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Details

Stereochemistry ACHIRAL
Molecular Formula C5H4FN5
Molecular Weight 153.1172
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 2-FLUOROADENINE

SMILES

NC1=NC(F)=NC2=C1NC=N2

InChI

InChIKey=WKMPTBDYDNUJLF-UHFFFAOYSA-N
InChI=1S/C5H4FN5/c6-5-10-3(7)2-4(11-5)9-1-8-2/h1H,(H3,7,8,9,10,11)

HIDE SMILES / InChI

Approval Year

PubMed

PubMed

TitleDatePubMed
Characterization of an engineered human purine nucleoside phosphorylase fused to an anti-her2/neu single chain Fv for use in ADEPT.
2009-12-03
Structural basis for enzymatic evolution from a dedicated ADP-ribosyl cyclase to a multifunctional NAD hydrolase.
2009-10-02
Diastereocontrolled electrophilic fluorinations of 2-deoxyribonolactone: syntheses of all corresponding 2-deoxy-2-fluorolactones and 2'-deoxy-2'-fluoro-NAD+s.
2009-08-21
A limited sampling schedule to estimate individual pharmacokinetic parameters of fludarabine in hematopoietic cell transplant patients.
2009-08-15
Selective killing of tumors deficient in methylthioadenosine phosphorylase: a novel strategy.
2009-05-29
Structure of a mutant human purine nucleoside phosphorylase with the prodrug, 2-fluoro-2'-deoxyadenosine and the cytotoxic drug, 2-fluoroadenine.
2009-05
Key labeling technologies to tackle sizeable problems in RNA structural biology.
2008-06
Prodrug converting enzyme gene delivery by L. monocytogenes.
2008-04-10
Cloning and functional expression of a novel Gi protein-coupled receptor for adenine from mouse brain.
2008-02
Comparison of gene targeting efficiencies in two mosses suggests that it is a conserved feature of Bryophyte transformation.
2007-10
[(3)H]Adenine is a suitable radioligand for the labeling of G protein-coupled adenine receptors but shows high affinity to bacterial contaminations in buffer solutions.
2007-09
Nicotinamide 2-fluoroadenine dinucleotide unmasks the NAD+ glycohydrolase activity of Aplysia californica adenosine 5'-diphosphate ribosyl cyclase.
2007-04-03
Preparation of a fludarabine intermediate via selective alkylation of 2-fluoroadenine.
2006
Cytosine arabinoside affects multiple cellular factors and induces drug resistance in human lymphoid cells.
2005-08-01
Identification of a subversive substrate of Trichomonas vaginalis purine nucleoside phosphorylase and the crystal structure of the enzyme-substrate complex.
2005-06-10
Oligotide, a defibrotide derivative, protects human microvascular endothelial cells against fludarabine-induced activation, damage and allogenicity.
2005-05
Evidence for the functional expression and pharmacological characterization of adenine receptors in native cells and tissues.
2005-03
Synthesis and biological activity of 2-fluoro adenine and 6-methyl purine nucleoside analogs as prodrugs for suicide gene therapy of cancer.
2005
Preclinical evaluation of a prostate-targeted gene-directed enzyme prodrug therapy delivered by ovine atadenovirus.
2004-11
Enzymatic synthesis and 19F NMR studies of 2-fluoroadenine-substituted RNA.
2004-09-29
Synthesis of 2',5'-dideoxy-2-fluoroadenosine and 2',5'-dideoxy-2,5'-difluoroadenosine: potent P-site inhibitors of adenylyl cyclase.
2004-02-26
Gene-directed enzyme prodrug therapy for prostate cancer in a mouse model that imitates the development of human disease.
2004-01
Synthesis of 2-fluoronoraristeromycin and its inhibitory activity against Plasmodium falciparum S-adenosyl-L-homocysteine hydrolase.
2003-11-17
Convenient synthesis of 2'-deoxy-2-fluoroadenosine from 2-fluoroadenine.
2003-10
Synthesis of carbocyclic and acyclic nucleosides possessing 2-fluoroadenine derivatives and their inhibitory activities against Plasmodium falciparum SAH hydrolase.
2003
Fludarabine induces apoptosis, activation, and allogenicity in human endothelial and epithelial cells: protective effect of defibrotide.
2002-07-01
Gene therapy for prostate cancer delivered by ovine adenovirus and mediated by purine nucleoside phosphorylase and fludarabine in mouse models.
2002-06
Interactions between 2-fluoroadenine 9-beta-D-arabinofuranoside and the kinase inhibitor UCN-01 in human leukemia and lymphoma cells.
2001-02
Name Type Language
2-FLUOROADENINE
Systematic Name English
NSC-27364
Preferred Name English
1H-PURIN-6-AMINE, 2-FLUORO-
Systematic Name English
2-FLUORO-6-AMINOPURINE
Systematic Name English
ADENINE, 2-FLUORO-
Systematic Name English
FLUDARABINE PHOSPHATE IMPURITY, 2-FLUOROADENINE- [USP IMPURITY]
Common Name English
2-FLUORO-1H-PURIN-6-AMINE
Systematic Name English
2-FLUORO-7H-PURIN-6-AMINE
Systematic Name English
FLUDARABINE PHOSPHATE IMPURITY D [EP IMPURITY]
Common Name English
9H-PURIN-6-AMINE, 2-FLUORO
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C45176
Created by admin on Mon Mar 31 21:27:55 GMT 2025 , Edited by admin on Mon Mar 31 21:27:55 GMT 2025
NCI_THESAURUS C45183
Created by admin on Mon Mar 31 21:27:55 GMT 2025 , Edited by admin on Mon Mar 31 21:27:55 GMT 2025
Code System Code Type Description
CHEBI
72457
Created by admin on Mon Mar 31 21:27:55 GMT 2025 , Edited by admin on Mon Mar 31 21:27:55 GMT 2025
PRIMARY
NCI_THESAURUS
C29794
Created by admin on Mon Mar 31 21:27:55 GMT 2025 , Edited by admin on Mon Mar 31 21:27:55 GMT 2025
PRIMARY
FDA UNII
2C8H3H4EBG
Created by admin on Mon Mar 31 21:27:55 GMT 2025 , Edited by admin on Mon Mar 31 21:27:55 GMT 2025
PRIMARY
CAS
700-49-2
Created by admin on Mon Mar 31 21:27:55 GMT 2025 , Edited by admin on Mon Mar 31 21:27:55 GMT 2025
PRIMARY
EPA CompTox
DTXSID80220264
Created by admin on Mon Mar 31 21:27:55 GMT 2025 , Edited by admin on Mon Mar 31 21:27:55 GMT 2025
PRIMARY
NSC
27364
Created by admin on Mon Mar 31 21:27:55 GMT 2025 , Edited by admin on Mon Mar 31 21:27:55 GMT 2025
PRIMARY
PUBCHEM
12790
Created by admin on Mon Mar 31 21:27:55 GMT 2025 , Edited by admin on Mon Mar 31 21:27:55 GMT 2025
PRIMARY