ARGININE PIDOLATE

First approved in 1957

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C6H14N4O2.C5H7NO3
Molecular Weight	303.3149
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)[C@@H]1CCC(=O)N1.N[C@@H](CCCNC(N)=N)C(O)=O

InChI

InChIKey=UYCAGRPOUWSBIQ-WOYAITHZSA-N

InChI=1S/C6H14N4O2.C5H7NO3/c7-4(5(11)12)2-1-3-10-6(8)9;7-4-2-1-3(6-4)5(8)9/h4H,1-3,7H2,(H,11,12)(H4,8,9,10);3H,1-2H2,(H,6,7)(H,8,9)/t4-;3-/m00/s1

HIDE SMILES / InChI

Molecular Formula	C5H7NO3
Molecular Weight	129.114
Charge	0
Count

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

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

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
Optimization of experimental conditions for RNA-based sequencing of MLH1 and MSH2 genes.	2001	11139242
Prevalence of mutations causing retinitis pigmentosa and other inherited retinopathies.	2001	11139241
Purification and characterization of calobin II, a second type of thrombin-like enzyme from Agkistrodon caliginosus (Korean viper).	2001 Apr	11024490
Nucleocytoplasmic shuttling of heterodimeric splicing factor U2AF.	2001 Apr 20	11118443
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
Abnormalities in response to vasopressin infusion in chronic fatigue syndrome.	2001 Feb	11087963
Characterization of homo- and heterodimerization of cardiac Csx/Nkx2.5 homeoprotein.	2001 Feb 16	11042197
Ligand-independent dimerization and activation of the oncogenic Xmrk receptor by two mutations in the extracellular domain.	2001 Feb 2	11038352
DNA recognition by the methyl-CpG binding domain of MeCP2.	2001 Feb 2	11035019
Human glutathione transferase T2-2 discloses some evolutionary strategies for optimization of the catalytic activity of glutathione transferases.	2001 Feb 23	11044441
Influence of microcystin-YR and nodularin on the activity of some proteolytic enzymes in mouse liver.	2001 Feb-Mar	10978764
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
Effect of AVT antisense oligodeoxynucleotides on AVT release induced by hypertonic stimulation in chicks.	2001 Jan	11137447
[Ca(2+)](i) signaling in renal arterial smooth muscle cells of pregnant rat is enhanced during inhibition of NOS.	2001 Jan	11124138
An extended hydrophobic interactive surface of Yersinia pestis Caf1M chaperone is essential for subunit binding and F1 capsule assembly.	2001 Jan	11123684
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
Regulatory role of arginase I and II in nitric oxide, polyamine, and proline syntheses in endothelial cells.	2001 Jan	11120661
Buffering action of endogenous nitric oxide on the adrenocortical secretagogue effect of endothelins in the rat.	2001 Jan	11115609
In vitro studies of a prolactin antagonist, hPRL-G129R in human breast cancer cells.	2001 Jan	11115535
Lower serum activity of prolyl endopeptidase in anorexia and bulimia nervosa.	2001 Jan	11070331
Nitric oxide production by coelomocytes of Asterias forbesi.	2001 Jan	10980315
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	11050089
Insights into the molecular basis for the carbenicillinase activity of PSE-4 beta-lactamase from crystallographic and kinetic studies.	2001 Jan 16	11148033
Upregulation of the nitric oxide-cGMP pathway in aged myocardium: physiological response to l-arginine.	2001 Jan 19	11139480
A proposed common structure of substrates bound to mitochondrial processing peptidase.	2001 Jan 19	11031253
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
Pharmacological profile of T-1032, a novel specific phosphodiesterase type 5 inhibitor, in isolated rat aorta and rabbit corpus cavernosum.	2001 Jan 5	11137871
Membrane binding motif of the P-type cardiotoxin.	2001 Jan 5	11114253
The function of Arg-94 in the oxidation and decarboxylation of glutaryl-CoA by human glutaryl-CoA dehydrogenase.	2001 Jan 5	11024031
L-ascorbic acid potentiates endothelial nitric oxide synthesis via a chemical stabilization of tetrahydrobiopterin.	2001 Jan 5	11022034
Rapid kinetic studies link tetrahydrobiopterin radical formation to heme-dioxy reduction and arginine hydroxylation in inducible nitric-oxide synthase.	2001 Jan 5	11020389
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	11013249
The modulation of oxygen radical production by nitric oxide in mitochondria.	2001 Mar 9	11106647
Sequence requirements for the N-methyl-D-aspartate receptor antagonist activity of conantokin-R.	2001 Mar 9	11096077
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	11069906

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 19:55:52 GMT 2025` Edited by `admin` on `Mon Mar 31 19:55:52 GMT 2025`
Record UNII	808T94CEU6
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ARGININE PCA

Preferred Name

English

ARGININE PIDOLATE

Common Name

English

ARGININE PYROGLUTAMATE

Preferred Name

English

ARGININE L-PYROGLUTAMATE

Common Name

English

L-ARGININE L-2 PYRROLIDONE-5-CARBOXYLATE

Common Name

English

ARGIDONE

Brand Name

English

L-PROLINE, 5-OXO-, COMPD. WITH L-ARGININE (1:1)

Systematic Name

English

Arginine pyroglutamate [WHO-DD]

Common Name

English

Classification Tree Code System Code

DSLD

3271 (Number of products:37)