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

Details

Stereochemistry ABSOLUTE
Molecular Formula C6H14N4O2.C4H6O5
Molecular Weight 308.2884
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ARGININE MALATE

SMILES

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

InChI

InChIKey=RUFJTBOKWJYXPM-WDIAKOBKSA-N
InChI=1S/C6H14N4O2.C4H6O5/c7-4(5(11)12)2-1-3-10-6(8)9;5-2(4(8)9)1-3(6)7/h4H,1-3,7H2,(H,11,12)(H4,8,9,10);2,5H,1H2,(H,6,7)(H,8,9)/t4-;2-/m01/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 C4H6O5
Molecular Weight 134.0874
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
Early glycation products produce pentosidine cross-links on native proteins. novel mechanism of pentosidine formation and propagation of glycation.
2001 Feb 9
The nutritional management of urea cycle disorders.
2001 Jan
Current strategies for the management of neonatal urea cycle disorders.
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
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
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
Altered endothelium-dependent relaxations in lambs with high pulmonary blood flow and pulmonary hypertension.
2001 Jan
Regulatory role of arginase I and II in nitric oxide, polyamine, and proline syntheses in endothelial cells.
2001 Jan
Buffering action of endogenous nitric oxide on the adrenocortical secretagogue effect of endothelins in the rat.
2001 Jan
Lower serum activity of prolyl endopeptidase in anorexia and bulimia nervosa.
2001 Jan
Nitric oxide production by coelomocytes of Asterias forbesi.
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
Specific interactions at the regulatory domain-substrate binding domain interface influence the cooperativity of inhibition and effector binding in Escherichia coli D-3-phosphoglycerate dehydrogenase.
2001 Jan 12
Amino acid residues in ribonuclease MC1 from bitter gourd seeds which are essential for uridine specificity.
2001 Jan 16
Strengthened arm-dimerization domain interactions in AraC.
2001 Jan 26
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
A single arginyl residue in plastocyanin and in cytochrome c(6) from the cyanobacterium Anabaena sp. PCC 7119 is required for efficient reduction of photosystem I.
2001 Jan 5
Eukaryotic translation initiation factor 5 functions as a GTPase-activating protein.
2001 Mar 2
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
Substrate-binding clusters of the K+-transporting Kdp ATPase of Escherichia coli investigated by amber suppression scanning mutagenesis.
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
Identification of the collagen-binding site of the von Willebrand factor A3-domain.
2001 Mar 30
Identification of the bile acid-binding site of the ileal lipid-binding protein by photoaffinity labeling, matrix-assisted laser desorption ionization-mass spectrometry, and NMR structure.
2001 Mar 9
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 Fri Dec 15 17:09:14 GMT 2023
Edited
by admin
on Fri Dec 15 17:09:14 GMT 2023
Record UNII
4ZWH2B7Q0Q
Record Status Validated (UNII)
Record Version
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Name Type Language
ARGININE MALATE
WHO-DD  
Common Name English
L-ARGININE, HYDROXYBUTANEDIOATE
Common Name English
L-ARGININE MALATE
Common Name English
Arginine malate [WHO-DD]
Common Name English
Classification Tree Code System Code
DSLD 3348 (Number of products:21)
Created by admin on Fri Dec 15 17:09:14 GMT 2023 , Edited by admin on Fri Dec 15 17:09:14 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID60194797
Created by admin on Fri Dec 15 17:09:14 GMT 2023 , Edited by admin on Fri Dec 15 17:09:14 GMT 2023
PRIMARY
PUBCHEM
76962777
Created by admin on Fri Dec 15 17:09:14 GMT 2023 , Edited by admin on Fri Dec 15 17:09:14 GMT 2023
PRIMARY
EVMPD
SUB00580MIG
Created by admin on Fri Dec 15 17:09:14 GMT 2023 , Edited by admin on Fri Dec 15 17:09:14 GMT 2023
PRIMARY
ECHA (EC/EINECS)
255-608-0
Created by admin on Fri Dec 15 17:09:14 GMT 2023 , Edited by admin on Fri Dec 15 17:09:14 GMT 2023
PRIMARY
FDA UNII
4ZWH2B7Q0Q
Created by admin on Fri Dec 15 17:09:14 GMT 2023 , Edited by admin on Fri Dec 15 17:09:14 GMT 2023
PRIMARY
WIKIPEDIA
ARGININE MALATE
Created by admin on Fri Dec 15 17:09:14 GMT 2023 , Edited by admin on Fri Dec 15 17:09:14 GMT 2023
PRIMARY
SMS_ID
100000085320
Created by admin on Fri Dec 15 17:09:14 GMT 2023 , Edited by admin on Fri Dec 15 17:09:14 GMT 2023
PRIMARY
CAS
41989-03-1
Created by admin on Fri Dec 15 17:09:14 GMT 2023 , Edited by admin on Fri Dec 15 17:09:14 GMT 2023
PRIMARY
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