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Details

Stereochemistry ABSOLUTE
Molecular Formula 2C6H14N4O2.C5H6O5
Molecular Weight 494.5001
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIARGININE OXOGLURATE

SMILES

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

InChI

InChIKey=NCRWNFFIHNRODM-SCGRZTRASA-N
InChI=1S/2C6H14N4O2.C5H6O5/c2*7-4(5(11)12)2-1-3-10-6(8)9;6-3(5(9)10)1-2-4(7)8/h2*4H,1-3,7H2,(H,11,12)(H4,8,9,10);1-2H2,(H,7,8)(H,9,10)/t2*4-;/m00./s1

HIDE SMILES / InChI

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

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

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

1973
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

1973
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

1973
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

1973
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
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
Purification and characterization of calobin II, a second type of thrombin-like enzyme from Agkistrodon caliginosus (Korean viper).
2001 Apr
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
Dose response of arginine vasopressin to the CCK-B agonist pentagastrin.
2001 Feb
Abnormalities in response to vasopressin infusion in chronic fatigue syndrome.
2001 Feb
Characterization of homo- and heterodimerization of cardiac Csx/Nkx2.5 homeoprotein.
2001 Feb 16
Ligand-independent dimerization and activation of the oncogenic Xmrk receptor by two mutations in the extracellular domain.
2001 Feb 2
DNA recognition by the methyl-CpG binding domain of MeCP2.
2001 Feb 2
The nutritional management of urea cycle disorders.
2001 Jan
Current strategies for the management of neonatal urea cycle disorders.
2001 Jan
Biglycan, a vascular proteoglycan, binds differently to HDL2 and HDL3: role of apoE.
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
[Ca(2+)](i) signaling in renal arterial smooth muscle cells of pregnant rat is enhanced during inhibition of NOS.
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
Altered TNF-alpha, glucose, insulin, and amino acids in islets of Langerhans cultured in a microgravity model system.
2001 Jan
The common Arg972 polymorphism in insulin receptor substrate-1 causes apoptosis of human pancreatic islets.
2001 Jan
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
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
A proposed common structure of substrates bound to mitochondrial processing peptidase.
2001 Jan 19
Exercise training in coronary artery disease and coronary vasomotion.
2001 Jan 2
Mutations that affect ligand binding to the Escherichia coli aspartate receptor: implications for transmembrane signaling.
2001 Jan 26
Pharmacological profile of T-1032, a novel specific phosphodiesterase type 5 inhibitor, in isolated rat aorta and rabbit corpus cavernosum.
2001 Jan 5
Membrane binding motif of the P-type cardiotoxin.
2001 Jan 5
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
The function of Arg-94 in the oxidation and decarboxylation of glutaryl-CoA by human glutaryl-CoA dehydrogenase.
2001 Jan 5
L-ascorbic acid potentiates endothelial nitric oxide synthesis via a chemical stabilization of tetrahydrobiopterin.
2001 Jan 5
Acetaldehyde, a metabolite of ethanol, activates the hypothalamic-pituitary-adrenal axis in the rat.
2001 Jan-Feb
Identification and analysis of the acyl carrier protein (ACP) docking site on beta-ketoacyl-ACP synthase III.
2001 Mar 16
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
A single histidine residue determines the pH sensitivity of the pacemaker channel HCN2.
2001 Mar 2
The molecular mechanism for the genetic disorder familial defective apolipoprotein B100.
2001 Mar 23
Effect of oxygen on induction of the cystine transporter by bacterial lipopolysaccharide in mouse peritoneal macrophages.
2001 Mar 30
Peptide leucine arginine, a potent immunomodulatory peptide isolated and structurally characterized from the skin of the Northern Leopard frog, Rana pipiens.
2001 Mar 30
The modulation of oxygen radical production by nitric oxide in mitochondria.
2001 Mar 9
The basis of prostaglandin synthesis in coral: molecular cloning and expression of a cyclooxygenase from the Arctic soft coral Gersemia fruticosa.
2001 Mar 9
Crystal structure of the ligand-binding domain of the ultraspiracle protein USP, the ortholog of retinoid X receptors in insects.
2001 Mar 9
Increased production of human proinsulin in the periplasmic space of Escherichia coli by fusion to DsbA.
2001 Nov 30
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 Dec 16 09:57:37 GMT 2023
Edited
by admin
on Sat Dec 16 09:57:37 GMT 2023
Record UNII
I9LFI257OB
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIARGININE OXOGLURATE
Common Name English
DIARGININE .ALPHA.-KETOGLUTARATE
Common Name English
L-ARGININE ALPHA KETO-GLUTARATE 2:1
Common Name English
ARGININE HEMOXOGLURATE
Common Name English
GLUTARIC ACID, 2-OXO-, COMPD. WITH ARGININE (1:2)
Systematic Name English
DIARGININE .ALPHA.-OXOGLUTARATE
Common Name English
ARGININE AKG 2:1
Common Name English
PENTANEDIOIC ACID, 2-OXO-, COMPD. WITH L-ARGININE (1:2)
Systematic Name English
DI-ARGICETO
Brand Name English
L-ARGININE, 2-OXOPENTANEDIOATE (2:1)
Systematic Name English
ARGININE AKG
Common Name English
L-ARGININE ALPHA-KETOGLUTARATE (2:1)
Common Name English
EUCOL
Brand Name English
DIARGININE OXOGLUTARATE
Common Name English
Classification Tree Code System Code
DSLD 2391 (Number of products:239)
Created by admin on Sat Dec 16 09:57:37 GMT 2023 , Edited by admin on Sat Dec 16 09:57:37 GMT 2023
DSLD 2618 (Number of products:151)
Created by admin on Sat Dec 16 09:57:37 GMT 2023 , Edited by admin on Sat Dec 16 09:57:37 GMT 2023
Code System Code Type Description
PUBCHEM
9957390
Created by admin on Sat Dec 16 09:57:37 GMT 2023 , Edited by admin on Sat Dec 16 09:57:37 GMT 2023
PRIMARY
CAS
556834-44-7
Created by admin on Sat Dec 16 09:57:37 GMT 2023 , Edited by admin on Sat Dec 16 09:57:37 GMT 2023
NON-SPECIFIC STOICHIOMETRY
CAS
533909-24-9
Created by admin on Sat Dec 16 09:57:37 GMT 2023 , Edited by admin on Sat Dec 16 09:57:37 GMT 2023
NON-SPECIFIC STOICHIOMETRY
CAS
5256-76-8
Created by admin on Sat Dec 16 09:57:37 GMT 2023 , Edited by admin on Sat Dec 16 09:57:37 GMT 2023
PRIMARY
ECHA (EC/EINECS)
226-059-4
Created by admin on Sat Dec 16 09:57:37 GMT 2023 , Edited by admin on Sat Dec 16 09:57:37 GMT 2023
PRIMARY
FDA UNII
I9LFI257OB
Created by admin on Sat Dec 16 09:57:37 GMT 2023 , Edited by admin on Sat Dec 16 09:57:37 GMT 2023
PRIMARY
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