ARGININE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C6H14N4O2
Molecular Weight	174.201
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

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

InChI

InChIKey=ODKSFYDXXFIFQN-BYPYZUCNSA-N

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

HIDE SMILES / InChI

Molecular Formula	C6H14N4O2
Molecular Weight	174.201
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

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

Description

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	Agonist 2,678		44.1 µM [EC50]

Conditions

Condition	Modality	Highest Phase	Product
Panhypopituitarism 13	Diagnostic	Approved 8,429	R-GENE 10
Pituitary dwarfism 13	Diagnostic	Approved 8,429	R-GENE 10
Acromegaly 21	Diagnostic	Approved 8,429	R-GENE 10
Gigantism 13	Diagnostic	Approved 8,429	R-GENE 10
Type 2 diabetes mellitus 259	Preventing	Phase III 656	Unknown
Preeclampsia 85	Preventing	Phase III 656	Unknown
Hypertension 567	Primary	Phase III 656	Unknown

C_max

Value	Dose	Analyte	Population
6219 μM	30 g single, intravenous	ARGININE plasma	Homo sapiens
882 μM	6 g single, intravenous	ARGININE plasma	Homo sapiens
310 μM	6 g single, oral	ARGININE plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
265435 M × min	30 g single, intravenous	ARGININE plasma	Homo sapiens
38223 M × min	6 g single, intravenous	ARGININE plasma	Homo sapiens
24788 M × min	6 g single, oral	ARGININE plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
41.6 min	30 g single, intravenous	ARGININE plasma	Homo sapiens
59.6 min	6 g single, intravenous	ARGININE plasma	Homo sapiens
77.5 min	6 g single, oral	ARGININE plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
100%			ARGININE plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
3.9 g/kg single, intravenous Accidental dose	unhealthy, 1.75	Disc. AE: Cardiopulmonary arrest, Metabolic acidosis...
200 mg/kg 3 times / day multiple, oral Highest studied dose	unhealthy, 24
15 g 2 times / day multiple, oral Studied dose	healthy, 34 ± 2.6
7 g 3 times / day multiple, oral Studied dose	unhealthy, 43± 16	DLT: Gastrointestinal discomfort...

Showing 1 to 4 of 4 entries

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AEs

Show entries

AE	Significance	Dose	Population
Cardiopulmonary arrest	Disc. AE	3.9 g/kg single, intravenous Accidental dose	unhealthy, 1.75
Metabolic acidosis	acute Disc. AE	3.9 g/kg single, intravenous Accidental dose	unhealthy, 1.75
Hyponatremia	severe Disc. AE	3.9 g/kg single, intravenous Accidental dose	unhealthy, 1.75
Gastrointestinal discomfort	20% DLT	7 g 3 times / day multiple, oral Studied dose	unhealthy, 43± 16

Showing 1 to 4 of 4 entries

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Sourcing

Sourcing

Show entries

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

Showing 1 to 5 of 6 entries

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PubMed

Show entries

Title	Date	PubMed
Signal-binding specificity of the mu4 subunit of the adaptor protein complex AP-4.	2001 Apr 20	11139587
Abnormalities in response to vasopressin infusion in chronic fatigue syndrome.	2001 Feb	11087963
Kinetics of CO and NO ligation with the Cys(331)-->Ala mutant of neuronal nitric-oxide synthase.	2001 Feb 16	11067850
Amino acid residues outside of the pore region contribute to N-type calcium channel permeation.	2001 Feb 23	11120735
The nutritional management of urea cycle disorders.	2001 Jan	11148548

Showing 1 to 5 of 29 entries

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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.