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 8429	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 504	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 656	Unknown Approved Use Unknown
Histidyl-tRNA synthetase deficiency 5 Sources: https://clinicaltrials.gov/ct2/show/NCT02924935	Primary	Phase I 428	Unknown Approved Use Unknown
Rheumatoid arthritis 316 Sources: https://www.ncbi.nlm.nih.gov/pubmed/342692	Primary	Not Provided 504	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Use of molecular beacons to verify that the serine hydroxymethyltransferase pseudogene SHMT-ps1 is unique to the order Primates.	2001	11182889
Protein histidine kinase.	2001	11100475
Disruption of an active site hydrogen bond converts human heme oxygenase-1 into a peroxidase.	2001 Apr 6	11121422
Pumping capacity of bacterial reaction centers and backpressure regulation of energy transduction.	2001 Feb	11179962
Genetic and transcriptional analysis of absA, an antibiotic gene cluster-linked two-component system that regulates multiple antibiotics in Streptomyces coelicolor.	2001 Feb	11169098
The folate cycle and disease in humans.	2001 Feb	11169015
Active site characterization of the single endo-polygalacturonase produced by Fusarium moniliforme NCIM 1276.	2001 Feb	11168425
Three-dimensional structure of the histidine-containing phosphocarrier protein (HPr) from Enterococcus faecalis in solution.	2001 Feb	11168402
The ptsH gene from Bacillus thuringiensis israelensis. Characterization of a new phosphorylation site on the protein HPr.	2001 Feb	11168390
Refolding and purification of Bothropstoxin-I, a Lys49-phospholipase A2 homologue, expressed as inclusion bodies in Escherichia coli.	2001 Feb	11162398
Molecular specificities of antibodies against ovine and murine recombinant prion proteins.	2001 Feb 16	11178966
Angiotensin I-converting enzyme transition state stabilization by HIS1089: evidence for a catalytic mechanism distinct from other gluzincin metalloproteinases.	2001 Feb 16	11067854
High resolution structure of the phosphohistidine-activated form of Escherichia coli cofactor-dependent phosphoglycerate mutase.	2001 Feb 2	11038361
Involvement of acetyl phosphate in the in vivo activation of the response regulator ComA in Bacillus subtilis.	2001 Feb 20	11179649
Kinetic and mechanistic properties of biotin sulfoxide reductase.	2001 Feb 6	11170471
Replacement of the axial histidine ligand with imidazole in cytochrome c peroxidase. 2. Effects on heme coordination and function.	2001 Feb 6	11170453
Replacement of the axial histidine ligand with imidazole in cytochrome c peroxidase. 1. Effects on structure.	2001 Feb 6	11170452
Crystal structure of auracyanin, a "blue" copper protein from the green thermophilic photosynthetic bacterium Chloroflexus aurantiacus.	2001 Feb 9	11178893
The pagetoid variant of urothelial carcinoma in situ of urinary bladder in a cow.	2001 Jan	11199158
An amicyanin C-terminal loop mutant where the active-site histidine donor cannot be protonated.	2001 Jan	11191220
Rapid deposition of wheat cell wall structural proteins in response to Fusarium-derived elicitors.	2001 Jan	11181716
The effect of amino acid-modifying reagents on chloroplast protein import and the formation of early import intermediates.	2001 Jan	11181713
Synergistic antidiabetic activities of zinc, cyclo (his-pro), and arachidonic acid.	2001 Jan	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 Jan	11169516
Proximal cysteine residue is essential for the enzymatic activities of cytochrome P450cam.	2001 Jan	11168358
Polyphyletic evolution of type II restriction enzymes revisited: two independent sources of second-hand folds revealed.	2001 Jan	11165501
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 Jan	11158442
In vitro catabolism of histidine by mixed rumen bacteria and protozoa.	2001 Jan	11116390
Regulation of a mammalian Shaker-related potassium channel, hKv1.5, by extracellular potassium and pH.	2001 Jan 12	11163793
Crystal structure of an enzyme-substrate complex provides insight into the interaction between human arylsulfatase A and its substrates during catalysis.	2001 Jan 12	11124905
Analysis of the subsite specificity of rat insulysin using fluorogenic peptide substrates.	2001 Jan 12	11042190
Structures of prolyl oligopeptidase substrate/inhibitor complexes. Use of inhibitor binding for titration of the catalytic histidine residue.	2001 Jan 12	11031266
The coenzyme b12 analog 5'-deoxyadenosylcobinamide-gdp supports catalysis by methylmalonyl-coa mutase in the absence of trans-ligand coordination.	2001 Jan 12	11031263
Site-directed mutagenesis of the bacterial metalloamidase UDP-(3-O-acyl)-N-acetylglucosamine deacetylase (LpxC). Identification of the zinc binding site.	2001 Jan 16	11148046
Effect of metal binding on electrogenic proton transfer associated with reduction of the secondary electron acceptor (QB) in Rhodobacter sphaeroides chromatophores.	2001 Jan 16	11148037
Expression and purification of polyhistidine-tagged firefly luciferase in insect cells--a potential alternative for process scale-up.	2001 Jan 23	11164962
Genotoxic effects of methyl isothiocyanate.	2001 Jan 25	11152966
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	11170431
Molecular engineering of myoglobin: the improvement of oxidation activity by replacing Phe-43 with tryptophan.	2001 Jan 30	11170427
Protein control of the redox potential of the primary quinone acceptor in reactioncCenters from Rhodobacter sphaeroides.	2001 Jan 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 Jan 30	11166366
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 Jan-Feb	11170371
Translocation breakpoints in FHIT and FRA3B in both homologs of chromosome 3 in an esophageal adenocarcinoma.	2001 Mar	11170287
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 Mar 1	11180942
Spectral and metal-binding properties of three single-point tryptophan mutants of the human transferrin N-lobe.	2001 Mar 1	11171122
Quaternary structure of rice nonsymbiotic hemoglobin.	2001 Mar 2	11106662
Role of two histidines in the (6-4) photolyase reaction.	2001 Mar 30	11124949
Identification of the collagen-binding site of the von Willebrand factor A3-domain.	2001 Mar 30	11098050
The basis of prostaglandin synthesis in coral: molecular cloning and expression of a cyclooxygenase from the Arctic soft coral Gersemia fruticosa.	2001 Mar 9	11085996
Ovarian tumor cells express a transmembrane serine protease: a potential candidate for early diagnosis and therapeutic intervention.	2001 Mar-Apr	11125283

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 `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

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Name

Type

Language

HISTIDINE

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

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

LOINC

27972-9