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 2578

PubMed

Title	Date	PubMed
Murine recombinant prion protein induces ordered aggregation of linear nucleic acids to condensed globular structures.	2001	11315641
Prophylaxis against herpesvirus infections in transplant recipients.	2001	11270937
Suicide gene therapy for pediatric tumors.	2001	11269507
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
Identification of genetic variants (g789C>T and G111S) in the human HSPB2 gene.	2001	11139265
T>C transition in codon 72 (TCG-->CCG), S72P, a putative hotspot in PMP22.	2001	11139264
A novel deletion (c663delC) at exon 5 of the proteolipid protein gene in Pelizaeus-Merzbacher disease.	2001	11139261
Suicide gene therapy: possible applications in haematopoietic disorders.	2001 Apr	11298856
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	11292409
DNA methylation learns to fly.	2001 Apr	11275305
Low-energy (5-40 eV) electron-stimulated desorption of anions from physisorbed DNA bases.	2001 Apr	11260665
Solution structure of the SL1 RNA of the M1 double-stranded RNA virus of Saccharomyces cerevisiae.	2001 Apr	11259308
Single molecule DNA sequencing in submicrometer channels: state of the art and future prospects.	2001 Apr 13	11257531
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
15-mer DNA duplexes containing an abasic site are thermodynamically more stable with adjacent purines than with pyrimidines.	2001 Apr 3	11300765
Changes in DNA methylation in neoplasia: pathophysiology and therapeutic implications.	2001 Apr 3	11281740
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
Characterization of DNA damage at purine residues in oligonucleotides and calf thymus DNA induced by the mutagen 1-nitrosoindole-3-acetonitrile.	2001 Feb	11258964
Differentiation of Streptococcus mutans and Streptococcus sobrinus via genotypic and phenotypic profiles from three different populations.	2001 Feb	11169134
Radiation concurrent with gemcitabine for locally advanced head and neck cancer: a phase I trial and intracellular drug incorporation study.	2001 Feb 1	11157033
Troxacitabine, a novel dioxolane nucleoside analog, has activity in patients with advanced leukemia.	2001 Feb 1	11157029
Alkylating agent and chromatin structure determine sequence context-dependent formation of alkylpurines.	2001 Feb 16	11237592
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
Isolation and analysis of an aciclovir-resistant murine cytomegalovirus mutant.	2001 Jan	11166858
Biochemical characterization of a neuroserpin variant associated with hereditary dementia.	2001 Jan	11141496
Usefulness of repeated direct intratumoral gene transfer using hemagglutinating virus of Japan-liposome method for cytosine deaminase suicide gene therapy.	2001 Jan 1	11196152
Regions of low single-nucleotide polymorphism incidence in human and orangutan xq: deserts and recent coalescences.	2001 Jan 1	11161800
Virological, clinical, and ophthalmologic features of cytomegalovirus retinitis after hematopoietic stem cell transplantation.	2001 Jan 15	11170910
Similarities in sunlight-induced mutational spectra of CpG-methylated transgenes and the p53 gene in skin cancer point to an important role of 5-methylcytosine residues in solar UV mutagenesis.	2001 Jan 19	11152598
Long-term remission of an AIDS-related primary effusion lymphoma with antiviral therapy.	2001 Jan 26	11216942
In-situ FTIR study on adsorption and oxidation of native and thermally denatured calf thymus DNA at glassy carbon electrodes.	2001 Jan 31	11246748
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
Epigenetic regulation of human bone morphogenetic protein 6 gene expression in prostate cancer.	2001 Mar	11277266
Topical cidofovir for bowenoid papulosis in an HIV-infected patient.	2001 Mar	11260042
Polymorphism of the WAF1 gene is related to susceptibility to cervical cancer in Japanese women.	2001 Mar	11179504
Atypical forms of incontinentia pigmenti in male individuals result from mutations of a cytosine tract in exon 10 of NEMO (IKK-gamma).	2001 Mar	11179023
High guanine-cytosine content is not an adaptation to high temperature: a comparative analysis amongst prokaryotes.	2001 Mar 7	11296861
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
Treatment of adenovirus infections in patients undergoing allogeneic hematopoietic stem cell transplantation.	2001 May 1	11303263
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 `Fri Dec 15 14:59:48 GMT 2023` Edited by `admin` on `Fri Dec 15 14:59:48 GMT 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