Identification

Summary

Cytidine is a drug used to manage neuropsychiatric deficits associated with cerebrovascular diseases in combination with uridine.

Generic Name
Cytidine
DrugBank Accession Number
DB02097
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 243.2166
Monoisotopic: 243.085520541
Chemical Formula
C9H13N3O5
Synonyms
  • 1-beta-D-Ribofuranosylcytosine
  • 1β-D-ribofuranosylcytosine
  • 4-amino-1-β-D-ribofuranosylpyrimidin-2(1H)-one
  • 4-amino-1β-D-ribofuranosyl-2(1H)-pyrimidinone
  • Citidina
  • Cytidin
  • Cytosine riboside
  • Zytidin

Pharmacology

Indication

Not Available

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UUridine-cytidine kinase 2Not AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

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Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as pyrimidine nucleosides. These are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Pyrimidine nucleosides
Sub Class
Not Available
Direct Parent
Pyrimidine nucleosides
Alternative Parents
Glycosylamines / Pentoses / Pyrimidones / Aminopyrimidines and derivatives / Imidolactams / Hydropyrimidines / Tetrahydrofurans / Heteroaromatic compounds / Secondary alcohols / Azacyclic compounds
show 6 more
Substituents
Alcohol / Amine / Aminopyrimidine / Aromatic heteromonocyclic compound / Azacycle / Glycosyl compound / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine / Imidolactam
show 18 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
cytidines (CHEBI:17562) / Ribonucleosides (C00475)
Affected organisms
Not Available

Chemical Identifiers

UNII
5CSZ8459RP
CAS number
65-46-3
InChI Key
UHDGCWIWMRVCDJ-XVFCMESISA-N
InChI
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
IUPAC Name
4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
SMILES
NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

References

Synthesis Reference

Kiyoshi Nakayama, Hiroshi Hagino, "Method for preparing cytidine diphosphate choline." U.S. Patent USRE0288861, issued August 15, 1972.

USRE0288861
General References
Not Available
Human Metabolome Database
HMDB0000089
KEGG Drug
D07769
KEGG Compound
C00475
PubChem Compound
6175
PubChem Substance
46507502
ChemSpider
5940
ChEBI
17562
ChEMBL
CHEMBL95606
ZINC
ZINC000002583632
PDBe Ligand
CTN
Wikipedia
Cytidine
PDB Entries
1uej / 2fr6 / 2v34 / 3ive / 3p0z / 3p10 / 3qhd / 3t80 / 3tka / 3w34
show 16 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2Unknown StatusTreatmentMyelodysplastic Syndromes (MDS)1
2WithdrawnTreatmentDepression, Bipolar2
1CompletedTreatmentMalignancies, Hematologic1
1CompletedTreatmentNon-Small Cell Lung Carcinoma (NSCLC)1
1, 2CompletedTreatmentMalignancies, Hematologic1
0CompletedTreatmentAdult Acute Megakaryoblastic Leukemia (M7) / Adult Acute Monoblastic Leukemia (M5a) / Adult Acute Monocytic Leukemia (M5b) / Adult Acute Myeloblastic Leukemia With Maturation (M2) / Adult Acute Myeloblastic Leukemia Without Maturation (M1) / Adult Acute Myeloid Leukemia With 11q23 (MLL) Abnormalities / Adult Acute Myeloid Leukemia With Del(5q) / Adult Acute Myeloid Leukemia With Inv(16)(p13;q22) / Adult Acute Myeloid Leukemia With T(16;16)(p13;q22) / Adult Acute Myeloid Leukemia With T(8;21)(q22;q22) / Adult Acute Myelomonocytic Leukemia (M4) / Adult Erythroleukemia (M6a) / Adult Pure Erythroid Leukemia (M6b) / Untreated Adult Acute Myeloid Leukemia1
Not AvailableWithdrawnNot AvailableMyalgic Encephalomyelitis (ME)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
InjectionIntramuscular; Intravenous
Injection, powder, for solutionIntramuscular; Intravenous
SolutionOral
TabletOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility43.8 mg/mLALOGPS
logP-2.2ALOGPS
logP-2.8ChemAxon
logS-0.74ALOGPS
pKa (Strongest Acidic)12.55ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area128.61 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity54.54 m3·mol-1ChemAxon
Polarizability22.4 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9623
Blood Brain Barrier+0.9465
Caco-2 permeable-0.8887
P-glycoprotein substrateNon-substrate0.798
P-glycoprotein inhibitor INon-inhibitor0.9686
P-glycoprotein inhibitor IINon-inhibitor0.9532
Renal organic cation transporterNon-inhibitor0.9519
CYP450 2C9 substrateNon-substrate0.793
CYP450 2D6 substrateNon-substrate0.8613
CYP450 3A4 substrateNon-substrate0.6203
CYP450 1A2 substrateNon-inhibitor0.9543
CYP450 2C9 inhibitorNon-inhibitor0.9638
CYP450 2D6 inhibitorNon-inhibitor0.9497
CYP450 2C19 inhibitorNon-inhibitor0.9489
CYP450 3A4 inhibitorNon-inhibitor0.9609
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.981
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9158
BiodegradationNot ready biodegradable0.7807
Rat acute toxicity1.7184 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.983
hERG inhibition (predictor II)Non-inhibitor0.911
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (5 TMS)GC-MSsplash10-0zfr-2951000000-7baf0e1ea8b1a34362e2
GC-MS Spectrum - GC-MS (4 TMS)GC-MSsplash10-0g4j-2980000000-9337623aef7fec22dd97
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-MSGC-MSsplash10-0zfr-2951000000-7baf0e1ea8b1a34362e2
GC-MS Spectrum - GC-MSGC-MSsplash10-0g4j-2980000000-9337623aef7fec22dd97
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-03di-0900000000-177050786fcbfaf2d270
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-03di-0900000000-1251248af66dca3401e2
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-03di-6900000000-c6b010a1d3e65a0942ee
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0006-0590100000-94eb2baae24aa405b1ba
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0006-9000000000-8155621584c25975ffa1
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-03di-0900000000-5065bc83a32bee37d07c
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0006-0590200000-4d5dc5376c40d083efbe
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-001i-0900000000-6ea86f62a48910b456a0
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-03di-0900000000-5c93b66b8899a4d3ce06
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0006-0090000000-f0e6ac0bacdbef1206b0
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-000f-0090010000-1cf915fa4dfb86b5861b
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0a4i-0900000000-6bb7990f165932decea7
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0006-0090000000-0b7dc368d61ee31afb78
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-000l-0090020000-fa04fb11f98259c403b6
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0006-0190172001-0671df3c315b8af9e13f
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0a4i-0900000000-8aa3fec051a7d9807888
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0006-0090000000-0563823e8f3a9def519a
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-004i-0028900000-f4b6c319a7e9fb17df2e
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-01ox-0590000000-d5d20f84ab30e96c30f6
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, PositiveLC-MS/MSsplash10-03di-0930000000-c4d3377790616b8b7869
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-0a4i-1930000000-faec28788ea577988b82
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4l-1940000000-c764d3c5062e8e006160
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0900000000-a9b5ac547307bf0a568d
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0090000000-0b7dc368d61ee31afb78
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0900000000-f8f5ef34bbf74fff6bdd
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0090000000-0563823e8f3a9def519a
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0a4i-1930000000-faec28788ea577988b82
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-0900000000-44127be30ae72f570759
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-9000000000-8155621584c25975ffa1
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-0900000000-5065bc83a32bee37d07c
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-0900000000-5c93b66b8899a4d3ce06
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-0090000000-f0e6ac0bacdbef1206b0
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-01ox-0590000000-d5d20f84ab30e96c30f6
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-03di-0930000000-c4d3377790616b8b7869
1H NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Uridine kinase activity
Specific Function
Phosphorylates uridine and cytidine to uridine monophosphate and cytidine monophosphate. Does not phosphorylate deoxyribonucleosides or purine ribonucleosides. Can use ATP or GTP as a phosphate don...
Gene Name
UCK2
Uniprot ID
Q9BZX2
Uniprot Name
Uridine-cytidine kinase 2
Molecular Weight
29298.92 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Drug created at June 13, 2005 13:24 / Updated at May 07, 2021 21:06