Cyclocreatine

Product NameCyclocreatine
CAS35404-50-3
MFC5H9N3O2
MW143.14
EINECS
MOL File35404-50-3.mol

Chemical Properties

Melting point	322-326C
storage temp.	-20°C Freezer
solubility	1 M HCl: soluble25mg/mL, clear, colorless
form	Solid
color	White to Off-White
InChI	InChI=1S/C5H9N3O2/c6-5-7-1-2-8(5)3-4(9)10/h1-3H2,(H2,6,7)(H,9,10)
InChIKey	AMHZIUVRYRVYBA-UHFFFAOYSA-N
SMILES	C1(N)N(CC(O)=O)CCN=1
CAS DataBase Reference	35404-50-3(CAS DataBase Reference)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-37/39
WGK Germany	3
HS Code	2940000080
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

Chemical Properties

White Solid

Uses

Can regulate creatine biosynthesis by suppressing the level of arginine:glycine amidinotransferase in chick liver

Uses

Cyclocreatine is used to regulate creatine biosynthesis by suppressing the level of arginine:glycine amidinotransferase in chick liver.

Biological Activity

Creatine analog th at protects tissues from ischemic damage; decreases the rate of ATP production via creatine kinase and reduces the proliferation of tumor cell lines th at are characterized by high levels of creatine kinase expression.

in vivo

Cyclocreatine (500 mg/kg, i.v., a single dose for 60 min) restores heart contractile function and shows markedly less myocardial cell injury when compared to the control (saline) group in the acute myocardial infarction (AMI) intact dog model^[1].
Cyclocreatine (0.28 mg/g, drink, supplementation daily from 10-week to 8 months) rescues microgliosis and clustering and moderates neurite dystrophy in TREM2^/ 5XFAD mice^[2].
Cyclocreatine (40 mg, gavage, daily for 1 month) significantly reduces liver metastatic burden and affects prostate cancer progression in a model of liver metastasis of mice^[3].

Animal Model:	AMI-intact dog model^[1]
Dosage:	500 mg/kg
Administration:	i.v., a single dose for 60 min
Result:	Preserved 85% of pre-ischemic ATP level (loss of only 15%) and 97% of the CrP (loss of 3%) during ischemia, as well as immediately restored over 80% of contractile function during the 2 h of reperfusion in AMI-intact dog model.

Animal Model:	5XFAD and TREM2^/ 5XFAD mice
Dosage:	0.28 mg/g
Administration:	Drinking water supplementation with cyclocreatine daily from 10-week to 8 months
Result:	Improved microglial metabolism and the protective response to Aβ plaques in TREM2-deficient 5XFAD mice.

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