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]
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
CHEBI:16436
CAS Number
987-78-0
DrugBank ID
DB12153
TTD ID
D02CFP
INTEDE ID
DR2077
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
Caspase-3 (CASP3) OTIJRBE7 CASP3_HUMAN Gene/Protein Processing [4]
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.