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

Details

Stereochemistry ABSOLUTE
Molecular Formula C6H14N4O2.C5H6O5
Molecular Weight 320.2996
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ARGININE OXOGLURATE

SMILES

C(C[C@@]([H])(C(=O)O)N)CNC(=N)N.C(CC(=O)O)C(=O)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 174.2012
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C5H6O5
Molecular Weight 146.0983
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Curator's Comment:: L-Arginine has the ability to cross the blood brain barrier.

Originator

Curator's Comment:: Arginine was first isolated from a lupin seedling extract in 1886 by the German chemist Ernst Schultze.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q5T6X5
Gene ID: 222545.0
Gene Symbol: GPRC6A
Target Organism: Homo sapiens (Human)
44.1 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
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

9.9705602E10
Diagnostic
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

9.9705602E10
Diagnostic
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

9.9705602E10
Diagnostic
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

9.9705602E10
Preventing
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
310 μM
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
6219 μM
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
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
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
24788 M × min
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
265435 M × min
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
77.5 min
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
41.6 min
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
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
100%
ARGININE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
3.9 g/kg single, intravenous
Accidental dose
Dose: 3.9 g/kg
Route: intravenous
Route: single
Dose: 3.9 g/kg
Sources: Page: p.621
unhealthy, 1.75
n = 1
Health Status: unhealthy
Condition: Short stature
Age Group: 1.75
Sex: F
Population Size: 1
Sources: Page: p.621
Disc. AE: Cardiopulmonary arrest, Metabolic acidosis...
AEs leading to
discontinuation/dose reduction:
Cardiopulmonary arrest
Metabolic acidosis (acute)
Hyponatremia (severe)
Sources: Page: p.621
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: Page: p.63
unhealthy, 24
n = 11
Health Status: unhealthy
Condition: Cystic fibrosis
Age Group: 24
Sex: M+F
Population Size: 11
Sources: Page: p.63
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: Page: p.1
healthy, 34 ± 2.6
n = 12
Health Status: healthy
Condition: Dietary supplementation
Age Group: 34 ± 2.6
Sex: M+F
Population Size: 12
Sources: Page: p.1
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: Page: p.200
unhealthy, 43± 16
n = 10
Health Status: unhealthy
Condition: Hypercholesterolaemia
Age Group: 43± 16
Sex: M+F
Population Size: 10
Sources: Page: p.200
DLT: Gastrointestinal discomfort...
Dose limiting toxicities:
Gastrointestinal discomfort (20%)
Sources: Page: p.200
AEs

AEs

AESignificanceDosePopulation
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: Page: p.621
unhealthy, 1.75
n = 1
Health Status: unhealthy
Condition: Short stature
Age Group: 1.75
Sex: F
Population Size: 1
Sources: Page: p.621
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: Page: p.621
unhealthy, 1.75
n = 1
Health Status: unhealthy
Condition: Short stature
Age Group: 1.75
Sex: F
Population Size: 1
Sources: Page: p.621
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: Page: p.621
unhealthy, 1.75
n = 1
Health Status: unhealthy
Condition: Short stature
Age Group: 1.75
Sex: F
Population Size: 1
Sources: Page: p.621
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: Page: p.200
unhealthy, 43± 16
n = 10
Health Status: unhealthy
Condition: Hypercholesterolaemia
Age Group: 43± 16
Sex: M+F
Population Size: 10
Sources: Page: p.200
PubMed

PubMed

TitleDatePubMed
Two novel mutations (Y141H; C214Y) and previously published mutation (R142W) in the RDS-peripherin gene in autosomal dominant macular dystrophies in Spanish families.
2001
A rare case of complete human erythrocyte AMP deaminase deficiency due to two novel missense mutations in AMPD3.
2001
Novel mutations in the GALK1 gene in patients with galactokinase deficiency.
2001
Optimization of experimental conditions for RNA-based sequencing of MLH1 and MSH2 genes.
2001
Prevalence of mutations causing retinitis pigmentosa and other inherited retinopathies.
2001
Renal response during acute unilateral ureteral obstruction in rats.
2001
The dialytic failure of the peritoneal membrane.
2001
Hemodialysis techniques and advanced glycation end products.
2001
AGE in micro- and macroangiopathy.
2001
Signal-binding specificity of the mu4 subunit of the adaptor protein complex AP-4.
2001 Apr 20
An intrahelical salt bridge within the trigger site stabilizes the GCN4 leucine zipper.
2001 Apr 27
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
Amino acid residues outside of the pore region contribute to N-type calcium channel permeation.
2001 Feb 23
The nutritional management of urea cycle disorders.
2001 Jan
Current strategies for the management of neonatal urea cycle disorders.
2001 Jan
Prevention of diabetes for up to 13 years by autoislet transplantation after pancreatectomy for chronic pancreatitis.
2001 Jan
Biglycan, a vascular proteoglycan, binds differently to HDL2 and HDL3: role of apoE.
2001 Jan
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
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
Effect of AVT antisense oligodeoxynucleotides on AVT release induced by hypertonic stimulation in chicks.
2001 Jan
Impaired renal vascular endothelial function in vitro in experimental hypercholesterolemia.
2001 Jan
How the Pseudomonas aeruginosa ExoS toxin downregulates Rac.
2001 Jan
Regulation of potassium channel Kir 1.1 (ROMK) abundance in the thick ascending limb of Henle's loop.
2001 Jan
Alteration of humoral and peripheral vascular responses during graded exercise in heart failure.
2001 Jan
Agmatine enhances the NADPH oxidase activity of neuronal NO synthase and leads to oxidative inactivation of the enzyme.
2001 Jan
[Ca(2+)](i) signaling in renal arterial smooth muscle cells of pregnant rat is enhanced during inhibition of NOS.
2001 Jan
An extended hydrophobic interactive surface of Yersinia pestis Caf1M chaperone is essential for subunit binding and F1 capsule assembly.
2001 Jan
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
A metabolic fragment of bradykinin, Arg-Pro-Pro-Gly-Phe, protects against the deleterious effects of lipopolysaccharide in rats.
2001 Jan
Altered endothelium-dependent relaxations in lambs with high pulmonary blood flow and pulmonary hypertension.
2001 Jan
Relationship between flow rate and NO production in postnatal mesenteric arteries.
2001 Jan
Altered TNF-alpha, glucose, insulin, and amino acids in islets of Langerhans cultured in a microgravity model system.
2001 Jan
Distinct T cell developmental consequences in humans and mice expressing identical mutations in the DLAARN motif of ZAP-70.
2001 Jan 1
Tec kinase signaling in T cells is regulated by phosphatidylinositol 3-kinase and the Tec pleckstrin homology domain.
2001 Jan 1
Substitution of Asp114 or Arg116 in the fingers domain of moloney murine leukemia virus reverse transcriptase affects interactions with the template-primer resulting in decreased processivity.
2001 Jan 12
Glutamine metabolism to glucosamine is necessary for glutamine inhibition of endothelial nitric oxide synthesis.
2001 Jan 15
Amino acid residues in ribonuclease MC1 from bitter gourd seeds which are essential for uridine specificity.
2001 Jan 16
Structure and organization of bacteriophage Pf3 probed by Raman and ultraviolet resonance Raman spectroscopy.
2001 Jan 16
Insights into the molecular basis for the carbenicillinase activity of PSE-4 beta-lactamase from crystallographic and kinetic studies.
2001 Jan 16
Strain is more important than electrostatic interaction in controlling the pKa of the catalytic group in aspartate aminotransferase.
2001 Jan 16
Upregulation of the nitric oxide-cGMP pathway in aged myocardium: physiological response to l-arginine.
2001 Jan 19
Exercise training in coronary artery disease and coronary vasomotion.
2001 Jan 2
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
Pharmacological profile of T-1032, a novel specific phosphodiesterase type 5 inhibitor, in isolated rat aorta and rabbit corpus cavernosum.
2001 Jan 5
The role of nitric oxide in bradycardia of rats with obstructive cholestasis.
2001 Jan 5
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
Acetaldehyde, a metabolite of ethanol, activates the hypothalamic-pituitary-adrenal axis in the rat.
2001 Jan-Feb
Effect of oxygen on induction of the cystine transporter by bacterial lipopolysaccharide in mouse peritoneal macrophages.
2001 Mar 30
Scanning mutagenesis reveals roles for helix n of the bacteriophage T7 RNA polymerase thumb subdomain in transcription complex stability, pausing, and termination.
2001 Mar 30
Rare somatic p53 mutation identified in breast cancer: a case report.
2001 Mar-Apr
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: I.V route is possible: The recommended adult dose is 30 g arginine hydrochloride (300 mL of R-Gene 10) administered by intravenous infusion over 30 minutes. The total dose should not exceed 30 g arginine hydrochloride. https://www.drugs.com/dosage/r-gene-10.html
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
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 Sat Jun 26 05:56:30 UTC 2021
Edited
by admin
on Sat Jun 26 05:56:30 UTC 2021
Record UNII
TVJ23A89RU
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ARGININE OXOGLURATE
MART.   WHO-DD  
Common 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
L-ARGININE 2-OXOPENTANEDIOATE
Common Name English
L-ARGININE 2-OXOGLUTARATE
Common Name English
ARGININE OXOGLURATE [MART.]
Common Name English
ARGININE OXOGLURATE [WHO-DD]
Common Name English
PENTANEDIOIC ACID, 2-OXO-, COMPD. WITH L-ARGININE (1:1)
Systematic Name English
ARGICETO-50
Brand Name English
Classification Tree Code System Code
DSLD 2391 (Number of products:239)
Created by admin on Sat Jun 26 05:56:31 UTC 2021 , Edited by admin on Sat Jun 26 05:56:31 UTC 2021
DSLD 2618 (Number of products:151)
Created by admin on Sat Jun 26 05:56:31 UTC 2021 , Edited by admin on Sat Jun 26 05:56:31 UTC 2021
Code System Code Type Description
FDA UNII
TVJ23A89RU
Created by admin on Sat Jun 26 05:56:31 UTC 2021 , Edited by admin on Sat Jun 26 05:56:31 UTC 2021
PRIMARY
CAS
556834-44-7
Created by admin on Sat Jun 26 05:56:31 UTC 2021 , Edited by admin on Sat Jun 26 05:56:31 UTC 2021
NON-SPECIFIC STOICHIOMETRY
CAS
499790-40-8
Created by admin on Sat Jun 26 05:56:31 UTC 2021 , Edited by admin on Sat Jun 26 05:56:31 UTC 2021
NON-SPECIFIC STEREOCHEMISTRY
CAS
533909-24-9
Created by admin on Sat Jun 26 05:56:31 UTC 2021 , Edited by admin on Sat Jun 26 05:56:31 UTC 2021
NON-SPECIFIC STOICHIOMETRY
PUBCHEM
11427178
Created by admin on Sat Jun 26 05:56:31 UTC 2021 , Edited by admin on Sat Jun 26 05:56:31 UTC 2021
PRIMARY
EVMPD
SUB00581MIG
Created by admin on Sat Jun 26 05:56:31 UTC 2021 , Edited by admin on Sat Jun 26 05:56:31 UTC 2021
PRIMARY
ECHA (EC/EINECS)
240-882-6
Created by admin on Sat Jun 26 05:56:31 UTC 2021 , Edited by admin on Sat Jun 26 05:56:31 UTC 2021
PRIMARY
CAS
16856-18-1
Created by admin on Sat Jun 26 05:56:31 UTC 2021 , Edited by admin on Sat Jun 26 05:56:31 UTC 2021
PRIMARY
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ACTIVE MOIETY