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

Molecular Formula	C5H5N5
Molecular Weight	135.1267
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
A novel polymorphism (-88 C>A) in the 5' UTR of the p53R2 gene.	2001	11139269
Metabolic fate of extracellular NAD in human skin fibroblasts.	2001	11135366
Molecular characterization of monoamine oxidases A and B.	2001	11008487
Quantum-chemical analysis of C-H...O and C-H...N interactions in RNA base pairs--H-bond versus anti-H-bond pattern.	2001 Feb	11245250
Structure of the N6-adenine DNA methyltransferase M.TaqI in complex with DNA and a cofactor analog.	2001 Feb	11175899
Origin of the cytoplasmic pH changes during anaerobic stress in higher plant cells. Carbon-13 and phosphorous-31 nuclear magnetic resonance studies.	2001 Feb	11161048
Differential actions of PKA and PKC in the regulation of glutamate release by group III mGluRs in the entorhinal cortex.	2001 Feb	11160494
Uric acid inhibits liver phosphorylase a activity under simulated in vivo conditions.	2001 Feb	11158927
Orexin A stimulates cortisol secretion from human adrenocortical cells through activation of the adenylate cyclase-dependent signaling cascade.	2001 Feb	11158046
Apoptosis induction by the photosensitizer verteporfin: identification of mitochondrial adenine nucleotide translocator as a critical target.	2001 Feb 15	11245415
In situ kinetic characterization of methylthioadenosine transport by the adenosine transporter (P2) of the African Trypanosoma brucei brucei and Trypanosoma brucei rhodesiense.	2001 Feb 15	11226379
Crystal structure of human cyclin-dependent kinase 2 in complex with the adenine-derived inhibitor H717.	2001 Feb 15	11170642
Thermodynamics of ion-induced RNA folding in the hammerhead ribozyme: an isothermal titration calorimetric study.	2001 Feb 6	11170470
Reduced hydrolysis of amelogenin may result in X-linked amelogenesis imperfecta.	2001 Jan	11223334
Duck hepatitis B virus polymerase gene mutants associated with resistance to lamivudine have a decreased replication capacity in vitro and in vivo.	2001 Jan	11211887
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
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
Molecular and biochemical characterization of a cytokinin oxidase from maize.	2001 Jan	11154345
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
Biochemical characterization of a neuroserpin variant associated with hereditary dementia.	2001 Jan	11141496
A functional genomics strategy that uses metabolome data to reveal the phenotype of silent mutations.	2001 Jan	11135551
Lysosomal involvement in hepatocyte cytotoxicity induced by Cu(2+) but not Cd(2+).	2001 Jan 1	11134899
A novel response of cancer cells to radiation involves autophagy and formation of acidic vesicles.	2001 Jan 15	11212227
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
2-Alkynyl-8-aryl-9-methyladenines as novel adenosine receptor antagonists: their synthesis and structure-activity relationships toward hepatic glucose production induced via agonism of the A(2B) receptor.	2001 Jan 18	11170626
Codon bias at the 3'-side of the initiation codon is correlated with translation initiation efficiency in Escherichia coli.	2001 Jan 24	11223267
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
Development of virus-specific immune responses in SHIV(KU)-infected macaques treated with PMPA.	2001 Jan 5	11145893
Signaling pathways involved in the A and B receptor-mediated cortisol secretagogue effect of endothelins in the human adrenal cortex.	2001 Mar	11179511
Adenosine increases ventilation rate, cardiac performance and haemolymph velocity in the American lobster Homarus americanus.	2001 Mar	11171418
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
Expression and mutagenesis of the NqrC subunit of the NQR respiratory Na(+) pump from Vibrio cholerae with covalently attached FMN.	2001 Mar 9	11248234
Solution structure of an A-tract DNA bend.	2001 Mar 9	11237619

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

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:57:19 GMT 2025` Edited by `admin` on `Mon Mar 31 18:57:19 GMT 2025`
Record UNII	364H11M7OD
Record Status	`Validated (UNII)`
Record Version

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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