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 8297

Conditions

Condition	Modality	Highest Phase	Product
Cytomegalovirus infection 6 Sources: https://clinicaltrials.gov/ct2/show/NCT00000981	Primary	Phase II 1132	Unknown Approved Use Unknown
Herpes simplex virus type 1 infection 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1983184	Primary	Phase II 1132	Unknown Approved Use Unknown
Herpes simplex virus type 2 infection 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1983184	Primary	Phase II 1132	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 Page: p.435	unhealthy n = 15 Health Status: unhealthy Condition: varicella Sex: M+F Food Status: UNKNOWN Population Size: 15 Sources: https://pubmed.ncbi.nlm.nih.gov/3525694 Page: p.435	Sources: https://pubmed.ncbi.nlm.nih.gov/3525694 Page: p.435

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
Lab Network	LN01343337	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01343337
MedChem Express	HY-50735	https://www.medchemexpress.com/search.html?q=HY-50735&ft=&fa=&fp=
MolPort	MolPort-020-006-030	https://www.molport.com/shop/molecule-link/MolPort-020-006-030
Molnova	M15648	https://www.molnova.com/en/serch-list.html?keywords=M15648
Toronto Research Chemicals	F371060	https://www.trc-canada.com/product-detail/?CatNum=F371060
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
mcule	MCULE-5047947693	https://mcule.com/MCULE-5047947693/
mcule	MCULE-9026756715	https://mcule.com/MCULE-9026756715/

PubMed

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

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 `Fri Dec 15 15:18:45 GMT 2023` Edited by `admin` on `Fri Dec 15 15:18:45 GMT 2023`
Record UNII	4058H365ZB
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FIACITABINE

Official 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

NSC-382097

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C29575

Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023

NCI_THESAURUS

C1557

Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023

NCI_THESAURUS

C281

Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023

Code System Code Type Description

NCI_THESAURUS

C73202

Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023

PRIMARY

EVMPD

SUB07621MIG

Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023

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FDA UNII

4058H365ZB

Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023

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ChEMBL

CHEMBL272557

Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023

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CAS

69123-90-6

Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023

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NSC

382097

Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023

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EPA CompTox

DTXSID8057807

Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023

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USAN

CC-20

Created by admin on Fri Dec 15 15:18:46 GMT 2023 , Edited by admin on Fri Dec 15 15:18:46 GMT 2023

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MESH

C026023

Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023

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SMS_ID

100000080984

Created by admin on Fri Dec 15 15:18:46 GMT 2023 , Edited by admin on Fri Dec 15 15:18:46 GMT 2023

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INN

6268

Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023

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PUBCHEM

50312

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DRUG BANK

DB12901

Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023

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Related Record Type Details


					4058H365ZB

FIACITABINE

ACTIVE MOIETY

Details

SMILES

InChI

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

Originator

Approval Year

Targets

Conditions

Approved Use

Approved Use

Approved Use

Doses

Sourcing

PubMed

Patents

Sample Use Guides

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