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69123-90-6

69123-90-6 structure
69123-90-6 structure
  • Name: Fiacitabine
  • Chemical Name: 4-amino-1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidin-2-one
  • CAS Number: 69123-90-6
  • Molecular Formula: C9H11FIN3O4
  • Molecular Weight: 371.104
  • Catalog: Signaling Pathways Anti-infection HSV
  • Create Date: 2018-02-15 08:00:00
  • Modify Date: 2024-01-04 18:42:40
  • 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].

Name 4-amino-1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidin-2-one
Synonyms 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
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
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.

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℃

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