ARGININE OXOGLURATE

First approved in 1957

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C6H14N4O2.C5H6O5
Molecular Weight	320.2991
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)CCC(=O)C(O)=O.N[C@@H](CCCNC(N)=N)C(O)=O

InChI

InChIKey=PGRNZHOQVAPMFX-WCCKRBBISA-N

InChI=1S/C6H14N4O2.C5H6O5/c7-4(5(11)12)2-1-3-10-6(8)9;6-3(5(9)10)1-2-4(7)8/h4H,1-3,7H2,(H,11,12)(H4,8,9,10);1-2H2,(H,7,8)(H,9,10)/t4-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	C6H14N4O2
Molecular Weight	174.201
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	C5H6O5
Molecular Weight	146.0981
Charge	0
Count

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

Description
Sources: https://www.drugs.com/npp/l-arginine.html | http://www.webmd.com/diet/supplement-guide-l-arginine#1

L-arginine is a nonessential amino acid that may play an important role in the treatment of cardiovascular disease due to its antiatherogenic, anti-ischemic, antiplatelet, and antithrombotic properties. It has been promoted as a growth stimulant and as a treatment for erectile dysfunction in men. L-arginine is a nonessential amino acid that may play an important role in the treatment of heart disease due to its block arterial plaque buildup, blood clots, platelet clumping, and to increase blood flow through the coronary artery. L-arginine is commonly sold as a health supplement claiming to improve vascular health and treat erectile dysfunction in men. L-arginine, which is promoted as a human growth stimulant, has also been used in bodybuilding. In the 1800s, it was first isolated from animal horn.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
G-protein coupled receptor family C group 6 member A 22 Target ID: Q5T6X5 Gene ID: 222545.0 Gene Symbol: GPRC6A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15576628	Agonist 2752		44.1 µM [EC50]

Conditions

Condition	Modality	Highest Phase	Product
Panhypopituitarism 13 Sources: http://labeling.pfizer.com/ShowLabeling.aspx?id=642	Diagnostic	Approved 8583	R-GENE 10 Approved Use R-Gene 10 is indicated as an intravenous stimulant to the pituitary for the release of human growth hormone in patients where the measurement of pituitary reserve for HGH can be of diagnostic usefulness. It can be used as a diagnostic aid in such conditions as panhypopituitarism, pituitary dwarfism, chromophobe adenoma, postsurgical craniopharyngioma, hypophysectomy, pituitary trauma, acromegaly, gigantism and problems of growth and stature. If the insulin hypoglycemia test has indicated a deficiency of pituitary reserve for HGH, a test with R-Gene 10 is advisable to confirm the negative response. This can be done after a waiting period of one day. As patients may not respond to R-Gene 10 (Arginine Hydrochloride Injection, USP) during the first test, the unresponsive patient should be tested again to confirm the negative result. A second test can be performed after a waiting period of one day. Some patients who respond to R-Gene 10 do not respond to insulin and vice versa. The rate of false positive responses for R-Gene 10 is approximately 32%, and the rate of false negatives is approximately 27%. Launch Date 1973
Pituitary dwarfism 13 Sources: http://labeling.pfizer.com/ShowLabeling.aspx?id=642	Diagnostic	Approved 8583	R-GENE 10 Approved Use R-Gene 10 is indicated as an intravenous stimulant to the pituitary for the release of human growth hormone in patients where the measurement of pituitary reserve for HGH can be of diagnostic usefulness. It can be used as a diagnostic aid in such conditions as panhypopituitarism, pituitary dwarfism, chromophobe adenoma, postsurgical craniopharyngioma, hypophysectomy, pituitary trauma, acromegaly, gigantism and problems of growth and stature. If the insulin hypoglycemia test has indicated a deficiency of pituitary reserve for HGH, a test with R-Gene 10 is advisable to confirm the negative response. This can be done after a waiting period of one day. As patients may not respond to R-Gene 10 (Arginine Hydrochloride Injection, USP) during the first test, the unresponsive patient should be tested again to confirm the negative result. A second test can be performed after a waiting period of one day. Some patients who respond to R-Gene 10 do not respond to insulin and vice versa. The rate of false positive responses for R-Gene 10 is approximately 32%, and the rate of false negatives is approximately 27%. Launch Date 1973
Acromegaly 21 Sources: http://labeling.pfizer.com/ShowLabeling.aspx?id=642	Diagnostic	Approved 8583	R-GENE 10 Approved Use R-Gene 10 is indicated as an intravenous stimulant to the pituitary for the release of human growth hormone in patients where the measurement of pituitary reserve for HGH can be of diagnostic usefulness. It can be used as a diagnostic aid in such conditions as panhypopituitarism, pituitary dwarfism, chromophobe adenoma, postsurgical craniopharyngioma, hypophysectomy, pituitary trauma, acromegaly, gigantism and problems of growth and stature. If the insulin hypoglycemia test has indicated a deficiency of pituitary reserve for HGH, a test with R-Gene 10 is advisable to confirm the negative response. This can be done after a waiting period of one day. As patients may not respond to R-Gene 10 (Arginine Hydrochloride Injection, USP) during the first test, the unresponsive patient should be tested again to confirm the negative result. A second test can be performed after a waiting period of one day. Some patients who respond to R-Gene 10 do not respond to insulin and vice versa. The rate of false positive responses for R-Gene 10 is approximately 32%, and the rate of false negatives is approximately 27%. Launch Date 1973
Gigantism 13 Sources: https://www.drugs.com/dosage/r-gene-10.html http://labeling.pfizer.com/ShowLabeling.aspx?id=642	Diagnostic	Approved 8583	R-GENE 10 Approved Use R-Gene 10 is indicated as an intravenous stimulant to the pituitary for the release of human growth hormone in patients where the measurement of pituitary reserve for HGH can be of diagnostic usefulness. It can be used as a diagnostic aid in such conditions as panhypopituitarism, pituitary dwarfism, chromophobe adenoma, postsurgical craniopharyngioma, hypophysectomy, pituitary trauma, acromegaly, gigantism and problems of growth and stature. If the insulin hypoglycemia test has indicated a deficiency of pituitary reserve for HGH, a test with R-Gene 10 is advisable to confirm the negative response. This can be done after a waiting period of one day. As patients may not respond to R-Gene 10 (Arginine Hydrochloride Injection, USP) during the first test, the unresponsive patient should be tested again to confirm the negative result. A second test can be performed after a waiting period of one day. Some patients who respond to R-Gene 10 do not respond to insulin and vice versa. The rate of false positive responses for R-Gene 10 is approximately 32%, and the rate of false negatives is approximately 27%. Launch Date 1973
Type 2 diabetes mellitus 262 Sources: https://clinicaltrials.gov/ct2/show/NCT00917449	Preventing	Phase III 665	Unknown Approved Use Unknown
Preeclampsia 85 Sources: https://clinicaltrials.gov/ct2/show/NCT02363348	Preventing	Phase III 665	Unknown Approved Use Unknown
Hypertension 575 Sources: https://clinicaltrials.gov/ct2/show/NCT02894723	Primary	Phase III 665	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
6219 μM EXPERIMENT https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1873701/	30 g single, intravenous dose: 30 g route of administration: Intravenous experiment type: SINGLE co-administered:	ARGININE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
882 μM EXPERIMENT https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1873701/	6 g single, intravenous dose: 6 g route of administration: Intravenous experiment type: SINGLE co-administered:	ARGININE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
310 μM EXPERIMENT https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1873701/	6 g single, oral dose: 6 g route of administration: Oral experiment type: SINGLE co-administered:	ARGININE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

AUC

Value	Dose	Analyte	Population
265435 M × min EXPERIMENT https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1873701/	30 g single, intravenous dose: 30 g route of administration: Intravenous experiment type: SINGLE co-administered:	ARGININE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
38223 M × min EXPERIMENT https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1873701/	6 g single, intravenous dose: 6 g route of administration: Intravenous experiment type: SINGLE co-administered:	ARGININE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
24788 M × min EXPERIMENT https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1873701/	6 g single, oral dose: 6 g route of administration: Oral experiment type: SINGLE co-administered:	ARGININE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

T_1/2

Value	Dose	Analyte	Population
41.6 min EXPERIMENT https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1873701/	30 g single, intravenous dose: 30 g route of administration: Intravenous experiment type: SINGLE co-administered:	ARGININE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
59.6 min EXPERIMENT https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1873701/	6 g single, intravenous dose: 6 g route of administration: Intravenous experiment type: SINGLE co-administered:	ARGININE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
77.5 min EXPERIMENT https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1873701/	6 g single, oral dose: 6 g route of administration: Oral experiment type: SINGLE co-administered:	ARGININE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

F_unbound

Value	Dose	Co-administered	Analyte	Population
100% EXPERIMENT https://www.jci.org/articles/view/103568			ARGININE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
3.9 g/kg single, intravenous Accidental dose Dose: 3.9 g/kg Route: intravenous Route: single Dose: 3.9 g/kg Sources: https://pubmed.ncbi.nlm.nih.gov/9365430/	unhealthy, 1.75 Health Status: unhealthy Age Group: 1.75 Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/9365430/	Disc. AE: Cardiopulmonary arrest, Metabolic acidosis... AEs leading to discontinuation/dose reduction: Cardiopulmonary arrest Metabolic acidosis (acute) Hyponatremia (severe) Sources: https://pubmed.ncbi.nlm.nih.gov/9365430/
200 mg/kg 3 times / day multiple, oral Highest studied dose Dose: 200 mg/kg, 3 times / day Route: oral Route: multiple Dose: 200 mg/kg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15640324	unhealthy, 24 Health Status: unhealthy Age Group: 24 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/15640324	Sources: https://pubmed.ncbi.nlm.nih.gov/15640324
15 g 2 times / day multiple, oral Studied dose Dose: 15 g, 2 times / day Route: oral Route: multiple Dose: 15 g, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/29858688	healthy, 34 ± 2.6 Health Status: healthy Age Group: 34 ± 2.6 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/29858688	Sources: https://pubmed.ncbi.nlm.nih.gov/29858688
7 g 3 times / day multiple, oral Studied dose Dose: 7 g, 3 times / day Route: oral Route: multiple Dose: 7 g, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9918901	unhealthy, 43± 16 Health Status: unhealthy Age Group: 43± 16 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/9918901	DLT: Gastrointestinal discomfort... Dose limiting toxicities: Gastrointestinal discomfort (20%) Sources: https://pubmed.ncbi.nlm.nih.gov/9918901

AEs

AE	Significance	Dose	Population
Cardiopulmonary arrest	Disc. AE	3.9 g/kg single, intravenous Accidental dose Dose: 3.9 g/kg Route: intravenous Route: single Dose: 3.9 g/kg Sources: https://pubmed.ncbi.nlm.nih.gov/9365430/	unhealthy, 1.75 Health Status: unhealthy Age Group: 1.75 Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/9365430/
Metabolic acidosis	acute Disc. AE	3.9 g/kg single, intravenous Accidental dose Dose: 3.9 g/kg Route: intravenous Route: single Dose: 3.9 g/kg Sources: https://pubmed.ncbi.nlm.nih.gov/9365430/	unhealthy, 1.75 Health Status: unhealthy Age Group: 1.75 Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/9365430/
Hyponatremia	severe Disc. AE	3.9 g/kg single, intravenous Accidental dose Dose: 3.9 g/kg Route: intravenous Route: single Dose: 3.9 g/kg Sources: https://pubmed.ncbi.nlm.nih.gov/9365430/	unhealthy, 1.75 Health Status: unhealthy Age Group: 1.75 Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/9365430/
Gastrointestinal discomfort	20% DLT	7 g 3 times / day multiple, oral Studied dose Dose: 7 g, 3 times / day Route: oral Route: multiple Dose: 7 g, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9918901	unhealthy, 43± 16 Health Status: unhealthy Age Group: 43± 16 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/9918901

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:29016	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:29016
ChemicalBook	CB0693158	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0693158
eMolecules	10311512	https://www.emolecules.com/cgi-bin/more?vid=10311512
eMolecules	478568	https://www.emolecules.com/cgi-bin/more?vid=478568
MolPort	MolPort-001-779-889	https://www.molport.com/shop/molecule-link/MolPort-001-779-889
MolPort	MolPort-006-118-537	https://www.molport.com/shop/molecule-link/MolPort-006-118-537

PubMed

Title	Date	PubMed
Postabsorptive plasma citrulline concentration is a marker of absorptive enterocyte mass and intestinal failure in humans.	2000 Dec	11113071
Two novel mutations (Y141H; C214Y) and previously published mutation (R142W) in the RDS-peripherin gene in autosomal dominant macular dystrophies in Spanish families.	2001	11139263
A rare case of complete human erythrocyte AMP deaminase deficiency due to two novel missense mutations in AMPD3.	2001	11139257
Novel mutations in the GALK1 gene in patients with galactokinase deficiency.	2001	11139256
Optimization of experimental conditions for RNA-based sequencing of MLH1 and MSH2 genes.	2001	11139242
Renal response during acute unilateral ureteral obstruction in rats.	2001	11135389
The dialytic failure of the peritoneal membrane.	2001	11125567
Hemodialysis techniques and advanced glycation end products.	2001	11125561
AGE in micro- and macroangiopathy.	2001	11125555
Signal-binding specificity of the mu4 subunit of the adaptor protein complex AP-4.	2001 Apr 20	11139587
Fructose-6-phosphate aldolase is a novel class I aldolase from Escherichia coli and is related to a novel group of bacterial transaldolases.	2001 Apr 6	11120740
Dose response of arginine vasopressin to the CCK-B agonist pentagastrin.	2001 Feb	11120398
Increased affinity of c-Myb for CREB-binding protein (CBP) after CBP-induced acetylation.	2001 Feb 2	11073948
Amino acid residues outside of the pore region contribute to N-type calcium channel permeation.	2001 Feb 23	11120735
Human glutathione transferase T2-2 discloses some evolutionary strategies for optimization of substrate binding to the active site of glutathione transferases.	2001 Feb 23	11044442
The nutritional management of urea cycle disorders.	2001 Jan	11148548
Current strategies for the management of neonatal urea cycle disorders.	2001 Jan	11148547
Biglycan, a vascular proteoglycan, binds differently to HDL2 and HDL3: role of apoE.	2001 Jan	11145944
Fibroblast growth factor-2 stimulates endothelial nitric oxide synthase expression and inhibits apoptosis by a nitric oxide-dependent pathway in Nb2 lymphoma cells.	2001 Jan	11145569
Differential effects of glucagon-like peptide-1 (7-36)amide versus cholecystokinin on arginine-induced islet hormone release in vivo and in vitro.	2001 Jan	11138972
How the Pseudomonas aeruginosa ExoS toxin downregulates Rac.	2001 Jan	11135665
Alteration of humoral and peripheral vascular responses during graded exercise in heart failure.	2001 Jan	11133893
Agmatine enhances the NADPH oxidase activity of neuronal NO synthase and leads to oxidative inactivation of the enzyme.	2001 Jan	11125020
Increased colocalization of corticotropin-releasing factor and arginine vasopressin in paraventricular neurones of the hypothalamus in lactating rats: evidence from immunotargeted lesions and immunohistochemistry.	2001 Jan	11123517
A metabolic fragment of bradykinin, Arg-Pro-Pro-Gly-Phe, protects against the deleterious effects of lipopolysaccharide in rats.	2001 Jan	11123364
Altered endothelium-dependent relaxations in lambs with high pulmonary blood flow and pulmonary hypertension.	2001 Jan	11123246
Relationship between flow rate and NO production in postnatal mesenteric arteries.	2001 Jan	11123196
Altered TNF-alpha, glucose, insulin, and amino acids in islets of Langerhans cultured in a microgravity model system.	2001 Jan	11120663
The common Arg972 polymorphism in insulin receptor substrate-1 causes apoptosis of human pancreatic islets.	2001 Jan	11099486
Lower serum activity of prolyl endopeptidase in anorexia and bulimia nervosa.	2001 Jan	11070331
Glutamine metabolism to glucosamine is necessary for glutamine inhibition of endothelial nitric oxide synthesis.	2001 Jan 15	11139387
Amino acid residues in ribonuclease MC1 from bitter gourd seeds which are essential for uridine specificity.	2001 Jan 16	11148047
Structure and organization of bacteriophage Pf3 probed by Raman and ultraviolet resonance Raman spectroscopy.	2001 Jan 16	11148039
Upregulation of the nitric oxide-cGMP pathway in aged myocardium: physiological response to l-arginine.	2001 Jan 19	11139480
Strengthened arm-dimerization domain interactions in AraC.	2001 Jan 26	11069917
Site-specific single amino acid changes to Lys or Arg in the central region of the movement protein of a hybrid bromovirus are required for adaptation to a nonhost.	2001 Jan 5	11145888
Membrane binding motif of the P-type cardiotoxin.	2001 Jan 5	11114253
Crystal structure and novel recognition motif of rho ADP-ribosylating C3 exoenzyme from Clostridium botulinum: structural insights for recognition specificity and catalysis.	2001 Jan 5	11114250
C60-Fullerene monomalonate adducts selectively inactivate neuronal nitric oxide synthase by uncoupling the formation of reactive oxygen intermediates from nitric oxide production.	2001 Jan 9	11141054
Acetaldehyde, a metabolite of ethanol, activates the hypothalamic-pituitary-adrenal axis in the rat.	2001 Jan-Feb	11139417
Translocation of jellyfish green fluorescent protein via the Tat system of Escherichia coli and change of its periplasmic localization in response to osmotic up-shock.	2001 Mar 16	11099493
Identification and analysis of the acyl carrier protein (ACP) docking site on beta-ketoacyl-ACP synthase III.	2001 Mar 16	11078736
Phage display-selected sequences of the heavy-chain CDR3 loop of the anti-digoxin antibody 26-10 define a high affinity binding site for position 16-substituted analogs of digoxin.	2001 Mar 16	11060305
Eukaryotic translation initiation factor 5 functions as a GTPase-activating protein.	2001 Mar 2	11092890
Substrate-binding clusters of the K+-transporting Kdp ATPase of Escherichia coli investigated by amber suppression scanning mutagenesis.	2001 Mar 30	11106663
Peptide leucine arginine, a potent immunomodulatory peptide isolated and structurally characterized from the skin of the Northern Leopard frog, Rana pipiens.	2001 Mar 30	11099505
Identification of the collagen-binding site of the von Willebrand factor A3-domain.	2001 Mar 30	11098050
The modulation of oxygen radical production by nitric oxide in mitochondria.	2001 Mar 9	11106647
The fission yeast TOR homolog, tor1+, is required for the response to starvation and other stresses via a conserved serine.	2001 Mar 9	11096119
Sequence requirements for the N-methyl-D-aspartate receptor antagonist activity of conantokin-R.	2001 Mar 9	11096077

Patents

Sample Use Guides

In Vivo Use Guide

L-arginine has been studied at oral doses of 6 to 30 g/day for a variety of conditions. Many formulations have been used.

Route of Administration: Oral

In Vitro Use Guide

A strong inward current in X. laevis oocytes expressing 5.24 (C terminus of the homologous goldfish 5.24 receptor) when L-Arg (L-arginine) was applied at 10 uM. When testing chimera h6A/5.24 (h6A/5.24, containing the ligand binding amino-terminal domain (ATD) of hGPRC6A with the signal transducing transmembrane and C terminus of the homologous goldfish 5.24 receptor) in this system, the responses were obtained with L-Arg at 100 uM.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:42:53 GMT 2025` Edited by `admin` on `Mon Mar 31 18:42:53 GMT 2025`
Record UNII	TVJ23A89RU
Record Status	`Validated (UNII)`
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Name

Type

Language

ARGININE OXOGLURATE

Common Name

English

ARGICETO-50

Preferred Name

English

L-ARGININE, 2-OXOPENTANEDIOATE (1:1)

Systematic Name

English

ARGININE, 2-OXOGLUTARATE (1:1), L-

Systematic Name

English

GLUTARIC ACID, 2-OXO-, COMPD. WITH L-ARGININE (1:1)

Systematic Name

English

ARGININE ALPHA-KETOGLUTARATE

Common Name

English

Arginine oxoglurate [WHO-DD]

Common Name

English

L-ARGININE 2-OXOPENTANEDIOATE

Common Name

English

L-ARGININE 2-OXOGLUTARATE

Common Name

English

ARGININE OXOGLURATE [MART.]

Common Name

English

PENTANEDIOIC ACID, 2-OXO-, COMPD. WITH L-ARGININE (1:1)

Systematic Name

English

Classification Tree Code System Code

DSLD

2391 (Number of products:239)