Valine

Identification

Summary

Valine is an amino acid commonly found as a component of total parenteral nutrition.

Brand Names
Aminosyn II 7 %, Sulfite-free, Aminosyn-PF 7%, Clinimix 2.75/5, Clinimix E 2.75/5, Clinisol 15, Freamine 6.9, Freamine III 10, Hepatamine 8, Nephramine, Olimel, Periolimel, Plenamine, Premasol, Primene, Procalamine 3, Prosol, Travasol 10, Trophamine 10 %
Generic Name
Valine
DrugBank Accession Number
DB00161
Background

Valine is a branched-chain essential amino acid that has stimulant activity. It promotes muscle growth and tissue repair. It is a precursor in the penicillin biosynthetic pathway.

Type
Small Molecule
Groups
Approved, Nutraceutical
Structure
Thumb
Weight
Average: 117.1463
Monoisotopic: 117.078978601
Chemical Formula
C5H11NO2
Synonyms
  • (2S)-2-Amino-3-methylbutanoic acid
  • (S)-Valine
  • 2-Amino-3-methylbutyric acid
  • L-(+)-alpha-Aminoisovaleric acid
  • L-alpha-Amino-beta-methylbutyric acid
  • L-valin
  • L-valine
  • Val
  • Valine

Pharmacology

Indication

Promotes mental vigor, muscle coordination, and calm emotions. May also be of use in a minority of patients with hepatic encephalopathy and in some with phenylketonuria.

Pharmacology
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Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

L-valine is a branched-chain essential amino acid (BCAA) that has stimulant activity. It promotes muscle growth and tissue repair. It is a precursor in the penicillin biosynthetic pathway. Valine is one of three branched-chain amino acids (the others are leucine and isoleucine) that enhance energy, increase endurance, and aid in muscle tissue recovery and repair. This group also lowers elevated blood sugar levels and increases growth hormone production. Supplemental valine should always be combined with isoleucine and leucine at a respective milligram ratio of 2:1:2. It is an essential amino acid found in proteins; important for optimal growth in infants and for growth in children and nitrogen balance in adults. The lack of L-valine may influence the growth of body, cause neuropathic obstacle, anaemia. It has wide applications in the field of pharmaceutical and food industry.

Mechanism of action

(Applies to Valine, Leucine and Isoleucine)
This group of essential amino acids are identified as the branched-chain amino acids, BCAAs. Because this arrangement of carbon atoms cannot be made by humans, these amino acids are an essential element in the diet. The catabolism of all three compounds initiates in muscle and yields NADH and FADH2 which can be utilized for ATP generation. The catabolism of all three of these amino acids uses the same enzymes in the first two steps. The first step in each case is a transamination using a single BCAA aminotransferase, with a-ketoglutarate as amine acceptor. As a result, three different a-keto acids are produced and are oxidized using a common branched-chain a-keto acid dehydrogenase, yielding the three different CoA derivatives. Subsequently the metabolic pathways diverge, producing many intermediates.
The principal product from valine is propionylCoA, the glucogenic precursor of succinyl-CoA. Isoleucine catabolism terminates with production of acetylCoA and propionylCoA; thus isoleucine is both glucogenic and ketogenic. Leucine gives rise to acetylCoA and acetoacetylCoA, and is thus classified as strictly ketogenic.
There are a number of genetic diseases associated with faulty catabolism of the BCAAs. The most common defect is in the branched-chain a-keto acid dehydrogenase. Since there is only one dehydrogenase enzyme for all three amino acids, all three a-keto acids accumulate and are excreted in the urine. The disease is known as Maple syrup urine disease because of the characteristic odor of the urine in afflicted individuals. Mental retardation in these cases is extensive. Unfortunately, since these are essential amino acids, they cannot be heavily restricted in the diet; ultimately, the life of afflicted individuals is short and development is abnormal The main neurological problems are due to poor formation of myelin in the CNS.

TargetActionsOrganism
UPropionyl-CoA carboxylase beta chain, mitochondrialNot AvailableHumans
UBranched-chain-amino-acid aminotransferase, cytosolicNot AvailableHumans
UValine--tRNA ligaseNot AvailableHumans
Absorption

Absorbed from the small intestine by a sodium-dependent active-transport process.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Hepatic

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Medicalerrors
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Toxicity

Symptoms of hypoglycemia, increased mortality in ALS patients taking large doses of BCAAs.

Pathways
PathwayCategory
Propanoate MetabolismMetabolic
2-Methyl-3-hydroxybutryl-CoA Dehydrogenase DeficiencyDisease
3-Methylglutaconic Aciduria Type IDisease
beta-Ketothiolase DeficiencyDisease
Clarithromycin Action PathwayDrug action
Roxithromycin Action PathwayDrug action
Gentamicin Action PathwayDrug action
Oxytetracycline Action PathwayDrug action
Tetracycline Action PathwayDrug action
Isovaleric AcidemiaDisease
Arbekacin Action PathwayDrug action
Troleandomycin Action PathwayDrug action
Josamycin Action PathwayDrug action
3-Hydroxy-3-methylglutaryl-CoA Lyase DeficiencyDisease
Malonic AciduriaDisease
Methylmalonic AciduriaDisease
Telithromycin Action PathwayDrug action
Amikacin Action PathwayDrug action
Spectinomycin Action PathwayDrug action
Demeclocycline Action PathwayDrug action
Doxycycline Action PathwayDrug action
Minocycline Action PathwayDrug action
Lymecycline Action PathwayDrug action
Isobutyryl-CoA Dehydrogenase DeficiencyDisease
Tigecycline Action PathwayDrug action
Paromomycin Action PathwayDrug action
Methacycline Action PathwayDrug action
Lincomycin Action PathwayDrug action
Chloramphenicol Action PathwayDrug action
Valine, Leucine, and Isoleucine DegradationMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
No interactions found.

Products

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
2.5% Travasol Amino Acid Injection With Electrolytes In 10% DextroseValine (145 mg / 100 mL) + Alanine (520 mg / 100 mL) + Arginine (290 mg / 100 mL) + Dextrose, unspecified form (10 g / 100 mL) + Dipotassium phosphate (130.5 mg / 100 mL) + Glycine (260 mg / 100 mL) + Histidine (120 mg / 100 mL) + Isoleucine (150 mg / 100 mL) + Leucine (182.5 mg / 100 mL) + Lysine (145 mg / 100 mL) + Magnesium chloride (25.5 mg / 100 mL) + Methionine (100 mg / 100 mL) + Phenylalanine (140 mg / 100 mL) + Proline (170 mg / 100 mL) + Serine (125 mg / 100 mL) + Sodium acetate (170 mg / 100 mL) + Sodium chloride (29.3 mg / 100 mL) + Threonine (105 mg / 100 mL) + Tryptophan (45 mg / 100 mL) + Tyrosine (10 mg / 100 mL)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-12-312015-08-05Canada flag
2.5% Travasol Amino Acid Injection With Electrolytes In 10% Dextrose ClinimixValine (115 mg / 100 mL) + Alanine (520 mg / 100 mL) + Arginine (260 mg / 100 mL) + Dextrose, unspecified form (10 g / 100 mL) + Dipotassium phosphate (130.5 mg / 100 mL) + Glycine (520 mg / 100 mL) + Histidine (110 mg / 100 mL) + Isoleucine (120 mg / 100 mL) + L-Leucine hydrochloride (155 mg / 100 mL) + Lysine hydrochloride (145 mg / 100 mL) + Magnesium chloride (25.5 mg / 100 mL) + Methionine (145 mg / 100 mL) + Phenylalanine hydrochloride (155 mg / 100 mL) + Proline (105 mg / 100 mL) + Sodium acetate (170 mg / 100 mL) + Sodium chloride (29.3 mg / 100 mL) + Threonine (105 mg / 100 mL) + Tryptophan (45 mg / 100 mL) + Tyrosine (10 mg / 100 mL)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1993-12-312015-08-05Canada flag
2.5% Travasol Amino Acid Injection Without Electrolytes In 10% Dextrose QuickmixValine (115 mg / 100 mL) + Alanine (520 mg / 100 mL) + Arginine (260 mg / 100 mL) + Dextrose, unspecified form (10 g / 100 mL) + Glycine (520 mg / 100 mL) + Histidine (110 mg / 100 mL) + Isoleucine (120 mg / 100 mL) + L-Leucine hydrochloride (155 mg / 100 mL) + Lysine hydrochloride (195 mg / 100 mL) + Methionine (195 mg / 100 mL) + Phenylalanine hydrochloride (155 mg / 100 mL) + Proline (105 mg / 100 mL) + Threonine (105 mg / 100 mL) + Tryptophan (45 mg / 100 mL) + Tyrosine (10 mg / 100 mL)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1995-12-312007-08-02Canada flag
2.5%travasol Amino Acid InJ.W.eleC.W.25%dexValine (145 mg / 100 mL) + Alanine (520 mg / 100 mL) + Arginine (290 mg / 100 mL) + Dextrose, unspecified form (25 g / 100 mL) + Dipotassium phosphate (130.5 mg / 100 mL) + Glycine (260 mg / 100 mL) + Histidine (120 mg / 100 mL) + Isoleucine (150 mg / 100 mL) + Leucine (182.5 mg / 100 mL) + Lysine (145 mg / 100 mL) + Magnesium chloride (25.5 mg / 100 mL) + Methionine (100 mg / 100 mL) + Phenylalanine (140 mg / 100 mL) + Proline (170 mg / 100 mL) + Serine (125 mg / 100 mL) + Sodium acetate (170 mg / 100 mL) + Sodium chloride (29.3 mg / 100 mL) + Threonine (105 mg / 100 mL) + Tryptophan (45 mg / 100 mL) + Tyrosine (10 mg / 100 mL)LiquidIntravenousClintec Nutrition Company1996-07-301998-08-13Canada flag
2.75% Travas. Amino Acid InJ.W.elecw.25%dexValine (159.5 mg / 100 mL) + Alanine (570 mg / 100 mL) + Arginine (316 mg / 100 mL) + Dextrose, unspecified form (25 g / 100 mL) + Dipotassium phosphate (261 mg / 100 mL) + Glycine (283 mg / 100 mL) + Histidine (132 mg / 100 mL) + Isoleucine (165 mg / 100 mL) + Leucine (201 mg / 100 mL) + Lysine (159.5 mg / 100 mL) + Magnesium chloride (51 mg / 100 mL) + Methionine (110 mg / 100 mL) + Phenylalanine (154 mg / 100 mL) + Proline (187 mg / 100 mL) + Serine (137.5 mg / 100 mL) + Sodium acetate (215.5 mg / 100 mL) + Sodium chloride (112 mg / 100 mL) + Threonine (115.5 mg / 100 mL) + Tryptophan (49.5 mg / 100 mL) + Tyrosine (11 mg / 100 mL)LiquidIntravenousClintec Nutrition Company1996-07-301998-08-13Canada flag
2.75% Travasol Amino Acid Injection With Electrolytes In 25% Dextrose QuickmixValine (126 mg / 100 mL) + Alanine (570 mg / 100 mL) + Arginine (285 mg / 100 mL) + Dextrose, unspecified form (25 g / 100 mL) + Dipotassium phosphate (261 mg / 100 mL) + Glycine (570 mg / 100 mL) + Histidine (120.5 mg / 100 mL) + Isoleucine (131.5 mg / 100 mL) + L-Leucine hydrochloride (170 mg / 100 mL) + Lysine hydrochloride (159 mg / 100 mL) + Magnesium chloride (51 mg / 100 mL) + Methionine (159 mg / 100 mL) + Phenylalanine hydrochloride (170 mg / 100 mL) + Proline (115 mg / 100 mL) + Sodium acetate (215.5 mg / 100 mL) + Sodium chloride (112 mg / 100 mL) + Threonine (115 mg / 100 mL) + Tryptophan (49.5 mg / 100 mL) + Tyrosine (11 mg / 100 mL)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-02-022007-08-02Canada flag
2.75% Travasol Amino Acid Injection With Electrolytes In 5% Dextrose QuickmixValine (126 mg / 100 mL) + Alanine (570 mg / 100 mL) + Arginine (285 mg / 100 mL) + Dextrose, unspecified form (5 g / 100 mL) + Dipotassium phosphate (215.5 mg / 100 mL) + Glycine (570 mg / 100 mL) + Histidine (120.5 mg / 100 mL) + Isoleucine (131.5 mg / 100 mL) + L-Leucine hydrochloride (170 mg / 100 mL) + Lysine hydrochloride (159 mg / 100 mL) + Magnesium chloride (51 mg / 100 mL) + Methionine (159 mg / 100 mL) + Phenylalanine hydrochloride (170 mg / 100 mL) + Proline (115 mg / 100 mL) + Sodium acetate (256 mg / 100 mL) + Sodium chloride (112 mg / 100 mL) + Threonine (115 mg / 100 mL) + Tryptophan (49.5 mg / 100 mL) + Tyrosine (11 mg / 100 mL)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1993-12-312007-08-02Canada flag
2.75%travasol Amino Acid InJ.W.eleC.W.5%dex.Valine (159.5 mg / 100 mL) + Alanine (570 mg / 100 mL) + Arginine (316 mg / 100 mL) + Dextrose, unspecified form (5 g / 100 mL) + Dipotassium phosphate (261 mg / 100 mL) + Glycine (283 mg / 100 mL) + Histidine (132 mg / 100 mL) + Isoleucine (165 mg / 100 mL) + Leucine (201 mg / 100 mL) + Lysine (159.5 mg / 100 mL) + Magnesium chloride (51 mg / 100 mL) + Methionine (110 mg / 100 mL) + Phenylalanine (154 mg / 100 mL) + Proline (187 mg / 100 mL) + Serine (137.5 mg / 100 mL) + Sodium acetate (215 mg / 100 mL) + Sodium chloride (112 mg / 100 mL) + Threonine (115.5 mg / 100 mL) + Tryptophan (49.5 mg / 100 mL) + Tyrosine (11 mg / 100 mL)LiquidIntravenousClintec Nutrition Company1996-12-311999-08-10Canada flag
20% ProsolValine (1.44 g) + Alanine (2.76 g) + Arginine (1.96 g) + Aspartic acid (0.6 g) + D-Methionine (0.76 g) + Glutamic acid (1.02 g) + Glycine (2.06 g) + Histidine (1.18 g) + Isoleucine (1.08 g) + Leucine (1.08 g) + Lysine (1.35 g) + Methionine (0.76 g) + Phenylalanine (1 g) + Proline (1.34 g) + Serine (1.02 g) + Threonine (0.98 g) + Tryptophan (0.32 g) + Tyrosine (0.05 g)LiquidIntravenousBaxter Laboratories1996-10-09Not applicableCanada flag
4.25% Amino Acid Injection Without Electrolytes In 20% Dextrose QuickmixValine (195 mg / 100 mL) + Alanine (880 mg / 100 mL) + Arginine (440 mg / 100 mL) + Dextrose, unspecified form (20 g / 100 mL) + Glycine (880 mg / 100 mL) + Histidine (186 mg / 100 mL) + Isoleucine (203 mg / 100 mL) + L-Leucine hydrochloride (263 mg / 100 mL) + Lysine hydrochloride (246 mg / 100 mL) + Methionine (246 mg / 100 mL) + Phenylalanine hydrochloride (263 mg / 100 mL) + Proline (178 mg / 100 mL) + Threonine (178 mg / 100 mL) + Tryptophan (76 mg / 100 mL) + Tyrosine (17 mg / 100 mL)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1995-12-312007-08-02Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ClinimixValine (4.93 g/2L) + Alanine (17.60 g/2L) + Arginine (9.78 g/2L) + Calcium chloride dihydrate (0.66 g/2L) + D-glucose monohydrate (300.00 g/2L) + Dipotassium phosphate (5.22 g/2L) + Glycine (8.76 g/2L) + Histidine (4.08 g/2L) + Isoleucine (5.10 g/2L) + Leucine (6.20 g/2L) + Lysine (4.93 g/2L) + Magnesium chloride hexahydrate (1.02 g/2L) + Methionine (3.40 g/2L) + Phenylalanine (4.76 g/2L) + Proline (5.78 g/2L) + Serine (4.25 g/2L) + Sodium acetate trihydrate (5.94 g/2L) + Sodium chloride (1.54 g/2L) + Threonine (3.57 g/2L) + Tryptophan (1.53 g/2L) + Tyrosine (0.34 g/2L)SolutionIntravenousBaxter Healthcare Corporation2017-10-252019-11-30US flag
ClinimixValine (1.60 g/1L) + Alanine (5.70 g/1L) + Arginine (3.17 g/1L) + Calcium chloride dihydrate (0.33 g/1L) + D-glucose monohydrate (75.00 g/1L) + Dipotassium phosphate (2.61 g/1L) + Glycine (2.84 g/1L) + Histidine (1.32 g/1L) + Isoleucine (1.65 g/1L) + Leucine (2.01 g/1L) + Lysine (2.00 g/1L) + Magnesium chloride hexahydrate (0.51 g/1L) + Methionine (1.10 g/1L) + Phenylalanine (1.54 g/1L) + Proline (1.87 g/1L) + Serine (1.38 g/1L) + Sodium acetate trihydrate (2.16 g/1L) + Sodium chloride (1.12 g/1L) + Threonine (1.16 g/1L) + Tryptophan (0.50 g/1L) + Tyrosine (0.11 g/1L)SolutionIntravenousBaxter Healthcare Corporation2017-10-252019-11-30US flag
ClinimixValine (1.60 g/1L) + Alanine (5.70 g/1L) + Arginine (3.17 g/1L) + Calcium chloride dihydrate (0.33 g/1L) + D-glucose monohydrate (100.00 g/1L) + Dipotassium phosphate (2.61 g/1L) + Glycine (2.84 g/1L) + Histidine (1.32 g/1L) + Isoleucine (1.65 g/1L) + Leucine (2.01 g/1L) + Lysine (2.00 g/1L) + Magnesium chloride hexahydrate (0.51 g/1L) + Methionine (1.10 g/1L) + Phenylalanine (1.54 g/1L) + Proline (1.87 g/1L) + Serine (1.38 g/1L) + Sodium acetate trihydrate (2.16 g/1L) + Sodium chloride (1.12 g/1L) + Threonine (1.16 g/1L) + Tryptophan (0.50 g/1L) + Tyrosine (0.11 g/1L)SolutionIntravenousBaxter Healthcare Corporation2017-10-252019-11-30US flag
FREAMINE III %10 1000 ML(SETLI)Valine (0.66 %) + Alanine (0.71 %) + Arginine (0.95 %) + Cysteine (0.016 %) + Glycine (1.4 %) + Histidine (0.28 %) + Isoleucine (0.69 %) + Leucine (0.91 %) + Lysine (0.73 %) + Methionine (0.53 %) + Phenylalanine (0.56 %) + Proline (1.12 %) + Serine (0.59 %) + Threonine (0.4 %) + Tryptophan (0.15 %)SolutionIntravenousECZACIBAŞI-BAXTER HASTANE ÜRÜNLERİ SAN.VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
FREAMINE III %10 1000 ML(SETSIZ)Valine (0.66 %) + Alanine (0.71 %) + Arginine (0.95 %) + Cysteine (0.016 %) + Glycine (1.4 %) + Histidine (0.28 %) + Isoleucine (0.69 %) + Leucine (0.91 %) + Lysine (0.73 %) + Methionine (0.53 %) + Phenylalanine (0.56 %) + Proline (1.12 %) + Serine (0.59 %) + Threonine (0.4 %) + Tryptophan (0.15 %)SolutionIntravenousECZACIBAŞI-BAXTER HASTANE ÜRÜNLERİ SAN.VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
FREAMINE III %10 500 ML(SETLI)Valine (0.66 %) + Alanine (0.71 %) + Arginine (0.95 %) + Cysteine (0.016 %) + Glycine (1.4 %) + Histidine (0.28 %) + Isoleucine (0.69 %) + Leucine (0.91 %) + Lysine (0.73 %) + Methionine (0.53 %) + Phenylalanine (0.56 %) + Proline (1.12 %) + Serine (0.59 %) + Threonine (0.4 %) + Tryptophan (0.15 %)SolutionIntravenousECZACIBAŞI-BAXTER HASTANE ÜRÜNLERİ SAN.VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
FREAMINE III %10 500 ML(SETSIZ)Valine (0.66 %) + Alanine (0.71 %) + Arginine (0.95 %) + Cysteine (0.016 %) + Glycine (1.4 %) + Histidine (0.28 %) + Isoleucine (0.69 %) + Leucine (0.91 %) + Lysine (0.73 %) + Methionine (0.53 %) + Phenylalanine (0.56 %) + Proline (1.12 %) + Serine (0.59 %) + Threonine (0.4 %) + Tryptophan (0.15 %)SolutionIntravenousECZACIBAŞI-BAXTER HASTANE ÜRÜNLERİ SAN.VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
FREAMINE III %8.5 500 ML(SETLI)Valine (0.56 %) + Alanine (0.6 %) + Arginine (0.81 %) + Cysteine (0.014 %) + Glycine (1.19 %) + Histidine (0.24 %) + Isoleucine (0.59 %) + Leucine (0.77 %) + Lysine (0.62 %) + Methionine (0.45 %) + Phenylalanine (0.48 %) + Proline (0.95 %) + Serine (0.5 %) + Threonine (0.34 %) + Tryptophan (0.13 %)SolutionIntravenousECZACIBAŞI-BAXTER HASTANE ÜRÜNLERİ SAN.VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
FREAMINE III %8.5 500 ML(SETSIZ)Valine (0.56 %) + Alanine (0.6 %) + Arginine (0.81 %) + Cysteine (0.014 %) + Glycine (1.19 %) + Histidine (0.24 %) + Isoleucine (0.59 %) + Leucine (0.77 %) + Lysine (0.62 %) + Methionine (0.45 %) + Phenylalanine (0.48 %) + Proline (0.95 %) + Serine (0.5 %) + Threonine (0.34 %) + Tryptophan (0.13 %)SolutionIntravenousECZACIBAŞI-BAXTER HASTANE ÜRÜNLERİ SAN.VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
FRESELAMIN %10 1000 ML SETLI SISEValine (0.66 %) + Alanine (0.71 %) + Arginine (0.95 %) + Cysteine (0.016 %) + Glycine (1.4 %) + Histidine (0.28 %) + Isoleucine (0.69 %) + Leucine (0.91 %) + Lysine (0.73 %) + Methionine (0.53 %) + Phenylalanine (0.56 %) + Proline (1.12 %) + Serine (0.59 %) + Threonine (0.4 %) + Tryptophan (0.15 %)SolutionIntravenousOSEL İLAÇ SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as valine and derivatives. These are compounds containing valine or a derivative thereof resulting from reaction of valine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Valine and derivatives
Alternative Parents
L-alpha-amino acids / Methyl-branched fatty acids / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Aliphatic acyclic compound / Alpha-amino acid / Amine / Amino acid / Branched fatty acid / Carbonyl group / Carboxylic acid / Fatty acid / Fatty acyl / Hydrocarbon derivative
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
proteinogenic amino acid, L-alpha-amino acid, valine, pyruvate family amino acid (CHEBI:16414) / Common amino acids (C00183)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
HG18B9YRS7
CAS number
72-18-4
InChI Key
KZSNJWFQEVHDMF-BYPYZUCNSA-N
InChI
InChI=1S/C5H11NO2/c1-3(2)4(6)5(7)8/h3-4H,6H2,1-2H3,(H,7,8)/t4-/m0/s1
IUPAC Name
(2S)-2-amino-3-methylbutanoic acid
SMILES
CC(C)[C@H](N)C(O)=O

References

Synthesis Reference

Hiroshi Matsui, Takayasu Tsuchida, Shigeru Nakamori, "Method for producing L-valine by fermentation." U.S. Patent US4391907, issued July, 1981.

US4391907
General References
Not Available
Human Metabolome Database
HMDB0000883
KEGG Drug
D00039
KEGG Compound
C00183
PubChem Compound
6287
PubChem Substance
46504886
ChemSpider
6050
BindingDB
50463208
RxNav
11115
ChEBI
16414
ChEMBL
CHEMBL43068
ZINC
ZINC000000895099
PharmGKB
PA451843
PDBe Ligand
VAL
PDRhealth
PDRhealth Drug Page
Wikipedia
Valine
MSDS
Download (72 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentCritically Ill Patients / Starvation1
4TerminatedSupportive CareCancer-related Malnutrition1
4TerminatedSupportive CareCritically Ill Patients1
4TerminatedSupportive CareParenteral Nutrition (No Primary Condition Studied)1
4WithdrawnSupportive CareMalnutrition1
3CompletedTreatmentCritically Ill Patients2
3CompletedTreatmentInfants, Premature / Low Birth Weight Infants / Newborn Infants / Septic / Small for Gestational Age Infants1
3CompletedTreatmentParenteral Feedings / Surgery1
3CompletedTreatmentParenteral Nutrition for Patients With Proven Insufficient Enteral Resorption1
3CompletedTreatmentParenteral Nutrition / Surgery1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • B. Braun Melsungen AG
  • Baxter International Inc.
  • Hospira Inc.
  • Spectrum Pharmaceuticals
  • V Sab Medical Labs Inc.
Dosage Forms
FormRouteStrength
LiquidIntravenous
SolutionParenteral
SolutionIntravenous2.453 g
Solution, concentrateIntravenous
TabletOral
Injection, solutionIntravenous
EmulsionParenteral
CapsuleOral
Injection, emulsionIntravenous
Injection, solution, concentrateIntravenous
Injection, emulsionParenteral
Injection, emulsion; injection, solutionIntravenous
EmulsionIntravenous
Injection, solution
Solution
Injection, solutionIntraperitoneal
LiquidHemodialysis
SolutionIntraperitoneal
EmulsionIntravenous4 g
EmulsionIntravenous3 g
SolutionIntravenous
InjectionIntravenous
Granule
Prices
Unit descriptionCostUnit
L-valine crystal3.19USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)315 °CPhysProp
water solubility5.85E+004 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-2.26HANSCH,C ET AL. (1995)
pKa2.3 (at 13 °C)KORTUM,G ET AL (1961)
Predicted Properties
PropertyValueSource
Water Solubility214.0 mg/mLALOGPS
logP-2.3ALOGPS
logP-2ChemAxon
logS0.26ALOGPS
pKa (Strongest Acidic)2.72ChemAxon
pKa (Strongest Basic)9.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity29.49 m3·mol-1ChemAxon
Polarizability12.19 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9527
Blood Brain Barrier+0.5852
Caco-2 permeable-0.8768
P-glycoprotein substrateNon-substrate0.7977
P-glycoprotein inhibitor INon-inhibitor0.9872
P-glycoprotein inhibitor IINon-inhibitor0.9955
Renal organic cation transporterNon-inhibitor0.9679
CYP450 2C9 substrateNon-substrate0.8395
CYP450 2D6 substrateNon-substrate0.873
CYP450 3A4 substrateNon-substrate0.7576
CYP450 1A2 substrateNon-inhibitor0.8276
CYP450 2C9 inhibitorNon-inhibitor0.9523
CYP450 2D6 inhibitorNon-inhibitor0.9583
CYP450 2C19 inhibitorNon-inhibitor0.9722
CYP450 3A4 inhibitorNon-inhibitor0.9359
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9916
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.5785
BiodegradationReady biodegradable0.646
Rat acute toxicity1.4765 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9943
hERG inhibition (predictor II)Non-inhibitor0.9795
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (7.74 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-0006-0910000000-23bfcf2795f71f458bda
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-0006-0920000000-7892bb9d4d9afcc23410
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-0006-0910000000-f2491152816b9c5dc7ed
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)GC-MSsplash10-0znj-1900000000-7c976d7c11a402db399f
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-00dl-8910000000-78e8ee971ad7298c23cd
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-00di-9200000000-805e6724e5181af78c81
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-0006-0910000000-a212771a5ea868139d5a
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-059t-0900000000-7b8e4e98ac9158bf26d9
GC-MS Spectrum - EI-BGC-MSsplash10-0006-0910000000-9079324093be9a14d47a
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0006-0910000000-23bfcf2795f71f458bda
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0006-0920000000-7892bb9d4d9afcc23410
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0006-0910000000-f2491152816b9c5dc7ed
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0znj-1900000000-7c976d7c11a402db399f
GC-MS Spectrum - GC-EI-QQGC-MSsplash10-000i-2920000000-1628d46d5520c5f20de8
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00dl-8910000000-78e8ee971ad7298c23cd
GC-MS Spectrum - GC-MSGC-MSsplash10-00di-9200000000-805e6724e5181af78c81
GC-MS Spectrum - GC-MSGC-MSsplash10-0006-0910000000-a212771a5ea868139d5a
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-00di-9000000000-67498a3295a1fe788c4b
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-0a4i-9000000000-fb359f44fcf1b83ee14d
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-0a4i-9000000000-8e5f620c04615765a062
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-014r-0900000000-619d80cc41221405e0bd
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-00di-9000000000-17ab53cec2e6b727c3e9
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-00di-9000000000-0dfbcc85d6423af91eda
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-014l-4900000000-c50d79ba3a5013bcf29f
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0uxr-0900000000-67a7784963ec75cecaa0
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-00di-9000000000-4569516f23d8a712b434
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-001i-0900000000-d928cac1226f19b8edc3
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0udi-0900000000-34059351f2cbd94a8acc
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-014i-0900000000-a36d8d68a6705027415f
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-014i-0900000000-1a5d8f4c1b293de18fed
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-014i-0900000000-b410df2c18dfc8ab7165
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-0gi0-6900000000-c87ff036e3a5d15b7670
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-00di-9000000000-561b3b28fa82e0b10658
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-05fr-9000000000-11e7c0a3d5cf8e4dedfe
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-0a4i-9000000000-6a6f8cd9629b0f09469c
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-0a4i-9000000000-4518f691bbda5739c0f1
MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , PositiveLC-MS/MSsplash10-014i-0900000000-a931cfc8207edac33775
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-00di-9000000000-430332b13b8c6368136b
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-014i-0900000000-ffb286a8ae38a0a3e6d2
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014i-0900000000-a36d8d68a6705027415f
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014i-0900000000-fd0315877791da7d0f73
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014i-0900000000-b410df2c18dfc8ab7165
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-014i-0900000000-ffb286a8ae38a0a3e6d2
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0gi0-6900000000-c87ff036e3a5d15b7670
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-9000000000-0541966936b0667a21ea
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-05fr-9000000000-11e7c0a3d5cf8e4dedfe
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4i-9000000000-2d3ef213c39969d98d2f
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4i-9000000000-4518f691bbda5739c0f1
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-00di-9000000000-5455b1ae1036ee8f1624
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-9000000000-17ab53cec2e6b727c3e9
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-9000000000-0dfbcc85d6423af91eda
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014l-4900000000-c50d79ba3a5013bcf29f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-9000000000-4569516f23d8a712b434
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-d77cafe24ec50283bbf8
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0900000000-34059351f2cbd94a8acc
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-9000000000-430332b13b8c6368136b
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Targets

Drugtargets
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Propionyl-coa carboxylase activity
Specific Function
Not Available
Gene Name
PCCB
Uniprot ID
P05166
Uniprot Name
Propionyl-CoA carboxylase beta chain, mitochondrial
Molecular Weight
58215.13 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Kim SN, Ryu KH, Lee EH, Kim JS, Hahn SH: Molecular analysis of PCCB gene in Korean patients with propionic acidemia. Mol Genet Metab. 2002 Nov;77(3):209-16. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
L-valine transaminase activity
Specific Function
Catalyzes the first reaction in the catabolism of the essential branched chain amino acids leucine, isoleucine, and valine.
Gene Name
BCAT1
Uniprot ID
P54687
Uniprot Name
Branched-chain-amino-acid aminotransferase, cytosolic
Molecular Weight
42965.815 Da
References
  1. Chen CD, Huang TF, Lin CH, Guan HH, Hsieh YC, Lin YH, Huang YC, Liu MY, Chang WC, Chen CJ: Purification, crystallization and preliminary X-ray crystallographic analysis of branched-chain aminotransferase from Deinococcus radiodurans. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2007 Jun 1;63(Pt 6):492-4. Epub 2007 May 5. [Article]
  2. Beck HC: Branched-chain fatty acid biosynthesis in a branched-chain amino acid aminotransferase mutant of Staphylococcus carnosus. FEMS Microbiol Lett. 2005 Feb 1;243(1):37-44. [Article]
  3. Saito M, Nishimura K, Wakabayashi S, Kurihara T, Nagata Y: Purification of branched-chain amino acid aminotransferase from Helicobacter pylori NCTC 11637. Amino Acids. 2007 Sep;33(3):445-9. Epub 2006 Nov 2. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Valine-trna ligase activity
Specific Function
Not Available
Gene Name
VARS
Uniprot ID
P26640
Uniprot Name
Valine--tRNA ligase
Molecular Weight
140474.755 Da
References
  1. Zhu B, Zhao MW, Eriani G, Wang ED: A present-day aminoacyl-tRNA synthetase with ancestral editing properties. RNA. 2007 Jan;13(1):15-21. Epub 2006 Nov 9. [Article]
  2. Laforest MJ, Delage L, Marechal-Drouard L: The T-domain of cytosolic tRNAVal, an essential determinant for mitochondrial import. FEBS Lett. 2005 Feb 14;579(5):1072-8. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Valine-trna ligase activity
Specific Function
Not Available
Gene Name
VARS
Uniprot ID
P26640
Uniprot Name
Valine--tRNA ligase
Molecular Weight
140474.755 Da
References
  1. Zhu B, Zhao MW, Eriani G, Wang ED: A present-day aminoacyl-tRNA synthetase with ancestral editing properties. RNA. 2007 Jan;13(1):15-21. Epub 2006 Nov 9. [Article]
  2. Laforest MJ, Delage L, Marechal-Drouard L: The T-domain of cytosolic tRNAVal, an essential determinant for mitochondrial import. FEBS Lett. 2005 Feb 14;579(5):1072-8. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Propionyl-coa carboxylase activity
Specific Function
Not Available
Gene Name
PCCB
Uniprot ID
P05166
Uniprot Name
Propionyl-CoA carboxylase beta chain, mitochondrial
Molecular Weight
58215.13 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Kim SN, Ryu KH, Lee EH, Kim JS, Hahn SH: Molecular analysis of PCCB gene in Korean patients with propionic acidemia. Mol Genet Metab. 2002 Nov;77(3):209-16. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
L-valine transaminase activity
Specific Function
Catalyzes the first reaction in the catabolism of the essential branched chain amino acids leucine, isoleucine, and valine.
Gene Name
BCAT1
Uniprot ID
P54687
Uniprot Name
Branched-chain-amino-acid aminotransferase, cytosolic
Molecular Weight
42965.815 Da
References
  1. Chen CD, Huang TF, Lin CH, Guan HH, Hsieh YC, Lin YH, Huang YC, Liu MY, Chang WC, Chen CJ: Purification, crystallization and preliminary X-ray crystallographic analysis of branched-chain aminotransferase from Deinococcus radiodurans. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2007 Jun 1;63(Pt 6):492-4. Epub 2007 May 5. [Article]
  2. Beck HC: Branched-chain fatty acid biosynthesis in a branched-chain amino acid aminotransferase mutant of Staphylococcus carnosus. FEMS Microbiol Lett. 2005 Feb 1;243(1):37-44. [Article]
  3. Saito M, Nishimura K, Wakabayashi S, Kurihara T, Nagata Y: Purification of branched-chain amino acid aminotransferase from Helicobacter pylori NCTC 11637. Amino Acids. 2007 Sep;33(3):445-9. Epub 2006 Nov 2. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transporter activity
Specific Function
Sodium-independent transporter that mediates the update of aromatic acid. Can function as a net efflux pathway for aromatic amino acids in the basosolateral epithelial cells (By similarity).
Gene Name
SLC16A10
Uniprot ID
Q8TF71
Uniprot Name
Monocarboxylate transporter 10
Molecular Weight
55492.07 Da
References
  1. Kim DK, Kanai Y, Chairoungdua A, Matsuo H, Cha SH, Endou H: Expression cloning of a Na+-independent aromatic amino acid transporter with structural similarity to H+/monocarboxylate transporters. J Biol Chem. 2001 May 18;276(20):17221-8. Epub 2001 Feb 20. [Article]

Drug created on June 13, 2005 13:24 / Updated on July 03, 2021 08:58