Details of the Drug

General Information of Drug (ID: DMI4XBM)

Drug Name
Citicoline
Synonyms Alphcolin; CerAxon; Citicholine; Hipercol; Neurex; Nicholin; Somazina; Trausan; Citicoline sodium; Cytidil diphosphocholine; CDP-choline; IP-302; Cytidine-5-diphosphocholine
Indication
Disease Entry ICD 11 Status REF
Cerebrovascular ischaemia 8B1Z Approved [1]
ATC Code
N06BX06: Citicoline
N06BX: Other psychostimulants and nootropics
N06B: PSYCHOSTIMULANTS, AGENTS USED FOR ADHD AND NOOTROPICS
N06: PSYCHOANALEPTICS
N: NERVOUS SYSTEM
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 2 Molecular Weight (mw) 488.32
Logarithm of the Partition Coefficient (xlogp) -4
Rotatable Bond Count (rotbonds) 10
Hydrogen Bond Donor Count (hbonddonor) 4
Hydrogen Bond Acceptor Count (hbondacc) 11
Chemical Identifiers
Formula
C14H26N4O11P2
IUPAC Name
[[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] 2-(trimethylazaniumyl)ethyl phosphate
Canonical SMILES
C[N+](C)(C)CCOP(=O)([O-])OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=CC(=NC2=O)N)O)O
InChI
InChI=1S/C14H26N4O11P2/c1-18(2,3)6-7-26-30(22,23)29-31(24,25)27-8-9-11(19)12(20)13(28-9)17-5-4-10(15)16-14(17)21/h4-5,9,11-13,19-20H,6-8H2,1-3H3,(H3-,15,16,21,22,23,24,25)/t9-,11-,12-,13-/m1/s1
InChIKey
RZZPDXZPRHQOCG-OJAKKHQRSA-N
Cross-matching ID
PubChem CID
13804
ChEBI ID
CHEMBL16436
CAS Number
987-78-0
UNII
536BQ2JVC7
DrugBank ID
DB12153
TTD ID
D02CFP
INTEDE ID
DR2077
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
ASM-like phosphodiesterase 3a (SMPDL3A) DEQJ8N3 ASM3A_HUMAN Substrate [2]
CDP-choline phosphohydrolase (ADPRM) DEH6S1Q ADPRM_HUMAN Substrate [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Poly polymerase 1 (PARP1) OT310QSG PARP1_HUMAN Gene/Protein Processing [4]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 The structure and catalytic mechanism of human sphingomyelin phosphodiesterase like 3a--an acid sphingomyelinase homologue with a novel nucleotide hydrolase activity. FEBS J. 2016 Mar;283(6):1107-23.
3 Molecular bases of catalysis and ADP-ribose preference of human Mn2+-dependent ADP-ribose/CDP-alcohol diphosphatase and conversion by mutagenesis to a preferential cyclic ADP-ribose phosphohydrolase. PLoS One. 2015 Feb 18;10(2):e0118680.
4 Citicoline increases glutathione redox ratio and reduces caspase-3 activation and cell death in staurosporine-treated SH-SY5Y human neuroblastoma cells. Brain Res. 2002 Dec 6;957(1):84-90. doi: 10.1016/s0006-8993(02)03605-3.