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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 of CYTIDINE

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

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
posilent

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Molecular cloning and functional characterization of inhibitor-sensitive (mENT1) and inhibitor-resistant (mENT2) equilibrative nucleoside transporters from mouse brain.
2000 Dec 1
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
Polymorphisms in the Mn-SOD and EC-SOD genes and their relationship to diabetic neuropathy in type 1 diabetes mellitus.
2001
Synthesis of novel 3'-C-methylene thymidine and 5-methyluridine/cytidine H-phosphonates and phosphonamidites for new backbone modification of oligonucleotides.
2001 Apr 20
6-oxocytidine containing oligonucleotides inhibit the HIV-1 integrase in vitro.
2001 Apr-Jul
Synthetic studies to improve the deuterium labelling in nucleosides for facilitating structural studies of large RNAs by high-field NMR spectroscopy.
2001 Apr-Jul
Phosphorylation is a regulatory mechanism in apolipoprotein B mRNA editing.
2001 Aug 1
A novel proton-dependent nucleoside transporter, CeCNT3, from Caenorhabditis elegans.
2001 Feb
Comments on: cylopentenyl cytosine inhibits cytidine triphosphate synthetase in paediatric acute non-lymphocytic leukaemia: a promising target for chemotherapy. A.C. Verschuur et al. Eur J Cancer 2000, 36, 627-635.
2001 Jan
Reduced hydrolysis of amelogenin may result in X-linked amelogenesis imperfecta.
2001 Jan
Induction of differentiation of acute promyelocytic leukemia cells by a cytidine deaminase-resistant analogue of 1-beta-D-arabinofuranosylcytosine, 1-(2-deoxy-2-methylene-beta-D-erythro-pentofuranosyl)cytidine.
2001 Jan 1
Simultaneous treatment with 1-beta-D-arabinofuranosylcytosine and daunorubicin induces cross-resistance to both drugs due to a combination-specific mechanism in HL60 cells.
2001 Jan 1
Purification method for the isolation of monophosphate nucleotides from Champagne wine and their identification by mass spectrometry.
2001 Jan 12
The RihA, RihB, and RihC ribonucleoside hydrolases of Escherichia coli. Substrate specificity, gene expression, and regulation.
2001 Jan 12
Temperature is a cue for gene expression in the post-infective L3 of the parasitic nematode Brugia pahangi.
2001 Jan 15
Probing structure and dynamics of DNA with 2-aminopurine: effects of local environment on fluorescence.
2001 Jan 30
RNA editing in higher plant plastids: oligoribonucleotide SSCP analysis allows the proof of base conversion directly at the RNA level.
2001 Jul
Correlated conformational fluctuations during enzymatic catalysis: Implications for catalytic rate enhancement.
2001 Jul
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
Screening of differentially expressed genes in 5-fluorouracil-resistant human gastrointestinal tumor cells.
2001 Jun
Elucidation of the initial step of oligonucleotide fragmentation in matrix-assisted laser desorption/ionization using modified nucleic acids.
2001 Jun
Na+ reabsorption in cultured rat epididymal epithelium via the Na+/nucleoside cotransporter.
2001 Mar
Ontogenic and longitudinal activity of Na(+)-nucleoside transporters in the human intestine.
2001 Mar
Cytosolic high K(m) 5'-nucleotidase and 5'(3')-deoxyribonucleotidase in substrate cycles involved in nucleotide metabolism.
2001 Mar 2
Effects of purine and pyrimidine nucleotides on intracellular Ca2+ in human eosinophils: activation of purinergic P2Y receptors.
2001 May
The RNA i-motif.
2001 May 25
Five-chlorodeoxycytidine, a tumor-selective enzyme-driven radiosensitizer, effectively controls five advanced human tumors in nude mice.
2001 Nov 1
Isolation, characterization and developmental regulation of the human apobec-1 complementation factor (ACF) gene.
2001 Nov 11
Quantitation of GSTP1 methylation in non-neoplastic prostatic tissue and organ-confined prostate adenocarcinoma.
2001 Nov 21
Anticodon domain methylated nucleosides of yeast tRNA(Phe) are significant recognition determinants in the binding of a phage display selected peptide.
2001 Nov 27
Phase I trial of weekly gemcitabine at 3-h infusion in refractory, heavily pretreated advanced solid tumors.
2001 Oct
Mechanisms of uptake and resistance to troxacitabine, a novel deoxycytidine nucleoside analogue, in human leukemic and solid tumor cell lines.
2001 Oct 1
The cytostatic- and differentiation-inducing effects of cyclopentenyl cytosine on neuroblastoma cell lines.
2001 Oct 15
Clonal instability of V region hypermutation in the Ramos Burkitt's lymphoma cell line.
2001 Sep
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
  • Download
Name Type Language
CYTIDINE
INCI   MART.   MI   WHO-DD  
INCI  
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)
Created by admin on Fri Dec 15 15:06:18 GMT 2023 , Edited by admin on Fri Dec 15 15:06:18 GMT 2023
NCI_THESAURUS C707
Created by admin on Fri Dec 15 15:06:18 GMT 2023 , Edited by admin on Fri Dec 15 15:06:18 GMT 2023
LOINC 79671-4
Created by admin on Fri Dec 15 15:06:18 GMT 2023 , Edited by admin on Fri Dec 15 15:06:18 GMT 2023
LOINC 79684-7
Created by admin on Fri Dec 15 15:06:18 GMT 2023 , Edited by admin on Fri Dec 15 15:06:18 GMT 2023
LOINC 79675-5
Created by admin on Fri Dec 15 15:06:18 GMT 2023 , Edited by admin on Fri Dec 15 15:06:18 GMT 2023
Code System Code Type Description
DRUG BANK
DB02097
Created by admin on Fri Dec 15 15:06:18 GMT 2023 , Edited by admin on Fri Dec 15 15:06:18 GMT 2023
PRIMARY
MERCK INDEX
m4053
Created by admin on Fri Dec 15 15:06:18 GMT 2023 , Edited by admin on Fri Dec 15 15:06:18 GMT 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
200-610-9
Created by admin on Fri Dec 15 15:06:18 GMT 2023 , Edited by admin on Fri Dec 15 15:06:18 GMT 2023
PRIMARY
EPA CompTox
DTXSID60891552
Created by admin on Fri Dec 15 15:06:18 GMT 2023 , Edited by admin on Fri Dec 15 15:06:18 GMT 2023
PRIMARY
CHEBI
17562
Created by admin on Fri Dec 15 15:06:18 GMT 2023 , Edited by admin on Fri Dec 15 15:06:18 GMT 2023
PRIMARY
NSC
20258
Created by admin on Fri Dec 15 15:06:18 GMT 2023 , Edited by admin on Fri Dec 15 15:06:18 GMT 2023
PRIMARY
EVMPD
SUB22640
Created by admin on Fri Dec 15 15:06:18 GMT 2023 , Edited by admin on Fri Dec 15 15:06:18 GMT 2023
PRIMARY
NCI_THESAURUS
C409
Created by admin on Fri Dec 15 15:06:18 GMT 2023 , Edited by admin on Fri Dec 15 15:06:18 GMT 2023
PRIMARY
WIKIPEDIA
CYTIDINE
Created by admin on Fri Dec 15 15:06:18 GMT 2023 , Edited by admin on Fri Dec 15 15:06:18 GMT 2023
PRIMARY
PUBCHEM
6175
Created by admin on Fri Dec 15 15:06:18 GMT 2023 , Edited by admin on Fri Dec 15 15:06:18 GMT 2023
PRIMARY
FDA UNII
5CSZ8459RP
Created by admin on Fri Dec 15 15:06:18 GMT 2023 , Edited by admin on Fri Dec 15 15:06:18 GMT 2023
PRIMARY
MESH
D003562
Created by admin on Fri Dec 15 15:06:18 GMT 2023 , Edited by admin on Fri Dec 15 15:06:18 GMT 2023
PRIMARY
CAS
65-46-3
Created by admin on Fri Dec 15 15:06:18 GMT 2023 , Edited by admin on Fri Dec 15 15:06:18 GMT 2023
PRIMARY
SMS_ID
100000089044
Created by admin on Fri Dec 15 15:06:18 GMT 2023 , Edited by admin on Fri Dec 15 15:06:18 GMT 2023
PRIMARY
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