CAS 69123-90-6|Fiacitabine

Introduction：Basic information about CAS 69123-90-6|Fiacitabine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Fiacitabine BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
MUTATION DATA
5. Synonyms

Common Name	Fiacitabine
CAS Number	69123-90-6	Molecular Weight	371.104
Density	2.4±0.1 g/cm3	Boiling Point	524.6±60.0 °C at 760 mmHg
Molecular Formula	C₉H₁₁FIN₃O₄	Melting Point	/
MSDS	/	Flash Point	271.1±32.9 °C

Names

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

Fiacitabine BiologicalActivity

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 >>HSVResearch 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.

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 >>HSVResearch 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.

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
InChIKey	GIMSJJHKKXRFGV-BYPJNBLXSA-N
SMILES	Nc1nc(=O)n(C2OC(CO)C(O)C2F)cc1I
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

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

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