016. Epub 2011 Dec 8. PubMed PMID: 22178244. 2: Ostrowski T, Golankiewicz B, De Clercq E, Andrei G, Snoeck R. Synthesis and anti-VZV activity of 6-heteroaryl derivatives of tricyclic acyclovir and 9-{[cis-1',2'-bis(hydroxymethyl)cycloprop-1'-yl]methyl}guanine analogues. Eur J Med Chem. 2009 Aug;44(8):3313-7. doi: 10.1016/j.ejmech.2009.03.005. Epub 2009 Mar 21. PubMed PMID: 19339082. 3: Itahashi M, Higaki S, Sugahara D, Sugioka K, Deai T, Takao K, Hayashi K, Shimomura Y. A-5021: a new acyclovir analogue inhibits murine herpetic keratitis. Cornea. 2008 Apr;27(3):334-8. doi: 10.1097/ICO.0b013e31815d889b. PubMed PMID: 18362663. 4: De Clercq E, Naesens L. In search of effective anti-HHV-6 agents. J Clin Virol. 2006 Dec;37 Suppl 1:S82-6. Review. PubMed PMID: 17276375. 5: Golankiewicz B, Ostrowski T. Tricyclic nucleoside analogues as antiherpes agents. Antiviral Res. 2006 Sep;71(2-3):134-40. Epub 2006 May 30. Review. PubMed PMID: 16780965. 6: Ostrowski T, Golankiewicz B, De Clercq E, Balzarini J. Synthesis and biological activity of tricyclic analogues of 9-[[cis-1',2'-bis(hydroxymethyl)cycloprop-1'-yl]methyl]guanine. Bioorg Med Chem. 2006 May 15;14(10):3535-42. Epub 2006 Feb 2. PubMed PMID: 16458009. 7: Onishi T, Sekiyama T, Tsuji T. Synthesis of phosphonate analogues of the antiviral cyclopropane nucleoside A-5021. Nucleosides Nucleotides Nucleic Acids. 2005;24(8):1187-97. PubMed PMID: 16270661. 8: De Clercq E. Highlights in the development of new antiviral agents. Mini Rev Med Chem. 2002 Apr;2(2):163-75. Review. PubMed PMID: 12370077. 9: Naesens L, De Clercq E. Recent developments in herpesvirus therapy. Herpes. 2001 Mar;8(1):12-6. Review. PubMed PMID: 11867011. 10: Onishi T, Tsuji T. Synthesis of cyclobutane analogues of the antiviral cyclopropane nucleoside A-5021. Nucleosides Nucleotides Nucleic Acids. 2001 Dec;20(12):1941-8. PubMed PMID: 11794799. 11: De Clercq E, Naesens L, De Bolle L, Schols D, Zhang Y, Neyts J. Antiviral agents active against human herpesviruses HHV-6, HHV-7 and HHV-8. Rev Med Virol. 2001 Nov-Dec;11(6):381-95. Review. PubMed PMID: 11747000. 12: De Clercq E, Andrei G, Snoeck R, De Bolle L, Naesens L, Degrève B, Balzarini J, Zhang Y, Schols D, Leyssen P, Ying C, Neyts J. Acyclic/carbocyclic guanosine analogues as anti-herpesvirus agents. Nucleosides Nucleotides Nucleic Acids. 2001 Apr-Jul;20(4-7):271-85. Review. PubMed PMID: 11563039. 13: Neyts J, De Clercq E. The anti-herpesvirus activity of (1'S,2'R)-9-[[1',2'-bis(hydroxymethyl)-cycloprop-1'-yl]methyl]guanine is markedly potentiated by the immunosuppressive agent mycophenolate mofetil. Antiviral Res. 2001 Feb;49(2):121-7. PubMed PMID: 11248364. 14: Neyts J, Naesens L, Ying C, De Bolle L, De Clercq E. Anti-herpesvirus activity of (1'S,2'R)-9-[[1',2'-bis(hydroxymethyl)-cycloprop-1'-yl]methyl] x guanine (A-5021) in vitro and in vivo. Antiviral Res. 2001 Feb;49(2):115-20. PubMed PMID: 11248363. 15: De Clercq E. Guanosine analogues as anti-herpesvirus agents. Nucleosides Nucleotides Nucleic Acids. 2000 Oct-Dec;19(10-12):1531-41. PubMed PMID: 11200257. 16: Wadden TA, Berkowitz RI, Sarwer DB, Prus-Wisniewski R, Steinberg C. Benefits of lifestyle modification in the pharmacologic treatment of obesity: a randomized trial. Arch Intern Med. 2001 Jan 22;161(2):218-27. PubMed PMID: 11176735. 17: Hasegawa Y, Nishiyama Y, Imaizumi K, Ono N, Kinoshita T, Hatano S, Saito H, Shimokata K. Avoidance of bone marrow suppression using A-5021 as a nucleoside analog for retrovirus-mediated herpes simplex virus type I thymidine kinase gene therapy. Cancer Gene Ther. 2000 Apr;7(4):557-62. PubMed PMID: 10811473. 18: Iwayama S, Ohmura Y, Suzuki K, Ono N, Nakazawa H, Aoki M, Tanabe I, Sekiyama T, Tsuji T, Okunishi M, Yamanishi K, Nishiyama Y. Evaluation of anti-herpesvirus activity of (1'S,2'R)-9-[[1',2'-bis(hydroxymethyl)cycloprop-1'-yl]methyl]- guanine (A-5021) in mice. Antiviral Res. 1999 Jun;42(2):139-48. PubMed PMID: 10389656. 19: Ono N, Iwayama S, Suzuki K, Sekiyama T, Nakazawa H, Tsuji T, Okunishi M, Daikoku T, Nishiyama Y. Mode of action of (1'S,2'R)-9-[[1',2'-bis(hydroxymethyl) cycloprop-1'-yl]methyl]guanine (A-5021) against herpes simplex virus type 1 and type 2 and varicella-zoster virus. Antimicrob Agents Chemother. 1998 Aug;42(8):2095-102. PubMed PMID: 9687413; PubMed Central PMCID: PMC105870. 20: Iwayama S, Ono N, Ohmura Y, Suzuki K, Aoki M, Nakazawa H, Oikawa M, Kato T, Okunishi M, Nishiyama Y, Yamanishi K. Antiherpesvirus activities of (1'S,2'R)-9-[[1',2'-bis(hydroxymethyl)cycloprop-1'-yl]methyl]guanine (A-5021) in cell culture. Antimicrob Agents Chemother. 1998 Jul;42(7):1666-70. PubMed PMID: 9661001; PubMed Central PMCID: PMC105663.