ALANINE

US Previously Marketed

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C3H7NO2
Molecular Weight	89.0932
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=QNAYBMKLOCPYGJ-REOHCLBHSA-N

InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m0/s1

HIDE SMILES / InChI

Description
Sources: Nelson, David L.; Cox, Michael M. (2005), Principles of Biochemistry (4th ed.), New York: W. H. Freeman.
Curator's Comment: description was created based on several sources, including https://www.drugbank.ca/drugs/DB00160

Alanine is a non-essential aminoacid encoded by GCU, GCC, GCA, and GCG codons. Besides being a building block of proteins, alanine plays a key role in glucose-alanine cycle. Alanine is medically used as a dietary supplement for conditions such as fructose intolerance, muscle atrophy, low birth weight.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Alanine aminotransferase 1 17 Target ID: CHEMBL5929 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6016324	Substrate 656

Conditions

Condition	Modality	Highest Phase	Product
Burns 17 Sources: https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=016822	Primary	Approved 8360	FREAMINE III 10% Approved Use Parenteral nutrition with 8.5% FreAmine® III (Amino Acid Injection) with Electrolytes is indicated to prevent nitrogen loss or treat negative nitrogen balance in adults and pediatric patients, where (1) the alimentary tract, by the oral, gastrostomy, or jejunostomy route, cannot or should not be used, or adequate protein intake is not feasible by these routes; (2) gastrointestinal absorption of protein is impaired; or (3) protein requirements are substantially increased as with extensive burns. Dosage, route of administration, and concomitant infusion of non-protein calories are dependent on various factors, such as nutritional metabolic status of the patient, anticipated duration of parenteral nutritional support, and vein tolerance Launch Date 5.4431998E10
Fructose intolerance 1 Sources: https://clinicaltrials.gov/ct2/show/NCT01185210	Primary	Natural Metabolite	Unknown Approved Use Unknown
Muscle atrophy 1 Sources: https://clinicaltrials.gov/ct2/show/NCT00760383	Primary	Natural Metabolite	Unknown Approved Use Unknown
Low birth weight 1 Sources: https://clinicaltrials.gov/ct2/show/NCT00005889	Primary	Natural Metabolite	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	SLC7A10 1 ASCT2 12

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
ASCT2 12	substrate 3326 Sources: https://rupress.org/jgp/article-abstract/151/3/357/124243 Page: -	yes
SLC7A10 1	substrate 3326 Sources: https://www.embopress.org/doi/full/10.15252/embr.201439561 Page: -	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:16449	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16449
ChemicalBook	CB9143191	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9143191
MolPort	MolPort-000-871-636	https://www.molport.com/shop/molecule-link/MolPort-000-871-636
MolPort	MolPort-001-573-589	https://www.molport.com/shop/molecule-link/MolPort-001-573-589
eMolecules	476064	https://www.emolecules.com/cgi-bin/more?vid=476064

PubMed

Title	Date	PubMed
Structure and function of branched chain aminotransferases.	2001	11642362
Catalysis of peptide formation by inorganic oxides: high efficiency of alumina under mild conditions on the Earth-like planets.	2001	11605636
The genome of Mycobacterium leprae: a minimal mycobacterial gene set.	2001	11532219
Water-soluble L-alanine and related oligopeptide conjugates with poly[(R,S)-3-hydroxybutanoic acid] oligomers, synthesis and structural studies by means of electrospray ionization multistage mass spectrometry.	2001	11484938
Preparation of and tissue response to DNA-lipid films.	2001 Aug	11669492
Comparison of the omega-transaminases from different microorganisms and application to production of chiral amines.	2001 Aug	11577718
Analysis of the role of bacterial endospore cortex structure in resistance properties and demonstration of its conservation amongst species.	2001 Aug	11473602
Enantioseparation of chiral amino acids as the N(O,S)-ethoxycarbonylated diastereomeric esters by achiral dual-capillary column gas chromatography.	2001 Dec	11814190
Isolation of Bacillus subtilis (chungkookjang), a poly-gamma-glutamate producer with high genetic competence.	2001 Dec	11778891
Antifungal alkyl amino alcohols from the tropical marine sponge Haliclona n. sp.	2001 Dec	11754615
Potential energy surfaces for the gas-phase interaction between alpha-alanine and alkali metal Ions (Li+, Na+, K+). A density functional study.	2001 Dec 3	11720499
Structure, activity and evolution of the group I thiolactone peptide quorum-sensing system of Staphylococcus aureus.	2001 Jul	11489134
Comparison of monomeric and polymeric amino acid based surfactants for chiral separations.	2001 Jul 13	11486879
Safinamide (Newron Pharmaceuticals).	2001 Jun	11572661
Oxygen K-edge X-ray absorption near edge structures (XANES) of sublimated films of amino acids.	2001 Mar 1	11512703
Relationship between hepatitis C virus infection and schistosomal liver disease: not simply an additive effect.	2001 Nov	11757747
Comparison of vaginal aminopeptidase enzymatic activities in various animals and in humans.	2001 Nov	11732752
pH and kinetic isotope effects in d-amino acid oxidase catalysis.	2001 Nov	11683874
Na+ transport by the neural glutamine transporter ATA1.	2001 Oct	11692272
Lactoferrin-induced reduction of vanB vancomycin resistance in enterococci.	2001 Oct	11691577
Evidence for altered hepatic gluconeogenesis in patients with cirrhosis using in vivo 31-phosphorus magnetic resonance spectroscopy.	2001 Oct	11559655
Human L-type amino acid transporter 1 (LAT1): characterization of function and expression in tumor cell lines.	2001 Oct 1	11557028
Glutamate 47 in 1-aminocyclopropane-1-carboxylate synthase is a major specificity determinant.	2001 Oct 16	11591146
Spider silk fibre extrusion: combined wide- and small-angle X-ray microdiffraction experiments.	2001 Oct 22	11589973
Biochemical characterization of a phosphinate inhibitor of Escherichia coli MurC.	2001 Oct 9	11580296
Sequential treatment with lamivudine and interferon monotherapies in patients with chronic hepatitis B not responding to interferon alone: results of a pilot study.	2001 Sep	11526544
Degradation signals in ErbB-2 dictate proteasomal processing and immunogenicity and resist protection by cis glycine-alanine repeat.	2001 Sep 15	11748930
Possible involvement of amino acid transporters on S-nitroso-cysteine-induced inhibition of arachidonic acid release in PC12 cells.	2001 Sep 28	11567792
Physiological roles of free D- and L-alanine in the crayfish Procambarus clarkii with special reference to osmotic and anoxic stress responses.	2002 Apr	11897200
Dye-linked D-proline dehydrogenase from hyperthermophilic archaeon Pyrobaculum islandicum is a novel FAD-dependent amino acid dehydrogenase.	2002 Apr 12	11823469
Antitumour and toxic effects on Wistar rats of two new platinum complexes.	2002 Feb	11895460
Preparation of optically active allothreonine via optical resolution by replacing crystallization.	2002 Feb	11848226
EPR dosimetric properties of 2-methylalanine: EPR, ENDOR and FT-EPR investigations.	2002 Feb	11835674
Analysis of the E. coli NifS CsdB protein at 2.0 A reveals the structural basis for perselenide and persulfide intermediate formation.	2002 Feb 1	11827487
Transport of D-serine via the amino acid transporter ATB(0,+) expressed in the colon.	2002 Feb 22	11846403
Mutations in the carboxyl-terminal domain of phospholipase C-beta 1 delineate the dimer interface and a potential Galphaq interaction site.	2002 Feb 8	11729196
Glycine and alanine dehydrogenase activities are catalyzed by the same protein in Mycobacterium smegmatis: upregulation of both activities under microaerophilic adaptation.	2002 Jan	11888165
Formation of D-alanyl-lipoteichoic acid is required for adhesion and virulence of Listeria monocytogenes.	2002 Jan	11849532
Highly selective molecularly imprinted overoxidized polypyrrole colloids: one-step preparation technique.	2002 Jan	11817725
The effect of Nigella sativa oil against the liver damage induced by Schistosoma mansoni infection in mice.	2002 Jan	11744288
Oligomeric beta(beta)(alpha) miniprotein motifs: pivotal role of single hinge residue in determining the oligomeric state.	2002 Jan 23	11792213
The unique ribbon morphology of the major ampullate silk of spiders from the genus Loxosceles (recluse spiders).	2002 Jan-Feb	11866550
In vitro hepatotoxicity of alachlor and its by-products.	2002 Jan-Feb	11807927
Nepenthes insignis uses a C2-portion of the carbon skeleton of L-alanine acquired via its carnivorous organs, to build up the allelochemical plumbagin.	2002 Mar	11867092
Glycine oxidase from Bacillus subtilis. Characterization of a new flavoprotein.	2002 Mar 1	11744710
A Y2 receptor mimetic aptamer directed against neuropeptide Y.	2002 Mar 29	11756401
Mechanisms of the protective effect of L-alanine to D-galactosamine-induced hepatocellular injury: comparative studies of L-alanine and pyruvate.	2002 Mar 8	11866426
Structural characterization of the M* partly folded intermediate of wild type and P138A aspartate aminotransferase from Escherichia coli.	2002 May 17	11875074
Reaction mechanism of alanine racemase from Bacillus stearothermophilus: x-ray crystallographic studies of the enzyme bound with N-(5'-phosphopyridoxyl)alanine.	2002 May 24	11886871
3-Hydroxykynurenine transaminase identity with alanine glyoxylate transaminase. A probable detoxification protein in Aedes aegypti.	2002 May 3	11880382

Patents

Sample Use Guides

In Vivo Use Guide

Alanine is a nutrient, available from animal and vegetarian sources. It could be administered intravenously.

Route of Administration: Other

In Vitro Use Guide

The extent of transamination was measured by measuring the pyruvate concentration after 10 minutes incubation period with the alanine aminotransferase. The Michaelis constant for alanine was shown to be 28 mM for alanine.

Name

Type

Language

ALANINE

Official Name

English

ALANINE [INCI]

Common Name

English

LYSINE ACETATE IMPURITY C [EP IMPURITY]

Common Name

English

SERINE IMPURITY A [EP IMPURITY]

Common Name

English

ALANINE [MI]

Common Name

English

VALINE IMPURITY A [EP IMPURITY]

Common Name

English

ALANINE [VANDF]

Common Name

English

ALANINE [USAN]

Common Name

English

ALANINE [USP MONOGRAPH]

Common Name

English

NSC-206315

Code

English

L-ALANINE [USP-RS]

Common Name

English

Alanine [WHO-DD]

Common Name

English

alanine [INN]

Common Name

English

(2S)-2-AMINOPROPANOIC ACID

Common Name

English

ALANINE [HSDB]

Common Name

English

L-ALANINE

Systematic Name

English

ALANINE [EP MONOGRAPH]

Common Name

English

ALANINE [II]

Common Name

English

L-ALANINE [JAN]

Common Name

English

ALANINE, L-

Systematic Name

English

L-ALANINE [FCC]

Common Name

English

L-2-AMINOPROPANOIC ACID

Common Name

English

Classification Tree Code System Code

LOINC

88018-7