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MedKoo Cat#: 326767 | Name: Fiacitabine
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Description:

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

Fiacitabine, also known as FIAC or DRG-0077, is a pyrimidine nucleoside analog reported to elicit potent anti-VZV activity both in vitro and in vivo. Fiacitabine has potent antiviral activity in vivo against herpes simplex virus types 1 and 2 and cytomegalovirus. Fiacitabine is therapeutically superior to ara-A for the treatment of varicella-zoster virus infections in immunosuppressed subjects.

Chemical Structure

Fiacitabine
Fiacitabine
CAS#69123-90-6

Theoretical Analysis

MedKoo Cat#: 326767

Name: Fiacitabine

CAS#: 69123-90-6

Chemical Formula: C9H11FIN3O4

Exact Mass: 370.9778

Molecular Weight: 371.11

Elemental Analysis: C, 29.13; H, 2.99; F, 5.12; I, 34.20; N, 11.32; O, 17.24

Price and Availability

Size Price Availability Quantity
5mg USD 750.00 2 Weeks
10mg USD 1,250.00 2 Weeks
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Related CAS #
No Data
Synonym
Fiacitabine; Fiacitabina; Fluoroiodoaracytidine; Fluorviodoaracytidine; Fiacitabinum; FIAC; FOAC; NSC 382097; NSC382097; NSC-382097;
IUPAC/Chemical Name
4-amino-1-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-iodopyrimidin-2(1H)-one
InChi Key
GIMSJJHKKXRFGV-BYPJNBLXSA-N
InChi Code
InChI=1S/C9H11FIN3O4/c10-5-6(16)4(2-15)18-8(5)14-1-3(11)7(12)13-9(14)17/h1,4-6,8,15-16H,2H2,(H2,12,13,17)/t4-,5+,6-,8-/m1/s1
SMILES Code
O=C1N=C(N)C(I)=CN1[C@H]2[C@@H](F)[C@@H]([C@@H](CO)O2)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

Preparing Stock Solutions

The following data is based on the product molecular weight 371.11 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: Coen N, Duraffour S, Topalis D, Snoeck R, Andrei G. Spectrum of activity and mechanisms of resistance of various nucleoside derivatives against gammaherpesviruses. Antimicrob Agents Chemother. 2014 Dec;58(12):7312-23. doi: 10.1128/AAC.03957-14. Epub 2014 Sep 29. PubMed PMID: 25267682; PubMed Central PMCID: PMC4249563. 2: Zhang G, Lan X, Yen TC, Chen Q, Pei Z, Qin C, Zhang Y. Therapeutic gene expression in transduced mesenchymal stem cells can be monitored using a reporter gene. Nucl Med Biol. 2012 Nov;39(8):1243-50. doi: 10.1016/j.nucmedbio.2012.06.010. Epub 2012 Jul 15. PubMed PMID: 22796395. 3: Chan PC, Wu CY, Chang WY, Chang WT, Alauddin M, Liu RS, Lin WJ, Chen FD, Chen CL, Wang HE. Evaluation of F-18-labeled 5-iodocytidine (18F-FIAC) as a new potential positron emission tomography probe for herpes simplex virus type 1 thymidine kinase imaging. Nucl Med Biol. 2011 Oct;38(7):987-95. doi: 10.1016/j.nucmedbio.2011.04.003. Epub 2011 Jun 22. PubMed PMID: 21982570. 4: Wu CY, Chan PC, Chang WT, Liu RS, Alauddin MM, Wang HE. Radiosynthesis of F-18 labeled cytidine analog 2'-fluoro-5-iodo-l-beta-d-arabinofuranosylcytosine ([(18)F]FIAC). Appl Radiat Isot. 2009 Jul-Aug;67(7-8):1362-5. doi: 10.1016/j.apradiso.2009.02.083. Epub 2009 Feb 28. PubMed PMID: 19324560. 5: 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. 6: Snoeck R, Andrei G, De Clercq E. Patterns of resistance and sensitivity to antiviral compounds of drug-resistant strains of human cytomegalovirus selected in vitro. Eur J Clin Microbiol Infect Dis. 1996 Jul;15(7):574-9. PubMed PMID: 8874075. 7: Gordon M. Severe toxicity of fialuridine (FIAU). N Engl J Med. 1996 Apr 25;334(17):1136-7; author reply 1137-8. PubMed PMID: 8598883. 8: Nikkels AF, Piérard GE. Recognition and treatment of shingles. Drugs. 1994 Oct;48(4):528-48. Review. PubMed PMID: 7528128. 9: Fourel I, Li J, Hantz O, Jacquet C, Fox JJ, Trépo C. Effects of 2'-fluorinated arabinosyl-pyrimidine nucleosides on duck hepatitis B virus DNA level in serum and liver of chronically infected ducks. J Med Virol. 1992 Jun;37(2):122-6. PubMed PMID: 1629711. 10: Neyts J, Snoeck R, Balzarini J, De Clercq E. Particular characteristics of the anti-human cytomegalovirus activity of (S)-1-(3-hydroxy-2-phosphonylmethoxypropyl)cytosine (HPMPC) in vitro. Antiviral Res. 1991 Jul;16(1):41-52. PubMed PMID: 1663729. 11: King DH. Fluorinated pyrimidines: a new change for old drugs. Transplant Proc. 1991 Jun;23(3 Suppl 3):168-70. Review. PubMed PMID: 1648825. 12: Veerisetty V, Balasubramaniam NK, Gentry GA. Equine herpes virus 1 and pseudorabies virus resistance to 2'-fluoropyrimidine analogs and to bromovinyldeoxyuridine: implications for dTMP kinase activity. Acta Virol. 1990 Dec;34(6):568-73. PubMed PMID: 1983184. 13: Fourel I, Hantz O, Watanabe KA, Jacquet C, Chomel B, Fox JJ, Trepo C. Inhibitory effects of 2'-fluorinated arabinosyl-pyrimidine nucleosides on woodchuck hepatitis virus replication in chronically infected woodchucks. Antimicrob Agents Chemother. 1990 Mar;34(3):473-5. PubMed PMID: 2334160; PubMed Central PMCID: PMC171618. 14: Pizer LI, Mitchell DH, Bentele B, Betz JL. A mammalian cell line designed to test the mutagenic activity of anti-herpes nucleosides. Int J Cancer. 1987 Jul 15;40(1):114-21. PubMed PMID: 3036717. 15: Rollinson EA. Comparative efficacy of three 2'-fluoropyrimidine nucleosides and 9-(1,3-dihydroxy-2-propoxymethyl)guanine (BW B759U) against pseudorabies and equine rhinopneumonitis virus infection in vitro and in laboratory animals. Antiviral Res. 1987 Jan;7(1):25-33. PubMed PMID: 3026244. 16: Sougawa M, Yoshii G, Tanaka Y. [Radiosensitization effects of nucleoside analogs]. Nihon Igaku Hoshasen Gakkai Zasshi. 1986 Dec 25;46(12):1415-20. Japanese. PubMed PMID: 3547318. 17: Leyland-Jones B, Donnelly H, Groshen S, Myskowski P, Donner AL, Fanucchi M, Fox J. 2'-Fluoro-5-iodoarabinosylcytosine, a new potent antiviral agent: efficacy in immunosuppressed individuals with herpes zoster. J Infect Dis. 1986 Sep;154(3):430-6. PubMed PMID: 3525694. 18: Chen MS, Van Nostrand M, Oshana SC. Quantitative determination of antiviral nucleoside analog in DNA. Anal Biochem. 1986 Aug 1;156(2):300-4. PubMed PMID: 3766933. 19: Colacino J, Brownridge E, Greenberg N, Lopez C. Enzymology and pathogenicity in mice of a herpes simplex virus type 1 mutant resistant to 2'-fluoro-2'-deoxy-1-beta-D-arabinofuranosyl-5-iodocytosine. Antimicrob Agents Chemother. 1986 May;29(5):877-82. PubMed PMID: 3015008; PubMed Central PMCID: PMC284171. 20: Fanucchi MP, Watanabe KA, Fox JJ, Chou TC. Kinetics and substrate specificity of human and canine cytidine deaminase. Biochem Pharmacol. 1986 Apr 1;35(7):1199-201. PubMed PMID: 3964296.