FIACITABINE

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

Structure Search

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

HIDE SMILES / InChI

Molecular Formula	C9H11FIN3O4
Molecular Weight	371.1042
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1983184 | https://www.ncbi.nlm.nih.gov/pubmed/1629711

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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
hepadnaviruses DNA polymerase 1 Target ID: hepadnaviruses DNA polymerase Sources: https://www.ncbi.nlm.nih.gov/pubmed/1629711	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Cytomegalovirus infection 6 Sources: https://clinicaltrials.gov/ct2/show/NCT00000981	Primary	Phase II 1147	Unknown Approved Use Unknown
Herpes simplex virus type 1 infection 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1983184	Primary	Phase II 1147	Unknown Approved Use Unknown
Herpes simplex virus type 2 infection 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1983184	Primary	Phase II 1147	Unknown Approved Use Unknown

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: https://pubmed.ncbi.nlm.nih.gov/3525694	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3525694	Sources: https://pubmed.ncbi.nlm.nih.gov/3525694

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00FCGN	https://www.1pchem.com/search?query=1P00FCGN
AK Scientific	3673AH	https://aksci.com/item_detail.php?cat=3673AH
AstaTech	F13670	http://astatechinc.com/CPSResult.php?CRNO=F13670
BLD Pharm	BD130360	http://www.bldpharm.com/search/Search.html?keyword=BD130360
BOC Sciences	69123-90-6	http://www.bocsci.com/description.asp?cas=69123-90-6
Capot Chemical	19114	https://www.capotchem.com/search.do?q=19114
Combi-Blocks	QV-1553	http://www.combi-blocks.com/cgi-bin/find.cgi?QV-1553
Debye Scientific	DB-024894	https://www.debyesci.com/index.php?id=product&ext[cno]=DB-024894
eMolecules	275118023	https://orderbb.emolecules.com/search/#?query=275118023
eMolecules	300556563	https://orderbb.emolecules.com/search/#?query=300556563
eMolecules	36557605	https://orderbb.emolecules.com/search/#?query=36557605
Lab Network	LN01343337	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01343337
mcule	MCULE-5047947693	https://mcule.com/MCULE-5047947693/
mcule	MCULE-9026756715	https://mcule.com/MCULE-9026756715/
MedChem Express	HY-50735	https://www.medchemexpress.com/search.html?q=HY-50735&ft=&fa=&fp=
Molnova	M15648	https://www.molnova.com/en/serch-list.html?keywords=M15648
MolPort	MolPort-020-006-030	https://www.molport.com/shop/molecule-link/MolPort-020-006-030
Toronto Research Chemicals	F371060	https://www.trc-canada.com/product-detail/?CatNum=F371060

PubMed

Title	Date	PubMed
Synthesis and antiviral activities of 1'-carbon-substituted 4'-thiothymidines.	2004-10-15	15388158
Anti-cowpox virus activities of certain adenosine analogs, arabinofuranosyl nucleosides, and 2'-fluoro-arabinofuranosyl nucleosides.	2004	15043161
Antiviral activity of selected acyclic nucleoside analogues against human herpesvirus 6.	1995-12	8669893
Susceptibilities of several drug-resistant herpes simplex virus type 1 strains to alternative antiviral compounds.	1995-07	7492121
Comparative activity of selected antiviral compounds against clinical isolates of varicella-zoster virus.	1995-04	7649195
Use of a standardized cell culture assay to assess activities of nucleoside analogs against hepatitis B virus replication.	1992-07-01	1444322
Particular characteristics of the anti-human cytomegalovirus activity of (S)-1-(3-hydroxy-2-phosphonylmethoxypropyl)cytosine (HPMPC) in vitro.	1991-07	1663729
Inhibitory effects of 2'-fluorinated arabinosyl-pyrimidine nucleosides on woodchuck hepatitis virus replication in chronically infected woodchucks.	1990-03	2334160
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.	1988-12-01	2852483
(S)-1-(3-hydroxy-2-phosphonylmethoxypropyl)cytosine, a potent and selective inhibitor of human cytomegalovirus replication.	1988-12	2854454
2'-Fluorinated arabinonucleosides of 5-(2-haloalkyl)uracil: synthesis and antiviral activity.	1987-07	3037079
In vitro and in vivo antiviral activity of 2'-fluorinated arabinosides of 5-(2-haloalkyl)uracil.	1987-06	2821896
Delayed treatment with combinations of antiviral drugs in mice infected with herpes simplex virus and application of the median effect method of analysis.	1986-09	3777913
Comparison of susceptibilities of varicella-zoster virus and herpes simplex viruses to nucleoside analogs.	1986-03	3013088
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.	1986-01	3015003
Comparative anti-herpesvirus activities of 9-(1,3-dihydroxy-2-propoxymethyl)guanine, acyclovir, and two 2'-fluoropyrimidine nucleosides.	1985-10	2998275
Comparative efficacy and selectivity of some nucleoside analogs against Epstein-Barr virus.	1985-06	2992367
In vitro and in vivo antiviral activity of 1-beta-D-arabinofuranosyl-E-5-(2-bromovinyl)uracil (BV-araU) and related compounds.	1984-06	6089657
Nucleosides. 129. Synthesis of antiviral nucleosides: 5-alkenyl-1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)uracils.	1984-01	6317862
Efficacy and selectivity of some nucleoside analogs as anti-human cytomegalovirus agents.	1983-10	6316843
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.	1983-09	6316849
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.	1983-07	6625559
Nucleosides. 123. Synthesis of antiviral nucleosides: 5-substituted 1-(2-deoxy-2-halogeno-beta-D-arabinofuranosyl)cytosines and -uracils. Some structure-activity relationships.	1983-02	6298422
Pulmonary and neurologic complications of treatment with FIAC (2'fluoro-5-iodo-aracytosine) in patients with acquired immune deficiency syndrome (AIDS).	1983-01-01	6100825
Inhibitory effects of antiherpesviral thymidine analogs against varicella-zoster virus.	1982-02	6280604
Differential activity of potential antiviral nucleoside analogs on herpes simplex virus-induced and human cellular thymidine kinases.	1981-09	6272634
Selective inhibition of herpesvirus deoxyribonucleic acid synthesis by acycloguanosine, 2'-fluoro-5-iodo-aracytosine, and (E)-5-(2-bromovinyl)-2'-deoxyuridine.	1981-05	6271053
2'-fluoro-5-iodo-aracytosine, a potent and selective anti-herpesvirus agent.	1980-05	6249196
Nucleosides. 110. Synthesis and antiherpes virus activity of some 2'-fluoro-2'-deoxyarabinofuranosylpyrimidine nucleosides.	1979-01	218006

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:53:40 GMT 2025` Edited by `admin` on `Mon Mar 31 17:53:40 GMT 2025`
Record UNII	4058H365ZB
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FIACITABINE

Official Name

English

NSC-382097

Preferred Name

English

FIACITABINE [USAN]

Common Name

English

FIACITABINE [MART.]

Common Name

English

2(1H)-PYRIMIDINONE, 4-AMINO-1-(2-DEOXY-2-FLUORO-.BETA.-D-ARABINOFURANOSYL)-5-IODO-

Common Name

English

fiacitabine [INN]

Common Name

English

1-(2-DEOXY-2-FLUORO-.BETA.-D-ARABINOFURANOSYL)-5-IODOCYTOSINE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29575