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Details

Stereochemistry ACHIRAL
Molecular Formula C4H5N3O
Molecular Weight 111.102
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYTOSINE

SMILES

NC1=NC(=O)NC=C1

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 111.102
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
A simple model based on mutation and selection explains trends in codon and amino-acid usage and GC composition within and across genomes.
2001
Prophylaxis against herpesvirus infections in transplant recipients.
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
A novel polymorphism (-88 C>A) in the 5' UTR of the p53R2 gene.
2001
A novel polymorphism IVS2+843C>T in the alternate promoter b1 of the human AE2 anion exchanger gene.
2001
A novel polymorphism (c288C>T) of the NPHS2 gene identified in a Taiwan Chinese family.
2001
A novel elastin gene mutation (1281delC) in a family with supravalvular aortic stenosis: a mutation cluster within exon 20.
2001
DNA methylation learns to fly.
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
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
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
Confounded cytosine! Tinkering and the evolution of DNA.
2001 Feb
Mildly eccentric 'E-DNA'.
2001 Feb
Structure of an RNA duplex with an unusual G.C pair in wobble-like conformation at 1.6 A resolution.
2001 Feb
Differentiation of Streptococcus mutans and Streptococcus sobrinus via genotypic and phenotypic profiles from three different populations.
2001 Feb
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
Reduction of wobble-position GC bases in Corynebacteria genes and enhancement of PCR and heterologous expression.
2001 Jan
Microsoft Word macro for analysis of cytosine methylation by the bisulfite deamination reaction.
2001 Jan
Spreadsheet-based program for the analysis of DNA methylation.
2001 Jan
In vitro effects of antiviral agents on human keratocytes.
2001 Jan
The use of bacterial choline oxidase, a glycinebetaine-synthesizing enzyme, to create stress-resistant transgenic plants.
2001 Jan
Usefulness of repeated direct intratumoral gene transfer using hemagglutinating virus of Japan-liposome method for cytosine deaminase suicide gene therapy.
2001 Jan 1
Virological, clinical, and ophthalmologic features of cytomegalovirus retinitis after hematopoietic stem cell transplantation.
2001 Jan 15
Long-term remission of an AIDS-related primary effusion lymphoma with antiviral therapy.
2001 Jan 26
Terpsichorean movements of pentaammineruthenium on pyrimidine and isocytosine ligands.
2001 Jan 29
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
Polymorphism of the WAF1 gene is related to susceptibility to cervical cancer in Japanese women.
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
Solution structure of an A-tract DNA bend.
2001 Mar 9
Molecular topology of polycyclic aromatic carcinogens determines DNA adduct conformation: a link to tumorigenic activity.
2001 Mar 9
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
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 Wed Jul 05 22:31:52 UTC 2023
Edited
by admin
on Wed Jul 05 22:31:52 UTC 2023
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
LAMIVUDINE IMPURITY C [USP IMPURITY]
Common Name English
4-AMINOURACIL
Common Name English
CYTOSINE [MI]
Common Name English
Cytosine [WHO-DD]
Common Name English
CYTOSINE [INCI]
Common Name English
CYTOSINIMINE
Systematic Name English
LAMIVUDINE IMPURITY E [EP IMPURITY]
Common Name English
CYTOSINE [USP-RS]
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 Wed Jul 05 22:31:52 UTC 2023 , Edited by admin on Wed Jul 05 22:31:52 UTC 2023
LOINC 79658-1
Created by admin on Wed Jul 05 22:31:52 UTC 2023 , Edited by admin on Wed Jul 05 22:31:52 UTC 2023
NCI_THESAURUS C789
Created by admin on Wed Jul 05 22:31:52 UTC 2023 , Edited by admin on Wed Jul 05 22:31:52 UTC 2023
LOINC 79655-7
Created by admin on Wed Jul 05 22:31:52 UTC 2023 , Edited by admin on Wed Jul 05 22:31:52 UTC 2023
LOINC 79683-9
Created by admin on Wed Jul 05 22:31:52 UTC 2023 , Edited by admin on Wed Jul 05 22:31:52 UTC 2023
Code System Code Type Description
RXCUI
1372540
Created by admin on Wed Jul 05 22:31:52 UTC 2023 , Edited by admin on Wed Jul 05 22:31:52 UTC 2023
PRIMARY RxNorm
DAILYMED
8J337D1HZY
Created by admin on Wed Jul 05 22:31:52 UTC 2023 , Edited by admin on Wed Jul 05 22:31:52 UTC 2023
PRIMARY
EVMPD
SUB34834
Created by admin on Wed Jul 05 22:31:52 UTC 2023 , Edited by admin on Wed Jul 05 22:31:52 UTC 2023
PRIMARY
MESH
D003596
Created by admin on Wed Jul 05 22:31:52 UTC 2023 , Edited by admin on Wed Jul 05 22:31:52 UTC 2023
PRIMARY
SMS_ID
100000128119
Created by admin on Wed Jul 05 22:31:52 UTC 2023 , Edited by admin on Wed Jul 05 22:31:52 UTC 2023
PRIMARY
RS_ITEM_NUM
1162148
Created by admin on Wed Jul 05 22:31:52 UTC 2023 , Edited by admin on Wed Jul 05 22:31:52 UTC 2023
PRIMARY
CAS
71-30-7
Created by admin on Wed Jul 05 22:31:52 UTC 2023 , Edited by admin on Wed Jul 05 22:31:52 UTC 2023
PRIMARY
FDA UNII
8J337D1HZY
Created by admin on Wed Jul 05 22:31:52 UTC 2023 , Edited by admin on Wed Jul 05 22:31:52 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-749-5
Created by admin on Wed Jul 05 22:31:52 UTC 2023 , Edited by admin on Wed Jul 05 22:31:52 UTC 2023
PRIMARY
NCI_THESAURUS
C410
Created by admin on Wed Jul 05 22:31:52 UTC 2023 , Edited by admin on Wed Jul 05 22:31:52 UTC 2023
PRIMARY
MERCK INDEX
M4062
Created by admin on Wed Jul 05 22:31:52 UTC 2023 , Edited by admin on Wed Jul 05 22:31:52 UTC 2023
PRIMARY Merck Index
WIKIPEDIA
CYTOSINE
Created by admin on Wed Jul 05 22:31:52 UTC 2023 , Edited by admin on Wed Jul 05 22:31:52 UTC 2023
PRIMARY
NSC
27787
Created by admin on Wed Jul 05 22:31:52 UTC 2023 , Edited by admin on Wed Jul 05 22:31:52 UTC 2023
PRIMARY
EPA CompTox
DTXSID4044456
Created by admin on Wed Jul 05 22:31:52 UTC 2023 , Edited by admin on Wed Jul 05 22:31:52 UTC 2023
PRIMARY
CHEBI
16040
Created by admin on Wed Jul 05 22:31:52 UTC 2023 , Edited by admin on Wed Jul 05 22:31:52 UTC 2023
PRIMARY
PUBCHEM
597
Created by admin on Wed Jul 05 22:31:52 UTC 2023 , Edited by admin on Wed Jul 05 22:31:52 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SOLVATE->ANHYDROUS
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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