ADENINE HYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C5H5N5.ClH
Molecular Weight	171.588
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.NC1=NC=NC2=C1N=CN2

InChI

InChIKey=UQVDQSWZQXDUJB-UHFFFAOYSA-N

InChI=1S/C5H5N5.ClH/c6-4-3-5(9-1-7-3)10-2-8-4;/h1-2H,(H3,6,7,8,9,10);1H

HIDE SMILES / InChI

Description
Sources: https://www.drugbank.ca/drugs/DB00173
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/25797921 | https://www.ncbi.nlm.nih.gov/pubmed/9046330 | https://www.ncbi.nlm.nih.gov/pubmed/2165159 | https://www.ncbi.nlm.nih.gov/pubmed/27776394 | https://www.ncbi.nlm.nih.gov/pubmed/26243842

Adenine is a nucleobase (a purine derivative). Its derivatives have a variety of roles in biochemistry including cellular respiration, in the form of both the energy-rich adenosine triphosphate (ATP) and the cofactors nicotinamide adenine dinucleotide (NAD) and flavin adenine dinucleotide (FAD). It also has functions in protein synthesis and as a chemical component of DNA and RNA. The shape of adenine is complementary to either thymine in DNA or uracil in RNA

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Phosphatidylinositol 4-kinase, PI4K 6 Target ID: CHEMBL2096619 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2165159	Inhibitor 8297	85.8 µM [Ki]
Cyclin-dependent kinase 1 27 Target ID: CHEMBL308 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9046330	Inhibitor 8297	200.0 µM [IC50]
Xanthine dehydrogenase 32 Target ID: CHEMBL1929 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17379526	Inhibitor 8297	10.89 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
preparation of red blood cells 5 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=fdd00e7b-039a-48a8-b654-941f85f5c00f	Diagnostic	Approved 8429	LEUKOTRAP WB SYSTEM Approved Use Indicated for collection of blood and preparation of red blood cells and plasma with pre-storage leukocyte reduction. Platelet concentrates are not intended to be made with this product.
Leukopenia associated with an overdose of antipsychotics 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27776394	Secondary	Not Provided 504	Unknown Approved Use Unknown
Neutropenia associated with an overdose of antipsychotics 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27776394	Secondary	Not Provided 504	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Drug therapy for hepatitis B.	2001	11147250
Molecular characterization of monoamine oxidases A and B.	2001	11008487
Renal interstitial adenosine metabolism during ischemia in dogs.	2001 Feb	11208598
Structure of the electron transfer complex between ferredoxin and ferredoxin-NADP(+) reductase.	2001 Feb	11175898
A Taq attack displaces bases.	2001 Feb	11175890
Maintenance of GABA receptor function of small-diameter cockroach neurons by adenine nucleotides.	2001 Feb	11164343
Uric acid inhibits liver phosphorylase a activity under simulated in vivo conditions.	2001 Feb	11158927
PTH and PTH-related peptide enhance steroid secretion from human adrenocortical cells.	2001 Feb	11158922
"Chemical preconditioning" by 3-nitropropionate reduces ischemia-reperfusion injury in cardiac-arrested rat lungs.	2001 Feb 15	11233893
Cytomegalovirus infection increases the expression and activity of ecto-ATPase (CD39) and ecto-5'nucleotidase (CD73) on endothelial cells.	2001 Feb 23	11226411
Quantum chemistry predicted correlations between geometric isomerism (conformation) of -OH and =NH substituents and typical group frequencies of nucleic acid bases: cytosine.	2001 Jan	11209867
Adenine and guanine nucleotide-specific succinyl-CoA synthetases in the clonal beta-cell mitochondria: implications in the beta-cell high-energy phosphate metabolism in relation to physiological insulin secretion.	2001 Jan	11206416
The physical basis of nucleic acid base stacking in water.	2001 Jan	11159389
Differential coupling of the human P2Y(11) receptor to phospholipase C and adenylyl cyclase.	2001 Jan	11156592
Activity of adenosine diphosphates and triphosphates on a P2Y(T) -type receptor in brain capillary endothelial cells.	2001 Jan	11156575
Extracellular ATP formation on vascular endothelial cells is mediated by ecto-nucleotide kinase activities via phosphotransfer reactions.	2001 Jan	11149913
Biochemical characterization of a neuroserpin variant associated with hereditary dementia.	2001 Jan	11141496
Development of cloned embryos from adult rabbit fibroblasts: effect of activation treatment and donor cell preparation.	2001 Jan	11133682
Oxidation of pyridine nucleotides during Fas- and ceramide-induced apoptosis in Jurkat cells: correlation with changes in mitochondria, glutathione depletion, intracellular acidification and caspase 3 activation.	2001 Jan 15	11139401
Phosphate exchange and ATP synthesis by DMSO-pretreated purified bovine mitochondrial ATP synthase.	2001 Jan 15	11139383
Activation of the insulin receptor's kinase domain changes the rate-determining step of substrate phosphorylation.	2001 Jan 16	11148045
Probing structure and dynamics of DNA with 2-aminopurine: effects of local environment on fluorescence.	2001 Jan 30	11170416
Regulation of protein degradation and protease expression by mannose in maize root tips. Pi sequestration by mannose may hinder the study of its signaling properties.	2001 Mar	11244127
Uptake of pentamidine in Trypanosoma brucei brucei is mediated by three distinct transporters: implications for cross-resistance with arsenicals.	2001 Mar	11179454
Adenosine increases ventilation rate, cardiac performance and haemolymph velocity in the American lobster Homarus americanus.	2001 Mar	11171418
Efficiency comparisons of rank and permutation tests based on summary statistics computed from repeated measures data.	2001 Mar 15	11241572
Crystal structure of paprika ferredoxin-NADP+ reductase. Implications for the electron transfer pathway.	2001 Mar 23	11053431

Patents

Sample Use Guides

In Vivo Use Guide

the daily dose of adenine is 10-60 mg/day

Route of Administration: Oral

In Vitro Use Guide

NIH/3T3 cells were plated at a density of 2 × 106 cells and left untreated overnight, cultural media was exchanged and experimental plates were exposed to adenine (200 -1200 mkM) for 24 hr. Cells were counted at various concentration of adenine or AICAR with a hemocytometer after diluting the sample 1:1 with 0.4% trypan blue solution (Sigma-Aldrich, St. Louis, MO, USA). Alternatively, the cell cytotoxicity of the cells was monitored with XTT assay. 50 μL of XTT reagent was added and the plates were then incubated for 4 hr at 37 °C in the dark. The absorbance at 490 nm with a reference wavelength set at 690 nm using VersaMax ELISA microplate reader

Name

Type

Language

ADENINE HYDROCHLORIDE

Systematic Name

English

6-AMINOPURINE HYDROCHLORIDE

Systematic Name

English

LEUCON

Brand Name

English

9H-PURIN-6-AMINE, HYDROCHLORIDE (1:1)

Systematic Name

English

Adenine hydrochloride [WHO-DD]

Common Name

English

Code System Code Type Description

SMS_ID

100000077959