HISTIDINE

US Previously Marketed

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 Search

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1123426
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histidine decarboxylase 9 Target ID: P19113 Gene ID: 3067.0 Gene Symbol: HDC Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/17965265 \| https://www.ncbi.nlm.nih.gov/pubmed/15612036	Substrate 661

Conditions

Condition	Modality	Highest Phase	Product
Burn 40 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/16822scs065_freamine_lbl.pdf	Primary	Approved 8583	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
Cholera 7 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15809910	Primary	Not Provided 511	Unknown Approved Use Unknown
Menkes disease 5 Sources: http://www.sciencedirect.com/science/article/pii/S0010854504002371 https://www.ncbi.nlm.nih.gov/pubmed/15862194 https://www.ncbi.nlm.nih.gov/pubmed/8223785 https://www.ncbi.nlm.nih.gov/pubmed/8229500 https://www.ncbi.nlm.nih.gov/pubmed/8528242	Primary	Phase III 665	Unknown Approved Use Unknown
Histidyl-tRNA synthetase deficiency 5 Sources: https://clinicaltrials.gov/ct2/show/NCT02924935	Primary	Phase I 438	Unknown Approved Use Unknown
Rheumatoid arthritis 320 Sources: https://www.ncbi.nlm.nih.gov/pubmed/342692	Primary	Not Provided 511	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Incomplete dialysis of protein samples containing 3-[(3-chlolamidopropyl)dimethylammonio]-1-propanesulfonate may lead to erroneous estimation of histidine content on amino acid analysis.	2001-03-01	11180942
Spectral and metal-binding properties of three single-point tryptophan mutants of the human transferrin N-lobe.	2001-03-01	11171122
Translocation breakpoints in FHIT and FRA3B in both homologs of chromosome 3 in an esophageal adenocarcinoma.	2001-03	11170287
Involvement of acetyl phosphate in the in vivo activation of the response regulator ComA in Bacillus subtilis.	2001-02-20	11179649
Molecular specificities of antibodies against ovine and murine recombinant prion proteins.	2001-02-16	11178966
Histidylated polylysine as DNA vector: elevation of the imidazole protonation and reduced cellular uptake without change in the polyfection efficiency of serum stabilized negative polyplexes.	2001-02-15	11170371
Abnormal secretion and function of recombinant human factor VII as the result of modification to a calcium binding site caused by a 15-base pair insertion in the F7 gene.	2001-02-15	11159523
Defective intracellular transport and processing of JAG1 missense mutations in Alagille syndrome.	2001-02-15	11157803
Crystal structure of auracyanin, a "blue" copper protein from the green thermophilic photosynthetic bacterium Chloroflexus aurantiacus.	2001-02-09	11178893
Kinetic and mechanistic properties of biotin sulfoxide reductase.	2001-02-06	11170471
Replacement of the axial histidine ligand with imidazole in cytochrome c peroxidase. 2. Effects on heme coordination and function.	2001-02-06	11170453
Replacement of the axial histidine ligand with imidazole in cytochrome c peroxidase. 1. Effects on structure.	2001-02-06	11170452
DNA-protein crosslinks induced by nickel compounds in isolated rat lymphocytes: role of reactive oxygen species and specific amino acids.	2001-02-01	11162780
Pumping capacity of bacterial reaction centers and backpressure regulation of energy transduction.	2001-02	11179962
Genetic and transcriptional analysis of absA, an antibiotic gene cluster-linked two-component system that regulates multiple antibiotics in Streptomyces coelicolor.	2001-02	11169098
The folate cycle and disease in humans.	2001-02	11169015
Active site characterization of the single endo-polygalacturonase produced by Fusarium moniliforme NCIM 1276.	2001-02	11168425
Three-dimensional structure of the histidine-containing phosphocarrier protein (HPr) from Enterococcus faecalis in solution.	2001-02	11168402
The ptsH gene from Bacillus thuringiensis israelensis. Characterization of a new phosphorylation site on the protein HPr.	2001-02	11168390
Cloning, expression, and purification of histidine-tagged preS domains of hepatitis B virus.	2001-02	11162405
Purification and kinetic characterization of CTP:phosphocholine cytidylyltransferase from Saccharomyces cerevisiae.	2001-02	11162399
Refolding and purification of Bothropstoxin-I, a Lys49-phospholipase A2 homologue, expressed as inclusion bodies in Escherichia coli.	2001-02	11162398
Purification and characterization of hexahistidine-tagged cyclohexanone monooxygenase expressed in Saccharomyces cerevisiae and Escherichia coli.	2001-02	11162390
Molecular genetics of glycogen-storage disease type 1a in Chinese patients of Taiwan.	2001-02	11161844
cDNA cloning and initial characterization of CYP3A43, a novel human cytochrome P450.	2001-02	11160876
Differential sensitivity of Kv1.4, Kv1.2, and their tandem channel to acidic pH: involvement of a histidine residue in high sensitivity to acidic pH.	2001-02	11160624
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.	2001-02	11158353
Direct evidence for the protonation of aspartate-75, proposed to be at a quinol binding site, upon reduction of cytochrome bo3 from Escherichia coli.	2001-01-30	11170431
Molecular engineering of myoglobin: the improvement of oxidation activity by replacing Phe-43 with tryptophan.	2001-01-30	11170427
Protein control of the redox potential of the primary quinone acceptor in reactioncCenters from Rhodobacter sphaeroides.	2001-01-30	11170424
Single-molecule measurements calibrate green fluorescent protein surface densities on transparent beads for use with 'knock-in' animals and other expression systems.	2001-01-30	11166366
Use of a Salmonella microsuspension bioassay to detect the mutagenicity of munitions compounds at low concentrations.	2001-01-25	11152971
Genotoxic effects of methyl isothiocyanate.	2001-01-25	11152966
Expression and purification of polyhistidine-tagged firefly luciferase in insect cells--a potential alternative for process scale-up.	2001-01-23	11164962
Site-directed mutagenesis of the bacterial metalloamidase UDP-(3-O-acyl)-N-acetylglucosamine deacetylase (LpxC). Identification of the zinc binding site.	2001-01-16	11148046
Effect of metal binding on electrogenic proton transfer associated with reduction of the secondary electron acceptor (QB) in Rhodobacter sphaeroides chromatophores.	2001-01-16	11148037
Three pairs of cysteine residues mediate both redox and zn2+ modulation of the nmda receptor.	2001-01-15	11160420
Regulation of a mammalian Shaker-related potassium channel, hKv1.5, by extracellular potassium and pH.	2001-01-12	11163793
The pagetoid variant of urothelial carcinoma in situ of urinary bladder in a cow.	2001-01	11199158
An amicyanin C-terminal loop mutant where the active-site histidine donor cannot be protonated.	2001-01	11191220
Rapid deposition of wheat cell wall structural proteins in response to Fusarium-derived elicitors.	2001-01	11181716
The effect of amino acid-modifying reagents on chloroplast protein import and the formation of early import intermediates.	2001-01	11181713
Synergistic antidiabetic activities of zinc, cyclo (his-pro), and arachidonic acid.	2001-01	11172475
Association of allelic loss at the FHIT locus and p53 alterations with tumour kinetics and chromosomal instability in non-small cell lung carcinomas (NSCLCs).	2001-01	11169516
Proximal cysteine residue is essential for the enzymatic activities of cytochrome P450cam.	2001-01	11168358
Polyphyletic evolution of type II restriction enzymes revisited: two independent sources of second-hand folds revealed.	2001-01	11165501
In vitro removal of human IgG autoantibodies by affinity filtration using immobilized L-histidine onto PEVA hollow fiber membranes.	2001-01	11163754
Two types of putative nuclear factors that physically interact with histidine-containing phosphotransfer (Hpt) domains, signaling mediators in His-to-Asp phosphorelay, in Arabidopsis thaliana.	2001-01	11158442
An increase of mature type skin collagen cross-link, histidinohydroxylysinonorleucine, in the sclerotic skin of morphea.	2001-01	11154869
Use of molecular beacons to verify that the serine hydroxymethyltransferase pseudogene SHMT-ps1 is unique to the order Primates.	2001	11182889

Patents

Sample Use Guides

In Vivo Use Guide

Rheumatoid arthritis patients were treated with L-histidine 4.5 g daily

Route of Administration: Oral

In Vitro Use Guide

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 `Mon Mar 31 17:35:14 GMT 2025` Edited by `admin` on `Mon Mar 31 17:35:14 GMT 2025`
Record UNII	4QD397987E
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

HISTIDINE

Official Name

English

L-HISTIDINE

Preferred Name

English

HISTIDINE [USAN]

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

(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

LOINC

27972-9