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 8 Target ID: CHEMBL2096619 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2165159	Inhibitor 8504	85.8 µM [Ki]
Cyclin-dependent kinase 1 27 Target ID: CHEMBL308 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9046330	Inhibitor 8504	200.0 µM [IC50]
Xanthine dehydrogenase 33 Target ID: CHEMBL1929 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17379526	Inhibitor 8504	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 8583	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 511	Unknown Approved Use Unknown
Neutropenia associated with an overdose of antipsychotics 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27776394	Secondary	Not Provided 511	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
6.8 μM OTHER GOV'T https://www.info.pmda.go.jp/go/interview/3/180095_4191001F1037_3_001_1F.pdf	27 μmol/kg single, oral dose: 27 μmol/kg route of administration: Oral experiment type: SINGLE co-administered:		ADENINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

PubMed

Title	Date	PubMed
UAG readthrough in mammalian cells: effect of upstream and downstream stop codon contexts reveal different signals.	2001	11242562
Ionization mechanism of oligonucleotides in matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.	2001	11135425
Mechanisms and modulation of intestinal epithelial repair.	2001 Feb	11233665
Renal interstitial adenosine metabolism during ischemia in dogs.	2001 Feb	11208598
Orexin A stimulates cortisol secretion from human adrenocortical cells through activation of the adenylate cyclase-dependent signaling cascade.	2001 Feb	11158046
RIZ, the retinoblastoma protein interacting zinc finger gene, is mutated in genetically unstable cancers of the pancreas, stomach, and colorectum.	2001 Feb	11135439
"Chemical preconditioning" by 3-nitropropionate reduces ischemia-reperfusion injury in cardiac-arrested rat lungs.	2001 Feb 15	11233893
Crystal structure of human cyclin-dependent kinase 2 in complex with the adenine-derived inhibitor H717.	2001 Feb 15	11170642
Cytomegalovirus infection increases the expression and activity of ecto-ATPase (CD39) and ecto-5'nucleotidase (CD73) on endothelial cells.	2001 Feb 23	11226411
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
Side chain-dependent binding of antitumor indoloquinoxaline derivatives to DNA: comparative spectroscopic and viscometric measurements.	2001 Jan	11201223
Molecular and biochemical characterization of a cytokinin oxidase from maize.	2001 Jan	11154345
Evolutionary optimization of metabolic pathways. Theoretical reconstruction of the stoichiometry of ATP and NADH producing systems.	2001 Jan	11146883
A functional genomics strategy that uses metabolome data to reveal the phenotype of silent mutations.	2001 Jan	11135551
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
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

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

LEUCON

Preferred Name

English

ADENINE HYDROCHLORIDE

Systematic Name

English

6-AMINOPURINE HYDROCHLORIDE

Systematic 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