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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: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

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

BEHAVIORAL: ANTIPSYCHOTIC

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

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
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.