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Encyclopedia > Creatine
Creatine
Creatine
IUPAC name 2-(carbamimidoyl-methyl- amino)acetic acid
Other names (α-methylguanido)acetic acid
Creatin
Kreatin
methylguanidinoacetic acid
N-amidinosarcosine
Identifiers
CAS number [57-00-1]
EINECS number 200-306-6
SMILES [NH2+]=C(N)N(C)CC([O-])=O
Properties
Molecular formula C4H9N3O2
Molar mass 131.13 g/mol
Melting point

dec. at 303 °C For the biochemistry and physiology of creatine, please see Creatine. ... Image File history File links Creatine2. ... Image File history File links No higher resolution available. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The EINECS number (for European Inventory of Existing Chemical Substances) is a registry number given to each chemical substance commercially available in the European Union between 1 January 1971 and 18 September 1981. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. ...

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Creatine is nitrogenous organic acid that occurs naturally in vertebrates and helps to supply energy to muscle and nerve cells. Creatine was identified in 1832 when Michel Eugène Chevreul discovered it as a component of skeletal muscle, which he later named creatine after the Greek word for flesh, Kreas. The plimsoll symbol as used in shipping In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals exactly). ... General Name, symbol, number nitrogen, N, 7 Chemical series nonmetals Group, period, block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... An organic acid is an organic compound that is an acid. ... This article does not cite any references or sources. ... For other uses of Muscles, see Muscles (disambiguation). ... Michel Eugène Chevreul (August 31, 1786 – April 9, 1889) was an important French chemist whose work with fatty acids led to early applications in the fields of art and science. ... A top-down view of skeletal muscle Skeletal muscle is a type of striated muscle, usually attached to the skeleton. ...

Contents

Function

Creatine by way of conversion to and from phosphocreatine is present and functions in all vertebrates, as well as some invertebrates, in conjunction with the enzyme creatine kinase. A similar system based on arginine/phosphoarginine operates in many invertebrates via the action of Arginine Kinase. The presence of this energy buffer system keeps the ATP/ADP ratio high at subcellular places where ATP is needed, which ensures that the free energy of ATP remains high and minimizes the loss of adenosine nucleotides, which would cause cellular dysfunction. Such high-energy phosphate buffers in the form of phosphocreatine or phosphoarginine are known as phosphagens. In addition, due to the presence of subcompartmentalized Creatine Kinase Isoforms at specific sites of the cell, the phosphocreatine/creatine kinase system also acts as an intracellular energy transport system from those places where ATP is generated (mitochondria and glycolysis) to those places where energy is needed and used, e.g., at the myofibrils for muscle contraction, at the sarcoplasmic reticulum (SR) for calcium pumping, and at the sites of many more biological processes that depend on ATP.[9,10] Phosphocreatine, also known as creatine phosphate or PCr, is a phosphorylated creatine molecule that is an important energy store in skeletal muscle. ... Creatine Kinase Creatine kinase (CK), also known as phosphocreatine kinase or creatine phosphokinase (CPK) is an enzyme (EC 2. ... Invertebrate is a term coined by Chevalier de Lamarck to describe any animal without a backbone or vertebra, like insects, squids and worms. ... Adenosine 5-triphosphate (ATP) is a multifunctional nucleotide that is most important as a molecular currency of intracellular energy transfer. ... Adenosine diphosphate, abbreviated ADP, is a nucleotide. ... The phosphagens are energy storage compounds, also known as high energy phosphate compounds, are chiefly found in muscular tissue in animals. ...


Biosynthesis

In the human body, approximately half of the daily creatine is biosynthesized mainly in the vertebrates by the use of parts from three different amino acids - arginine, glycine, and methionine. The rest is taken in by alimentary sources mainly from fresh fish and meat. Ninety-five percent of creatine is later stored in the skeletal muscles, with the rest in the brain, heart, testes, inner ear, hair cells, and other organs and cells. This article is about the class of chemicals. ... Arginine (abbreviated as Arg or R)[1] is an α-amino acid. ... For the plant, see Glycine (plant). ... Methionine is an α-amino acid with the chemical formula HO2CCH(NH2)CH2CH2SCH3. ... Human brain In animals, the brain (enkephale) (Greek for in the skull), is the control center of the central nervous system, responsible for behavior. ... The heart and lungs, from an older edition of Grays Anatomy. ... Human male anatomy The testicles, known medically as testes (singular testis), are the male generative glands in animals. ... Inner ear The inner ear is the bony labyrinth, a system of passages comprising two main functional parts: the organ of hearing, or cochlea and the vestibular apparatus, the organ of balance that consists of three semicircular canals and the vestibule. ... Hair cells are the sensory cells of the auditory system that are found within the cochleas organ of Corti. ...

The pathway for the synthesis of creatineArg - Arginine; GAMT - Guanidinoacetate N-methyltransferase; GAMT - Glycine amidinotransferase; Gly - Glycine; Met - Methionine; SAH - S-adenosyl homocysteine; SAM - S-adenosyl methionine.The color scheme is as follows:enzymes, coenzymes and the Met part, substrate names, the Gly part, the Arg part
The pathway for the synthesis of creatine
Arg - Arginine; GAMT - Guanidinoacetate N-methyltransferase; GAMT - Glycine amidinotransferase; Gly - Glycine; Met - Methionine; SAH - S-adenosyl homocysteine; SAM - S-adenosyl methionine.
The color scheme is as follows:enzymes, coenzymes and the Met part, substrate names, the Gly part, the Arg part

The enzyme GAMT (guanidinoacetate N-methyltransferase, also known as L-arginine:glycine amidinotransferase (AGAT), EC 2.1.4.1) is a mitochondrial enzyme responsible for catalyzing the first rate-limiting step of creatine biosynthesis, and is primarily expressed in the kidneys and pancreas[1]. For the plant, see Glycine (plant). ... Methionine is an α-amino acid with the chemical formula HO2CCH(NH2)CH2CH2SCH3. ... S-adenosylhomocysteine is an intermediate in the synthesis of cysteine. ... This article does not cite its references or sources. ... Ribbon diagram of the enzyme TIM, surrounded by the space-filling model of the protein. ... Arginine (abbreviated as Arg or R)[1] is an α-amino acid. ... For the plant, see Glycine (plant). ... ... Ribbon diagram of the enzyme TIM, surrounded by the space-filling model of the protein. ... Kidneys viewed from behind with spine removed The kidneys are bean-shaped excretory organs in vertebrates. ...


The second enzyme in the pathway (GAMT, guanidinoacetate N-methyltransferase, EC:2.1.1.2) is primarily expressed in the liver and pancreas[2].


Genetic deficiencies in the creatine biosynthetic pathway lead to various severe neurological defects[3].


Controversy

Whilst creatine's effectiveness in the treatment of many muscular, neuromuscular and neuro-degenerative diseases is documented [1], its utility as a performance enhancing food supplement in sports has been questioned[2] (see Creatine supplements for more information). Despite this, and perhaps because of its popularity [3], some have proposed that its use as a performance enhancer should be banned[4]. Food additives are substances added to food to preserve flavor or improve its taste and appearance. ... For the biochemistry and physiology of creatine, please see Creatine. ...


Side Effects

Continuous intake of excessively high dosages of creatine may lead to any of several possible side-effects. It has been hypothesized that consistently high doses could lead to hypertension due to increased water retention [5]. It can also cause dehydration by another mechanism.[citation needed] There is some discussion of kidney problems resulting from supplementation, as excess creatine is not broken down into nitrogenous wastes but instead released in a more benign form [6].


Creatine supplementation utilizing proper cycling and dosages, however, has not been linked with any adverse side-effects beyond occasional dehydration due to increased muscular water uptake from the rest of the body.[7]


According to the opinion statement of the European Food Safety Authorities (EFSA) published in 2004 it was concluded that "The safety and bioavailability of the requested source of creatine, creatine monohydrate in foods for particular nutritional uses, is not a matter of concern provided that there is adequate control of the purity of this source of creatine (minimum 99.95%) with respect to dicyandiamide and dihydro-1,3,5-triazine derivatives, as well as heavy metal contamination. The EFSA Panel endorses the previous opinion of the SCF that high loading doses (20 gram / day) of creatine should be avoided. Provided high purity creatine monohydrate is used in foods for particular nutritional uses, the Panel considers that the consumption of doses of up to 3g/day of supplemental creatine, similar to the daily turnover rate of creatine, is unlikely to pose any risk". Publication date of the EFSA Statement is 26/04/2006. EFSA statement


This opinion is corroborated by the fact that creatine is a natural component in mothers milk and that creatine is absolutely necessary for brain development in the human embryo and the baby, as well as for optimal physiological functioning of the adult human body, especially the brain, nervous system, the muscles and other organs and cells of high energy expenditure, where the creatine kinase (CK) system is highly expressed and creatine levels are high. For a scientific update on CK and creatine function see the recently published book Function of CK and Creatine in Health and Disease.


Sources

In humans, approximately half of stored creatine originates from food (mainly from fresh meat and fish). Since vegetables do not contain creatine, vegetarians clearly show lower levels of muscle creatine which, upon creatine supplementation, rise to a level higher than in meat-eaters.[8] This article is about the food. ... For other uses, see Fish (disambiguation). ...


Creatine and the treatment of muscular diseases

Creatine supplementation has been, and continues to be, investigated as a possible therapeutic approach for the treatment of muscular, neuromuscular, neurological and neurodegenerative diseases (arthritis, congestive heart failure, Parkinson's disease, disuse atrophy, gyrate atrophy, McArdle's disease, Huntington's disease, miscellaneous neuromuscular diseases, mitochondrial diseases, muscular dystrophy, neuroprotection, etc.). Arthritis (from Greek arthro-, joint + -itis, inflammation; plural: arthritides) is a group of conditions where there is damage caused to the joints of the body. ... Congestive heart failure (CHF), also called congestive cardiac failure (CCF) or just heart failure, is a condition that can result from any structural or functional cardiac disorder that impairs the ability of the heart to fill with or pump a sufficient amount of blood throughout the body. ... Glycogen storage disease type V is a metabolic disorder, more specifically a glycogen storage disease, caused by a deficiency of myophosphorylase, the muscle isoform of the enzyme glycogen phosphorylase. ... Mitochondrial diseases are a group of disorders relating to the mitochondria, the organelles that are the powerhouses of the eukaryotic cells that comprise higher-order lifeforms (including humans). ... Muscular dystrophy refers to a group of genetic, hereditary muscle diseases that cause progressive muscle weakness. ... The term neuroprotection means mechanisms within the nervous system which protect neurons from apoptosis or degeneration, for example following a brain injury or as a result of chronic neurodegenerative diseases. ...


Two studies have indicated that creatine may be beneficial for neuromuscular disorders. First, a study demonstrated that creatine is twice as effective as the prescription drug riluzole in extending the lives of mice with the degenerative neural disease amyotrophic lateral sclerosis (ALS, or Lou Gehrig's disease)[9]. The neuroprotective effects of creatine in the mouse model of ALS may be due either to an increased availability of energy to injured nerve cells or to a blocking of the chemical pathway that leads to cell death. Riluzole is a drug used to treat amyotrophic lateral sclerosis. ... Amyotrophic Lateral Sclerosis (ALS, sometimes called Lou Gehrigs Disease, or Maladie de Charcot) is a progressive, usually fatal, neurodegenerative disease caused by the degeneration of motor neurons, the nerve cells in the central nervous system that control voluntary muscle movement. ... Programmed cell death (PCD) is the deliberate suicide of an unwanted cell in a multicellular organism. ...


Second, creatine has been demonstrated to cause modest increases in strength in people with a variety of neuromuscular disorders[10].


Third, creatine has been shown to be beneficial as an adjuvant treatment for several neuro-muscular and neuro-degenerative diseases (11,12) and its potential is just beginning to be explored in several multi-center clinical studies in the USA and elsewhere.


See also

Adenosine 5-triphosphate (ATP) is a multifunctional nucleotide that is most important as a molecular currency of intracellular energy transfer. ... In biochemistry, beta-alanine (or β-alanine) is the only naturally occurring beta amino acid, which are amino acids in which the amino group is at the β-position from the carboxylate group (i. ... Creatine Kinase Creatine kinase (CK), also known as phosphocreatine kinase or creatine phosphokinase (CPK) is an enzyme (EC 2. ... Overview of the citric acid cycle The citric acid cycle (also known as the tricarboxylic acid cycle, the TCA cycle, or the Krebs cycle, after Hans Adolf Krebs who identified the cycle) is a series of chemical reactions of central importance in all living cells that use oxygen as part... Creatine ethyl ester, also known as creatine ester, cre-ester and CEE, is a substance sold as an aid for athletic performance and for muscle development in bodybuilding. ... Coenzyme Q (CoQ), also known as ubiquinone or ubiquinol, is a biologically active quinone with an isoprenoid side chain, related in structure to vitamin K and vitamin E. The oxidized structure of CoQ, or Q, is given here: The various kinds of Coenzyme Q can be distinguished by the number... This article does not cite any references or sources. ... Lipoic acid, also known as α-lipoic acid (alpha lipoic acid) or thioctic acid, has formula C8H14S2O2 and systematic name 5-(1,2-dithiolan-3-yl)pentanoic acid. ... Nootropics are drugs that are used to enhance mental performance in healthy individuals. ... Pantothenic acid, also called vitamin B5, is an antioxidant water-soluble vitamin needed to break down carbohydrates, proteins, and fats. ... R-phrases , , , , S-phrases , , , Except where noted otherwise, data are given for materials in their standard state (at 25 Â°C, 100 kPa) Infobox disclaimer and references Nitric oxide or Nitrogen monoxide is a chemical compound with chemical formula NO. This gas is an important signaling molecule in the body of...

References

  1. ^ Creatine and Creatine Kinase in Health and Disease (2007) Series: Subcellular Biochemistry , Vol. 46 Salomons, Gajja S.; Wyss, Markus (Eds.) 2007, XVIII, 352 p., Hardcover ISBN: 978-1-4020-6485-2
  2. ^ Edward G. McFarland, M.D. (2002-10-04). Sports Enhancers - The Good, the Questionable and the Dangerous. Johns Hopkins Hospital. Retrieved on 2008-01-08.
  3. ^ "Creatine sales totaled $193 million in 2003 — or roughly 10% of the $1.9-billion sports supplement market, according to the San Diego-based Nutrition Business Journal." Joshua Tompkins (2004-05-03). The creatine edge. LA Times. Retrieved on 2008-01-08.
  4. ^ Consumer Review: Creatine Monohydrate: The Next Drug To Be Banned By The NCAA?.
  5. ^ http://www.teengrowth.com/index.cfm?action=info_advice&ID_Advice=2406&category=sports&catdesc=Sports&subdesc=Steroids
  6. ^ http://www.drugdigest.org/DD/PrintablePages/herbMonograph/0,11475,4045,00.html
  7. ^ Bizzarini E, De Angelis L. (December 2004). "Is the use of oral creatine supplementation safe?". J Sports Med Phys Fitness.. PMID 15758854.
  8. ^ Burke DG, Chilibeck PD, Parise G, Candow DG, Mahoney D, Tarnopolsky M (2003). "Effect of creatine and weight training on muscle creatine and performance in vegetarians". Medicine and science in sports and exercise 35 (11): 1946–55. doi:10.1249/01.MSS.0000093614.17517.79. PMID 14600563.
  9. ^ Klivenyi P, Ferrante RJ, Matthews RT, Bogdanov MB, Klein AM, Andreassen OA, Mueller G, Wermer M, Kaddurah-Daouk R, Beal MF. (mar 1999). "Neuroprotective effects of creatine in a transgenic animal model of amyotrophic lateral sclerosis.". Nature Medicine. 5 (3): 347-350. PMID 10086395.
  10. ^ Tarnopolsky M, Martin J (1999). "Creatine monohydrate increases strength in patients with neuromuscular disease". Neurology 52 (4): 854–7. PMID 10078740.


10. Schlattner U, Tokarska-Schlattner M, Wallimann T. (2006) Mitochondrial creatine kinase in human health and disease. Biochim Biophys Acta. 2006 Feb;1762(2):164-80. Review Also see: 2002 (number). ... is the 277th day of the year (278th in leap years) in the Gregorian calendar. ... 2008 (MMVIII) is the current year, a leap year that started on Tuesday of the Anno Domini (or common era), in accordance to the Gregorian calendar. ... is the 8th day of the year in the Gregorian calendar. ... Year 2004 (MMIV) was a leap year starting on Thursday of the Gregorian calendar. ... is the 123rd day of the year (124th in leap years) in the Gregorian calendar. ... 2008 (MMVIII) is the current year, a leap year that started on Tuesday of the Anno Domini (or common era), in accordance to the Gregorian calendar. ... is the 8th day of the year in the Gregorian calendar. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ...


11. Wallimann T, Wyss M, Brdiczka D, Nicolay K, Eppenberger HM. (1992) Intracellular compartmentation, structure and function of creatine kinase isoenzymes in tissues with high and fluctuating energy demands: the 'phosphocreatine circuit' for cellular energy homeostasis. Biochem J. 1992 Jan 1;281 ( Pt 1):21-40. Review.


12. Creatine and Creatine Kinase in Health and Disease (2007) Series: Subcellular Biochemistry , Vol. 46 Salomons, Gajja S.; Wyss, Markus (Eds.) 2007, XVIII, 352 p., Hardcover ISBN: 978-1-4020-6485-2


12. Wallimann T, Tokarska-Schlattner M, Neumann D, Epand RM, Epand RF, Andres RH, Widmer HR, Hornemann T, Saks VA, Agarkova I, Schlattner U. (2007) The phospho-creatine circuit: molecular and cellular physiology of creatine kinases, sensitivity to free radicals and enhancement by creatine supplementation. In: Molecular Systems Bioenergetics: Energy for Life, Basic Principles, Organization and Dynamics of Cellular Energetics (Saks, V.A., Editor), Wiley-VCH, Weinheim, Germany, pp. 195-264 (2007)


External links

A dietary supplement is intended to supply nutrients, (vitamins, minerals, fatty acids or amino acids) that are missing or not consumed in sufficient quantity in a persons diet. ... An essential amino acid or indispensable amino acid is an amino acid that cannot be synthesized de novo by the organism (usually referring to humans), and therefore must be supplied in the diet. ... Many supplements come in capsule form. ... A variety of energy drinks are available; the skinny bullet can shape is popular. ... An energy bar is a dietary supplement often consumed by athletes or other physically active people to maintain their caloric needs in light of their strenuous physical activity. ... Essential fatty acids, or EFAs, are fatty acids that cannot be constructed within an organism from other components (generally all references are to humans) by any known chemical pathways; and therefore must be obtained from the diet. ... Herbalism is a traditional medicinal or folk medicine practice based on the use of plants and plant extracts. ... mccall is cooool Dietary minerals are the chemical elements required by living organisms, other than the four elements carbon, hydrogen, nitrogen, and oxygen which are present in common organic molecules. ... The word prebiotic has two separate and disparate meanings: Before Life From the roots pre (meaning before) and biotic (referring to life), the word prebiotic can refer to the time before life appeared on the earth or any other planet with the capacity to harbor it. ... Probiotics are dietary supplements containing potentially beneficial bacteria or yeasts. ... Species L. acidophilus L. brevis L. delbrueckii subsp. ... Bifidobacteria (genus Bifidobacterium) are a group of anaerobic bacteria and a form of probiotic that is thought to have health-promoting properties for humans. ... Retinol (Vitamin A) A vitamin is a nutrient that is an organic compound required in tiny amounts for essential metabolic reactions in a living organism. ... Whole food supplements comprise a unique class within the food supplement industry. ... Retinol (Vitamin A) A vitamin is a nutrient that is an organic compound required in tiny amounts for essential metabolic reactions in a living organism. ... mccall is cooool Dietary minerals are the chemical elements required by living organisms, other than the four elements carbon, hydrogen, nitrogen, and oxygen which are present in common organic molecules. ... The structure of retinol, the most common dietary form of vitamin A Vitamin A is an essential human nutrient. ... The B vitamins are eight water-soluble vitamins that play important roles in cell metabolism. ... For the similarly spelled nucleic acid, see Thymine Thiamine or thiamin, also known as vitamin B1, is one of the B vitamins. ... 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  Results from FactBites:
 
Creatine Supplementation (1832 words)
Creatine supplementation is claimed to increase muscle power by playing a role in the transfer of energy to help the muscle contract.
Supplement labels state that "creatine is converted to phosphocreatine, which is important for short energy bursts such as sprinting and weight lifting" and that "depletion of phosphocreatine can result in muscle fatigue and fading muscle power." Claims are also made that supplementation increases muscle body mass.
Creatine is not subjected to FDA testing, and the purity and hygienic condition of commercial creatine products may be questionable [21].
Creatine kinase - Wikipedia, the free encyclopedia (406 words)
Creatine kinase (CK), also known as phosphocreatine kinase or creatine phosphokinase (CPK) is an enzyme (EC 2.7.3.2) expressed by various tissue types.
Its function is the catalysis of the conversion of creatine to phosphocreatine, consuming adenosine triphosphate (ATP) and generating adenosine diphosphate (ADP) and the reverse reaction.
In tissues that consume ATP rapidly, especially skeletal muscle, but also brain and smooth muscle, creatine phosphate serves as an energy reservoir for the rapid regeneration of ATP, the major source of energy in biochemical reactions.
  More results at FactBites »

 
 

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