CYTOSINE

Possibly Marketed Outside US

First approved in 2014

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 Search

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

Description
Sources: https://themedicalbiochemistrypage.org/nucleic-acids.php | https://library.med.utah.edu/NetBiochem/pupyr/pp.htm

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

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2565

PubMed

Title	Date	PubMed
Murine recombinant prion protein induces ordered aggregation of linear nucleic acids to condensed globular structures.	2001	11315641
A simple model based on mutation and selection explains trends in codon and amino-acid usage and GC composition within and across genomes.	2001	11305938
Prophylaxis against herpesvirus infections in transplant recipients.	2001	11270937
Imaging biochemistry: applications to breast cancer.	2001	11250743
UAG readthrough in mammalian cells: effect of upstream and downstream stop codon contexts reveal different signals.	2001	11242562
Regulation of gene expression by GC-rich DNA cis-elements.	2001	11237405
A novel polymorphism (-88 C>A) in the 5' UTR of the p53R2 gene.	2001	11139269
A novel polymorphism IVS2+843C>T in the alternate promoter b1 of the human AE2 anion exchanger gene.	2001	11139268
A novel polymorphism (c288C>T) of the NPHS2 gene identified in a Taiwan Chinese family.	2001	11139267
A novel elastin gene mutation (1281delC) in a family with supravalvular aortic stenosis: a mutation cluster within exon 20.	2001	11139266
DNA methylation learns to fly.	2001 Apr	11275305
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	11254879
Association study of CAG repeats in the KCNN3 gene in Japanese patients with schizophrenia, schizoaffective disorder and bipolar disorder.	2001 Apr 15	11311923
Potent inhibition of hemangiosarcoma development in mice by cidofovir.	2001 Apr 15	11291040
Glucocorticoid-induced DNA demethylation and gene memory during development.	2001 Apr 17	11296230
Changes in DNA methylation in neoplasia: pathophysiology and therapeutic implications.	2001 Apr 3	11281740
Suicide gene therapy for premalignant disease: a new strategy for the treatment of intraepithelial neoplasia.	2001 Feb	11313795
Isolation and frontier molecular orbital investigation of bioactive quinone-methide triterpenoids from the bark of Salacia petenensis.	2001 Feb	11270725
Size constraints for targeting post-transcriptional gene silencing and for RNA-directed methylation in Nicotiana benthamiana using a potato virus X vector.	2001 Feb	11260498
Confounded cytosine! Tinkering and the evolution of DNA.	2001 Feb	11252956
Mildly eccentric 'E-DNA'.	2001 Feb	11175893
Structure of an RNA duplex with an unusual G.C pair in wobble-like conformation at 1.6 A resolution.	2001 Feb	11173467
Differentiation of Streptococcus mutans and Streptococcus sobrinus via genotypic and phenotypic profiles from three different populations.	2001 Feb	11169134
Surveying CpG methylation at 5'-CCGG in the genomes of rice cultivars.	2001 Jan	11247604
Diagnostic and therapeutic dilemmas of a large scrotal lesion in an AIDS patient.	2001 Jan	11215088
Reduction of wobble-position GC bases in Corynebacteria genes and enhancement of PCR and heterologous expression.	2001 Jan	11200224
Microsoft Word macro for analysis of cytosine methylation by the bisulfite deamination reaction.	2001 Jan	11196301
Spreadsheet-based program for the analysis of DNA methylation.	2001 Jan	11196300
In vitro effects of antiviral agents on human keratocytes.	2001 Jan	11189008
The use of bacterial choline oxidase, a glycinebetaine-synthesizing enzyme, to create stress-resistant transgenic plants.	2001 Jan	11154327
Usefulness of repeated direct intratumoral gene transfer using hemagglutinating virus of Japan-liposome method for cytosine deaminase suicide gene therapy.	2001 Jan 1	11196152
Virological, clinical, and ophthalmologic features of cytomegalovirus retinitis after hematopoietic stem cell transplantation.	2001 Jan 15	11170910
Long-term remission of an AIDS-related primary effusion lymphoma with antiviral therapy.	2001 Jan 26	11216942
Terpsichorean movements of pentaammineruthenium on pyrimidine and isocytosine ligands.	2001 Jan 29	11209605
The mechanism of DNA cytosine-5 methylation. Kinetic and mutational dissection of Hhai methyltransferase.	2001 Jun 15	11283006
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	11320667
Early diagnosis of adenovirus infection and treatment with cidofovir after bone marrow transplantation in children.	2001 Mar	11319592
Effect of chemical modifications of cytosine and guanine in a CpG-motif of oligonucleotides: structure-immunostimulatory activity relationships.	2001 Mar	11310616
Polymorphism of the WAF1 gene is related to susceptibility to cervical cancer in Japanese women.	2001 Mar	11179504
Tetraplex formation by the progressive myoclonus epilepsy type-1 repeat: implications for instability in the repeat expansion diseases.	2001 Mar 2	11240124
A-like guanine-guanine stacking in the aqueous DNA duplex of d(GGGGCCCC).	2001 Mar 23	11254379
Solution structure of an A-tract DNA bend.	2001 Mar 9	11237619
Molecular topology of polycyclic aromatic carcinogens determines DNA adduct conformation: a link to tumorigenic activity.	2001 Mar 9	11237618
Pseudogenes, junk DNA, and the dynamics of Rickettsia genomes.	2001 May	11319266
The elevated GC content at exonic third sites is not evidence against neutralist models of isochore evolution.	2001 May	11319260
Actinomycin D binds strongly to d(TGTCATTG), a single-stranded DNA devoid of GpC sites.	2001 May 1	11318644
Catechol estrogens induce oxidative DNA damage and estradiol enhances cell proliferation.	2001 May 1	11291067
Cytosine methylation enhances mitoxantrone-DNA adduct formation at CpG dinucleotides.	2001 May 11	11278477
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	11279060
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	11278705

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

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