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Details

Stereochemistry ACHIRAL
Molecular Formula C4H9N3O5P.Na
Molecular Weight 233.0949
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MONOSODIUM PHOSPHOCREATINE

SMILES

[Na+].CN(CC(O)=O)C(=N)NP(O)([O-])=O

InChI

InChIKey=ZKXLDDHHUCNNBQ-UHFFFAOYSA-M
InChI=1S/C4H10N3O5P.Na/c1-7(2-3(8)9)4(5)6-13(10,11)12;/h2H2,1H3,(H,8,9)(H4,5,6,10,11,12);/q;+1/p-1

HIDE SMILES / InChI

Description
Curator's Comment: The description was created based on several sources, including https://www.drugbank.ca/drugs/DB13191 | https://clinicaltrials.gov/ct2/show/NCT02757443 | https://clinicaltrials.gov/ct2/show/NCT03138681 | https://www.drugs.com/dict/phosphocreatine.html | https://www.rlsnet.ru/tn_index_id_3865.htm#pokazaniya-preparata-neoton | https://www.ncbi.nlm.nih.gov/pubmed/26795537

Phosphocreatine (creatine phosphate, PCr, PC) is the phosphorylated form of endogenous creatine that serves as a rapidly mobilizable reserve of high-energy phosphates in skeletal muscle and the brain of vertebrates. Phosphocreatine is a key component in the intracellular system of energy buffering and transports from the site of energy production to the site of energy utilization to ensure that supply meets the high and dynamic demands of the heart. Phosphocreatine can anaerobically donate a phosphate group to ADP to form ATP during the first two to seven seconds following an intense muscular or neuronal effort. Conversely, excess ATP can be used during a period of low effort to convert creatine to phosphocreatine. The reversible phosphorylation of creatine is catalyzed by several creatine kinases. Particularly, PCr makes the energy of phosphoryl bonds of adenosine triphosphate (ATP) available at the myofibrillar creatine kinase that allows myocardium contraction. Supplementation with PCr was, therefore, suggested as potentially beneficial in patients with acute and chronic myocardial ischaemic injury. Phosphocreatine has been tried in the treatment of cardiac disorders and has been added to cardioplegic solutions. Phosphocreatine is used intravenously in hospitals in some parts of the world for cardiovascular problems under the name Neoton and also used by some professional athletes, as it is not a controlled substance.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Neonon

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Energy metabolism in single human muscle fibres during intermittent contraction with occluded circulation.
1993 Jan
Calf muscle mitochondrial and glycogenolytic ATP synthesis in patients with claudication due to peripheral vascular disease analysed using 31P magnetic resonance spectroscopy.
1995 Dec
Carbohydrate ingestion augments skeletal muscle creatine accumulation during creatine supplementation in humans.
1996 Nov
Effect of L-carnitine on myocardial metabolism: results of a balanced, placebo-controlled, double-blind study in patients undergoing open heart surgery.
1998 Feb
Skeletal muscle metabolism during exercise in humans.
2000 Mar
Creatine supplementation improves sprint performance in male sprinters.
2001 Apr
Control of glycolysis in contracting skeletal muscle. II. Turning it off.
2002 Jan
Severely altered guanidino compound levels, disturbed body weight homeostasis and impaired fertility in a mouse model of guanidinoacetate N-methyltransferase (GAMT) deficiency.
2004 May 1
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: https://clinicaltrials.gov/ct2/show/NCT03138681 | https://clinicaltrials.gov/ct2/show/NCT02757443
Acute myocardial infarction: the first day - intravenous rapid infusion of Neoton in a dose of 2-4 g (the drug is diluted with water for injection in a volume of 0.05 L) followed by intravenous infusion over 2 hours 8-16 g of powder in 0.2 L 5 % Glucose / dextrose solution; The second day, 2 times a day, intravenously drip (duration of infusion - from 1/2 hour), inject 2-4 g Neoton (the drug is diluted with water for injection in the volume of 0.05 l); On the third day of therapy, the solution is administered according to the same schedule at a dose of 2 g (if necessary, therapy is continued for 6 days); Heart failure (with chronic course): therapy can begin with shock doses - 5-10 g Neoton in 0.2 L 5% dextrose / glucose solution intravenously drip, the rate of administration - 4-5 g per hour, the duration of therapy - from 3 Up to 5 days. Further, maintenance doses are prescribed - intravenously drip (duration of infusion is from 1/2 hour) 1-2 g of powder in water for injection in a volume of 0.05 L, with a frequency of 2 times a day, the average duration of treatment is 2 to 6 weeks . If the patient's condition allows, therapy immediately begins with the use of maintenance doses according to the scheme described above; Intraoperative ischemia of the lower extremities: before surgery - rapid infusion of 2-4 g of powder in water for injection in a volume of 0.05 l; During the operation and during the reperfusion period, 8-10 g Neoton is dripped intravenously into 0.2 L of 5% glucose / dextrose solution at a rate of 4 to 5 g per hour; Intraoperative myocardial ischemia: intravenously drip (duration of infusion - from 1/2 hour) 2 g of powder diluted in water for injection in a volume of 0.05 l, with a frequency of administration 2 times a day. The course should be started 3-5 days before the surgery and continue for 1-2 days after it. During the operation, Neoton solution should be added to the usual cardioplegic solution (concentration - 10 mmol / l) or immediately before administration (dose - 2.5 g / l).
Route of Administration: Intravenous
Cell viability was evaluated by MTT cytotoxic assay kit (Sigma, USA). HUVECs (5 x 10^8 cells/ml) were plated in 6-well plates, incubated at 37 C for 24 h and pretreated with 5–20 mM PCr (Phosphocreatine) for 6 h respectively, then stimulated with lipopolsaccharide (LPS) (1 mkg/ml) for 24 h. After that, 20 mlL MTT solution was added into each well and incubated at 37 C for 1 h. The absorbance values of all the samples were recorded by using a microplate reader (Model 354, Thermo, USA) at a wavelength of 570 nm.
Name Type Language
MONOSODIUM PHOSPHOCREATINE
Systematic Name English
GLYCINE, N-(IMINO(PHOSPHONOAMINO)METHYL)-N-METHYL-, SODIUM SALT (1:1)
Systematic Name English
Code System Code Type Description
PUBCHEM
118406
Created by admin on Sat Dec 16 10:17:20 GMT 2023 , Edited by admin on Sat Dec 16 10:17:20 GMT 2023
PRIMARY
EPA CompTox
DTXSID30886293
Created by admin on Sat Dec 16 10:17:20 GMT 2023 , Edited by admin on Sat Dec 16 10:17:20 GMT 2023
PRIMARY
ECHA (EC/EINECS)
261-462-9
Created by admin on Sat Dec 16 10:17:20 GMT 2023 , Edited by admin on Sat Dec 16 10:17:20 GMT 2023
PRIMARY
FDA UNII
2NQ8WWR2PX
Created by admin on Sat Dec 16 10:17:20 GMT 2023 , Edited by admin on Sat Dec 16 10:17:20 GMT 2023
PRIMARY
CAS
58823-91-9
Created by admin on Sat Dec 16 10:17:20 GMT 2023 , Edited by admin on Sat Dec 16 10:17:20 GMT 2023
PRIMARY