Deoxycytidine

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Deoxycytidine
Skeletal formula of deoxycytidine
Ball-and-stick model of the deoxycytidine molecule
Names
IUPAC name
2′-deoxycytidine
Systematic IUPAC name
4-Amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2(1H)-one
Other names
doxecitine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.012.231 Edit this at Wikidata
MeSH Deoxycytidine
UNII
  • InChI=1S/C9H13N3O4/c10-7-1-2-12(9(15)11-7)8-3-5(14)6(4-13)16-8/h1-2,5-6,8,13-14H,3-4H2,(H2,10,11,15)/t5-,6+,8+/m0/s1
    Key: CKTSBUTUHBMZGZ-SHYZEUOFSA-N
  • InChI=1/C9H13N3O4/c10-7-1-2-12(9(15)11-7)8-3-5(14)6(4-13)16-8/h1-2,5-6,8,13-14H,3-4H2,(H2,10,11,15)/t5-,6+,8+/m0/s1
    Key: CKTSBUTUHBMZGZ-SHYZEUOFBO
  • c1cn(c(=O)nc1N)[C@H]2C[C@@H]([C@H](O2)CO)O
Properties
C9H13N3O4
Molar mass 227.217
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Deoxycytidine is a deoxyribonucleoside, a component of deoxyribonucleic acid. It is similar to the ribonucleoside cytidine, but with one hydroxyl group removed from the C2' position. Deoxycytidine can be phosphorylated at C5' of the deoxyribose by deoxycytidine kinase, converting it to deoxycytidine monophosphate (dCMP), a DNA precursor.[1] dCMP can be converted to dUMP and dTMP.[citation needed]

Doxecitine is the international nonproprietary name.[2]

Clinical significance

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Deoxycytidine can be used as a precursor for 5-aza-2′-deoxycytidine, a treatment for people with myelodysplastic syndrome. This compound slows the cell cycle by interfering with the methylation of the P15/INK4B gene, increasing the expression of P15/INK4B protein which subdues the transformation of MDS to leukemia.[3]

Deoxycytidine can serve as a biomarker for tumor diagnosis. Deoxycytidine can be used as a biomarker for breast cancer patients and healthy individuals. 5-(Hydroxymethyl)-2′-deoxycytidine (5-hmdC), 5-(formyl)-2′-deoxycytidine (5-fodC), and 5-(carboxyl)-2′-deoxycytidine (5-cadC) are intermediates in the DNA demethylation pathway and can act as biomarkers. 5-hmdC levels were significantly reduced in urine samples of breast cancer patients, while 5-fodC and 5-cadC levels were elevated.[4]

Doxecitine is a component of the medication doxecitine/doxribtimine used for the treatment of thymidine kinase 2 deficiency.[5]

References

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  1. ^ Staub M, Eriksson S (2006). "The Role of Deoxycytidine Kinase in DNA Synthesis and Nucleoside Analog Activation". In Peters GJ (ed.). Deoxynucleoside Analogs In Cancer Therapy. Cancer Drug Discovery and Development. Humana Press. pp. 29–52. doi:10.1007/978-1-59745-148-2_2. ISBN 978-1-59745-148-2.
  2. ^ World Health Organization (2022). "International nonproprietary names for pharmaceutical substances (INN): recommended INN: list 87". WHO Drug Information. 36 (1). hdl:10665/352794.
  3. ^ Kim KW, Roh JK, Wee HJ, Kim C (2016). "Molecular Targeted Anticancer Drugs". In Kim KW, Roh JK, Wee HJ, Kim C (eds.). Cancer Drug Discovery: Science and History. Springer Netherlands. pp. 175–238. doi:10.1007/978-94-024-0844-7_9. ISBN 978-94-024-0844-7.
  4. ^ Guo M, Zhang L, Du Y, Du W, Liu D, Guo C, et al. (March 2018). "Enrichment and Quantitative Determination of 5-(Hydroxymethyl)-2'-deoxycytidine, 5-(Formyl)-2'-deoxycytidine, and 5-(Carboxyl)-2'-deoxycytidine in Human Urine of Breast Cancer Patients by Magnetic Hyper-Cross-Linked Microporous Polymers Based on Polyionic Liquid". Analytical Chemistry. 90 (6): 3906–3913. doi:10.1021/acs.analchem.7b04755. PMID 29316399.
  5. ^ "FDA approves 1st drug for thymidine kinase 2 deficiency". U.S. Food and Drug Administration. 3 November 2025. Retrieved 4 November 2025. Public Domain This article incorporates text from this source, which is in the public domain.
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