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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
Adenosine analogues as substrates and inhibitors of S-adenosylhomocysteine hydrolase.
1981 Jan 6
Broad-spectrum antiviral activity of the carbocyclic analog of 3-deazaadenosine.
1983 Mar
Broad-spectrum antiviral activity of adenosine analogues.
1984 Jun
Structure-activity relationship of novel oligopeptide antiviral and antitumor agents related to netropsin and distamycin.
1986 Jul
Inhibitory effect of selected antiviral compounds on measles (SSPE) virus replication in vitro.
1989 Sep
3-Deaza-adenosine and inhibition of HIV.
1992 Feb 15
Synthesis and antiviral activity of some new S-adenosyl-L-homocysteine derivatives.
1992 Nov 27
Inhibitory activity of S-adenosylhomocysteine hydrolase inhibitors against human cytomegalovirus replication.
1993 Jul
Anti-human immunodeficiency virus 1 (HIV-1) activities of 3-deazaadenosine analogs: increased potency against 3'-azido-3'-deoxythymidine-resistant HIV-1 strains.
1995 Jan 3
The role of phosphatidylethanolamine methylation in the secretion of very low density lipoproteins by cultured rat hepatocytes: rapid inhibition of phosphatidylethanolamine methylation by bezafibrate increases the density of apolipoprotein B48-containing lipoproteins.
1996 Nov 11
Extracellular ATP and adenosine cause apoptosis of pulmonary artery endothelial cells.
1997 Aug
Characterization of glycine N-methyltransferase from rabbit liver.
2004 Jun
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
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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