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Substance Name: Citicoline [INN:JAN]
RN: 987-78-0
UNII: 536BQ2JVC7
InChIKey: RZZPDXZPRHQOCG-OJAKKHQRSA-N

Note

  • Donor of choline in biosynthesis of choline-containing phosphoglycerides.

Molecular Formula

  • C14-H26-N4-O11-P2

Molecular Weight

  • 488.3244
 

Classification Codes

  • Central Nervous System Agents
  • Drug / Therapeutic Agent
  • Nootropic Agents
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Names and Synonyms

Name of Substance

  • Citicoline [INN:JAN]
  • Cytidine diphosphate choline

MeSH Heading

  • Cytidine diphosphate choline

Synonyms

  • BRN 4170138
  • CDP-cholin
  • CDP-cholin [German]
  • CDP-choline
  • CDP-colina
  • CDP-colina [Spanish]
  • Cereb
  • Choline 5'-cytidine diphosphate
  • Choline cytidine 5'-pyrophosphate ester
  • Choline cytidine diphosphate
  • Choline, ester with cytidine 5'-pyrophosphate
  • Citicholine
  • Citicolina
  • Citicolina [INN-Spanish]
  • Citicoline
  • Citicolinum
  • Citicolinum [INN-Latin]
  • Citidin difosfato de colina
  • Citidin difosfato de colina [Spanish]
  • Citidoline
  • Colite
  • Cyscholin
  • Cytidindiphosphocholin
  • Cytidindiphosphocholin [German]
  • Cytidine 5'-(choline diphosphate)
  • Cytidine 5'-(cholinyl pyrophosphate)
  • Cytidine 5'-(trihydrogen diphosphate), p'-(2-(trimethylammonio)ethyl) ester, inner salt
  • Cytidine 5'-diphosphate choline
  • Cytidine 5'-diphosphocholine
  • Cytidine 5'-diphosphoric choline
  • Cytidine 5-diphosphocholine
  • Cytidine choline diphosphate
  • Cytidine diphosphate cholin ester
  • Cytidine diphosphate choline
  • Cytidine diphosphate choline ester
  • Cytidine diphosphocholine
  • Cytidine diphosphorylcholine
  • Cytidine, 5'-pyrophosphate, ester with choline
  • Cytidinediphosphoric choline
  • Cytidoline
  • Difosfocin
  • EINECS 213-580-7
  • Emicholin
  • Ensign
  • Haocolin
  • IP 302
  • IP-302
  • Meibis
  • Nicholin
  • Niticolin
  • NSC 122002
  • Recofnan
  • Recognan
  • Somazina
  • Startonyl
  • Suncholin
  • Ubelin
  • UNII-536BQ2JVC7

Systematic Names

  • Choline, hydroxide, 5'-ester with cytidine 5'-(trihydrogen pyrophosphate), inner salt
  • Citicoline
  • Cytidine 5'-(trihydrogen diphosphate), mono(2-(trimethylammonio)ethyl) ester, hydroxide, inner salt
  • Cytidine 5'-(trihydrogen diphosphate), p'-(2-(trimethylammonio)ethyl) ester, inner salt

Registry Numbers

CAS Registry Number

  • 987-78-0

FDA UNII

  • 536BQ2JVC7

Other Registry Number

  • 1477-47-0

System Generated Number

  • 0000987780

Structure Descriptors

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

Smiles

C[N+](C)(C)CCOP(=O)([O-])OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)n2ccc(nc2=O)N)O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intramuscular 4472mg/kg (4472mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: ANTIPSYCHOTIC

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Oyo Yakuri. Pharmacometrics. Vol. 20, Pg. 109, 1980.
mouse LD50 intraperitoneal 5393mg/kg (5393mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: ANTIPSYCHOTIC

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Oyo Yakuri. Pharmacometrics. Vol. 20, Pg. 109, 1980.
mouse LD50 intravenous 4150mg/kg (4150mg/kg)   Drugs in Japan Vol. -, Pg. 531, 1995.
mouse LD50 oral 27142mg/kg (27142mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Oyo Yakuri. Pharmacometrics. Vol. 20, Pg. 109, 1980.
mouse LD50 subcutaneous 6485mg/kg (6485mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Oyo Yakuri. Pharmacometrics. Vol. 20, Pg. 109, 1980.
rabbit LD50 intravenous 1950mg/kg (1950mg/kg)   Drugs in Japan Vol. 6, Pg. 322, 1982.
rat LD50 intramuscular 3750mg/kg (3750mg/kg)   Drugs in Japan Vol. -, Pg. 531, 1995.
rat LD50 intraperitoneal 5344mg/kg (5344mg/kg) BEHAVIORAL: ANTIPSYCHOTIC

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Oyo Yakuri. Pharmacometrics. Vol. 20, Pg. 109, 1980.
rat LD50 intravenous 2973mg/kg (2973mg/kg) BEHAVIORAL: ANTIPSYCHOTIC

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Oyo Yakuri. Pharmacometrics. Vol. 20, Pg. 109, 1980.
rat LD50 oral 18501mg/kg (18501mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Oyo Yakuri. Pharmacometrics. Vol. 20, Pg. 109, 1980.
rat LD50 subcutaneous 8218mg/kg (8218mg/kg) BEHAVIORAL: ANTIPSYCHOTIC

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Oyo Yakuri. Pharmacometrics. Vol. 20, Pg. 109, 1980.

Physical Properties

Physical Property Value Units Temp (deg C) Source
pKa Dissociation Constant 4.4 (none)   EXP
log P (octanol-water) -6.940 (none)   EST
Atmospheric OH Rate Constant 1.81E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.