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 504	posilent Approved Use Unknown

PubMed

Title	Date	PubMed
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
Hydrogen-bond-mediated photoinduced electron-transfer: novel dimethylaniline-anthracene ensembles formed via Watson-Crick base-pairing.	2001 Apr 25	11457097
Site-directed alkylation to cytidine within duplex by the oligonucleotides containing functional nucleobases.	2001 Apr-Jul	11563144
Unnatural enantiomers of 5-azacytidine analogues: syntheses and enzymatic properties.	2001 Apr-Jul	11563127
1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine (ECyd, TAS-106)1: antitumor effect and mechanism of action.	2001 Apr-Jul	11563078
6-oxocytidine containing oligonucleotides inhibit the HIV-1 integrase in vitro.	2001 Apr-Jul	11563063
Synthetic studies to improve the deuterium labelling in nucleosides for facilitating structural studies of large RNAs by high-field NMR spectroscopy.	2001 Apr-Jul	11563016
Hypochlorite-induced damage to nucleosides: formation of chloramines and nitrogen-centered radicals.	2001 Aug	11511181
Phosphorylation is a regulatory mechanism in apolipoprotein B mRNA editing.	2001 Aug 1	11463337
Cleavage of 3',5'-pyrophosphate-linked dinucleotides by ribonuclease A and angiogenin.	2001 Aug 28	11513604
ARCD-1, an apobec-1-related cytidine deaminase, exerts a dominant negative effect on C to U RNA editing.	2001 Dec	11698249
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 Dec 14	11577082
Hepatitis C virus RNA-dependent RNA polymerase (NS5B) as a mediator of the antiviral activity of ribavirin.	2001 Dec 7	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 Dec 7	11571303
Stability and structure of RNA duplexes containing isoguanosine and isocytidine.	2001 Feb 21	11456697
RNA editing in higher plant plastids: oligoribonucleotide SSCP analysis allows the proof of base conversion directly at the RNA level.	2001 Jul	11525414
Linking class-switch recombination with somatic hypermutation.	2001 Jul	11433363
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 Jul 11	11470507
A phase I trial of topotecan and gemcitabine administered weekly for 3 consecutive weeks to patients with advanced tumors.	2001 Jul 15	11466697
Intracellular trafficking determinants in APOBEC-1, the catalytic subunit for cytidine to uridine editing of apolipoprotein B mRNA.	2001 Jul 15	11426934
Solution structure of the pseudoknot of SRV-1 RNA, involved in ribosomal frameshifting.	2001 Jul 27	11501999
Effects of tomato extract on human platelet aggregation in vitro.	2001 Jun	11454256
Screening of differentially expressed genes in 5-fluorouracil-resistant human gastrointestinal tumor cells.	2001 Jun	11429060
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 Jun 1	11446636
The RNA i-motif.	2001 May 25	11491284
Resistance to 2-chloro-2'-deoxyadenosine of the human B-cell leukemia cell line EHEB.	2001 Nov	11705877
Five-chlorodeoxycytidine, a tumor-selective enzyme-driven radiosensitizer, effectively controls five advanced human tumors in nude mice.	2001 Nov 1	11697326
Essential role of Stat5 for IL-5-dependent IgH switch recombination in mouse B cells.	2001 Nov 1	11673510
Isolation, characterization and developmental regulation of the human apobec-1 complementation factor (ACF) gene.	2001 Nov 11	11718896
Quantitation of GSTP1 methylation in non-neoplastic prostatic tissue and organ-confined prostate adenocarcinoma.	2001 Nov 21	11717336
Biosynthesis of vitamin B(6) in yeast: incorporation pattern of glucose.	2001 Nov 21	11707109
Anticodon domain methylated nucleosides of yeast tRNA(Phe) are significant recognition determinants in the binding of a phage display selected peptide.	2001 Nov 27	11714272
Phase I trial of weekly gemcitabine at 3-h infusion in refractory, heavily pretreated advanced solid tumors.	2001 Oct	11593051
Use of isogenic human cancer cells for high-throughput screening and drug discovery.	2001 Oct	11581659
Cyclopentenyl cytosine induces apoptosis and increases cytarabine-induced apoptosis in a T-lymphoblastic leukemic cell-line.	2001 Oct	11532523
Mechanisms of uptake and resistance to troxacitabine, a novel deoxycytidine nucleoside analogue, in human leukemic and solid tumor cell lines.	2001 Oct 1	11585758
In situ class switching and differentiation to IgA-producing cells in the gut lamina propria.	2001 Oct 11	11675788
Cloning and verification of the Lactococcus lactis pyrG gene and characterization of the gene product, CTP synthase.	2001 Oct 12	11500486
The cytostatic- and differentiation-inducing effects of cyclopentenyl cytosine on neuroblastoma cell lines.	2001 Oct 15	11597578
A new reactive nucleoside analogue for highly reactive and selective cross-linking reaction to cytidine under neutral conditions.	2001 Oct 8	11551753
Selection of drug-resistant transduced cells with cytosine nucleoside analogs using the human cytidine deaminase gene.	2001 Sep	11593336
A novel affinity chromatography method for the co-purification of deoxycytidine kinase and cytidine deaminase.	2001 Sep	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 Sep	11544457
Clonal instability of V region hypermutation in the Ramos Burkitt's lymphoma cell line.	2001 Sep	11526098
Cloning and expression of uridine/cytidine kinase cDNA from human fibrosarcoma cells.	2001 Sep	11494055
Kinetic properties of the acylneuraminate cytidylyltransferase from Pasteurella haemolytica A2.	2001 Sep 15	11577688
Site-bound water and the shortcomings of a less than perfect transition state analogue.	2001 Sep 25	11560484
Synthesis and biological evaluation of L- and D-configurations of 2',3'-dideoxy-4'-C-methyl-3'-oxacytidine analogues.	2001 Sep 3	11527719

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 `Fri Dec 15 15:06:18 GMT 2023` Edited by `admin` on `Fri Dec 15 15:06:18 GMT 2023`
Record UNII	5CSZ8459RP
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CYTIDINE

Official Name

English

CYTIDINE [INCI]

Common Name

English

CYTIDINE [MI]

Common Name

English

Cytidine [WHO-DD]

Common Name

English

CYTIDINE [MART.]

Common Name

English

NSC-20258

Code

English

Classification Tree Code System Code

DSLD

4271 (Number of products:1)