ADENINE SULFATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	2C5H5N5.H2O4S
Molecular Weight	368.332
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OS(O)(=O)=O.NC1=C2N=CNC2=NC=N1.NC3=C4N=CNC4=NC=N3

InChI

InChIKey=LQXHSCOPYJCOMD-UHFFFAOYSA-N

InChI=1S/2C5H5N5.H2O4S/c2*6-4-3-5(9-1-7-3)10-2-8-4;1-5(2,3)4/h2*1-2H,(H3,6,7,8,9,10);(H2,1,2,3,4)

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
Molecular characterization of monoamine oxidases A and B.	2001	11008487
De novo mutation in the mitochondrial tRNALeu(UUR) gene (A3243G) with rapid segregation resulting in MELAS in the offspring.	2001 Feb	11168879
RIZ, the retinoblastoma protein interacting zinc finger gene, is mutated in genetically unstable cancers of the pancreas, stomach, and colorectum.	2001 Feb	11135439
Crystal structure of human cyclin-dependent kinase 2 in complex with the adenine-derived inhibitor H717.	2001 Feb 15	11170642
Anatomy of a preferred target site for the bacterial insertion sequence IS903.	2001 Feb 23	11178901
Thermodynamics of ion-induced RNA folding in the hammerhead ribozyme: an isothermal titration calorimetric study.	2001 Feb 6	11170470
FRET analysis indicates that the two ATPase active sites of the P-glycoprotein multidrug transporter are closely associated.	2001 Feb 6	11170469
A nucleotide insertion and frameshift cause albumin Kénitra, an extended and O-glycosylated mutant of human serum albumin with two additional disulfide bridges.	2001 Jan	11168369
The physical basis of nucleic acid base stacking in water.	2001 Jan	11159389
Activity of adenosine diphosphates and triphosphates on a P2Y(T) -type receptor in brain capillary endothelial cells.	2001 Jan	11156575
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
Inosine-5'-monophosphate dehydrogenase is required for mitogenic competence of transformed pancreatic beta cells.	2001 Jan	11145582
Type 2 iodothyronin deiodinase transgene expression in the mouse heart causes cardiac-specific thyrotoxicosis.	2001 Jan	11145561
Developmental potential and transgene expression of porcine nuclear transfer embryos using somatic cells.	2001 Jan	11144215
Development of cloned embryos from adult rabbit fibroblasts: effect of activation treatment and donor cell preparation.	2001 Jan	11133682
Regulation of BK(Ca) channels expressed in human embryonic kidney 293 cells by epoxyeicosatrienoic acid.	2001 Jan	11125019
Lysosomal involvement in hepatocyte cytotoxicity induced by Cu(2+) but not Cd(2+).	2001 Jan 1	11134899
Vasoactive intestinal peptide-stimulated adenosine 3',5'-cyclic monophosphate formation in cerebral cortex and hypothalamus of chick and rat: comparison of the chicken and mammalian peptide.	2001 Jan 12	11121878
The structure of the chloroplast F1-ATPase at 3.2 A resolution.	2001 Jan 12	11032839
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
Activation of the insulin receptor's kinase domain changes the rate-determining step of substrate phosphorylation.	2001 Jan 16	11148045
Selectively suppressed Ca2+-induced Ca2+ release activity of alpha-ryanodine receptor (alpha-RyR) in frog skeletal muscle sarcoplasmic reticulum: potential distinct modes in Ca2+ release between alpha- and beta-RyR.	2001 Jan 26	11054412
Conformation and dynamics of abasic sites in DNA investigated by time-resolved fluorescence of 2-aminopurine.	2001 Jan 30	11170417
Enhanced cellular immune response and reduced CD8(+) lymphocyte apoptosis in acutely SIV-infected Rhesus macaques after short-term antiretroviral treatment.	2001 Jan 5	11145904
The XRCC1 399 glutamine allele is a risk factor for adenocarcinoma of the lung.	2001 Jan 5	11104903
Successful nonfreezing, subzero preservation of rat liver with 2,3-butanediol and type I antifreeze protein.	2001 Mar	11180993
Signaling pathways involved in the A and B receptor-mediated cortisol secretagogue effect of endothelins in the human adrenal cortex.	2001 Mar	11179511
Polymorphism of the WAF1 gene is related to susceptibility to cervical cancer in Japanese women.	2001 Mar	11179504
Adenosine signaling in outer medullary descending vasa recta.	2001 Mar	11171666
Role of adenosine kinase in Saccharomyces cerevisiae: identification of the ADO1 gene and study of the mutant phenotypes.	2001 Mar 15	11223943
A(1) or A(3) adenosine receptors induce late preconditioning against infarction in conscious rabbits by different mechanisms.	2001 Mar 16	11249876
Crystal structure of paprika ferredoxin-NADP+ reductase. Implications for the electron transfer pathway.	2001 Mar 23	11053431
Specific labeling of the bovine heart mitochondrial phosphate carrier with fluorescein 5-isothiocyanate: roles of Lys185 and putative adenine nucleotide recognition site in phosphate transport.	2001 Mar 30	11133984
Expression and mutagenesis of the NqrC subunit of the NQR respiratory Na(+) pump from Vibrio cholerae with covalently attached FMN.	2001 Mar 9	11248234

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

6-AMINOPURINE HEMISULFATE SALT

Preferred Name

English

ADENINE SULFATE

Common Name

English

ADENINE HEMISULFATE SALT

Common Name

English

Code System Code Type Description

FDA UNII

741GJF3K9M