U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C4H5N3O
Molecular Weight 111.1022
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYTOSINE

SMILES

c1cnc([nH]c1=N)O

InChI

InChIKey=OPTASPLRGRRNAP-UHFFFAOYSA-N
InChI=1S/C4H5N3O/c5-3-1-2-6-4(8)7-3/h1-2H,(H3,5,6,7,8)

HIDE SMILES / InChI

Molecular Formula C4H5N3O
Molecular Weight 111.1022
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Cytosine is a pyrimidine nucleobase, one of the five main bases of nucleic acids. In DNA and RNA cytosine is paired with guanine. Only small amounts of cytosine administered with food are incorporated in DNA. The majority of cytosine is synthesized de-novo starting from carbamoyl phosphate.

CNS Activity

Curator's Comment:: Cytosine administered with food does not pass through blood-brain barrier. Cytosine is synthesized in the brain de-novo.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Murine recombinant prion protein induces ordered aggregation of linear nucleic acids to condensed globular structures.
2001
Prophylaxis against herpesvirus infections in transplant recipients.
2001
Suicide gene therapy for pediatric tumors.
2001
Imaging biochemistry: applications to breast cancer.
2001
UAG readthrough in mammalian cells: effect of upstream and downstream stop codon contexts reveal different signals.
2001
Regulation of gene expression by GC-rich DNA cis-elements.
2001
Suicide gene therapy: possible applications in haematopoietic disorders.
2001 Apr
The ganciclovir implant plus oral ganciclovir versus parenteral cidofovir for the treatment of cytomegalovirus retinitis in patients with acquired immunodeficiency syndrome: The Ganciclovir Cidofovir Cytomegalovirus Retinitis Trial.
2001 Apr
DNA methylation learns to fly.
2001 Apr
Low-energy (5-40 eV) electron-stimulated desorption of anions from physisorbed DNA bases.
2001 Apr
Solution structure of the SL1 RNA of the M1 double-stranded RNA virus of Saccharomyces cerevisiae.
2001 Apr
Base sequence-specific attack of stilbene estrogen metabolite(s) on the mitochondrial DNA: implications in the induction of instability in the mitochondrial genome in the kidney of Syrian hamsters.
2001 Apr
Single molecule DNA sequencing in submicrometer channels: state of the art and future prospects.
2001 Apr 13
Association study of CAG repeats in the KCNN3 gene in Japanese patients with schizophrenia, schizoaffective disorder and bipolar disorder.
2001 Apr 15
Potent inhibition of hemangiosarcoma development in mice by cidofovir.
2001 Apr 15
Glucocorticoid-induced DNA demethylation and gene memory during development.
2001 Apr 17
15-mer DNA duplexes containing an abasic site are thermodynamically more stable with adjacent purines than with pyrimidines.
2001 Apr 3
Changes in DNA methylation in neoplasia: pathophysiology and therapeutic implications.
2001 Apr 3
Suicide gene therapy for premalignant disease: a new strategy for the treatment of intraepithelial neoplasia.
2001 Feb
Isolation and frontier molecular orbital investigation of bioactive quinone-methide triterpenoids from the bark of Salacia petenensis.
2001 Feb
Size constraints for targeting post-transcriptional gene silencing and for RNA-directed methylation in Nicotiana benthamiana using a potato virus X vector.
2001 Feb
Characterization of DNA damage at purine residues in oligonucleotides and calf thymus DNA induced by the mutagen 1-nitrosoindole-3-acetonitrile.
2001 Feb
Confounded cytosine! Tinkering and the evolution of DNA.
2001 Feb
Host responses and persistence of vector genome following intrabronchial administration of an E1(-)E3(-) adenovirus gene transfer vector to normal individuals.
2001 Feb
Alkylating agent and chromatin structure determine sequence context-dependent formation of alkylpurines.
2001 Feb 16
Surveying CpG methylation at 5'-CCGG in the genomes of rice cultivars.
2001 Jan
Diagnostic and therapeutic dilemmas of a large scrotal lesion in an AIDS patient.
2001 Jan
Quantum chemistry predicted correlations between geometric isomerism (conformation) of -OH and =NH substituents and typical group frequencies of nucleic acid bases: cytosine.
2001 Jan
Terpsichorean movements of pentaammineruthenium on pyrimidine and isocytosine ligands.
2001 Jan 29
In-situ FTIR study on adsorption and oxidation of native and thermally denatured calf thymus DNA at glassy carbon electrodes.
2001 Jan 31
The mechanism of DNA cytosine-5 methylation. Kinetic and mutational dissection of Hhai methyltransferase.
2001 Jun 15
Comparative study of a novel nucleoside analogue (Troxatyl, troxacitabine, BCH-4556) and AraC against leukemic human tumor xenografts expressing high or low cytidine deaminase activity.
2001 Mar
Early diagnosis of adenovirus infection and treatment with cidofovir after bone marrow transplantation in children.
2001 Mar
Effect of chemical modifications of cytosine and guanine in a CpG-motif of oligonucleotides: structure-immunostimulatory activity relationships.
2001 Mar
Epigenetic regulation of human bone morphogenetic protein 6 gene expression in prostate cancer.
2001 Mar
Topical cidofovir for bowenoid papulosis in an HIV-infected patient.
2001 Mar
Tetraplex formation by the progressive myoclonus epilepsy type-1 repeat: implications for instability in the repeat expansion diseases.
2001 Mar 2
A-like guanine-guanine stacking in the aqueous DNA duplex of d(GGGGCCCC).
2001 Mar 23
Hierarchy of DNA damage recognition in Escherichia coli nucleotide excision repair.
2001 Mar 6
High guanine-cytosine content is not an adaptation to high temperature: a comparative analysis amongst prokaryotes.
2001 Mar 7
Solution structure of an A-tract DNA bend.
2001 Mar 9
Evolution of endogenous retrovirus-like elements of the woolly mammoth (Mammuthus primigenius) and its relatives.
2001 May
Pseudogenes, junk DNA, and the dynamics of Rickettsia genomes.
2001 May
The elevated GC content at exonic third sites is not evidence against neutralist models of isochore evolution.
2001 May
Actinomycin D binds strongly to d(TGTCATTG), a single-stranded DNA devoid of GpC sites.
2001 May 1
Treatment of adenovirus infections in patients undergoing allogeneic hematopoietic stem cell transplantation.
2001 May 1
Catechol estrogens induce oxidative DNA damage and estradiol enhances cell proliferation.
2001 May 1
Cytosine methylation enhances mitoxantrone-DNA adduct formation at CpG dinucleotides.
2001 May 11
Chimeras between single-stranded DNA-binding proteins from Escherichia coli and Mycobacterium tuberculosis reveal that their C-terminal domains interact with uracil DNA glycosylases.
2001 May 18
Optimized RNA targets of two closely related triple KH domain proteins, heterogeneous nuclear ribonucleoprotein K and alphaCP-2KL, suggest Distinct modes of RNA recognition.
2001 May 18
Patents

Patents

Sample Use Guides

In Vivo Use Guide
As a component of DNA, cytosine is ingested with a normal diet. Normally, a major amount of cytosine is excreted, and a small amount is incorporated into DNA of the gastrointestinal tract.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Jun 26 06:28:23 UTC 2021
Edited
by admin
on Sat Jun 26 06:28:23 UTC 2021
Record UNII
8J337D1HZY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CYTOSINE
INCI   MI   USP-RS  
INCI  
Official Name English
NSC-27787
Code English
4-AMINOURACIL
Common Name English
LAMIVUDINE IMPURITY E [EP]
Common Name English
CYTOSINE [MI]
Common Name English
CYTOSINE [INCI]
Common Name English
LAMIVUDINE IMPURITY C [USP]
Common Name English
CYTOSINIMINE
Systematic Name English
CYTOSINE [USP-RS]
Common Name English
LAMIVUDINE IMPURITY C RS [USP]
Common Name English
4-AMINOPYRIMIDIN-2(1H)-ONE
Systematic Name English
Classification Tree Code System Code
EU-Orphan Drug EU/3/07/476
Created by admin on Sat Jun 26 06:28:23 UTC 2021 , Edited by admin on Sat Jun 26 06:28:23 UTC 2021
LOINC 79658-1
Created by admin on Sat Jun 26 06:28:23 UTC 2021 , Edited by admin on Sat Jun 26 06:28:23 UTC 2021
NCI_THESAURUS C789
Created by admin on Sat Jun 26 06:28:23 UTC 2021 , Edited by admin on Sat Jun 26 06:28:23 UTC 2021
LOINC 79655-7
Created by admin on Sat Jun 26 06:28:23 UTC 2021 , Edited by admin on Sat Jun 26 06:28:23 UTC 2021
LOINC 79683-9
Created by admin on Sat Jun 26 06:28:23 UTC 2021 , Edited by admin on Sat Jun 26 06:28:23 UTC 2021
Code System Code Type Description
RXCUI
1372540
Created by admin on Sat Jun 26 06:28:23 UTC 2021 , Edited by admin on Sat Jun 26 06:28:23 UTC 2021
PRIMARY RxNorm
EVMPD
SUB34834
Created by admin on Sat Jun 26 06:28:23 UTC 2021 , Edited by admin on Sat Jun 26 06:28:23 UTC 2021
PRIMARY
MESH
D003596
Created by admin on Sat Jun 26 06:28:23 UTC 2021 , Edited by admin on Sat Jun 26 06:28:23 UTC 2021
PRIMARY
CAS
71-30-7
Created by admin on Sat Jun 26 06:28:23 UTC 2021 , Edited by admin on Sat Jun 26 06:28:23 UTC 2021
PRIMARY
FDA UNII
8J337D1HZY
Created by admin on Sat Jun 26 06:28:23 UTC 2021 , Edited by admin on Sat Jun 26 06:28:23 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-749-5
Created by admin on Sat Jun 26 06:28:23 UTC 2021 , Edited by admin on Sat Jun 26 06:28:23 UTC 2021
PRIMARY
NCI_THESAURUS
C410
Created by admin on Sat Jun 26 06:28:23 UTC 2021 , Edited by admin on Sat Jun 26 06:28:23 UTC 2021
PRIMARY
MERCK INDEX
M4062
Created by admin on Sat Jun 26 06:28:23 UTC 2021 , Edited by admin on Sat Jun 26 06:28:23 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
CYTOSINE
Created by admin on Sat Jun 26 06:28:23 UTC 2021 , Edited by admin on Sat Jun 26 06:28:23 UTC 2021
PRIMARY
EPA CompTox
71-30-7
Created by admin on Sat Jun 26 06:28:23 UTC 2021 , Edited by admin on Sat Jun 26 06:28:23 UTC 2021
PRIMARY
PUBCHEM
597
Created by admin on Sat Jun 26 06:28:23 UTC 2021 , Edited by admin on Sat Jun 26 06:28:23 UTC 2021
PRIMARY
USP_CATALOG
1162148
Created by admin on Sat Jun 26 06:28:23 UTC 2021 , Edited by admin on Sat Jun 26 06:28:23 UTC 2021
PRIMARY USP-RS
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
PARENT -> IMPURITY
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY