Ompenaclid

Details

Stereochemistry	ACHIRAL
Molecular Formula	C4H9N3O2
Molecular Weight	131.1332
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC(=N)NCCC(O)=O

InChI

InChIKey=KMXXSJLYVJEBHI-UHFFFAOYSA-N

InChI=1S/C4H9N3O2/c5-4(6)7-2-1-3(8)9/h1-2H2,(H,8,9)(H4,5,6,7)

HIDE SMILES / InChI

Molecular Formula	C4H9N3O2
Molecular Weight	131.1332
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Mitochondrial intermembrane inclusion bodies: the common denominator between human mitochondrial myopathies and creatine depletion, due to impairment of cellular energetics.	1997 Sep	9309701
Effect of creatine manipulation on fast-twitch skeletal muscle of the mouse.	2002 Dec	12390299
AMP kinase is required for mitochondrial biogenesis in skeletal muscle in response to chronic energy deprivation.	2002 Dec 10	12444247
The blood-brain barrier creatine transporter is a major pathway for supplying creatine to the brain.	2002 Nov	12439290
Human, rat and chicken small intestinal Na+ - Cl- -creatine transporter: functional, molecular characterization and localization.	2002 Nov 15	12433955
Effects of creatine loading and depletion on rat skeletal muscle contraction.	2002 Oct	12207567
Metabolic modulation of muscle fiber properties unrelated to mechanical stimuli.	2003 Dec	15038837
A role for guanidino compounds in the brain.	2003 Feb	12701810
Creatine transporter activity and content in the rat heart supplemented by and depleted of creatine.	2003 Feb	12531746
Anti-inflammatory activity of creatine supplementation in endothelial cells in vitro.	2003 Jun	12812994
Muscle creatine uptake and creatine transporter expression in response to creatine supplementation and depletion.	2003 Jun	12611762
Inhibition of the mitochondrial permeability transition by creatine kinase substrates. Requirement for microcompartmentation.	2003 May 16	12621025
The aminoguanidine carboxylate BVT.12777 activates ATP-sensitive K+ channels in the rat insulinoma cell line, CRI-G1.	2004 Aug 24	15329154
Stimulation of HSP72 expression following ATP depletion and short-term exercise training in fast-twitch muscle.	2004 Jan	14706115
Taurine-induced long-lasting potentiation in the rat hippocampus shows a partial dissociation from total hippocampal taurine content and independence from activation of known taurine transporters.	2004 Jun	15147512
Functional characterization of sodium- and chloride-dependent taurine transport in human keratinocytes.	2004 Mar	15018993
Effect of muscle creatine content manipulation on contractile properties in mouse muscles.	2004 Mar	14981743
Plasma protein aspartyl damage is increased in hemodialysis patients: studies on causes and consequences.	2004 Oct	15466280
Activation of hypothalamic ATP-sensitive K+ channels by the aminoguanidine carboxylate BVT.12777.	2005 Apr	15842236
Pseudomonas aeruginosa PAO1 genes for 3-guanidinopropionate and 4-guanidinobutyrate utilization may be derived from a common ancestor.	2005 Dec	16339950
Possible involvement of glutamic and/or aspartic acid residue(s) and requirement of mitochondrial integrity for the protective effect of creatine against inhibition of cardiac mitochondrial respiration by methylglyoxal.	2005 Mar	15881668
Novel parent structures for inhibitors of the murine GABA transporters mGAT3 and mGAT4.	2005 Sep 5	16111674
Increased guanidino species in murine and human succinate semialdehyde dehydrogenase (SSADH) deficiency.	2006 Apr	16504488
Overexpression of wild-type creatine transporter (SLC6A8) restores creatine uptake in primary SLC6A8-deficient fibroblasts.	2006 Apr-Jun	16763899
Electrolysis stimulates creatine transport and transporter cell surface expression in incubated mouse skeletal muscle: potential role of ROS.	2006 Dec	16849631
Possible role of creatine concentrations in the brain in regulating appetite and weight.	2006 Jul 26	16781683
Increased resistance to fatigue in creatine kinase deficient muscle is not due to improved contractile economy.	2006 Jun	16491397
The creatine transporter mediates the uptake of creatine by brain tissue, but not the uptake of two creatine-derived compounds.	2006 Nov 3	16949212
Anisoin: a useful pre-chromatographic derivatization fluorogenic reagent for LC analysis of guanidino compounds.	2006 Sep 11	16460903
In vivo effects of myocardial creatine depletion on left ventricular function, morphology, and energy metabolism--consequences in acute myocardial infarction.	2007 Apr	17448422
Aging-associated reductions in AMP-activated protein kinase activity and mitochondrial biogenesis.	2007 Feb	17276357
BVT.3531 reduces body weight and activates K(ATP) channels in isolated arcuate neurons in rats.	2007 Jun 7	17346811
Ontogeny up-regulates renal Na(+)/Cl(-)/creatine transporter in rat.	2007 Nov	17916324
Arginine and glycine stimulate creatine synthesis in creatine transporter 1-deficient lymphoblasts.	2008 Apr 1	18258176
Cardiac structure and function during ageing in energetically compromised Guanidinoacetate N-methyltransferase (GAMT)-knockout mice - a one year longitudinal MRI study.	2008 Feb 6	18275592
[Effects of creatine phosphokinase competitive inhibitor on system and tissue energy metabolism in rats in the norm and during unloading].	2008 Jul-Aug	19140471
Accumulation of methylguanidine and changes in guanidino compound levels in plasma, urine, and kidneys of furosemide-treated rats.	2008 Jun	18502263
In vivo effects of myocardial creatine depletion on left ventricular function morphology and lipid metabolism: study in a mouse model.	2008 Mar	18325464
LKB1 and AMPK and the regulation of skeletal muscle metabolism.	2008 May	18403917
Metabolic transformation of rabbit skeletal muscle cells in primary culture in response to low glucose.	2008 May	18211829
Decreasing intramuscular phosphagen content simultaneously increases plasma membrane FAT/CD36 and GLUT4 transporter abundance.	2008 Sep	18650314
Impaired PGC-1alpha function in muscle in Huntington's disease.	2009 Aug 15	19460884
Muscle-specific differences in the response of mitochondrial proteins to beta-GPA feeding: an evaluation of potential mechanisms.	2009 Jun	19318515
The orally active antihyperglycemic drug beta-guanidinopropionic acid is transported by the human proton-coupled amino acid transporter hPAT1.	2009 May-Jun	19358571
Guanidino acids act as rho1 GABA(C) receptor antagonists.	2009 Oct	19387831
Impairment of PGC-1alpha expression, neuropathology and hepatic steatosis in a transgenic mouse model of Huntington's disease following chronic energy deprivation.	2010 Aug 15	20529956
Na(+)/Cl(-)/creatine transporter activity and expression in rat brain synaptosomes.	2010 Jan 13	19804817
Amino acid derivatives from Lucilia sericata excretions/secretions may contribute to the beneficial effects of maggot therapy via increased angiogenesis.	2010 Mar	19799603
Effects of creatine and β-guanidinopropionic acid and alterations in creatine transporter and creatine kinases expression in acute seizure and chronic epilepsy models.	2010 Oct 28	20979657
Could early ischemic arrhythmia triggered by purinergic activation of the transient receptor potential channels be prevented by creatine?	2010 Winter	21264067

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:31:25 GMT 2023` Edited by `admin` on `Fri Dec 15 15:31:25 GMT 2023`
Record UNII	UL1984YRKA
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Ompenaclid

Official Name

English

3-Guanidinopropanoic acid

Systematic Name

English

ORISTAR GPA

Brand Name

English

AMIDINO BETA-ALANINE [INCI]

Common Name

English

RGX 202 [WHO-DD]

Common Name

English

OMPENACLID [USAN]

Common Name

English

PNU-10483

Code

English

3-(carbamimidoylamino)propanoic acid

Systematic Name

English

AMIDINO .BETA.-ALANINE

Systematic Name

English

GUANIDINOPROPIONIC ACID

Systematic Name

English

N-carbamimidoyl-β-alanine

Common Name

English

β-Alanine, N-(aminoiminomethyl)-

Systematic Name

English

RGX-202

Code

English

RGX202

Code

English

ompenaclid [INN]

Common Name

English

Classification Tree Code System Code

DSLD

1758 (Number of products:1)