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About This Item
Empirical Formula (Hill Notation):
C5H9N3O2
CAS Number:
Molecular Weight:
143.14
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Quality Level
Assay
98%
form
solid
solubility
1 M HCl: soluble 25 mg/mL, clear, colorless
functional group
carboxylic acid
SMILES string
OC(=O)CN1CCNC1=N
InChI
1S/C5H9N3O2/c6-5-7-1-2-8(5)3-4(9)10/h1-3H2,(H2,6,7)(H,9,10)
InChI key
AMHZIUVRYRVYBA-UHFFFAOYSA-N
General description
2-Imino-1-imidazolidineacetic acid (cyclocreatine) is an analog of creatine. It is reported to exhibit antitumour effect in some transplanted human and rodent tumours in vivo. It is reported as an efficient substrate for creatine kinase. It is an anticancer and neuroprotective agent. The crystal structure of cyclocreatine has been studied by X-ray diffraction methods. It is reported to crystallize as a zwitterion in the monoclinic system.
Application
2-Imino-1-imidazolidineacetic acid (cyclocreatine) is suitable for use in a study to investigate the growth inhibitory effects of cyclocreatine on LS174T human colon adenocarcinoma implanted subdermally in nude mice. It may be used to evaluate the brain-type creatine kinase (CKB), to study the role of CKB in cigarette smoke-induced bronchial epithelial cell senescence.
Protectant against inhibition of cardiac mitochondrial respiration by methylglyoxal
Growth inhibition of Hodgkin disease-derived cell lines
Investigations into effects in rat hepatocarcinogenesis model
Growth inhibition of Hodgkin disease-derived cell lines
Investigations into effects in rat hepatocarcinogenesis model
Biochem/physiol Actions
Creatine analog that protects tissues from ischemic damage; decreases the rate of ATP production via creatine kinase and reduces the proliferation of tumor cell lines that are characterized by high levels of creatine kinase expression.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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