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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H12FN5O4
Molecular Weight 285.2318
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 2-FLUOROADENOSINE

SMILES

NC1=NC(F)=NC2=C1N=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O

InChI

InChIKey=HBUBKKRHXORPQB-UUOKFMHZSA-N
InChI=1S/C10H12FN5O4/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,14,15)/t3-,5-,6-,9-/m1/s1

HIDE SMILES / InChI
2-Fluoroadenosine (F-Ado) was developed at Southern Research Institute in 1957 as a potential anticancer drug. 2-Fluoroadenosine is not deaminated by adenosine deaminase but metabolized to triphosphate as shown in vitro. The drug was also shown to be a potent inhibitor of lymphocyte-mediated cytolysis.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Purine analogs as potential anticytomegalovirus agents.
1969 Sep
Stereoselective synthesis and antiviral activity of D-2',3'-didehydro-2',3'-dideoxy-2'-fluoro-4'-thionucleosides.
2002 Oct 24
Partial agonists for A(3) adenosine receptors.
2004
Identification of a subversive substrate of Trichomonas vaginalis purine nucleoside phosphorylase and the crystal structure of the enzyme-substrate complex.
2005 Jun 10
Biodistribution and PET imaging of [(18)F]-fluoroadenosine derivatives.
2007 Apr
Nicotinamide 2-fluoroadenine dinucleotide unmasks the NAD+ glycohydrolase activity of Aplysia californica adenosine 5'-diphosphate ribosyl cyclase.
2007 Apr 3
[(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 Sep
High resolution crystal structures of Mycobacterium tuberculosis adenosine kinase: insights into the mechanism and specificity of this novel prokaryotic enzyme.
2007 Sep 14
Crystal structures of Mycobacterium tuberculosis S-adenosyl-L-homocysteine hydrolase in ternary complex with substrate and inhibitors.
2008 Dec
Characterization of an engineered human purine nucleoside phosphorylase fused to an anti-her2/neu single chain Fv for use in ADEPT.
2009 Dec 3
[The preparative method for 2-fluoroadenosine synthesis].
2009 Mar-Apr
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
The cytotoxic lymphocytes (2.5*10(5) cells/ml) were preincubated for 60 min at 37 degree Celsius with 2-fluoroadenosine at concentrations from 0.5 to 50 uM and then the mixture was added to EL4 cells. IC50 for the inhibition of cytolysis was 6.1 uM. In a preliminary test, 2-fluoroadenosine inhibited the growth of Human Epidermoid Carcinoma at 10(-8) g./ml.
Name Type Language
2-FLUOROADENOSINE
Systematic Name English
2-FLUORO-9-.BETA.-D-RIBOFURANOSYLADENINE
Common Name English
PURINE, 6-AMINO-2-FLUORO-9-.BETA.-D-RIBOFURANOSYL-
Common Name English
NSC-30605
Code English
ADENOSINE, 2-FLUORO-
Systematic Name English
Code System Code Type Description
CHEBI
39740
Created by admin on Fri Dec 15 17:54:06 GMT 2023 , Edited by admin on Fri Dec 15 17:54:06 GMT 2023
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NSC
30605
Created by admin on Fri Dec 15 17:54:06 GMT 2023 , Edited by admin on Fri Dec 15 17:54:06 GMT 2023
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DRUG BANK
DB04441
Created by admin on Fri Dec 15 17:54:06 GMT 2023 , Edited by admin on Fri Dec 15 17:54:06 GMT 2023
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EPA CompTox
DTXSID70163252
Created by admin on Fri Dec 15 17:54:06 GMT 2023 , Edited by admin on Fri Dec 15 17:54:06 GMT 2023
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PUBCHEM
8975
Created by admin on Fri Dec 15 17:54:06 GMT 2023 , Edited by admin on Fri Dec 15 17:54:06 GMT 2023
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MESH
C034064
Created by admin on Fri Dec 15 17:54:06 GMT 2023 , Edited by admin on Fri Dec 15 17:54:06 GMT 2023
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FDA UNII
0S67290CRJ
Created by admin on Fri Dec 15 17:54:06 GMT 2023 , Edited by admin on Fri Dec 15 17:54:06 GMT 2023
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CAS
146-78-1
Created by admin on Fri Dec 15 17:54:06 GMT 2023 , Edited by admin on Fri Dec 15 17:54:06 GMT 2023
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