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Details

Stereochemistry ABSOLUTE
Molecular Formula C11H14N4O4
Molecular Weight 266.2533
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 3-DEAZAADENOSINE

SMILES

NC1=NC=CC2=C1N=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O

InChI

InChIKey=DBZQFUNLCALWDY-PNHWDRBUSA-N
InChI=1S/C11H14N4O4/c12-10-7-5(1-2-13-10)15(4-14-7)11-9(18)8(17)6(3-16)19-11/h1-2,4,6,8-9,11,16-18H,3H2,(H2,12,13)/t6-,8-,9-,11-/m1/s1

HIDE SMILES / InChI

Molecular Formula C11H14N4O4
Molecular Weight 266.2533
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/19372464

3-Deaza-adenosine (BW 91Y) is a potent inhibitor of adenosine deaminase and S-Adenosylhomocysteine (SAH) hydrolase, with potent antitumor activity against a range of leukemia cell lines. 3-Deaza-adenosine has anti-inflammatory properties, inhibiting leukocyte adhesion and chemotaxis, lymphocyte-mediated cytolysis, phagocytosis, degranulation, and NF-κB signaling. 3-Deaza-adenosine also has antiviral and antibacterial activities. 3-Deaza-adenosine has previously been shown to inhibit a variety of cellular functions, which could be critical for the development of atherosclerosis and restenosis. These include the thrombin-stimulated production of platelet-derived growth factor and the expression of endothelial leukocyte adhesion molecule-1 as well as cellular arachidonic acid and ROS production. Moreover, c3Ado prevents tumor necrosis factor (TNF)-alpha production, reduces TNF- alpha-induced macrophage adhesion to endothelial cells in vitro via the inhibition of ICAM-1 synthesis, and promotes monocyte apoptosis.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
360.0 µM [Ki]
4.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Broad-spectrum antiviral activity of the carbocyclic analog of 3-deazaadenosine.
1983 Mar
Broad-spectrum antiviral activity of adenosine analogues.
1984 Jun
Inhibitory effect of selected antiviral compounds on arenavirus replication in vitro.
1990 Oct-Nov
Extracellular ATP and adenosine cause apoptosis of pulmonary artery endothelial cells.
1997 Aug
Vaccinia virus inhibitors as a paradigm for the chemotherapy of poxvirus infections.
2001 Apr
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Evaluation of 3-deaza-adenosine analogues as ligands for adenosine kinase and inhibitors of Mycobacterium tuberculosis growth.
2007 Jan
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
Human coronary artery smooth muscle cells (VSMCs; Clonetics, Verviers, Belgium) were grown in 500 mkL of supplemented growth medium containing 5% FCS (SmGM-2; Clonetics, Verviers, Belgium) in 24-well culture dishes. 10, 50 and 100 mkM of c3Ado (3-Deazaadenosine) were added to the growth medium. After 48 hours of incubation at 37°C/5% CO2, cells were trypsinized and counted using a hemocytometer.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:05:48 GMT 2023
Edited
by admin
on Fri Dec 15 15:05:48 GMT 2023
Record UNII
037V4520IY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
3-DEAZAADENOSINE
Common Name English
1H-IMIDAZO(4,5-C)PYRIDIN-4-AMINE, 1-.BETA.-D-RIBOFURANOSYL
Systematic Name English
ADENOSINE, 3-DEAZA-
Common Name English
NSC-167897
Code English
Code System Code Type Description
PUBCHEM
23190
Created by admin on Fri Dec 15 15:05:48 GMT 2023 , Edited by admin on Fri Dec 15 15:05:48 GMT 2023
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NSC
167897
Created by admin on Fri Dec 15 15:05:48 GMT 2023 , Edited by admin on Fri Dec 15 15:05:48 GMT 2023
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EPA CompTox
DTXSID2040941
Created by admin on Fri Dec 15 15:05:48 GMT 2023 , Edited by admin on Fri Dec 15 15:05:48 GMT 2023
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FDA UNII
037V4520IY
Created by admin on Fri Dec 15 15:05:48 GMT 2023 , Edited by admin on Fri Dec 15 15:05:48 GMT 2023
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CAS
6736-58-9
Created by admin on Fri Dec 15 15:05:48 GMT 2023 , Edited by admin on Fri Dec 15 15:05:48 GMT 2023
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DRUG BANK
DB04546
Created by admin on Fri Dec 15 15:05:48 GMT 2023 , Edited by admin on Fri Dec 15 15:05:48 GMT 2023
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