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Fiacitabine

Names

[ CAS No. ]:
69123-90-6

[ Name ]:
Fiacitabine

[Synonym ]:
1-(2-Deoxy-2-fluoro-b-D-arabinofuranosyl)-5-iodocytosine
2'-Fluoro-5-iodo-1-b-D-arabinofuranosylcytosine
4-Amino-1-(2-deoxy-2-fluoro-b-D-arabinofuranosyl)-5-iodo-2(1H)-pyrimidinone
FIAC
2'-Fluoro-5-iodo-aracytosine
2'-fluoro-5-iodoarabinosylcytosine
Fluorviodoaracytidine
DRG-0077
4-Amino-1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-iodo-2(1H)-pyrimidinone
4-Amino-1-(2-deoxy-2-fluor-β-D-arabinofuranosyl)-5-iodpyrimidin-2(1H)-on
2(1H)-Pyrimidinone, 4-amino-1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-iodo-
4-Amino-1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-iodopyrimidin-2(1H)-one
Fluoroiodoaracytidine
Fiacitabine

Biological Activity

[Description]:

Fiacitabine(NSC 382097; FIAC; FOAC) is a selective inhibitior of DNA replication of herpes simplex virus(HSV) with IC50 values of 2.5 nM and 12.6 nM for HSV1 and HSV2, respectively. IC50 value: 2.5/12.6 nM (HSV1/2) [2]Target: HSVFIAC suppressed by 90% the replication of various strains of herpes simplex virus types 1 and 2 at concentrations of 0.0025 to 0.0126 microM. Cytotoxicity was minimal, as determined by trypan blue dye exclusion with norman Vero, WI-38, and NC-37 cell proliferation; the 50% inhibitory dose was 4 to 10 microM in a 4-day assay. FIAC was active at much lower concentrations than arabinosylcytosine, iododeoxyuridine, and arabinosyladenine. It was slightly more active against herpes simplex virus type 1 than acycloquanosine and slightly more toxic to normal cells. FIAC was about 8,000 times more active against the replication of wild-type herpes simplex virus type 1 than against a mutant strain lacking the expression of virus-specified thymidine kinase [2].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> HSV
Research Areas >> Infection

[References]

[1]. Allaudeen HS, et al. Selective inhibition of DNA replication in herpes simplex virus infected cells by 1-(2'-deoxy-2'-fluoro-beta-D-arabinofuranosyl)-5-iodocytosine. J Biol Chem. 1982 Oct 25;257(20):11879-82.

[2]. Lopez C, et al. 2'-fluoro-5-iodo-aracytosine, a potent and selective anti-herpesvirus agent. Antimicrob Agents Chemother. 1980 May;17(5):803-6.


[Related Small Molecules]

Vidarabine | BAY 57-1293 | Acyclovir | idoxuridine | Valacyclovir hydrochloride | Amenamevir | Penciclovir | 1-Docosanol | Tromantadine | B220 | BRL44385

Chemical & Physical Properties

[ Density]:
2.4±0.1 g/cm3

[ Boiling Point ]:
524.6±60.0 °C at 760 mmHg

[ Molecular Formula ]:
C9H11FIN3O4

[ Molecular Weight ]:
371.104

[ Flash Point ]:
271.1±32.9 °C

[ Exact Mass ]:
370.977814

[ PSA ]:
110.60000

[ LogP ]:
-0.27

[ Vapour Pressure ]:
0.0±3.1 mmHg at 25°C

[ Index of Refraction ]:
1.791

[ Storage condition ]:
2-8℃

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UW7353000
CHEMICAL NAME :
2(1H)-Pyrimidinone, 4-amino-1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)- 5-iodo-
CAS REGISTRY NUMBER :
69123-90-6
LAST UPDATED :
199612
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C9-H11-F-I-N3-O4
MOLECULAR WEIGHT :
371.13
WISWESSER LINE NOTATION :
T6NVMYJ DUM EI A- BT5OTJ CF DQ E1Q

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :
DNA inhibition
TEST SYSTEM :
Rodent - mouse Leukocyte
DOSE/DURATION :
353 umol/L
REFERENCE :
CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 42,3957,1982

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream