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C0256

Sigma-Aldrich

Cytidine 5′-diphosphocholine sodium salt dihydrate

~98%, from yeast, solid

Synonyme(s) :

CDP-coline, Citicoline sodique, P′-[2-(Triméthylammonio)­éthyl]­ester cytidine 5′-(tri­hydro­gène di­phos­phate) sel interne monosodique

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About This Item

Formule empirique (notation de Hill):
C14H25N4NaO11P2 · 2H2O
Numéro CAS:
33818-15-4
Poids moléculaire :
546.34
Numéro Beilstein :
4110040
Numéro MDL:
MFCD00150508
Code UNSPSC :
41106300
ID de substance PubChem :
24278064
Nomenclature NACRES :
NA.77

Source biologique

yeast

Pureté

~98%

Forme

solid

Couleur

white

Solubilité

H2O: 100 mg/mL

Température de stockage

−20°C

Chaîne SMILES 

[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

Clé InChI

YWAFNFGRBBBSPD-MBWJOHGMSA-M

Description générale

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 .

Actions biochimiques/physiologiques

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.

Attention

Hygroscopic

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Consulter la Bibliothèque de documents

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
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
Adibhatla R M and Hatcher J F
Neurochemical Research, 30(1), 15-23 (2005)
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.
W M Clark et al.
Neurology, 49(3), 671-678 (1997-09-26)
Citicoline (CDP-choline) is a key intermediary in the biosynthesis of phosphatidylcholine, an important component of the neural cell membrane. It has been shown to produce beneficial effects in both animal models and non-US clinical stroke trials. This study comprised a
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