U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C6H9N3O2
Molecular Weight 155.1546
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HISTIDINE

SMILES

N[C@@H](CC1=CNC=N1)C(O)=O

InChI

InChIKey=HNDVDQJCIGZPNO-YFKPBYRVSA-N
InChI=1S/C6H9N3O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1,7H2,(H,8,9)(H,10,11)/t5-/m0/s1

HIDE SMILES / InChI

Molecular Formula C6H9N3O2
Molecular Weight 155.1546
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/15612036 | http://www.sciencedirect.com/science/article/pii/S0010854504002371 | https://www.drugs.com/drp/custodiol-htk-solution.html | http://www.pharmanovia.com/fileadmin/user_upload/Pdf_filer/Custodiol_Package_Insert_09-04-03.pdf

Histidine is an essential amino acid. L-histidine is converted to histamine by histidine decarboxylase, a pyridoxal 5'-phosphate-dependent enzyme. The copper(II)–l-histidine (1:2 complex at physiological pH) has been widely used in the treatment of Menkes disease (a genetic neurodegenerative disorder that leads to early death in the children due to impaired copper metabolism) and more recent use has been reported in the treatment of infantile hypertrophic cardioencephalomyopathy (a condition caused by mutations in SCO2, a cytochrome c oxidase assembly gene). CUSTODIOL HTK (Histidine-tryptophan-ketoglutarate) Solution is indicated for perfusion and flushing of donor kidneys, liver, and heart prior to removal from the donor or immediately after removal from the donor.

Originator

Sources: Kossel, A., 2. physiol. Chem., 1896, xxii, 176. | Hedin, S. G., 2. physiol. Chem., 1896, xxii, 191.
Curator's Comment: Histidine was discovered simultaneously by Kossel and by Hedin. http://www.jbc.org/content/78/3/627.full.pdf

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P19113
Gene ID: 3067.0
Gene Symbol: HDC
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
FreAmine III

Approved Use

3% FreAmine® III (Amino Acid Injection) with Electrolytes is designed for peripheral administration to well-nourished mildly catabolic adult patients who require only short-term parenteral nutrition. In medical or routine postsurgical patients where enteral nutrition is not desirable or cannot be tolerated, protein sparing can be achieved by the peripheral infusion of amino acid solutions with or without nonprotein calories.

Launch Date

1971
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
L-amino acid sensing by the extracellular Ca2+-sensing receptor.
2000 Apr 25
Primary structure, genomic organization, and functional and electrogenic characteristics of human system N 1, a Na+- and H+-coupled glutamine transporter.
2000 Aug 4
Protein histidine kinase.
2001
The ptsH gene from Bacillus thuringiensis israelensis. Characterization of a new phosphorylation site on the protein HPr.
2001 Feb
Cloning, expression, and purification of histidine-tagged preS domains of hepatitis B virus.
2001 Feb
Refolding and purification of Bothropstoxin-I, a Lys49-phospholipase A2 homologue, expressed as inclusion bodies in Escherichia coli.
2001 Feb
Molecular genetics of glycogen-storage disease type 1a in Chinese patients of Taiwan.
2001 Feb
cDNA cloning and initial characterization of CYP3A43, a novel human cytochrome P450.
2001 Feb
A soluble two-component regulatory system controls expression of quinoprotein ethanol dehydrogenase (QEDH) but not expression of cytochrome c(550) of the ethanol-oxidation system in Pseudomonas aeruginosa.
2001 Feb
Defective intracellular transport and processing of JAG1 missense mutations in Alagille syndrome.
2001 Feb 15
Molecular specificities of antibodies against ovine and murine recombinant prion proteins.
2001 Feb 16
Angiotensin I-converting enzyme transition state stabilization by HIS1089: evidence for a catalytic mechanism distinct from other gluzincin metalloproteinases.
2001 Feb 16
High resolution structure of the phosphohistidine-activated form of Escherichia coli cofactor-dependent phosphoglycerate mutase.
2001 Feb 2
Purification and characterization of a novel calcium-binding protein from the extrapallial fluid of the mollusc, Mytilus edulis.
2001 Feb 9
Modification of surface histidine residues abolishes the cytotoxic activity of Clostridium difficile toxin A.
2001 Feb-Mar
Expression and characterization of Flag-epitope- and hexahistidine-tagged derivatives of saxiphilin for use in detection and assay of saxitoxin.
2001 Feb-Mar
An increase of mature type skin collagen cross-link, histidinohydroxylysinonorleucine, in the sclerotic skin of morphea.
2001 Jan
Characterization of the Co(2+) and Ni(2+) binding amino-acid residues of the N-terminus of human albumin. An insight into the mechanism of a new assay for myocardial ischemia.
2001 Jan
An in vivo study of ovine placental transport of essential amino acids.
2001 Jan
Multiple regions with allelic loss at chromosome 3 in superficial multifocal bladder tumors.
2001 Jan
Targeting of cytoskeletal proteins to the flagellum of Trypanosoma brucei.
2001 Jan
Analysis of the subsite specificity of rat insulysin using fluorogenic peptide substrates.
2001 Jan 12
Structures of prolyl oligopeptidase substrate/inhibitor complexes. Use of inhibitor binding for titration of the catalytic histidine residue.
2001 Jan 12
Site-directed mutagenesis of the bacterial metalloamidase UDP-(3-O-acyl)-N-acetylglucosamine deacetylase (LpxC). Identification of the zinc binding site.
2001 Jan 16
Effect of metal binding on electrogenic proton transfer associated with reduction of the secondary electron acceptor (QB) in Rhodobacter sphaeroides chromatophores.
2001 Jan 16
Chemical rescue of phosphoryl transfer in a cavity mutant: a cautionary tale for site-directed mutagenesis.
2001 Jan 16
Use of a Salmonella microsuspension bioassay to detect the mutagenicity of munitions compounds at low concentrations.
2001 Jan 25
Genotoxic effects of methyl isothiocyanate.
2001 Jan 25
Mutations that affect ligand binding to the Escherichia coli aspartate receptor: implications for transmembrane signaling.
2001 Jan 26
Direct evidence for the protonation of aspartate-75, proposed to be at a quinol binding site, upon reduction of cytochrome bo3 from Escherichia coli.
2001 Jan 30
Protein control of the redox potential of the primary quinone acceptor in reactioncCenters from Rhodobacter sphaeroides.
2001 Jan 30
Single-molecule measurements calibrate green fluorescent protein surface densities on transparent beads for use with 'knock-in' animals and other expression systems.
2001 Jan 30
Amino acid residues involved in the coordination and assembly of the manganese cluster of photosystem II. Proton-coupled electron transport of the redox-active tyrosines and its relationship to water oxidation.
2001 Jan 5
Translocation breakpoints in FHIT and FRA3B in both homologs of chromosome 3 in an esophageal adenocarcinoma.
2001 Mar
Quaternary structure of rice nonsymbiotic hemoglobin.
2001 Mar 2
A single histidine residue determines the pH sensitivity of the pacemaker channel HCN2.
2001 Mar 2
Substrate-binding clusters of the K+-transporting Kdp ATPase of Escherichia coli investigated by amber suppression scanning mutagenesis.
2001 Mar 30
Zinc release from the CH2C6 zinc finger domain of FILAMENTOUS FLOWER protein from Arabidopsis thaliana induces self-assembly.
2001 Mar 9
Flavohemoglobin, a globin with a peroxidase-like catalytic site.
2001 Mar 9
The two major plant plasma membrane H+-ATPases display different regulatory properties.
2001 Mar 9
Identification of the bile acid-binding site of the ileal lipid-binding protein by photoaffinity labeling, matrix-assisted laser desorption ionization-mass spectrometry, and NMR structure.
2001 Mar 9
Identification of a heparin binding domain in the N-terminal cleavage site of pro-islet amyloid polypeptide. Implications for islet amyloid formation.
2001 May 18
Patents

Sample Use Guides

In Vivo Use Guide
Rheumatoid arthritis patients were treated with L-histidine 4.5 g daily
Route of Administration: Oral
Histidine significantly inhibited both hydrogen peroxide- and TNF-alpha-induced IL-8 secretion and mRNA expression in Caco-2 cells and HT-29 cells. These inhibitions were dose dependent and the inhibition rate of hydrogen peroxide-induced IL-8 secretion reached more than 50% at a concentration of 25 mM, with over 95% inhibition at a concentration of 50 mM.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:00:54 GMT 2023
Edited
by admin
on Fri Dec 15 15:00:54 GMT 2023
Record UNII
4QD397987E
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
HISTIDINE
EP   HSDB   II   INCI   INN   MART.   MI   USAN   USP   VANDF   WHO-DD  
USAN   INN   INCI  
Official Name English
HISTIDINE [USAN]
Common Name English
HISTIDINE [INCI]
Common Name English
HISTIDINE [VANDF]
Common Name English
histidine [INN]
Common Name English
NSC-137773
Code English
L-HISTIDINE [FHFI]
Common Name English
HISTIDINE [HSDB]
Common Name English
FEMA NO. 3694
Code English
L-HISTIDINE [FCC]
Common Name English
SERINE IMPURITY C [EP IMPURITY]
Common Name English
HISTIDINE [USP MONOGRAPH]
Common Name English
HISTIDINE [MART.]
Common Name English
HISTIDINE [EP MONOGRAPH]
Common Name English
HISTIDINE [II]
Common Name English
L-HISTIDINE
FCC   FHFI   JAN   USP-RS  
Systematic Name English
(2S)-2-AMINO-3-(IMIDAZOL-4-YL)PROPANOIC ACID
Systematic Name English
L-HISTIDINE [JAN]
Common Name English
Histidine [WHO-DD]
Common Name English
HISTIDINE [MI]
Common Name English
L-HISTIDINE [USP-RS]
Common Name English
HISTIDINE, L-
Systematic Name English
Classification Tree Code System Code
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JECFA EVALUATION L-HISTIDINE
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DSLD 1766 (Number of products:719)
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DSLD 176 (Number of products:100)
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CFR 21 CFR 172.320
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Code System Code Type Description
CHEBI
29979
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PRIMARY
MERCK INDEX
m6028
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PRIMARY Merck Index
MESH
D006639
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PRIMARY
FDA UNII
4QD397987E
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PRIMARY
NSC
137773
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PRIMARY
CHEBI
57595
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PRIMARY
ECHA (EC/EINECS)
200-745-3
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PRIMARY
JECFA MONOGRAPH
1421
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PRIMARY
RXCUI
5340
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PRIMARY RxNorm
HSDB
1810
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PRIMARY
DRUG BANK
DB00117
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PRIMARY
ChEMBL
CHEMBL17962
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PRIMARY
DAILYMED
4QD397987E
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PRIMARY
CHEBI
15971
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PRIMARY
DRUG CENTRAL
1377
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PRIMARY
EVMPD
SUB20034
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PRIMARY
CAS
71-00-1
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PRIMARY
CHEBI
27570
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PRIMARY
EPA CompTox
DTXSID9023126
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PRIMARY
EVMPD
SUB08045MIG
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PRIMARY
SMS_ID
100000092646
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PRIMARY
RS_ITEM_NUM
1308505
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PRIMARY
WIKIPEDIA
HISTIDINE
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PRIMARY
INN
6163
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PRIMARY
PUBCHEM
6274
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PRIMARY
NCI_THESAURUS
C29597
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PRIMARY
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