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Chemistry

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Also known as: L-arginine, 74-79-3, L-(+)-arginine, L(+)-arginine, L-arg, (s)-2-amino-5-guanidinopentanoic acid
Molecular Formula
C6H14N4O2
Molecular Weight
174.20  g/mol
InChI Key
ODKSFYDXXFIFQN-BYPYZUCNSA-N
FDA UNII
94ZLA3W45F

L-Arginine
An essential amino acid that is physiologically active in the L-form.
1 2D Structure

L-Arginine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S)-2-amino-5-(diaminomethylideneamino)pentanoic acid
2.1.2 InChI
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
2.1.3 InChI Key
ODKSFYDXXFIFQN-BYPYZUCNSA-N
2.1.4 Canonical SMILES
C(CC(C(=O)O)N)CN=C(N)N
2.1.5 Isomeric SMILES
C(C[C@@H](C(=O)O)N)CN=C(N)N
2.2 Other Identifiers
2.2.1 UNII
94ZLA3W45F
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Arginine Hydrochloride

2. Arginine, L Isomer

3. Arginine, L-isomer

4. Dl Arginine Acetate, Monohydrate

5. Dl-arginine Acetate, Monohydrate

6. Hydrochloride, Arginine

7. L Arginine

8. L-arginine

9. L-isomer Arginine

10. Monohydrate Dl-arginine Acetate

2.3.2 Depositor-Supplied Synonyms

1. L-arginine

2. 74-79-3

3. L-(+)-arginine

4. L(+)-arginine

5. L-arg

6. (s)-2-amino-5-guanidinopentanoic Acid

7. H-arg-oh

8. (l)-arginine

9. Arginina

10. Arginine, L-

11. Arginine (van)

12. L-arginin

13. Argininum [inn-latin]

14. Arginina [inn-spanish]

15. L-ornithine, N5-(aminoiminomethyl)-

16. Argamine

17. Argivene

18. Detoxargin

19. Levargin

20. L-alpha-amino-delta-guanidinovaleric Acid

21. Arg

22. Minophagen A

23. 1-amino-4-guanidovaleric Acid

24. Ccris 3609

25. (s)-(+)-arginine

26. Nsc 206269

27. Chebi:16467

28. Hsdb 1429

29. Ai3-24165

30. (s)-2-amino-5-((aminoiminomethyl)amino)pentanoic Acid

31. (s)-2-amino-5-guanidinovaleric Acid

32. Brn 1725413

33. L-norvaline, 5-((aminoiminomethyl)amino)-

34. 2-amino-5-guanidinovaleric Acid

35. Chembl1485

36. (2s)-2-amino-5-guanidinopentanoic Acid

37. (s)-2-amino-5-[(aminoiminomethyl)amino]pentanoic Acid

38. (2s)-2-amino-5-(diaminomethylideneamino)pentanoic Acid

39. 94zla3w45f

40. Pentanoic Acid, 2-amino-5-((aminoiminomethyl)amino)-, (s)-

41. (2s)-2-amino-5-(carbamimidamido)pentanoic Acid

42. L-arginine, Monohydrochloride

43. Nsc-206269

44. Arginine (l-arginine)

45. R-gene

46. L-norvaline, 5-[(aminoiminomethyl)amino]-

47. (2s)-2-amino-5-carbamimidamidopentanoic Acid

48. Dsstox_cid_21056

49. Dsstox_rid_79618

50. Dsstox_gsid_41056

51. Argininum

52. Pentanoic Acid, 2-amino-5-[(aminoiminomethyl)amino]-, (s)-

53. Arginine [usan:inn]

54. Cas-74-79-3

55. Arginine [usp:inn]

56. Einecs 200-811-1

57. Mfcd00002635

58. 2-amino-5-guanidino-pentanoic Acid

59. Unii-94zla3w45f

60. Nsc203450

61. 3h-l-arginine

62. L-arginine, Labeled With Tritium

63. 1laf

64. L-a-amino-d-guanidinovaleric Acid

65. Ncgc00015064-02

66. (s)-arginine

67. L(+) Arginine

68. L-aryginine,(s)

69. H-arg

70. L-(+) Arginine

71. L(+)-arginine;

72. L-arginine (9ci)

73. Arginine (usp/inn)

74. Tocris-0663

75. (2s)-2-amino-5-guanidino-pentanoic Acid

76. Arginine [hsdb]

77. Arginine [inci]

78. L-arginine (jp17)

79. Arginine [inn]

80. Arginine [ii]

81. Arginine [mi]

82. Arginine [vandf]

83. Gnd

84. Lopac-a-5006

85. Arginine, L- (8ci)

86. Arginine [mart.]

87. L-arginine [fcc]

88. L-arginine [jan]

89. Arginine [who-dd]

90. Bmse000029

91. Bmse000899

92. Bmse000919

93. Epitope Id:140084

94. L-arginine (h-arg-oh)

95. L-arginine [fhfi]

96. Ec 200-811-1

97. Schembl1791

98. 2-amino-5-guanidinovalerate

99. Lopac0_000077

100. Arginine Hydrochloride(usan)

101. Gtpl721

102. L-arginine [usp-rs]

103. 4-04-00-02648 (beilstein Handbook Reference)

104. L-a-amino-d-guanidinovalerate

105. L-amino-4-guanidovaleric Acid

106. Arginine [ep Impurity]

107. Us9138393, L-arginine

108. Us9144538, L-arginine

109. 1-amino-4-guanidovalerlic Acid

110. Arginine [ep Monograph]

111. Arginine [usp Monograph]

112. Dtxsid6041056

113. Bdbm21959

114. L-arginine, 99%, Fcc, Fg

115. Bdbm181132

116. Hms3260o15

117. N5-(aminoiminomethyl)-l-ornithine

118. Hy-n0455

119. Zinc1532525

120. L-arginine, Vetec(tm), 98.5%

121. Tox21_113046

122. Tox21_500077

123. Ac-083

124. L-2-amino-5-guanidinopentanoic Acid

125. L-alpha-amino-delta-guanidinovalerate

126. L-arginine, Reagent Grade, >=98%

127. S5634

128. Akos006239069

129. Akos015854096

130. Tox21_113046_1

131. Am81500

132. Ccg-204172

133. Db00125

134. Lp00077

135. Sdccgsbi-0050065.p002

136. L-arginine, 99%, Natural, Fcc, Fg

137. (s)-2-amino-5-guanidino-pentanoic Acid

138. 5-[(aminoiminomethyl)amino]-l-norvaline

139. Ncgc00015064-01

140. Ncgc00024715-01

141. Ncgc00024715-02

142. Ncgc00024715-03

143. Ncgc00024715-04

144. Ncgc00024715-05

145. Ncgc00024715-10

146. Ncgc00260762-01

147. 4455-52-1

148. As-14190

149. L-arginine, Bioultra, >=99.5% (nt)

150. Sbi-0207062.p001

151. A0526

152. A7079

153. Eu-0100077

154. L-arginine, Saj Special Grade, >=98.0%

155. A 5006

156. C00062

157. D02982

158. L-arginine, Vetec(tm) Reagent Grade, >=98%

159. Lysine Acetate Impurity F [ep Impurity]

160. M02981

161. 2-azaniumyl-5-(diaminomethyleneammonio)pentanoate

162. Ab00374192_03

163. Norvaline, 5-[(aminoiminomethyl)amino]-, (l)-

164. 002a635

165. A837397

166. A929348

167. Q173670

168. Sr-01000075479

169. Sr-01000597671

170. (s)-2-amino-5-[(aminoiminomethyl)amino]-pentanoate

171. (s)-2-amino-5-[(aminoiminomethyl)amino]pentanoate

172. Sr-01000075479-1

173. Sr-01000597671-1

174. W-104410

175. (s)-2-amino-5-[(aminoiminomethyl)amino]-pentanoic Acid

176. Arginine, European Pharmacopoeia (ep) Reference Standard

177. (2s)-2-amino-5-[(diaminomethylidene)amino]pentanoic Acid

178. 7f15b0c7-356d-45d7-ac33-03aee4394a0e

179. S-(+)-2-amino-5-[(aminoiminomethyl)amino]pentanoic Acid

180. (2s)-2-azanyl-5-[bis(azanyl)methylideneamino]pentanoic Acid

181. L-arginine, United States Pharmacopeia (usp) Reference Standard

182. L-arginine, Pharmaceutical Secondary Standard; Certified Reference Material

183. L-

184. L-arginine, From Non-animal Source, Meets Ep, Usp Testing Specifications, Suitable For Cell Culture, 98.5-101.0%

185. L-arginine, Pharmagrade, Ajinomoto, Ep, Usp, Manufactured Under Appropriate Gmp Controls For Pharma Or Biopharmaceutical Production, Suitable For Cell Culture

2.3.3 Other Synonyms

1. L-arginine

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 174.20 g/mol
Molecular Formula C6H14N4O2
XLogP3-4.2
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count4
Rotatable Bond Count5
Exact Mass174.11167570 g/mol
Monoisotopic Mass174.11167570 g/mol
Topological Polar Surface Area128 Ų
Heavy Atom Count12
Formal Charge0
Complexity176
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameR-gene 10
Active IngredientArginine hydrochloride
Dosage FormInjectable
RouteInjection
Strength10gm/100ml
Market StatusPrescription
CompanyPharmacia And Upjohn

2 of 2  
Drug NameR-gene 10
Active IngredientArginine hydrochloride
Dosage FormInjectable
RouteInjection
Strength10gm/100ml
Market StatusPrescription
CompanyPharmacia And Upjohn

4.2 Therapeutic Uses

EXPTL USE: IN MICE, L-ARGININE-HCL HAD AN INHIBITORY EFFECT ON MURINE SARCOMA VIRUS-MOLONEY & C3H BREAST ADENOCARCINOMA TUMOR SYSTEMS.

CRITSELIS AN ET AL; L-ARGININE INCREASES RESISTANCE TO TUMORS; CURR CHEMOTHER PROC INT CONGR CHEMOTHER, 10TH, VOL 2, 1978, 1122-4


EXPTL USE: EXPTL DIETS GIVEN 10 DAYS AFTER WALKER 256 CARCINOSARCOMA CELLS INOCULATED INTO RATS, RESULTED IN LOWER TUMOR WEIGHTS.

TAKAMURA C; INHIBITORY EFFECT OF ARGININE-SUPPLEMENTED DIETS ON GROWTH OF WALKER 256 CARCINOSARCOMA; KANSAI IKA DAIGAKU ZASSHI 29(3) 519 (1977)


EXPTL USE: L-ARGININE-HCL INCR IN VITRO MOTILITY IN SPECIMENS OF HUMAN SEMEN EXHIBITING SUBNORMAL MOTILITY. EFFECT WAS DOSE DEPENDENT.

KELLER DW ET AL; L-ARGININE STIMULATION OF HUMAN SPERM MOTILITY IN VITRO; BIOL REPROD 13(2) 154 (1975)


EXPTL USE: ARGININE (1% IN DIET) GIVEN TO RATS INCR THYMIC SIZE & PREVENTED THYMIC INVOLUTION WHICH OCCURS WITH INJURY. ARGININE PROMOTED WOUND HEALING IN RATS.

BARBUL A ET AL; ARGININE: A THYMOTROPIC & WOUND-HEALING PROMOTING AGENT; SURG FORUM 28: 101 (1977)


For more Therapeutic Uses (Complete) data for (L)-ARGININE (6 total), please visit the HSDB record page.


4.3 Drug Indication

Used for nutritional supplementation, also for treating dietary shortage or imbalance.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Studies have shown that is has improved immune responses to bacteria, viruses and tumor cells; promotes wound healing and regeneration of the liver; causes the release of growth hormones; considered crucial for optimal muscle growth and tissue repair.


5.2 Absorption, Distribution and Excretion

Absorption

Absorbed from the lumen of the small intestine into the enterocytes. Absorption is efficient and occurs by an active transport mechanism.


5.3 Metabolism/Metabolites

Some metabolism of L-arginine takes place in the enterocytes. L-arginine not metabolized in the enterocytes enters the portal circulation from whence it is transported to the liver, where again some portion of the amino acid is metabolized.


PRODUCT OF OXIDATIVE DEAMINATION OR TRANSAMINATION OF L-ARGININE IS ALPHA-KETO-GAMMA-GUANIDOVALERIC ACID; PRODUCT OF DECARBOXYLATION IS AGMATINE. PATHWAYS & PRODUCTS OF METABOLISM: ARGININE YIELDS ORNITHINE + UREA; ARGININE YIELDS CITRULLINE + NH3; ARGININE + GLYCINE YIELDS GUANIDOACETIC ACID + ORNITHINE /FROM TABLE/

Fenaroli's Handbook of Flavor Ingredients. Volume 2. Edited, translated, and revised by T.E. Furia and N. Bellanca. 2nd ed. Cleveland: The Chemical Rubber Co., 1975., p. 829


5.4 Mechanism of Action

Many of supplemental L-arginine's activities, including its possible anti-atherogenic actions, may be accounted for by its role as the precursor to nitric oxide or NO. NO is produced by all tissues of the body and plays very important roles in the cardiovascular system, immune system and nervous system. NO is formed from L-arginine via the enzyme nitric oxide synthase or synthetase (NOS), and the effects of NO are mainly mediated by 3,'5' -cyclic guanylate or cyclic GMP. NO activates the enzyme guanylate cyclase, which catalyzes the synthesis of cyclic GMP from guanosine triphosphate or GTP. Cyclic GMP is converted to guanylic acid via the enzyme cyclic GMP phosphodiesterase. NOS is a heme-containing enzyme with some sequences similar to cytochrome P-450 reductase. Several isoforms of NOS exist, two of which are constitutive and one of which is inducible by immunological stimuli. The constitutive NOS found in the vascular endothelium is designated eNOS and that present in the brain, spinal cord and peripheral nervous system is designated nNOS. The form of NOS induced by immunological or inflammatory stimuli is known as iNOS. iNOS may be expressed constitutively in select tissues such as lung epithelium. All the nitric oxide synthases use NADPH (reduced nicotinamide adenine dinucleotide phosphate) and oxygen (O2) as cosubstrates, as well as the cofactors FAD (flavin adenine dinucleotide), FMN (flavin mononucleotide), tetrahydrobiopterin and heme. Interestingly, ascorbic acid appears to enhance NOS activity by increasing intracellular tetrahydrobiopterin. eNOS and nNOS synthesize NO in response to an increased concentration of calcium ions or in some cases in response to calcium-independent stimuli, such as shear stress. In vitro studies of NOS indicate that the Km of the enzyme for L-arginine is in the micromolar range. The concentration of L-arginine in endothelial cells, as well as in other cells, and in plasma is in the millimolar range. What this means is that, under physiological conditions, NOS is saturated with its L-arginine substrate. In other words, L-arginine would not be expected to be rate-limiting for the enzyme, and it would not appear that supraphysiological levels of L-arginine which could occur with oral supplementation of the amino acid^would make any difference with regard to NO production. The reaction would appear to have reached its maximum level. However, in vivo studies have demonstrated that, under certain conditions, e.g. hypercholesterolemia, supplemental L-arginine could enhance endothelial-dependent vasodilation and NO production.


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