Details of the Drug

General Information of Drug (ID: DMQTREB)

Drug Name
Uridine
Synonyms
uridine; 58-96-8; Uridin; Uracil riboside; beta-Uridine; d-uridine; CHEBI:16704; b-Uridine; UNII-WHI7HQ7H85; Urd; AI3-52690; EINECS 200-407-5; WHI7HQ7H85; MLS000069625; Uracil-1-beta-d-ribofuranoside; C9H12N2O6; DRTQHJPVMGBUCF-XVFCMESISA-N; SMR000058222; 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione; 1-beta-D-ribofuranosylpyrimidine-2,4(1H,3H)-dione
Indication
Disease Entry ICD 11 Status REF
Depression 6A70-6A7Z Approved [1], [2]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 244.2
Topological Polar Surface Area (xlogp) -2
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 4
Hydrogen Bond Acceptor Count (hbondacc) 6
Chemical Identifiers
Formula
C9H12N2O6
IUPAC Name
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
Canonical SMILES
C1=CN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O
InChI
InChI=1S/C9H12N2O6/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16/h1-2,4,6-8,12,14-15H,3H2,(H,10,13,16)/t4-,6-,7-,8-/m1/s1
InChIKey
DRTQHJPVMGBUCF-XVFCMESISA-N
Cross-matching ID
PubChem CID
6029
ChEBI ID
CHEBI:16704
CAS Number
58-96-8
DrugBank ID
DB02745
TTD ID
D0Y7DP
VARIDT ID
DR00321
INTEDE ID
DR2135

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Thymidine phosphorylase (TYMP) TTO0IB8 TYPH_HUMAN Inhibitor [3]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Concentrative nucleoside transporter 1 (SLC28A1) DT0EQPW S28A1_HUMAN Substrate [4]
Concentrative nucleoside transporter 2 (SLC28A2) DT82KPY S28A2_HUMAN Substrate [5]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Uridine-cytidine kinase 1 (UCK1) DE478BP UCK1_HUMAN Substrate [6]
Nicotinamide riboside kinase 1 (NRK1) DENV24I NRK1_HUMAN Substrate [7]
Nicotinamide riboside kinase 2 (NRK2) DE8DJ3N NRK2_HUMAN Substrate [7]
Uridine-cytidine kinase 2 (UCK2) DETN1O0 UCK2_HUMAN Substrate [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Depression
ICD Disease Classification 6A70-6A7Z
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Thymidine phosphorylase (TYMP) DTT TYMP 6.50E-01 -0.03 -0.25
Concentrative nucleoside transporter 2 (SLC28A2) DTP CNT2 1.04E-01 -4.21E-02 -3.44E-01
Concentrative nucleoside transporter 1 (SLC28A1) DTP CNT1 3.82E-01 3.88E-02 2.66E-01
Nicotinamide riboside kinase 1 (NRK1) DME NMRK1 5.11E-01 1.57E-02 4.25E-02
Nicotinamide riboside kinase 2 (NRK2) DME NMRK2 5.46E-01 -4.62E-02 -2.57E-01
Uridine-cytidine kinase 1 (UCK1) DME UCK1 4.70E-01 -3.84E-02 -2.47E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4566).
2 ClinicalTrials.gov (NCT00210080) A Study to Diagnose Lung Cancer by Sputum Cytology (01-312). U.S. National Institutes of Health.
3 Enzymatic activities of uridine and thymidine phosphorylase in normal and cancerous uterine cervical tissues. Hum Cell. 2007 Nov;20(4):107-10.
4 Electrophysiological recordings of CNT1 (SLC28A1) activity on Nanions SURFE2R N1.
5 Transport of ribavirin across the rat and human placental barrier: Roles of nucleoside and ATP-binding cassette drug efflux transporters. Biochem Pharmacol. 2019 May;163:60-70.
6 Phosphorylation of uridine and cytidine nucleoside analogs by two human uridine-cytidine kinases. Mol Pharmacol. 2001 May;59(5):1181-6.
7 Nicotinamide riboside kinase structures reveal new pathways to NAD+. PLoS Biol. 2007 Oct 2;5(10):e263.
8 FLT3 is implicated in cytarabine transport by human equilibrative nucleoside transporter 1 in pediatric acute leukemia. Oncotarget. 2016 Aug 2;7(31):49786-49799.
9 Pancreatic Cancer Chemoresistance to Gemcitabine. Cancers (Basel). 2017 Nov 16;9(11).
10 Lonsurf, INN-trifluridine/tipiracil.
11 PharmGKB: A worldwide resource for pharmacogenomic information. Wiley Interdiscip Rev Syst Biol Med. 2018 Jul;10(4):e1417. (ID: PA2040)
12 Multiple SLC and ABC Transporters Contribute to the Placental Transfer of Entecavir. Drug Metab Dispos. 2017 Mar;45(3):269-278.
13 Identification and functional analysis of variants in the human concentrative nucleoside transporter 2, hCNT2 (SLC28A2) in Chinese, Malays and Indians. Pharmacogenet Genomics. 2007 Sep;17(9):783-6.
14 Clinical Nephrotoxins: Renal Injury from Drugs and Chemicals.
15 Design and synthesis of novel 5,6-disubstituted uracil derivatives as potent inhibitors of thymidine phosphorylase. Bioorg Med Chem Lett. 2006 Mar 1;16(5):1335-7.
16 The role of phosphate in the action of thymidine phosphorylase inhibitors: Implications for the catalytic mechanism. Bioorg Med Chem Lett. 2010 Mar 1;20(5):1648-51.
17 Discovery of 5-substituted-6-chlorouracils as efficient inhibitors of human thymidine phosphorylase. J Med Chem. 2007 Nov 29;50(24):6016-23.
18 5'-O-tritylinosine and analogues as allosteric inhibitors of human thymidine phosphorylase. J Med Chem. 2006 Sep 7;49(18):5562-70.