CYTIDINE

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C9H13N3O5
Molecular Weight	243.2166
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=NC(=O)N(C=C1)[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O

InChI

InChIKey=UHDGCWIWMRVCDJ-XVFCMESISA-N

InChI=1S/C9H13N3O5/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16)/t4-,6-,7-,8-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C9H13N3O5
Molecular Weight	243.2166
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28458037

Cytidine is a substrate of the uridine-cytidine kinase and is a part nucleic acids. It can serve as a substrate for the salvage pathway of pyrimidine nucleotide synthesis, as a precursor of the cytidine triphosphate (CTP) needed in the phosphatidylcholine (PC) and phosphatidylethanolamine (PE) biosynthetic pathway. Cytidine was also used under the brand name posilent in Germany for the treatment of muscular, accommodative, and nervous eye disorders.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Uridine-cytidine kinase 3 Target ID: CHEMBL3542438 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28458037	Substrate 661

Conditions

Condition	Modality	Targets	Highest Phase	Product
Muscular, accommodative, and nervous eye disorders 1 Sources: http://www.ndrugs.com/?s=posilent	Primary		Not Provided 511	posilent Approved Use Unknown

PubMed

Title	Date	PubMed
Novel role for RNA-binding protein CUGBP2 in mammalian RNA editing. CUGBP2 modulates C to U editing of apolipoprotein B mRNA by interacting with apobec-1 and ACF, the apobec-1 complementation factor.	2001-12-14	11577082
Hepatitis C virus RNA-dependent RNA polymerase (NS5B) as a mediator of the antiviral activity of ribavirin.	2001-12-07	11602568
Mutagenesis of apobec-1 complementation factor reveals distinct domains that modulate RNA binding, protein-protein interaction with apobec-1, and complementation of C to U RNA-editing activity.	2001-12-07	11571303
ARCD-1, an apobec-1-related cytidine deaminase, exerts a dominant negative effect on C to U RNA editing.	2001-12	11698249
Anticodon domain methylated nucleosides of yeast tRNA(Phe) are significant recognition determinants in the binding of a phage display selected peptide.	2001-11-27	11714272
Quantitation of GSTP1 methylation in non-neoplastic prostatic tissue and organ-confined prostate adenocarcinoma.	2001-11-21	11717336
Biosynthesis of vitamin B(6) in yeast: incorporation pattern of glucose.	2001-11-21	11707109
Isolation, characterization and developmental regulation of the human apobec-1 complementation factor (ACF) gene.	2001-11-11	11718896
Five-chlorodeoxycytidine, a tumor-selective enzyme-driven radiosensitizer, effectively controls five advanced human tumors in nude mice.	2001-11-01	11697326
Essential role of Stat5 for IL-5-dependent IgH switch recombination in mouse B cells.	2001-11-01	11673510
Resistance to 2-chloro-2'-deoxyadenosine of the human B-cell leukemia cell line EHEB.	2001-11	11705877
The cytostatic- and differentiation-inducing effects of cyclopentenyl cytosine on neuroblastoma cell lines.	2001-10-15	11597578
Cloning and verification of the Lactococcus lactis pyrG gene and characterization of the gene product, CTP synthase.	2001-10-12	11500486
In situ class switching and differentiation to IgA-producing cells in the gut lamina propria.	2001-10-11	11675788
A new reactive nucleoside analogue for highly reactive and selective cross-linking reaction to cytidine under neutral conditions.	2001-10-08	11551753
Mechanisms of uptake and resistance to troxacitabine, a novel deoxycytidine nucleoside analogue, in human leukemic and solid tumor cell lines.	2001-10-01	11585758
Phase I trial of weekly gemcitabine at 3-h infusion in refractory, heavily pretreated advanced solid tumors.	2001-10	11593051
Use of isogenic human cancer cells for high-throughput screening and drug discovery.	2001-10	11581659
Cyclopentenyl cytosine induces apoptosis and increases cytarabine-induced apoptosis in a T-lymphoblastic leukemic cell-line.	2001-10	11532523
Site-bound water and the shortcomings of a less than perfect transition state analogue.	2001-09-25	11560484
Site-directed alkylation to cytidine within duplex by the oligonucleotides containing functional nucleobases.	2001-09-21	11563144
Unnatural enantiomers of 5-azacytidine analogues: syntheses and enzymatic properties.	2001-09-21	11563127
1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine (ECyd, TAS-106)1: antitumor effect and mechanism of action.	2001-09-21	11563078
6-oxocytidine containing oligonucleotides inhibit the HIV-1 integrase in vitro.	2001-09-21	11563063
Synthetic studies to improve the deuterium labelling in nucleosides for facilitating structural studies of large RNAs by high-field NMR spectroscopy.	2001-09-21	11563016
Kinetic properties of the acylneuraminate cytidylyltransferase from Pasteurella haemolytica A2.	2001-09-15	11577688
Synthesis and biological evaluation of L- and D-configurations of 2',3'-dideoxy-4'-C-methyl-3'-oxacytidine analogues.	2001-09-03	11527719
Selection of drug-resistant transduced cells with cytosine nucleoside analogs using the human cytidine deaminase gene.	2001-09	11593336
A novel affinity chromatography method for the co-purification of deoxycytidine kinase and cytidine deaminase.	2001-09	11580191
Association between a new polymorphism in the activation-induced cytidine deaminase gene and atopic asthma and the regulation of total serum IgE levels.	2001-09	11544457
Clonal instability of V region hypermutation in the Ramos Burkitt's lymphoma cell line.	2001-09	11526098
Cloning and expression of uridine/cytidine kinase cDNA from human fibrosarcoma cells.	2001-09	11494055
Cleavage of 3',5'-pyrophosphate-linked dinucleotides by ribonuclease A and angiogenin.	2001-08-28	11513604
Phosphorylation is a regulatory mechanism in apolipoprotein B mRNA editing.	2001-08-01	11463337
Hypochlorite-induced damage to nucleosides: formation of chloramines and nitrogen-centered radicals.	2001-08	11511181
Solution structure of the pseudoknot of SRV-1 RNA, involved in ribosomal frameshifting.	2001-07-27	11501999
A phase I trial of topotecan and gemcitabine administered weekly for 3 consecutive weeks to patients with advanced tumors.	2001-07-15	11466697
Intracellular trafficking determinants in APOBEC-1, the catalytic subunit for cytidine to uridine editing of apolipoprotein B mRNA.	2001-07-15	11426934
Full-sized RanBPM cDNA encodes a protein possessing a long stretch of proline and glutamine within the N-terminal region, comprising a large protein complex.	2001-07-11	11470507
RNA editing in higher plant plastids: oligoribonucleotide SSCP analysis allows the proof of base conversion directly at the RNA level.	2001-07	11525414
Linking class-switch recombination with somatic hypermutation.	2001-07	11433363
An efficient method for the preparation of 1'alpha-branched-chain sugar pyrimidine ribonucleosides from uridine: the first conversion of a natural nucleoside into 1'-substituted ribonucleosides.	2001-06-01	11446636
Effects of tomato extract on human platelet aggregation in vitro.	2001-06	11454256
Screening of differentially expressed genes in 5-fluorouracil-resistant human gastrointestinal tumor cells.	2001-06	11429060
The RNA i-motif.	2001-05-25	11491284
Hydrogen-bond-mediated photoinduced electron-transfer: novel dimethylaniline-anthracene ensembles formed via Watson-Crick base-pairing.	2001-04-25	11457097
Stability and structure of RNA duplexes containing isoguanosine and isocytidine.	2001-02-21	11456697
Mutant loxP vectors for selectable marker recycle and conditional knock-outs.	2001	11591226
Comparative histochemical study of Bowen's disease and actinic keratosis: preserved normal basal cells in Bowen's disease.	2001	11512639
Cytostatic effect of inostamycin, an inhibitor of cytidine 5'-diphosphate 1,2-diacyl-sn-glycerol (CDP-DG): inositol transferase, on oral squamous cell carcinoma cell lines.	2001	11448100

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

In the proliferating normal human T lymphocytes similar patterns of incorporation of [14C]uridine were observed in the presence of the physiological concentration of cytidine and after addition of 2 microM of cytidine. In contrast, in the MOLT-3 cells after addition of 2 microM of cytidine the proportion of CTP synthesized by conversion of UTP into CTP was substantially decreased, whereas the salvage of cytidine was proportionally increased. It was concluded that the reutilization of uridine is a preferred route in the synthesis of CTP for MOLT-3 cells at physiological concentrations of uridine and cytidine, whereas in proliferating normal human T lymphocytes CTP is largely synthesized through reutilization of cytidine. This difference in salvage of pyrimidine ribonucleosides may be exploited for selective chemotherapy.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:46:34 GMT 2025` Edited by `admin` on `Mon Mar 31 17:46:34 GMT 2025`
Record UNII	5CSZ8459RP
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CYTIDINE

Official Name

English

NSC-20258

Preferred Name

English

CYTIDINE [MI]

Common Name

English

Cytidine [WHO-DD]

Common Name

English

CYTIDINE [MART.]

Common Name

English

Classification Tree Code System Code

DSLD

4271 (Number of products:1)