View source for Cytidine

{{distinguish|cytosine|cysteine|cystine|cytisine}}
{{chembox
| Watchedfields = changed
| verifiedrevid = 443554948
| ImageFile = Cytidin.svg
| ImageSize = 150px
| ImageAlt = Skeletal formula of cytidine
| ImageFile1 = Cytidine 3D ball.png
| ImageAlt1 = Ball-and-stick model of the cytidine molecule
| IUPACName = Cytidine
| SystematicName = 4-Amino-1-[(2''R'',3''R'',4''S'',5''R'')-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2(1''H'')-one
| OtherNames = 4-Amino-1-β-<small>D</small>-ribofuranosyl-2(1''H'')-pyrimidinone<ref name="crc97">{{cite book | author=William M. Haynes | title=CRC Handbook of Chemistry and Physics | edition=97th | year=2016 | publisher=CRC Press | location=Boca Raton | isbn=978-1-4987-5429-3 | pages=3–140 | url=https://books.google.com/books?id=VVezDAAAQBAJ}}</ref><br>4-Amino-1-[3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one
|Section1={{Chembox Identifiers
| IUPHAR_ligand = 4728
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5940
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07769
| InChI = 1/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
| InChIKey = UHDGCWIWMRVCDJ-XVFCMESIBD
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 95606
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = UHDGCWIWMRVCDJ-XVFCMESISA-N
| CASNo=65-46-3
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem=6175
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 5CSZ8459RP
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 17562
| SMILES = O=C1/N=C(/N)\C=C/N1[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)CO
| MeSHName=Cytidine
  }}
|Section2={{Chembox Properties
| C=9 | H=13 | N=3 | O=5
| MolarMass=243.217
| Appearance= white, crystalline powder<ref name="hawleys">{{cite book | author=Robert A. Lewis, Michael D. Larrañaga, Richard J. Lewis Sr. | title=Hawley's Condensed Chemical Dictionary | edition=16th | year=2016 | publisher=John Wiley & Sons, Inc. | location=Hoboken, New Jersey | isbn=978-1-118-13515-0 | page=688}}</ref>
| Density=
| MeltingPt=230 °C (decomposes)<ref name="crc97"/>
| BoilingPt=
| Solubility=
| MagSus = −123.7·10<sup>−6</sup> cm<sup>3</sup>/mol
  }}
|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
  }}
}}

'''Cytidine''' ([[nucleoside#List of nucleosides and corresponding nucleobases|symbol]] '''C''' or '''Cyd''') is a [[nucleoside]] [[molecule]] that is formed when [[cytosine]] is attached to a [[ribose]] ring (also known as a [[ribofuranose]]) via a β-N<sub>1</sub>-[[glycosidic bond]]. Cytidine is a component of [[RNA]]. It is a white water-soluble solid<ref name="hawleys"/> that is only slightly soluble in [[ethanol]].<ref name="crc97"/>

==Dietary sources==
Dietary sources of cytidine include foods with high RNA (ribonucleic acid) content,<ref name=Jonas>{{cite journal |author=Jonas DA |title=Safety considerations of DNA in food |journal=Ann Nutr Metab |volume=45 |issue=6 |pages=235–54 |year=2001 |pmid=11786646 |url=http://content.karger.com/produktedb/produkte.asp?typ=fulltext&file=anm45235 |doi=10.1159/000046734 |author2=Elmadfa I |author3=Engel KH |display-authors=3 |last4=Heller |first4=K.J. |last5=Kozianowski |first5=G. |last6=kÖNig |first6=A. |last7=mÜLler |first7=D. |last8=Narbonne |first8=J.F. |last9=Wackernagel |first9=W.|doi-access=free |url-access=subscription }}</ref> such as organ meats, brewer's yeast, as well as pyrimidine-rich foods such as beer. During digestion, RNA-rich foods are broken-down into ribosyl pyrimidines (cytidine and [[uridine]]), which are absorbed intact.<ref name=Jonas/>  In humans, dietary cytidine is converted into uridine,<ref>{{cite journal |vauthors=Wurtman RJ, Regan M, Ulus I, Yu L |title=Effect of oral CDP-choline on plasma choline and uridine levels in humans |journal=Biochem. Pharmacol. |volume=60 |issue=7 |pages=989–92 |date=Oct 2000 |pmid=10974208 |doi=10.1016/S0006-2952(00)00436-6|s2cid=18687483 }}</ref> which is probably the compound behind cytidine's metabolic effects.

==Cytidine analogues==
A variety of cytidine [[analog (chemistry)|analogues]] are known, some with potentially useful pharmacology. For example, [[KP-1461]] is an [[AIDS drug|anti-HIV agent]] that works as a viral mutagen,<ref>{{cite web | url = http://www.aidsnews.org/2007/10/kp-1461.html | title = New Kind of Antiretroviral, KP-1461 | author = John S. James | publisher = AIDS Treatment News | access-date = 2012-03-23 | archive-url = https://web.archive.org/web/20190330230051/http://www.aidsnews.org/2007/10/kp-1461.html | archive-date = 2019-03-30 | url-status = dead }}</ref> and [[zebularine]] exists in ''[[Escherichia coli|E. coli]]'' and is being examined for chemotherapy.  Low doses of [[azacitidine]] and its analog [[decitabine]] have shown results against cancer through [[epigenetic]] demethylation.<ref>{{cite web | url = http://medicalxpress.com/news/2012-03-scientists-reprogram-cancer-cells-doses.html | title = Scientists reprogram cancer cells with low doses of epigenetic drugs | date = March 22, 2012 | publisher = Medical XPress}}</ref>

==Biological actions==
In addition to its role as a [[pyrimidine]] component of RNA, cytidine has been found to control [[neuron]]al-[[glia]]l [[glutamate]] cycling, with supplementation decreasing midfrontal/cerebral glutamate/[[glutamine]] levels.<ref name="Machado-VieiraSalvadore2010">{{cite journal|last1=Machado-Vieira|first1=Rodrigo|last2=Salvadore|first2=Giacomo|last3=DiazGranados|first3=Nancy|last4=Ibrahim|first4=Lobna|last5=Latov|first5=David|last6=Wheeler-Castillo|first6=Cristina|last7=Baumann|first7=Jacqueline|last8=Henter|first8=Ioline D.|last9=Zarate|first9=Carlos A.|title=New Therapeutic Targets for Mood Disorders|journal=The Scientific World Journal|volume=10|year=2010|pages=713–726|issn=1537-744X|doi=10.1100/tsw.2010.65|pmid=20419280|pmc=3035047 |doi-access=free }}</ref> As such, cytidine has generated interest as a potential [[glutamatergic]] [[antidepressant]] drug.<ref name="Machado-VieiraSalvadore2010" />

==Related compounds==
* [[Deoxycytidine]] is [[cytosine]] attached to a [[deoxyribose]].

==References==
{{Reflist|2}}

==External links==
* [https://web.archive.org/web/20160303223452/http://gmd.mpimp-golm.mpg.de/Spectrums/2af6fe93-60d8-48bf-95c0-9b1dde66da88.aspx Cytidine MS Spectrum]

{{Nucleobases, nucleosides, and nucleotides}}
{{Purinergics}}
{{Glutamatergics}}

[[Category:Nucleosides]]
[[Category:Pyrimidones]]
[[Category:Hydroxymethyl compounds]]