Identification
- Generic Name
- Creatine
- DrugBank Accession Number
- DB00148
- Background
An amino acid derivative that occurs in vertebrate tissues and in urine. In muscle tissue, creatine generally occurs as phosphocreatine. Creatine is excreted as creatinine in the urine.
- Type
- Small Molecule
- Groups
- Approved, Investigational, Nutraceutical
- Structure
Structure for Creatine (DB00148)
- Weight
- Average: 131.1332
Monoisotopic: 131.069476547 - Chemical Formula
- C4H9N3O2
- Synonyms
- ((amino(Imino)methyl)(methyl)amino)acetic acid
- (alpha-Methylguanido)acetic acid
- (N-methylcarbamimidamido)acetic acid
- (α-methylguanido)acetic acid
- alpha-Methylguanidino acetic acid
- Creatin
- Creatine
- Kreatin
- Methylglycocyamine
- N-(aminoiminomethyl)-N-methylglycine
- N-amidinosarcosine
- N-carbamimidoyl-N-methylglycine
- N-methyl-N-guanylglycine
Pharmacology
- Indication
For nutritional supplementation, also for treating dietary shortage or imbalance.
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Creatine is a essential, non-proteinaceous amino acid derivative found in all animals. It is synthesized in the kidney, liver, and pancreas from L-arginine, glycine and L-methionine. Following its biosynthesis, creatine is transported to the skeletal muscle, heart, brain and other tissues. Most of the creatine is metabolized in these tissues to phosphocreatine (creatine phosphate). Phosphocreatine is a major energy storage form in the body. Supplemental creatine may have an energy-generating action during anaerobic exercise and may also have neuroprotective and cardioprotective actions.
- Mechanism of action
In the muscles, a fraction of the total creatine binds to phosphate - forming creatine phosphate. The reaction is catalysed by creatine kinase, and the result is phosphocreatine (PCr). Phosphocreatine binds with adenosine diphosphate to convert it back to ATP (adenosine triphosphate), an important cellular energy source for short term ATP needs prior to oxidative phosphorylation.
Target Actions Organism ACreatine kinase M-type ligandHumans ACreatine kinase U-type, mitochondrial ligandHumans ACreatine kinase B-type ligandHumans ACreatine kinase S-type, mitochondrial ligandHumans ASodium- and chloride-dependent creatine transporter 1 Not Available Humans AGuanidinoacetate N-methyltransferase product ofHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
3 hours
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- No interactions found.
Products
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Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Ginsamin Energy Creatine (10000 mg/20g) + Ascorbic acid (1000 mg/20g) + Ginkgo biloba (160 mg/20g) + Ginseng (200 mg/20g) + Taurine (1000 mg/20g) Liquid Oral Biogrand Co., Ltd 2010-03-07 Not applicable US 
- Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Ginsamin Energy Creatine (10000 mg/20g) + Ascorbic acid (1000 mg/20g) + Ginkgo biloba (160 mg/20g) + Ginseng (200 mg/20g) + Taurine (1000 mg/20g) Liquid Oral Biogrand Co., Ltd 2010-03-07 Not applicable US
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Alpha amino acids and derivatives
- Alternative Parents
- Guanidines / Monocarboxylic acids and derivatives / Carboxylic acids / Carboximidamides / Organopnictogen compounds / Organic oxides / Imines / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Aliphatic acyclic compound / Alpha-amino acid or derivatives / Carbonyl group / Carboximidamide / Carboxylic acid / Guanidine / Hydrocarbon derivative / Imine / Monocarboxylic acid or derivatives / Organic nitrogen compound
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- glycine derivative, guanidines (CHEBI:16919)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- MU72812GK0
- CAS number
- 57-00-1
- InChI Key
- CVSVTCORWBXHQV-UHFFFAOYSA-N
- InChI
- InChI=1S/C4H9N3O2/c1-7(4(5)6)2-3(8)9/h2H2,1H3,(H3,5,6)(H,8,9)
- IUPAC Name
- 2-(N-methylcarbamimidamido)acetic acid
- SMILES
- CN(CC(O)=O)C(N)=N
References
- Synthesis Reference
Stefan Weiss, Helmut Krommer, "Process for the preparation of a creatine or creatine monohydrate." U.S. Patent US5719319, issued September, 1963.
US5719319- General References
- Burke DG, Chilibeck PD, Parise G, Tarnopolsky MA, Candow DG: Effect of alpha-lipoic acid combined with creatine monohydrate on human skeletal muscle creatine and phosphagen concentration. Int J Sport Nutr Exerc Metab. 2003 Sep;13(3):294-302. [Article]
- Dangott B, Schultz E, Mozdziak PE: Dietary creatine monohydrate supplementation increases satellite cell mitotic activity during compensatory hypertrophy. Int J Sports Med. 2000 Jan;21(1):13-6. [Article]
- Hespel P, Op't Eijnde B, Van Leemputte M, Urso B, Greenhaff PL, Labarque V, Dymarkowski S, Van Hecke P, Richter EA: Oral creatine supplementation facilitates the rehabilitation of disuse atrophy and alters the expression of muscle myogenic factors in humans. J Physiol. 2001 Oct 15;536(Pt 2):625-33. [Article]
- Hultman E, Soderlund K, Timmons JA, Cederblad G, Greenhaff PL: Muscle creatine loading in men. J Appl Physiol (1985). 1996 Jul;81(1):232-7. [Article]
- Juhn M: Popular sports supplements and ergogenic aids. Sports Med. 2003;33(12):921-39. [Article]
- External Links
- Human Metabolome Database
- HMDB0000064
- KEGG Compound
- C00300
- PubChem Compound
- 586
- PubChem Substance
- 46504868
- ChemSpider
- 566
- BindingDB
- 50357229
- 2907
- ChEBI
- 16919
- ChEMBL
- CHEMBL283800
- ZINC
- ZINC000003861770
- PharmGKB
- PA164778930
- PDBe Ligand
- CRN
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Creatine
- PDB Entries
- 1v7z / 3a6j / 3b6r
- MSDS
- Download (73.1 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Major Depressive Disorder (MDD) 2 4 Recruiting Treatment Major Depressive Disorder (MDD) 1 4 Terminated Treatment Major Depressive Disorder (MDD) 1 4 Withdrawn Treatment Major Depressive Disorder (MDD) 1 3 Completed Prevention Schizophrenia 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- National Vitamin Company
- Professional Co.
- Solace Nutrition
- Dosage Forms
Form Route Strength Liquid Oral - Prices
Unit description Cost Unit Creatine monohydrate powder 0.81USD g Cytotine 1.5 g/15 ml liquid 0.07USD ml Creatine powder 0.01USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 255 dec °C PhysProp water solubility 1.33E+004 mg/L (at 18 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP -0.2 Not Available - Predicted Properties
Property Value Source Water Solubility 4.11 mg/mL ALOGPS logP -1.6 ALOGPS logP -2.9 Chemaxon logS -1.5 ALOGPS pKa (Strongest Acidic) 3.5 Chemaxon pKa (Strongest Basic) 12.43 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 90.41 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 42.01 m3·mol-1 Chemaxon Polarizability 12.17 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9605 Blood Brain Barrier + 0.6849 Caco-2 permeable - 0.6228 P-glycoprotein substrate Non-substrate 0.5275 P-glycoprotein inhibitor I Non-inhibitor 0.9704 P-glycoprotein inhibitor II Non-inhibitor 0.8744 Renal organic cation transporter Non-inhibitor 0.8321 CYP450 2C9 substrate Non-substrate 0.7916 CYP450 2D6 substrate Non-substrate 0.767 CYP450 3A4 substrate Non-substrate 0.7585 CYP450 1A2 substrate Non-inhibitor 0.9136 CYP450 2C9 inhibitor Non-inhibitor 0.9068 CYP450 2D6 inhibitor Non-inhibitor 0.8954 CYP450 2C19 inhibitor Non-inhibitor 0.9157 CYP450 3A4 inhibitor Non-inhibitor 0.9346 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9969 Ames test Non AMES toxic 0.7522 Carcinogenicity Non-carcinogens 0.8138 Biodegradation Not ready biodegradable 0.7859 Rat acute toxicity 2.0088 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9653 hERG inhibition (predictor II) Non-inhibitor 0.9649
Spectra
- Mass Spec (NIST)
- Download (8.81 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 123.2857626 predictedDarkChem Lite v0.1.0 [M-H]- 123.2423626 predictedDarkChem Lite v0.1.0 [M-H]- 123.3093626 predictedDarkChem Lite v0.1.0 [M-H]- 123.4018626 predictedDarkChem Lite v0.1.0 [M-H]- 125.553024 predictedDeepCCS 1.0 (2019) [M+H]+ 124.3097626 predictedDarkChem Lite v0.1.0 [M+H]+ 124.2666626 predictedDarkChem Lite v0.1.0 [M+H]+ 124.2621626 predictedDarkChem Lite v0.1.0 [M+H]+ 124.3332626 predictedDarkChem Lite v0.1.0 [M+H]+ 127.62428 predictedDeepCCS 1.0 (2019) [M+Na]+ 124.3442626 predictedDarkChem Lite v0.1.0 [M+Na]+ 124.3034626 predictedDarkChem Lite v0.1.0 [M+Na]+ 124.3524626 predictedDarkChem Lite v0.1.0 [M+Na]+ 124.3629626 predictedDarkChem Lite v0.1.0 [M+Na]+ 136.62532 predictedDeepCCS 1.0 (2019)
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Ligand
- General Function
- Creatine kinase activity
- Specific Function
- Reversibly catalyzes the transfer of phosphate between ATP and various phosphogens (e.g. creatine phosphate). Creatine kinase isoenzymes play a central role in energy transduction in tissues with l...
- Gene Name
- CKM
- Uniprot ID
- P06732
- Uniprot Name
- Creatine kinase M-type
- Molecular Weight
- 43100.91 Da
References
- Zeng L, Hu Q, Wang X, Mansoor A, Lee J, Feygin J, Zhang G, Suntharalingam P, Boozer S, Mhashilkar A, Panetta CJ, Swingen C, Deans R, From AH, Bache RJ, Verfaillie CM, Zhang J: Bioenergetic and functional consequences of bone marrow-derived multipotent progenitor cell transplantation in hearts with postinfarction left ventricular remodeling. Circulation. 2007 Apr 10;115(14):1866-75. Epub 2007 Mar 26. [Article]
- Zhou DQ, Hu Y, Liu G, Gong L, Xi Y, Wen L: Muscle-specific creatine kinase gene polymorphism and running economy responses to an 18-week 5000-m training programme. Br J Sports Med. 2006 Dec;40(12):988-91. Epub 2006 Sep 25. [Article]
- Wallimann T, Wyss M, Brdiczka D, Nicolay K, Eppenberger HM: 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Ligand
- General Function
- Creatine kinase activity
- Specific Function
- Reversibly catalyzes the transfer of phosphate between ATP and various phosphogens (e.g. creatine phosphate). Creatine kinase isoenzymes play a central role in energy transduction in tissues with l...
- Gene Name
- CKMT1A
- Uniprot ID
- P12532
- Uniprot Name
- Creatine kinase U-type, mitochondrial
- Molecular Weight
- 47036.3 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Slenzka K, Appel R, Kappel Th, Rahmann H: Influence of altered gravity on brain cellular energy and plasma membrane metabolism of developing lower aquatic vertebrates. Adv Space Res. 1996;17(6-7):125-8. [Article]
- Wyss M, Schlegel J, James P, Eppenberger HM, Wallimann T: Mitochondrial creatine kinase from chicken brain. Purification, biophysical characterization, and generation of heterodimeric and heterooctameric molecules with subunits of other creatine kinase isoenzymes. J Biol Chem. 1990 Sep 15;265(26):15900-8. [Article]
- Muhlebach SM, Wirz T, Brandle U, Perriard JC: Evolution of the creative kinases. The chicken acidic type mitochondrial creatine kinase gene as the first nonmammalian gene. J Biol Chem. 1996 May 17;271(20):11920-9. [Article]
- Wallimann T, Wyss M, Brdiczka D, Nicolay K, Eppenberger HM: 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Ligand
- General Function
- Ubiquitin protein ligase binding
- Specific Function
- Reversibly catalyzes the transfer of phosphate between ATP and various phosphogens (e.g. creatine phosphate). Creatine kinase isoenzymes play a central role in energy transduction in tissues with l...
- Gene Name
- CKB
- Uniprot ID
- P12277
- Uniprot Name
- Creatine kinase B-type
- Molecular Weight
- 42643.95 Da
References
- Tian XF, Zhang XS, Li YH, Wang ZZ, Zhang F, Wang LM, Yao JH: Proteasome inhibition attenuates lung injury induced by intestinal ischemia reperfusion in rats. Life Sci. 2006 Oct 26;79(22):2069-76. Epub 2006 Jun 23. [Article]
- Debrincat MA, Zhang JG, Willson TA, Silke J, Connolly LM, Simpson RJ, Alexander WS, Nicola NA, Kile BT, Hilton DJ: Ankyrin repeat and suppressors of cytokine signaling box protein asb-9 targets creatine kinase B for degradation. J Biol Chem. 2007 Feb 16;282(7):4728-37. Epub 2006 Dec 5. [Article]
- Burklen TS, Hirschy A, Wallimann T: Brain-type creatine kinase BB-CK interacts with the Golgi Matrix Protein GM130 in early prophase. Mol Cell Biochem. 2007 Mar;297(1-2):53-64. Epub 2006 Oct 12. [Article]
- Wallimann T, Wyss M, Brdiczka D, Nicolay K, Eppenberger HM: 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Ligand
- General Function
- Creatine kinase activity
- Specific Function
- Reversibly catalyzes the transfer of phosphate between ATP and various phosphogens (e.g. creatine phosphate). Creatine kinase isoenzymes play a central role in energy transduction in tissues with l...
- Gene Name
- CKMT2
- Uniprot ID
- P17540
- Uniprot Name
- Creatine kinase S-type, mitochondrial
- Molecular Weight
- 47504.08 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Koufen P, Ruck A, Brdiczka D, Wendt S, Wallimann T, Stark G: Free radical-induced inactivation of creatine kinase: influence on the octameric and dimeric states of the mitochondrial enzyme (Mib-CK). Biochem J. 1999 Dec 1;344 Pt 2:413-7. [Article]
- Wyss M, James P, Schlegel J, Wallimann T: Limited proteolysis of creatine kinase. Implications for three-dimensional structure and for conformational substrates. Biochemistry. 1993 Oct 12;32(40):10727-35. [Article]
- Stachowiak O, Dolder M, Wallimann T, Richter C: Mitochondrial creatine kinase is a prime target of peroxynitrite-induced modification and inactivation. J Biol Chem. 1998 Jul 3;273(27):16694-9. [Article]
- Wallimann T, Wyss M, Brdiczka D, Nicolay K, Eppenberger HM: 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- General Function
- Neurotransmitter:sodium symporter activity
- Specific Function
- Required for the uptake of creatine in muscles and brain.
- Gene Name
- SLC6A8
- Uniprot ID
- P48029
- Uniprot Name
- Sodium- and chloride-dependent creatine transporter 1
- Molecular Weight
- 70522.17 Da
References
- Rosenberg EH, Munoz CM, Degrauw TJ, Jakobs Cn, Salomons GS: Overexpression of wild-type creatine transporter (SLC6A8) restores creatine uptake in primary SLC6A8-deficient fibroblasts. J Inherit Metab Dis. 2006 Apr-Jun;29(2-3):345-6. [Article]
- Derave W, Straumann N, Olek RA, Hespel P: Electrolysis stimulates creatine transport and transporter cell surface expression in incubated mouse skeletal muscle: potential role of ROS. Am J Physiol Endocrinol Metab. 2006 Dec;291(6):E1250-7. Epub 2006 Jul 18. [Article]
- Lunardi G, Parodi A, Perasso L, Pohvozcheva AV, Scarrone S, Adriano E, Florio T, Gandolfo C, Cupello A, Burov SV, Balestrino M: The creatine transporter mediates the uptake of creatine by brain tissue, but not the uptake of two creatine-derived compounds. Neuroscience. 2006 Nov 3;142(4):991-7. Epub 2006 Sep 1. [Article]
- Campistol J, Arias-Dimas A, Poo P, Pineda M, Hoffman M, Vilaseca MA, Artuch R, Ribes A: [Cerebral creatine transporter deficiency: an infradiagnosed neurometabolic disease]. Rev Neurol. 2007 Mar 16-31;44(6):343-7. [Article]
- Wang L, Zhang Y, Shao M, Zhang H: Spatiotemporal expression of the creatine metabolism related genes agat, gamt and ct1 during zebrafish embryogenesis. Int J Dev Biol. 2007;51(3):247-53. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Product of
- General Function
- Methyltransferase activity
- Specific Function
- Not Available
- Gene Name
- GAMT
- Uniprot ID
- Q14353
- Uniprot Name
- Guanidinoacetate N-methyltransferase
- Molecular Weight
- 26317.925 Da
References
- Almeida LS, Vilarinho L, Darmin PS, Rosenberg EH, Martinez-Munoz C, Jakobs C, Salomons GS: A prevalent pathogenic GAMT mutation (c.59G>C) in Portugal. Mol Genet Metab. 2007 May;91(1):1-6. Epub 2007 Mar 1. [Article]
- Kan HE, Meeuwissen E, van Asten JJ, Veltien A, Isbrandt D, Heerschap A: Creatine uptake in brain and skeletal muscle of mice lacking guanidinoacetate methyltransferase assessed by magnetic resonance spectroscopy. J Appl Physiol (1985). 2007 Jun;102(6):2121-7. Epub 2007 Mar 8. [Article]
- Wang L, Zhang Y, Shao M, Zhang H: Spatiotemporal expression of the creatine metabolism related genes agat, gamt and ct1 during zebrafish embryogenesis. Int J Dev Biol. 2007;51(3):247-53. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Symporter activity
- Specific Function
- Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cat...
- Gene Name
- SLC22A5
- Uniprot ID
- O76082
- Uniprot Name
- Solute carrier family 22 member 5
- Molecular Weight
- 62751.08 Da
References
- Ohashi R, Tamai I, Yabuuchi H, Nezu JI, Oku A, Sai Y, Shimane M, Tsuji A: Na(+)-dependent carnitine transport by organic cation transporter (OCTN2): its pharmacological and toxicological relevance. J Pharmacol Exp Ther. 1999 Nov;291(2):778-84. [Article]
Drug created at June 13, 2005 13:24 / Updated at January 02, 2024 23:42