Key Documents

Cytidine 5′-diphosphocholine sodium salt dihydrate

Name: Cytidine 5′-diphosphocholine sodium salt dihydrate
Brand: SIGMA

~98%, from yeast, solid

Synonym(s):

CDP-choline-Na, CDP-coline, Citicoline sodium, P′-[2-(Trimethylammonio)ethyl]ester cytidine 5′-(trihydrogen diphosphate) inner salt monosodium

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About This Item

Empirical Formula (Hill Notation):

C₁₄H₂₅N₄NaO₁₁P₂ · 2H₂O

CAS Number:

33818-15-4

Molecular Weight:

546.34

UNSPSC Code:

41106300

NACRES:

NA.77

PubChem Substance ID:

24278064

MDL number:

MFCD00150508

Beilstein/REAXYS Number:

4110040

Assay:

~98%

Form:

solid

Quality level:

200

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Properties

biological source

yeast

Quality Level

200

assay

~98%

form

solid

color

white

solubility

H₂O: 100 mg/mL

storage temp.

−20°C

SMILES string

[Na+].C[N+](C)(C)CCOP([O-])(=O)OP([O-])(=O)OCC1OC([C@H](O)[C@@H]1O)N2C=CC(N)=NC2=O

InChI

1S/C14H26N4O11P2.Na/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);/q;+1/p-1/t9?,11-,12-,13?;/m1./s1

InChI key

YWAFNFGRBBBSPD-MBWJOHGMSA-M

Description

General description

Cytidine 5′-diphosphocholine (CDP-choline) contains cytidine and choline linked via a diphosphate bridge.

Application

Cytidine 5′-diphosphocholine sodium salt dihydrate has been used as a physiological metabolite for the identification of gemcitabine diphosphate choline (GdPC) by liquid chromatography-mass spectrometry (LC-MS/MS) method in the Kennedy pathway [1].

Biochem/physiol Actions

Cytidine 5′-diphosphocholine (CDP-choline) plays an important role in the synthesis of phosphatidylcholine. It is also involved in the biosynthesis of acetylcholine, a neurotransmitter. CDP-choline has therapeutic effects against hypoxia, cerebral ischemia and traumatic brain injury. It also exhibits therapeutic effects against learning and memory disorders, drug addiction and Alzheimer′s and Parkinson′s diseases.

Disclaimer

Hygroscopic

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This Item	30290	C9630	A6885
Sigma-Aldrich C0256 Cytidine 5′-diphosphocholine sodium salt dihydrate	Sigma-Aldrich 30290 Cytidine 5′-diphosphocholine sodium salt hydrate	Sigma-Aldrich C9630 Cytidine 2′:3′-cyclic monophosphate monosodium salt	Sigma-Aldrich A6885 Adenosine 3′,5′-cyclic monophosphate sodium salt monohydrate
form solid	form powder	form powder	form powder
assay ~98%	assay ≥99.0% (HPLC)	assay ≥95% (HPLC)	assay ≥98.0% (HPLC)
Quality Level 200	Quality Level 100	Quality Level 200	Quality Level 200
storage temp. −20°C	storage temp. 2-8°C	storage temp. −20°C	storage temp. −20°C
solubility H₂O: 100 mg/mL	solubility -	solubility water: 50 mg/mL, clear, colorless	solubility H₂O: 10 mg/mL
color white	color -	color -	color white

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Synergistic effects of citicoline and MK-801 in temporary experimental focal ischemia in rats.

M Z Onal et al.

Stroke, 28(5), 1060-1065 (1997-05-01)

Citicoline, a naturally occurring precursor of phosphatidylcholine, is neuroprotective and is currently being assessed in clinical trials. To evaluate potential synergistic neuroprotective effects of prolonged citicoline treatment and early N-methyl-D-aspartate (NMDA) antagonist therapy, suboptimal treatment regimens of citicoline and MK-801

Cytidine 5'-diphosphocholine (CDP-choline) in stroke and other CNS disorders.

Rao Muralikrishna Adibhatla et al.

Neurochemical research, 30(1), 15-23 (2005-03-11)

Brain phosphatidylcholine (PC) levels are regulated by a balance between synthesis and hydrolysis. Pro-inflammatory cytokines such as tumor necrosis factor-alpha (TNF-alpha) and interleukin-1 (IL-1alpha/beta) activate phospholipase A(2) (PLA(2)) and PC-phospholipase C (PC-PLC) to hydrolyze PC. PC hydrolysis by PLA(2) releases

The effects of prolonged treatment with citicoline in temporary experimental focal ischemia.

W R Schäbitz et al.

Journal of the neurological sciences, 138(1-2), 21-25 (1996-06-01)

Potential therapeutic effects of cytidine 5-diphosphocholine (citicoline), a key intermediary in the biosynthesis of the membrane phospholipid, phosphatidylcholine, are presumably related to enhanced phospholipid synthesis in the ischemic brain. We evaluated prolonged citicoline treatment in a temporary focal ischemia model.

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Global Trade Item Number

SKU	GTIN
C0256-500MG	04061838352903
C0256-1G	04061833450352
C0256-100MG	04061833450345

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