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

Details

Stereochemistry ACHIRAL
Molecular Formula C4H8N3O5P.2Na
Molecular Weight 255.0767
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHOSPHOCREATINE SODIUM

SMILES

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

InChI

InChIKey=RNTXMYSPASRLFT-UHFFFAOYSA-L
InChI=1S/C4H10N3O5P.2Na/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;2*+1/p-2

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C4H8N3O5P
Molecular Weight 209.0972
Charge -2
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
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
Creatine supplementation improves sprint performance in male sprinters.
2001 Apr
Muscle oxygen uptake and energy turnover during dynamic exercise at different contraction frequencies in humans.
2001 Oct 1
Creatine supplementation: a comparison of loading and maintenance protocols on creatine uptake by human skeletal muscle.
2003 Mar
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
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 Sat Dec 16 20:02:26 GMT 2023
Edited
by admin
on Sat Dec 16 20:02:26 GMT 2023
Record UNII
79577SJY6E
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PHOSPHOCREATINE SODIUM
WHO-DD  
Systematic Name English
PHOSPHOCREATINE SODIUM SALT
MI  
Common Name English
EPG
Brand Name English
PHOSPHOCREATINE SODIUM SALT [MI]
Common Name English
GLYCINE, N-(IMINO(PHOSPHONOAMINO)METHYL)-N-METHYL-, SODIUM SALT (1:2)
Systematic Name English
SARCOSINE, N-(PHOSPHONOAMIDINO)-, SODIUM SALT
Systematic Name English
DISODIUM PHOSPHOCREATINE
INCI  
INCI  
Official Name English
SODIUM PHOSPHOCREATINE
Systematic Name English
DISODIUM PHOSPHOCREATINE [INCI]
Common Name English
Phosphocreatine sodium [WHO-DD]
Common Name English
Code System Code Type Description
FDA UNII
79577SJY6E
Created by admin on Sat Dec 16 20:02:26 GMT 2023 , Edited by admin on Sat Dec 16 20:02:26 GMT 2023
PRIMARY
PUBCHEM
71588
Created by admin on Sat Dec 16 20:02:26 GMT 2023 , Edited by admin on Sat Dec 16 20:02:26 GMT 2023
PRIMARY
MERCK INDEX
m8722
Created by admin on Sat Dec 16 20:02:26 GMT 2023 , Edited by admin on Sat Dec 16 20:02:26 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID40919309
Created by admin on Sat Dec 16 20:02:26 GMT 2023 , Edited by admin on Sat Dec 16 20:02:26 GMT 2023
PRIMARY
CAS
922-32-7
Created by admin on Sat Dec 16 20:02:26 GMT 2023 , Edited by admin on Sat Dec 16 20:02:26 GMT 2023
PRIMARY
CAS
33166-68-6
Created by admin on Sat Dec 16 20:02:26 GMT 2023 , Edited by admin on Sat Dec 16 20:02:26 GMT 2023
SUPERSEDED
SMS_ID
100000153536
Created by admin on Sat Dec 16 20:02:26 GMT 2023 , Edited by admin on Sat Dec 16 20:02:26 GMT 2023
PRIMARY
EVMPD
SUB127604
Created by admin on Sat Dec 16 20:02:26 GMT 2023 , Edited by admin on Sat Dec 16 20:02:26 GMT 2023
PRIMARY
DRUG BANK
DBSALT002491
Created by admin on Sat Dec 16 20:02:26 GMT 2023 , Edited by admin on Sat Dec 16 20:02:26 GMT 2023
PRIMARY
ECHA (EC/EINECS)
213-074-6
Created by admin on Sat Dec 16 20:02:26 GMT 2023 , Edited by admin on Sat Dec 16 20:02:26 GMT 2023
PRIMARY
CAS
1159882-55-9
Created by admin on Sat Dec 16 20:02:26 GMT 2023 , Edited by admin on Sat Dec 16 20:02:26 GMT 2023
ALTERNATIVE
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY