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

Topological Polar Surface Area (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

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]

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Molecular Interaction Atlas (MIA)

MIA Detail

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.