7340. Phosphocreatine

Nomenclature

CAS number: 67-07-2
N-[Imino(phosphonoamino)methyl]-N-methylglycine; N-(phosphonoamidino)sarcosine; creatine phosphate; creatinephosphoric acid; PC.
C4H10N3O5P; mol wt 211.11.
C 22.76%, H 4.77%, N 19.90%, O 37.89%, P 14.67%.

Description and references

Phosphorylated form of creatine, q.v. Occurs primarily in skeletal muscle; also found in heart and brain. Involved in the transfer of high energy phosphate to ADP. Isoln from frog muscle: Eggleton, Biochem. J. 21, 190 (1927); from cat muscle: Fiske, Subbarow, J. Biol. Chem. 81, 629 (1929). Synthesis by phosphorylation of creatine: Zeile, Fawaz, Z. Physiol. Chem. 256, 193 (1938); Ennor, Stocken, Biochem. J. 43, 190 (1948). Enzymic determn in skeletal muscle: K. Yoshikawa et al., Anal. Biochem. 159, 303 (1986). HPLC determn in cardiac muscle: T. Teerlink et al., Anal. Biochem. 214, 278 (1993). Clinical trial as cardioprotective: M. L. Semenovsky et al., J. Thorac. Cardiovasc. Surg. 94, 762 (1987); as antiarrhythmic: M. Y. Ruda et al., Am. Heart J. 116, 393 (1988). Review of role in energy metabolism: S. P. Bessman, C. L. Carpenter, Annu. Rev. Biochem. 54, 831-862 (1985).

Chemical structure

Derivative

Sodium salt.

Nomenclature

Creatergyl (Sanofi-Synthelabo); Neoton (Alfa).
C4H8N3Na2O5P; mol wt 255.08.
C 18.83%, H 3.16%, N 16.47%, Na 18.03%, O 31.36%, P 12.14%.

Properties

Occurs as the hexahydrate, platelets from water + ethanol. Very sol in water. (Free acid, pKa2 is 4.6).

Derivative

Calcium salt tetrahydrate.
C4H8CaN3O5P.4H2O; mol wt 321.24.
C 14.96%, H 5.02%, Ca 12.48%, N 13.08%, O 44.82%, P 9.64%.

Properties

Hygroscopic crystals. Sol in water; sparingly sol in alcohol.

Note

The term phosphagen, originally a synonym for phosphocreatine, has since been used to describe any naturally occurring phosphorylated guanidine compd.

Therapeutic Category

Cardioprotective.