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Chemistry

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Also known as: Creatine phosphate, Phosphorylcreatine, N-phosphocreatine, Fosfocreatine, Creatine-p, 67-07-2
Molecular Formula
C4H10N3O5P
Molecular Weight
211.11  g/mol
InChI Key
DRBBFCLWYRJSJZ-UHFFFAOYSA-N
FDA UNII
020IUV4N33

Phosphocreatine
An endogenous substance found mainly in skeletal muscle of vertebrates. It has been tried in the treatment of cardiac disorders and has been added to cardioplegic solutions. (Reynolds JEF(Ed): Martindale: The Extra Pharmacopoeia (electronic version). Micromedex, Inc, Englewood, CO, 1996)
1 2D Structure

Phosphocreatine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-[methyl-[(E)-N'-phosphonocarbamimidoyl]amino]acetic acid
2.1.2 InChI
InChI=1S/C4H10N3O5P/c1-7(2-3(8)9)4(5)6-13(10,11)12/h2H2,1H3,(H,8,9)(H4,5,6,10,11,12)
2.1.3 InChI Key
DRBBFCLWYRJSJZ-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CN(CC(=O)O)C(=NP(=O)(O)O)N
2.1.5 Isomeric SMILES
CN(CC(=O)O)/C(=N/P(=O)(O)O)/N
2.2 Other Identifiers
2.2.1 UNII
020IUV4N33
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Creatine Phosphate

2. Disodium Salt Phosphocreatine

3. Neoton

4. Phosphate, Creatine

5. Phosphocreatine, Disodium Salt

6. Phosphorylcreatine

2.3.2 Depositor-Supplied Synonyms

1. Creatine Phosphate

2. Phosphorylcreatine

3. N-phosphocreatine

4. Fosfocreatine

5. Creatine-p

6. 67-07-2

7. N-(phosphonoamidino)sarcosine

8. N-phosphorylcreatine

9. Phosphagen

10. Creatinephosphoric Acid

11. N-(phosphonoamidino)-sarcosine

12. Creatine Phosphic Acid

13. N-(n-phosphonoamido)sarcosine

14. Chebi:17287

15. 020iuv4n33

16. 2-(1-methyl-3-phosphonoguanidino)acetic Acid

17. Glycine, N-(imino(phosphonoamino)methyl)-n-methyl-

18. 2-(3-methyl-1-phosphonocarbamimidamido)acetic Acid

19. Glycine, N-[imino(phosphonoamino)methyl]-n-methyl-

20. N-phosphorocreatine

21. Einecs 200-643-9

22. [[imino(phosphonoamino)methyl](methyl)amino]acetic Acid

23. {[imino(phosphonoamino)methyl](methyl)amino}acetic Acid

24. Unii-020iuv4n33

25. N-methyl-n-(n-phosphonocarbamimidoyl)glycine

26. N(omega)-phosphonocreatine

27. Bmse000079

28. Phosphocreatine [mi]

29. Chembl1204644

30. Dtxsid0058776

31. Creatine Phosphate [mart.]

32. Creatine Phosphate [who-dd]

33. Hy-d0885

34. Mfcd00152044

35. Stl452993

36. Akos027340220

37. Db13191

38. As-12479

39. 2-(1-methyl-3-phosphonoguanidino)aceticacid

40. Cs-0013742

41. C02305

42. N-[imino(phosphonoamino)methyl]-n-methyl-glycine

43. 067c072

44. A917893

45. 2-(1-methyl-3-phosphonocarbamimidamido)acetic Acid

46. W-104734

47. 2-[methyl-(n'-phosphonocarbamimidoyl)amino]acetic Acid

2.4 Create Date
2006-10-04
3 Chemical and Physical Properties
Molecular Weight 211.11 g/mol
Molecular Formula C4H10N3O5P
XLogP3-2.6
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count6
Rotatable Bond Count4
Exact Mass211.03580743 g/mol
Monoisotopic Mass211.03580743 g/mol
Topological Polar Surface Area136 Ų
Heavy Atom Count13
Formal Charge0
Complexity271
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Phosphocreatine is a naturally occuring substance that is found predominantly in the skeletal muscles of vertebrates. Its primary utility within the body is to serve in the maintanence and recycling of adenosine triphosphate (ATP) for muscular activity like contractions. Given this utility of phosphocreatine to recycle ATP, the most plausible therapeutic potentials for its use involve conditions caused by energy shortage or by increased energy requirements - such as in ischemic stroke and other cerebrovascular diseases. It is important to note however that relatively little clinical research has been done to significantly further the evidence for any such indications, although it is administered intravenously for cardiovascular conditions in some countries. Additionally, because phosphocreatine is not regulated as a controlled substance it is taken as a supplement by some professional athletes as a means to perhaps increase short bursts of muscle strength or energy for professional athletics.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Creatine is a naturally occurring chemical within the body and is primarily stored in skeletal muscle in both free and phosphorylated forms. Phosphocreatine is the name given to the phosphorylated form of creatine. Additionally, phosphocreatine can also be found in other areas of the body like the kidneys, liver, and brain. In fact, most *in vivo* synthesis of creatine occurs in the liver where amidine groups from arginine are transfered to glycine with the help of the glycine transaminidase enzyme to form guanidinoacetic acid. This acid is then methylated with the methyl group of S-adenosylmethionine via guanidinoacetate methyltransferase to generate creatine. The synthesized creatine is transported to storage sites in skeletal muscle via the bloodstream. The phosphorylation of creatine is reversible in both a forwards and backwards reaction. That is, while phosphocreatine is capable of anaerobically donating a phosphate group to adenosine diphosphate (ADP) to regenerate ATP, at the same time excess ATP can be dephosphorylated during periods of low muscle activity to convert creatine to phosphocreatine. This dual activity in synthesizing phosphocreatine from excess levels of ATP during rest and use of phosphocreatine to regenerate ATP during high activity demonstrates the crucial utility of phosphocreatine in acting as an energy buffer in body mucle cells. Phosphocreatine's fast regeneration of ATP is considered a coupled reaction - in essence, the energy released from transferring a donating a phosphate group from phosphocreatine is used to regenerate ATP. Phosphocreatine consequently plays an essential role in body tissues that have high, fluctuating energy requirments like muscle and brain tissues.


5.2 MeSH Pharmacological Classification

Cardiotonic Agents

Agents that have a strengthening effect on the heart or that can increase cardiac output. They may be CARDIAC GLYCOSIDES; SYMPATHOMIMETICS; or other drugs. They are used after MYOCARDIAL INFARCT; CARDIAC SURGICAL PROCEDURES; in SHOCK; or in congestive heart failure (HEART FAILURE). (See all compounds classified as Cardiotonic Agents.)


5.3 ATC Code

C - Cardiovascular system

C01 - Cardiac therapy

C01E - Other cardiac preparations

C01EB - Other cardiac preparations

C01EB06 - Fosfocreatine


5.4 Absorption, Distribution and Excretion

Route of Elimination

Phosphocreatine is eliminated renally. The end result of creatine degredation is the product creatinine, which enters the bloodstream from its storage sites in body muscle. When creatinine enters the renal parenchyma it is filtered in the renal glomerulus to be excreted in the urine.


5.5 Mechanism of Action

Adenosine triphosphate (ATP) is the primary source of chemical energy that body muscles use to perform contractions. During such contraction processes, ATP molecules are depleted as they undergo hydrolysis reactions and become adenosine diphosphate (ADP). To maintain homeostasis in muscle activity, the ATP supply of muscles must be regenerated regularly. Phosphocreatine occurs naturally within the body and is capable of regenerating ATP by transferring a high-energy phosphate from itself to ADP, resulting in the formation of ATP and creatine. This kind of regeneration of ATP with phosphocreatine typically occurs within seconds of intense muscular or neuronal effort, acting as a quickly accessible reserve of high-energy phosphates for the recycling of ATP in body muscle tissues. ATP recycling from phosphocreatine is in fact known as the quickest form of ATP regeneration.


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02-Apr-2021
23-Sep-2024
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