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
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
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
PubMed
| Title | Date | PubMed |
|---|---|---|
| Purine analogs as potential anticytomegalovirus agents. | 1969 Sep |
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| Partial agonists for A(3) adenosine receptors. | 2004 |
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| Identification of a subversive substrate of Trichomonas vaginalis purine nucleoside phosphorylase and the crystal structure of the enzyme-substrate complex. | 2005 Jun 10 |
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| Biodistribution and PET imaging of [(18)F]-fluoroadenosine derivatives. | 2007 Apr |
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| Nicotinamide 2-fluoroadenine dinucleotide unmasks the NAD+ glycohydrolase activity of Aplysia californica adenosine 5'-diphosphate ribosyl cyclase. | 2007 Apr 3 |
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| [(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 |
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| High resolution crystal structures of Mycobacterium tuberculosis adenosine kinase: insights into the mechanism and specificity of this novel prokaryotic enzyme. | 2007 Sep 14 |
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| Crystal structures of Mycobacterium tuberculosis S-adenosyl-L-homocysteine hydrolase in ternary complex with substrate and inhibitors. | 2008 Dec |
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| 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
Sample Use Guides
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.
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39740
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30605
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DB04441
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DTXSID70163252
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8975
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C034064
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0S67290CRJ
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146-78-1
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SUBSTANCE RECORD
