THREONINE

US Previously Marketed

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C4H9NO3
Molecular Weight	119.1192
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=AYFVYJQAPQTCCC-GBXIJSLDSA-N

InChI=1S/C4H9NO3/c1-2(6)3(5)4(7)8/h2-3,6H,5H2,1H3,(H,7,8)/t2-,3+/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10780944 | https://www.ncbi.nlm.nih.gov/pubmed/28337245 | https://www.ncbi.nlm.nih.gov/pubmed/12361482
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/8296531 | https://www.ncbi.nlm.nih.gov/pubmed/1905383 | https://www.ncbi.nlm.nih.gov/pubmed/12523390

L-threonine is an essential amino acid. Threonine is a precursor of glycine. The biochemical studies on rats proved that glycine is synthesized from threonine (through threonine dehydrogenase pathway). Threonine dehydrogenase is the key enzyme in mammals like pigs, cat, and rats for degradation of 80% threonine. In adult humans, degradation of 7–11% of threonine is done by threonine dehydrogenase. The human L-threonine 3-dehydrogenase gene (GeneID: 157739, UniProtKB: Q8IZJ6 (TDH_HUMAN)) is an expressed pseudogene having lost the splice acceptor site preceding exon 6 and codon arginine-214 (CGA) is mutated to a stop codon (TGA). A few trials demonstrated that oral L-threonine may alleviate clinical signs of amyotrophic lateral sclerosis and spasticity in humans. L-Threonine has recently been brought into agricultural industry for balancing the livestock feed.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
EC 1.1.1.103 3 Target ID: EC 1.1.1.103 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10780944/	Substrate 661

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 8429	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 1971
Amyotrophic lateral sclerosis 41 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1905383 https://www.ncbi.nlm.nih.gov/pubmed/1353011 https://www.ncbi.nlm.nih.gov/pubmed/8909433	Primary	Phase II 1132	Unknown Approved Use Unknown
Multiple sclerosis 104 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1520082	Primary	Phase II 1132	Unknown Approved Use Unknown
Spasticity 11 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1742749 https://www.ncbi.nlm.nih.gov/pubmed/1520082 https://www.ncbi.nlm.nih.gov/pubmed/8296531 https://www.ncbi.nlm.nih.gov/pubmed/6809303	Primary	Phase II 1132	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
200 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/685879/	15 mg/kg single, intravenous dose: 15 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		THREONINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
300 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/685879/	15 mg/kg single, intravenous dose: 15 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		THREONINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/685879/	15 mg/kg single, intravenous dose: 15 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		THREONINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY438198
001 Chemical	NO18664
1PlusChem LLC	1P00359M
1PlusChem LLC	1P00IB51
1PlusChem LLC	1P01DL1Y
A2B Chem	AB45994
A2B Chem	AI53445
AA Blocks	AA002PJH
AA Blocks	AA0034Q6
AA Blocks	AA00FTGT
AA Blocks	AA00I5B7
AA Blocks	AA00IB39
AK Scientific	G142
AK Scientific	K436
AKOS	AKOS028109055
Accela ChemBio Inc	SY020053
Acros Organics	13893
Acros Organics	13894
Alfa Chemistry	A10606
Alfa Chemistry	A16851
Alfa Chemistry	ACM72195
Ambeed	A110778
Ambeed	A153173
Ambeed	A222119
Angene	AGN-PC-0OH2VW
Angene	AGN-PC-0WACXX
Apollo Scientific	BIT0719
Apollo Scientific	BIT0724
Apollo Scientific	BIT0801
Apollo Scientific	OR2477
AstaTech	39304
BLD Pharm	BD225703
BLD Pharm	BD2391
BLD Pharm	BD31226
BLD Pharm	BD756801
BOC Sciences	72-19-5
BOC Sciences	80-68-2
BOC Sciences	82650-07-5
Bachem	E-2420
Bachem	F-2635
Bide Pharmatech	BD2391
Bide Pharmatech	BD31226
BioSynth	Q-201331
Biopurify Phytochemicals	BP3526
BlocksMatrix Scientific	139694
BlocksMatrix Scientific	75268
Bosche Scientific	T0933
Capot Chemical	12340
Capot Chemical	20724
Chem Scene	CS-0031488
Chem Scene	CS-W020046
Chem-Impex International	282
Chemspace	CSC000185852
Chemspace	CSC009817209
Chemspace	CSC010423990
Combi-Blocks	QJ-7920
Compound Cloud	6288
Creative Peptides	CP01901
Creative Peptides	CP01902
Creative Peptides	CP01903
Creative Peptides	CP01904
Creative Peptides	CP01906
Debye Scientific	DB-029984
Enamine	BBV-38272790
Enamine	BBV-38791000
Enamine	BBV-45226436
Enamine	EN300-18051
Enamine	EN300-270140
Fluorochem	517689
Fluorochem	M02962
Frontier Scientific Services	500043031
Frontier Scientific Services	500054449
Hairui	HR126335
Hairui	HR128851
Hairui	HR129491
Hairui	HR135216
Hairui	HR138779
Hangzhou APIChem Technology	AC-11296
Hangzhou Yuhao Chemical Technology	JZ0528
Heteroz	6845
IBScreen	BB_NC-03162
IBScreen	BB_SC-09459
IRIS Biotech	HAA1131
Indofine	04-2494
Indofine	25644
Innovapharm	BBS-00021069
Innovapharm	STT-00389248
KeyOrganics	AS-12789
KeyOrganics	AS-14237
KeyOrganics	CS-15694
Lab Network	LN00173147
Lab Network	LN00198741
Lab Network	LN01814138
Lab Network	LN04550472
Lab Seeker	SC-09866
Lab Seeker	SC-09869
Lan Pharmatech	LQT-B48531
Life Chemicals	F8881-8883
MedChem Express	HY-N0658
MolPort	MolPort-001-780-280
MolPort	MolPort-003-939-608
MolPort	MolPort-044-560-773
MolPort	MolPort-044-567-341
Molcore	CS16722
Molcore	CS22619
Molcore	MC438198
Molcore	MC438199
Molcore	MC438200
Molnova	M19037
MuseChem	R014505
NCI Plated 2007	16589
NCI Plated 2007	206267
NCI Plated 2007	41828
NCI Plated 2007	46701
NCI Plated 2007	46702
Nanjing Pope Bio-tech	NSTH-D07039
Nanjing Pope Bio-tech	NSTH-D14439
Norris Pharm	NSTH-D07039
Norris Pharm	NSTH-D14439
Oakwood	222028
Oakwood	M02962
PI Chemicals	PI-15755
PI Chemicals	PI-16564
PI Chemicals	PI-27180
Pharmeks	PHBB_SC-06218
Princeton BioMolecular Research	OSSL_783105
Scientific Exchange	F-415596
Selleck Chemicals	S4951
Sigma Aldrich	1667202
Sigma Aldrich	61506
Sigma Aldrich	61506\|SIAL
Sigma Aldrich	69356\|SIAL
Sigma Aldrich	PHR1242\|SIAL
StruChem	SC-09866
StruChem	SC-09869
SynQuest	4157-1-X7
SynQuest	64452
Synthonix	T61081
TargetMol	72-19-5
TargetMol	HMDB0000167
TargetMol	T2O2777
Tetrahedron	TS32381
Tetrahedron	TS74521
TimTec	SBB061654
TimTec	ST45312853
Toronto Research Chemicals	A614555
Toronto Research Chemicals	C349130
Toronto Research Chemicals	T405500
Vesino Industrial Co Ltd	VC30839
Vesino Industrial Co Ltd	VC31011
Vitas-M Laboratory	BBL011585
Vitas-M Laboratory	STL163323
W&J PharmaChem	50A131924
W&J PharmaChem	50A589311
Wonderchem	WD0384G
Wonderchem	WD03V5S
Wonderchem	WD040NS
Wonderchem	WD06QRS
ZINC	ZINC000000895103	http://zinc15.docking.org/substances/ZINC000000895103
eMolecules	109656846
eMolecules	208168342
eMolecules	299996263
eMolecules	532410
eMolecules	93430221
eNovation Chemicals	D380617
eNovation Chemicals	D692371
mcule	MCULE-1563595722
mcule	MCULE-2676185993
mcule	MCULE-5505393195
mcule	MCULE-6095200760
mcule	MCULE-7379719940

PubMed

Title	Date	PubMed
Ras activation of the Raf kinase: tyrosine kinase recruitment of the MAP kinase cascade.	2001	11237210
The first constant-domain (CH1) exon of human IGHG2 is polymorphic and in strong linkage disequilibrium with the CH2 exon polymorphism encoding the G2m(n+) allotype in Caucasians.	2001	11220626
Deficiency of Pten accelerates mammary oncogenesis in MMTV-Wnt-1 transgenic mice.	2001	11178110
A single amino-acid in the TM1 domain is an important determinant of the desensitization kinetics of recombinant human and guinea pig alpha-homomeric 5-hydroxytryptamine type 3 receptors.	2001 Apr	11259629
Direct and differential interaction of beta-arrestins with the intracellular domains of different opioid receptors.	2001 Apr	11259620
Phosphoserine/threonine-binding domains.	2001 Apr	11248545
Starvation-induced lysosomal degradation of aldolase B requires glutamine 111 in a signal sequence for chaperone-mediated transport.	2001 Apr	11241348
F X Nottingham and F X Taunton. Two novel mutations in factor X resulting in loss of functional activity and an interpretation using molecular modelling.	2001 Feb	11246545
Mutation at codon 130 in hepatitis B virus (HBV) core region increases markedly during acute exacerbation of hepatitis in chronic HBV carriers.	2001 Feb	11227666
Tyrosine phosphorylation of p120(ctn) in v-Src transfected L cells depends on its association with E-cadherin and reduces adhesion activity.	2001 Feb	11171320
Molecular interactions between the specialist herbivore Manduca sexta (Lepidoptera, Sphingidae) and its natural host Nicotiana attenuata. II. Accumulation of plant mRNAs in response to insect-derived cues.	2001 Feb	11161027
Kinase suppressor of ras is necessary for tumor necrosis factor alpha activation of extracellular signal-regulated kinase/mitogen-activated protein kinase in intestinal epithelial cells.	2001 Feb 1	11221891
Electrophysiologic endpoint measures in a multicenter ALS drug trial.	2001 Feb 15	11231032
The ATP-dependent CodWX (HslVU) protease in Bacillus subtilis is an N-terminal serine protease.	2001 Feb 15	11179218
LIM-kinase 2 induces formation of stress fibres, focal adhesions and membrane blebs, dependent on its activation by Rho-associated kinase-catalysed phosphorylation at threonine-505.	2001 Feb 15	11171090
Ceramide induces the dephosphorylation and inhibition of constitutively activated Akt in PTEN negative U87mg cells.	2001 Feb 2	11162641
Role of Thr(11) in the binding of omega-conotoxin MVIIC to N-type Ca2+ channels.	2001 Feb 23	11226434
Blunted cardiac responses to receptor activation in subjects with Thr164Ile beta(2)-adrenoceptors.	2001 Feb 27	11222464
Site-directed mutation in a conserved kinase domain of human cytomegalovirus-pp65 with preservation of cytotoxic T lymphocyte targeting.	2001 Feb 8	11166885
Inhibition of PP-2A upregulates CaMKII in rat forebrain and induces hyperphosphorylation of tau at Ser 262/356.	2001 Feb 9	11172803
Thr226 is a key residue for bioluminescence spectra determination in beetle luciferases.	2001 Feb 9	11162668
Reduced hydrolysis of amelogenin may result in X-linked amelogenesis imperfecta.	2001 Jan	11223334
Rapid deposition of wheat cell wall structural proteins in response to Fusarium-derived elicitors.	2001 Jan	11181716
Near-infrared reflectance spectroscopy enables the fast and accurate prediction of the essential amino acid contents in soy, rapeseed meal, sunflower meal, peas, fishmeal, meat meal products, and poultry meal.	2001 Jan	11170560
Identification of tyrosine-phosphorylated proteins associated with the nuclear envelope.	2001 Jan	11168378
An HphI polymorphism in the E-selectin gene is associated with premature coronary artery disease.	2001 Jan	11168027
FMN is covalently attached to a threonine residue in the NqrB and NqrC subunits of Na(+)-translocating NADH-quinone reductase from Vibrio alginolyticus.	2001 Jan 12	11163785
Differential effects of the allosteric enhancer (2-amino-4,5-dimethyl-trienyl)[3-trifluoromethyl) phenyl]methanone (PD81,723) on agonist and antagonist binding and function at the human wild-type and a mutant (T277A) adenosine A1 receptor.	2001 Jan 15	11163328
Serotonin activates S6 kinase in a rapamycin-sensitive manner in Aplysia synaptosomes.	2001 Jan 15	11160419
Follicle-stimulating-hormone receptor and twinning.	2001 Jan 20	11213123
A molecular marker for chloroquine-resistant falciparum malaria.	2001 Jan 25	11172152
Protein control of the redox potential of the primary quinone acceptor in reactioncCenters from Rhodobacter sphaeroides.	2001 Jan 30	11170424
Increased p53 phosphorylation after microtubule disruption is mediated in a microtubule inhibitor- and cell-specific manner.	2001 Jan 4	11244509
Electrical activity regulates AChR gene expression via JNK, PKCzeta and Sp1 in skeletal chick muscle.	2001 Jan 5	11163354
Phase-feeding supports maximum growth performance of broiler chicks from forty-three to seventy-one days of age.	2001 Mar	11261566
Studies on feeding peanut meal as a protein source for broiler chickens.	2001 Mar	11261561
A novel mechanism controls anaerobic and catabolite regulation of the Escherichia coli tdc operon.	2001 Mar	11251844
Biochemical characterization of cholesterol-3-sulfate as the sole effector for the phosphorylation of HMG1 by casein kinase I in vitro.	2001 Mar	11243881
Cytoplasmic localization of p21Cip1/WAF1 by Akt-induced phosphorylation in HER-2/neu-overexpressing cells.	2001 Mar	11231573
Isolation and characterisation of genomic and cDNA clones coding for a serine-, alanine-, and proline-rich protein of Trypanosoma cruzi.	2001 Mar	11226452
Three-dimensional structure of human follicle-stimulating hormone.	2001 Mar	11222739
Topology and structure of the C1q-binding site on C-reactive protein.	2001 Mar 15	11238646
Hydrophobic analogues of the winter flounder 'antifreeze' protein.	2001 Mar 2	11240143
Structural and functional analysis of the HIV gp41 core containing an Ile573 to Thr substitution: implications for membrane fusion.	2001 Mar 6	11258890
Expression and mutagenesis of the NqrC subunit of the NQR respiratory Na(+) pump from Vibrio cholerae with covalently attached FMN.	2001 Mar 9	11248234
The F-box protein SKP2 binds to the phosphorylated threonine 380 in cyclin E and regulates ubiquitin-dependent degradation of cyclin E.	2001 Mar 9	11237742
Phosphorylation-dependent conformation and proteolytic stability of c-Myb.	2001 Mar-Apr	11259165
Sodium-substrate cotransport in bacteria.	2001 May 1	11248194
Recent progress in the Na(+)-translocating NADH-quinone reductase from the marine Vibrio alginolyticus.	2001 May 1	11248187
Synthesis of bisaminoacylated pdCpAs and tandemly activated transfer RNAs.	2007 Jul 1	17490885

Patents

Sample Use Guides

In Vivo Use Guide

L-threonine (4 g daily) with pyridoxal phosphate (160 mg daily) for six months in patients with amyotrophic lateral sclerosis. Threonine supplementation (500 mg/day) was given to 6 patients with genetic spasticity syndromes for a period of 12 months, followed by a 4-month observation period without medication. Oral L-threonine at 6 g/day in patients with spinal spasticity.

Route of Administration: Oral

In Vitro Use Guide

20 mM L-Threonine increases heat shock protein (HSP)70 and HSP25 expression and protects intestinal epithelial cells from heat stress injury

Name

Type

Language

THREONINE

Official Name

English

THREONINE, L-

Systematic Name

English

THREONINE [MART.]

Common Name

English

THREONINE [MI]

Common Name

English

(2S,3R)-2-AMINO-3-HYDROXYBUTYRIC ACID

Systematic Name

English

NSC-46701

Code

English

Threonine [WHO-DD]

Common Name

English

THREONINE [USP MONOGRAPH]

Common Name

English

L-THREONINE [JAN]

Common Name

English

THREONINE [EP MONOGRAPH]

Common Name

English

THREONINE [II]

Common Name

English

NSC-16589

Code

English

(R-(R*,S*))-2-AMINO-3-HYDROXYBUTANOIC ACID

Systematic Name

English

THREONINE [INCI]

Common Name

English

L-THREONINE [FCC]

Common Name

English

LYSINE HYDROCHLORIDE IMPURITY C [EP IMPURITY]

Common Name

English

FEMA NO. 4710

Code

English

THREONINE [HSDB]

Common Name

English

THREONINE [VANDF]

Common Name

English

(S)-THREONINE

Systematic Name

English

L-THREONINE [USP-RS]

Common Name

English

threonine [INN]

Common Name

English

THREONINE [USAN]

Common Name

English

L-THREONINE

Systematic Name

English

THR

Common Name

English

Classification Tree Code System Code

LOINC

3010-6