Details
Stereochemistry | ACHIRAL |
Molecular Formula | C4H10N3O5P |
Molecular Weight | 211.1131 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(CC(O)=O)C(=N)NP(O)(O)=O
InChI
InChIKey=DRBBFCLWYRJSJZ-UHFFFAOYSA-N
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)
Molecular Formula | C4H10N3O5P |
Molecular Weight | 211.1131 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/27318357Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27318357
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.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2656 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16236486 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Neonon Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Early time course of N-acetylaspartate, creatine and phosphocreatine, and compounds containing choline in the brain after acute stroke. A proton magnetic resonance spectroscopy study. | 1992 Nov |
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Energy metabolism in single human muscle fibres during intermittent contraction with occluded circulation. | 1993 Jan |
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Calf muscle mitochondrial and glycogenolytic ATP synthesis in patients with claudication due to peripheral vascular disease analysed using 31P magnetic resonance spectroscopy. | 1995 Dec |
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A relationship between impaired fetal growth and reduced muscle glycolysis revealed by 31P magnetic resonance spectroscopy. | 1995 Oct |
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Carbohydrate ingestion augments skeletal muscle creatine accumulation during creatine supplementation in humans. | 1996 Nov |
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Effect of L-carnitine on myocardial metabolism: results of a balanced, placebo-controlled, double-blind study in patients undergoing open heart surgery. | 1998 Feb |
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Skeletal muscle metabolism during exercise in humans. | 2000 Mar |
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Creatine supplementation improves sprint performance in male sprinters. | 2001 Apr |
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Muscle oxygen uptake and energy turnover during dynamic exercise at different contraction frequencies in humans. | 2001 Oct 1 |
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Control of glycolysis in contracting skeletal muscle. II. Turning it off. | 2002 Jan |
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The yo-yo intermittent recovery test: physiological response, reliability, and validity. | 2003 Apr |
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Effects of creatine supplementation in cystic fibrosis: results of a pilot study. | 2003 Dec |
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Creatine supplementation: a comparison of loading and maintenance protocols on creatine uptake by human skeletal muscle. | 2003 Mar |
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Metabolic effects of induced alkalosis during progressive forearm exercise to fatigue. | 2004 Jun |
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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 |
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Neuromechanism of developing methamphetamine psychosis: a neuroimaging study. | 2004 Oct |
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High-energy phosphate metabolism in the calf muscle during moderate isotonic exercise under different degrees of cuff compression: a phosphorus 31 magnetic resonance spectroscopy study. | 2005 Aug |
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Energy system contribution to 1500- and 3000-metre track running. | 2005 Oct |
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Effects of creatine supplementation on aerobic power and cardiovascular structure and function. | 2005 Sep |
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Effect of temperature on skeletal muscle energy turnover during dynamic knee-extensor exercise in humans. | 2006 Jul |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: http://en.remedy-info.com/ovr0_neoton.html
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26708229
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 17:18:18 GMT 2023
by
admin
on
Fri Dec 15 17:18:18 GMT 2023
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Record UNII |
020IUV4N33
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Record Status |
Validated (UNII)
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Record Version |
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WHO-VATC |
QC01EB06
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WHO-ATC |
C01EB06
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DSLD |
1146 (Number of products:2)
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67-07-2
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3464
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CHEMBL1204644
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DTXSID0058776
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020IUV4N33
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200-643-9
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PHOSPHOCREATINE
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DB13191
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SUB14849MIG
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17287
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D010725
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100000079437
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m8722
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587
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ACTIVE MOIETY |