U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of PHOSPHOCREATINE

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)

HIDE SMILES / InChI

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

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
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
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
A relationship between impaired fetal growth and reduced muscle glycolysis revealed by 31P magnetic resonance spectroscopy.
1995 Oct
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
Muscle oxygen uptake and energy turnover during dynamic exercise at different contraction frequencies in humans.
2001 Oct 1
Control of glycolysis in contracting skeletal muscle. II. Turning it off.
2002 Jan
The yo-yo intermittent recovery test: physiological response, reliability, and validity.
2003 Apr
Effects of creatine supplementation in cystic fibrosis: results of a pilot study.
2003 Dec
Creatine supplementation: a comparison of loading and maintenance protocols on creatine uptake by human skeletal muscle.
2003 Mar
Metabolic effects of induced alkalosis during progressive forearm exercise to fatigue.
2004 Jun
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
Neuromechanism of developing methamphetamine psychosis: a neuroimaging study.
2004 Oct
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
Energy system contribution to 1500- and 3000-metre track running.
2005 Oct
Effects of creatine supplementation on aerobic power and cardiovascular structure and function.
2005 Sep
Effect of temperature on skeletal muscle energy turnover during dynamic knee-extensor exercise in humans.
2006 Jul
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:18:18 UTC 2023
Edited
by admin
on Fri Dec 15 17:18:18 UTC 2023
Record UNII
020IUV4N33
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PHOSPHOCREATINE
MI  
Systematic Name English
CREATINE-P
Common Name English
CREATINE PHOSPHATE
MART.   WHO-DD  
Common Name English
PHOSPHAGEN
Common Name English
PHOSPHOCREATINE [MI]
Common Name English
Creatine Phosphate [WHO-DD]
Common Name English
FOSFOCREATINE
Common Name English
CREATINE PHOSPHATE [MART.]
Common Name English
Classification Tree Code System Code
WHO-VATC QC01EB06
Created by admin on Fri Dec 15 17:18:18 UTC 2023 , Edited by admin on Fri Dec 15 17:18:18 UTC 2023
WHO-ATC C01EB06
Created by admin on Fri Dec 15 17:18:18 UTC 2023 , Edited by admin on Fri Dec 15 17:18:18 UTC 2023
DSLD 1146 (Number of products:2)
Created by admin on Fri Dec 15 17:18:18 UTC 2023 , Edited by admin on Fri Dec 15 17:18:18 UTC 2023
Code System Code Type Description
CAS
67-07-2
Created by admin on Fri Dec 15 17:18:18 UTC 2023 , Edited by admin on Fri Dec 15 17:18:18 UTC 2023
PRIMARY
DRUG CENTRAL
3464
Created by admin on Fri Dec 15 17:18:18 UTC 2023 , Edited by admin on Fri Dec 15 17:18:18 UTC 2023
PRIMARY
ChEMBL
CHEMBL1204644
Created by admin on Fri Dec 15 17:18:18 UTC 2023 , Edited by admin on Fri Dec 15 17:18:18 UTC 2023
PRIMARY
EPA CompTox
DTXSID0058776
Created by admin on Fri Dec 15 17:18:18 UTC 2023 , Edited by admin on Fri Dec 15 17:18:18 UTC 2023
PRIMARY
FDA UNII
020IUV4N33
Created by admin on Fri Dec 15 17:18:18 UTC 2023 , Edited by admin on Fri Dec 15 17:18:18 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-643-9
Created by admin on Fri Dec 15 17:18:18 UTC 2023 , Edited by admin on Fri Dec 15 17:18:18 UTC 2023
PRIMARY
WIKIPEDIA
PHOSPHOCREATINE
Created by admin on Fri Dec 15 17:18:18 UTC 2023 , Edited by admin on Fri Dec 15 17:18:18 UTC 2023
PRIMARY
DRUG BANK
DB13191
Created by admin on Fri Dec 15 17:18:18 UTC 2023 , Edited by admin on Fri Dec 15 17:18:18 UTC 2023
PRIMARY
EVMPD
SUB14849MIG
Created by admin on Fri Dec 15 17:18:18 UTC 2023 , Edited by admin on Fri Dec 15 17:18:18 UTC 2023
PRIMARY
CHEBI
17287
Created by admin on Fri Dec 15 17:18:18 UTC 2023 , Edited by admin on Fri Dec 15 17:18:18 UTC 2023
PRIMARY
MESH
D010725
Created by admin on Fri Dec 15 17:18:18 UTC 2023 , Edited by admin on Fri Dec 15 17:18:18 UTC 2023
PRIMARY
SMS_ID
100000079437
Created by admin on Fri Dec 15 17:18:18 UTC 2023 , Edited by admin on Fri Dec 15 17:18:18 UTC 2023
PRIMARY
MERCK INDEX
m8722
Created by admin on Fri Dec 15 17:18:18 UTC 2023 , Edited by admin on Fri Dec 15 17:18:18 UTC 2023
PRIMARY Merck Index
PUBCHEM
587
Created by admin on Fri Dec 15 17:18:18 UTC 2023 , Edited by admin on Fri Dec 15 17:18:18 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
METABOLITE -> PARENT
PARENT -> METABOLITE
Related Record Type Details
ACTIVE MOIETY