Synonym
Ara-fluorocytosine; NSC 529180; NSC-529180; NSC529180
IUPAC/Chemical Name
1-beta-D-Arabinofuranosyl-5-fluorocytosine
InChi Key
STRZQWQNZQMHQR-MNCSTQPFSA-N
InChi Code
InChI=1S/C9H12FN3O5/c10-3-1-13(9(17)12-7(3)11)8-6(16)5(15)4(2-14)18-8/h1,4-6,8,14-16H,2H2,(H2,11,12,17)/t4-,5-,6+,8-/m1/s1
SMILES Code
O=C1N([C@H]2[C@H]([C@@H]([C@@H](CO)O2)O)O)C=C(F)C(N)=N1
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
261.21
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: Siddiqui MA, Driscoll JS, Marquez VE, Roth JS, Shirasaka T, Mitsuya H, Barchi JJ Jr, Kelley JA. Chemistry and anti-HIV properties of 2'-fluoro-2',3'-dideoxyarabinofuranosylpyrimidines. J Med Chem. 1992 Jun 12;35(12):2195-201. PubMed PMID: 1351945.
2: Thaler M, Bacher J, O'Leary T, Pizzo PA. Evaluation of single-drug and combination antifungal therapy in an experimental model of candidiasis in rabbits with prolonged neutropenia. J Infect Dis. 1988 Jul;158(1):80-8. PubMed PMID: 3392423.
3: Snyder RD, van Houten B, Regan JD. The inhibition of ultraviolet radiation-induced DNA repair in human diploid fibroblasts by arabinofuranosyl nucleosides. Chem Biol Interact. 1984 Jun;50(1):1-14. PubMed PMID: 6733802.
4: Mertelsmann R, Drapkin RL, Gee TS, Kempin S, Passe S, Thaler HT, Arlin Z, Dowling M, Dufour P, McKenzie S, To L, Comacho E, Oettgen HF, Burchenal JH, Clarkson B. Treatment of acute nonlymphocytic leukemia in adults: response to 2,2-anhydro-1-B-D-arabinofuranosyl-5-fluorocytosine and thioguanine on the L-12 protocol. Cancer. 1981 Nov 15;48(10):2136-42. PubMed PMID: 6170414.
5: Watanabe KA, Reichman U, Chu CK, Hollenberg DH, Fox JJ. Nucleosides. 116. 1-(beta-D-Xylofuranosyl)-5-fluorocytosines with a leaving group on the 3' position. Potential double-barreled masked precursors of anticancer nucleosides. J Med Chem. 1980 Oct;23(10):1088-94. PubMed PMID: 7420353.
6: Brugarolas A, Buesa JM, Lacave AJ, Gracia Marco M, Valle Pereda M. Phase I and II clinical study of anhydro-ara-5-fluorocytosine (AAFC) and ICRF-159 combination in adenocarcinoma of digestive origin. Cancer Clin Trials. 1978 Winter;1(4):289-95. PubMed PMID: 93030.
7: Kreis W, Woodcock TM, Meyers MB, Carlevarini LA, Krakoff IH. Physiologic disposition of cytosine arabinoside and its derivatives in man. Cancer Treat Rep. 1977 Jul;61(4):723-6. PubMed PMID: 195729.
8: Cook AF. Fluorinated Pyrimidine nucleosides. 1. Synthesis of a nitrogen analogue of the antitumor agent 2,2'-anhydro-1-beta-D-arabinofuranosyl-5-fluorocytosine hydrochloride. J Med Chem. 1977 Mar;20(3):344-8. PubMed PMID: 66315.
9: Basler GA, Shapiro WR. Comparison of 2,2'-anhydro-1-beta-D-arabinofuranosyl-5-fluorocytosine and cytosine arabinoside in the treatment of murine brain tumor. Cancer Treat Rep. 1976 Jul;60(7):875-9. PubMed PMID: 64295.
10: Schneyer CA, Galbraith WM. Evaluation of sialogogic action of cyclocytidine (NSC-145668) and anhydro-ara-5-fluorocytidine (NSC-166641). Cancer Chemother Rep. 1975 Sep-Oct;59(5):1019. PubMed PMID: 1203892.
11: Burchenal JH. Murine and human leukemias. Bibl Haematol. 1975;(40):665-77. Review. PubMed PMID: 1100047.
