Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C9H11FIN3O4 |
| Molecular Weight | 371.1042 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NC(=O)N(C=C1I)[C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2F
InChI
InChIKey=GIMSJJHKKXRFGV-BYPJNBLXSA-N
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
Fiacitabine, also known as FIAC, is a pyrimidine nucleoside, which had been in phase II clinical trilas for the treatment Cytomegalovirus infections and Herpes simplex virus infections. However, these researches have been discontinued. It was also shown the inhibitor activity of FIAC against the DNA polymerase of hepadnaviruses.
Approval Year
Doses
| Dose | Population | Adverse events |
|---|---|---|
200 mg/m2 2 times / day multiple, intravenous Studied dose Dose: 200 mg/m2, 2 times / day Route: intravenous Route: multiple Dose: 200 mg/m2, 2 times / day Sources: Page: p.435 |
unhealthy n = 15 Health Status: unhealthy Condition: varicella Sex: M+F Food Status: UNKNOWN Population Size: 15 Sources: Page: p.435 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Nucleosides. 110. Synthesis and antiherpes virus activity of some 2'-fluoro-2'-deoxyarabinofuranosylpyrimidine nucleosides. | 1979 Jan |
|
| 2'-fluoro-5-iodo-aracytosine, a potent and selective anti-herpesvirus agent. | 1980 May |
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| Selective inhibition of herpesvirus deoxyribonucleic acid synthesis by acycloguanosine, 2'-fluoro-5-iodo-aracytosine, and (E)-5-(2-bromovinyl)-2'-deoxyuridine. | 1981 May |
|
| Differential activity of potential antiviral nucleoside analogs on herpes simplex virus-induced and human cellular thymidine kinases. | 1981 Sep |
|
| Inhibitory effects of antiherpesviral thymidine analogs against varicella-zoster virus. | 1982 Feb |
|
| Nucleosides. 123. Synthesis of antiviral nucleosides: 5-substituted 1-(2-deoxy-2-halogeno-beta-D-arabinofuranosyl)cytosines and -uracils. Some structure-activity relationships. | 1983 Feb |
|
| Therapeutic activities of 1-(2-fluoro-2-deoxy-beta-D-arabinofuranosyl)-5-iodocytosine and -thymine alone and in combination with acyclovir and vidarabine in mice infected intracerebrally with herpes simplex virus. | 1983 Jul |
|
| Efficacy and selectivity of some nucleoside analogs as anti-human cytomegalovirus agents. | 1983 Oct |
|
| Antiherpes activity of (E)-5-(2-bromovinyl)- and 5-vinyl-1-beta-D-arabinofuranosyluracil and some other 5-substituted uracil arabinosyl nucleosides in two different cell lines. | 1983 Sep |
|
| Pulmonary and neurologic complications of treatment with FIAC (2'fluoro-5-iodo-aracytosine) in patients with acquired immune deficiency syndrome (AIDS). | 1983-1984 |
|
| Nucleosides. 129. Synthesis of antiviral nucleosides: 5-alkenyl-1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)uracils. | 1984 Jan |
|
| In vitro and in vivo antiviral activity of 1-beta-D-arabinofuranosyl-E-5-(2-bromovinyl)uracil (BV-araU) and related compounds. | 1984 Jun |
|
| Comparative efficacy and selectivity of some nucleoside analogs against Epstein-Barr virus. | 1985 Jun |
|
| Comparative anti-herpesvirus activities of 9-(1,3-dihydroxy-2-propoxymethyl)guanine, acyclovir, and two 2'-fluoropyrimidine nucleosides. | 1985 Oct |
|
| Activities of 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-iodocytosine and its metabolites against herpes simplex virus types 1 and 2 in cell culture and in mice infected intracerebrally with herpes simplex virus type 2. | 1986 Jan |
|
| Comparison of susceptibilities of varicella-zoster virus and herpes simplex viruses to nucleoside analogs. | 1986 Mar |
|
| Delayed treatment with combinations of antiviral drugs in mice infected with herpes simplex virus and application of the median effect method of analysis. | 1986 Sep |
|
| 2'-Fluorinated arabinonucleosides of 5-(2-haloalkyl)uracil: synthesis and antiviral activity. | 1987 Jul |
|
| In vitro and in vivo antiviral activity of 2'-fluorinated arabinosides of 5-(2-haloalkyl)uracil. | 1987 Jun |
|
| (S)-1-(3-hydroxy-2-phosphonylmethoxypropyl)cytosine, a potent and selective inhibitor of human cytomegalovirus replication. | 1988 Dec |
|
| Incorporation and metabolism of 2'-fluoro-5-substituted arabinosyl pyrimidines and their selective inhibition of viral DNA synthesis in herpes simplex virus type 1 (HSV-1)-infected and mock-infected Vero cells. | 1988 Dec 1 |
|
| Inhibitory effects of 2'-fluorinated arabinosyl-pyrimidine nucleosides on woodchuck hepatitis virus replication in chronically infected woodchucks. | 1990 Mar |
|
| Particular characteristics of the anti-human cytomegalovirus activity of (S)-1-(3-hydroxy-2-phosphonylmethoxypropyl)cytosine (HPMPC) in vitro. | 1991 Jul |
|
| Use of a standardized cell culture assay to assess activities of nucleoside analogs against hepatitis B virus replication. | 1992 Jul 1 |
|
| Comparative activity of selected antiviral compounds against clinical isolates of varicella-zoster virus. | 1995 Apr |
|
| Antiviral activity of selected acyclic nucleoside analogues against human herpesvirus 6. | 1995 Dec |
|
| Susceptibilities of several drug-resistant herpes simplex virus type 1 strains to alternative antiviral compounds. | 1995 Jul |
|
| Anti-cowpox virus activities of certain adenosine analogs, arabinofuranosyl nucleosides, and 2'-fluoro-arabinofuranosyl nucleosides. | 2004 |
|
| Synthesis and antiviral activities of 1'-carbon-substituted 4'-thiothymidines. | 2004 Oct 15 |
Patents
Sample Use Guides
immunosuppressed patients with herpesvirus infection: fiacitabine (FIAC) was administrated to 32 host compromised patients, 30 with advanced cancer, who were experiencing acute herpesvirus infections (varicella zoster, 29; HSV-1, 2; HSV-2, 1); the drug was given by 20 min i.v. infusion twice a day for 7 days. The dosage levels explored were 60, 120, 240, 400, and 600 mg/sq m/day.
Route of Administration:
Other
2-Fluoro-5-iodo-ara-C (FIAC/Fiacitabine) was tested for antiviral activity against several strains of herpes simplex virus (HSV), types 1 and 2. Effective dose-50% (ED-50) determinations for FIAC ranged from 0.023 to 0.51 muM for HSV-2. FIAC-treated cells did not exhibit any toxicity until the drug concentration was increased 2000-fold above the ED-50 level.
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NCI_THESAURUS |
C29575
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C1557
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C281
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C73202
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SUB07621MIG
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4058H365ZB
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CHEMBL272557
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69123-90-6
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382097
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DTXSID8057807
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CC-20
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C026023
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100000080984
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6268
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50312
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DB12901
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ACTIVE MOIETY
