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

Details

Stereochemistry ABSOLUTE
Molecular Formula C6H9N3O2.ClH.H2O
Molecular Weight 209.631
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HISTIDINE MONOHYDROCHLORIDE MONOHYDRATE

SMILES

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

InChI

InChIKey=CMXXUDSWGMGYLZ-XRIGFGBMSA-N
InChI=1S/C6H9N3O2.ClH.H2O/c7-5(6(10)11)1-4-2-8-3-9-4;;/h2-3,5H,1,7H2,(H,8,9)(H,10,11);1H;1H2/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

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Use of molecular beacons to verify that the serine hydroxymethyltransferase pseudogene SHMT-ps1 is unique to the order Primates.
2001
Two novel mutations (Y141H; C214Y) and previously published mutation (R142W) in the RDS-peripherin gene in autosomal dominant macular dystrophies in Spanish families.
2001
Multiple conformations of catalytic serine and histidine in acetylxylan esterase at 0.90 A.
2001 Apr 6
Pumping capacity of bacterial reaction centers and backpressure regulation of energy transduction.
2001 Feb
Genetic and transcriptional analysis of absA, an antibiotic gene cluster-linked two-component system that regulates multiple antibiotics in Streptomyces coelicolor.
2001 Feb
The folate cycle and disease in humans.
2001 Feb
Active site characterization of the single endo-polygalacturonase produced by Fusarium moniliforme NCIM 1276.
2001 Feb
Three-dimensional structure of the histidine-containing phosphocarrier protein (HPr) from Enterococcus faecalis in solution.
2001 Feb
The ptsH gene from Bacillus thuringiensis israelensis. Characterization of a new phosphorylation site on the protein HPr.
2001 Feb
Purification and kinetic characterization of CTP:phosphocholine cytidylyltransferase from Saccharomyces cerevisiae.
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
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 Feb
DNA-protein crosslinks induced by nickel compounds in isolated rat lymphocytes: role of reactive oxygen species and specific amino acids.
2001 Feb 1
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 Feb 15
Defective intracellular transport and processing of JAG1 missense mutations in Alagille syndrome.
2001 Feb 15
Involvement of acetyl phosphate in the in vivo activation of the response regulator ComA in Bacillus subtilis.
2001 Feb 20
Replacement of the axial histidine ligand with imidazole in cytochrome c peroxidase. 1. Effects on structure.
2001 Feb 6
Crystal structure of auracyanin, a "blue" copper protein from the green thermophilic photosynthetic bacterium Chloroflexus aurantiacus.
2001 Feb 9
The pagetoid variant of urothelial carcinoma in situ of urinary bladder in a cow.
2001 Jan
An amicyanin C-terminal loop mutant where the active-site histidine donor cannot be protonated.
2001 Jan
Rapid deposition of wheat cell wall structural proteins in response to Fusarium-derived elicitors.
2001 Jan
The effect of amino acid-modifying reagents on chloroplast protein import and the formation of early import intermediates.
2001 Jan
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
Proximal cysteine residue is essential for the enzymatic activities of cytochrome P450cam.
2001 Jan
Polyphyletic evolution of type II restriction enzymes revisited: two independent sources of second-hand folds revealed.
2001 Jan
In vitro removal of human IgG autoantibodies by affinity filtration using immobilized L-histidine onto PEVA hollow fiber membranes.
2001 Jan
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
Group A streptococcal growth phase-associated virulence factor regulation by a novel operon (Fas) with homologies to two-component-type regulators requires a small RNA molecule.
2001 Jan
Ischemic preconditioning with opening of mitochondrial adenosine triphosphate-sensitive potassium channels or Na/H exchange inhibition: which is the best protective strategy for heart transplants?
2001 Jan
Monoclonal antibody that binds to the central loop of the Tn10-encoded metal tetracycline/H+ antiporter of Escherichia coli.
2001 Jan
Regulation of a mammalian Shaker-related potassium channel, hKv1.5, by extracellular potassium and pH.
2001 Jan 12
Crystal structure of an enzyme-substrate complex provides insight into the interaction between human arylsulfatase A and its substrates during catalysis.
2001 Jan 12
Three pairs of cysteine residues mediate both redox and zn2+ modulation of the nmda receptor.
2001 Jan 15
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
Solution structure and dynamic character of the histidine-containing phosphotransfer domain of anaerobic sensor kinase ArcB from Escherichia coli.
2001 Jan 16
Expression and purification of polyhistidine-tagged firefly luciferase in insect cells--a potential alternative for process scale-up.
2001 Jan 23
Use of a Salmonella microsuspension bioassay to detect the mutagenicity of munitions compounds at low concentrations.
2001 Jan 25
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
Role of the conserved acidic residue Asp21 in the structure of phosphatidylinositol 3-kinase Src homology 3 domain: circular dichroism and nuclear magnetic resonance studies.
2001 Jan 9
Outer sphere mutations perturb metal reactivity in manganese superoxide dismutase.
2001 Jan 9
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
Translocation breakpoints in FHIT and FRA3B in both homologs of chromosome 3 in an esophageal adenocarcinoma.
2001 Mar
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
Role of two histidines in the (6-4) photolyase reaction.
2001 Mar 30
Ovarian tumor cells express a transmembrane serine protease: a potential candidate for early diagnosis and therapeutic intervention.
2001 Mar-Apr
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 15:26:39 GMT 2023
Edited
by admin
on Fri Dec 15 15:26:39 GMT 2023
Record UNII
X573657P6P
Record Status Validated (UNII)
Record Version
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Name Type Language
HISTIDINE MONOHYDROCHLORIDE MONOHYDRATE
Systematic Name English
HISTIDINE HYDROCHLORIDE MONOHYDRATE
EP  
Systematic Name English
L-Histidine Monohydrochloride [FCC]
Common Name English
L-Histidine Hydrochloride Hydrate [JAN]
Common Name English
L-HISTIDINE MONOHYDROCHLORIDE MONOHYDRATE [USP-RS]
Common Name English
HISTIDINE MONOHYDROCHLORIDE MONOHYDRATE, (-)-
Systematic Name English
HISTIDINE, L-, MONOHYDROCHLORIDE MONOHYDRATE
Common Name English
HISTIDINE HYDROCHLORIDE MONOHYDRATE [EP MONOGRAPH]
Common Name English
L-HISTIDINE, HYDROCHLORIDE, HYDRATE (1:1:1)
Systematic Name English
L-HISTIDINE MONOHYDROCHLORIDE MONOHYDRATE
USP-RS  
Systematic Name English
HISTIDINE, L-, HYDROCHLORIDE MONOHYDRATE
Systematic Name English
Code System Code Type Description
EVMPD
SUB22401
Created by admin on Fri Dec 15 15:26:39 GMT 2023 , Edited by admin on Fri Dec 15 15:26:39 GMT 2023
PRIMARY
PUBCHEM
165377
Created by admin on Fri Dec 15 15:26:39 GMT 2023 , Edited by admin on Fri Dec 15 15:26:39 GMT 2023
PRIMARY
EPA CompTox
DTXSID00208089
Created by admin on Fri Dec 15 15:26:39 GMT 2023 , Edited by admin on Fri Dec 15 15:26:39 GMT 2023
PRIMARY
RS_ITEM_NUM
1308550
Created by admin on Fri Dec 15 15:26:39 GMT 2023 , Edited by admin on Fri Dec 15 15:26:39 GMT 2023
PRIMARY
CAS
5934-29-2
Created by admin on Fri Dec 15 15:26:39 GMT 2023 , Edited by admin on Fri Dec 15 15:26:39 GMT 2023
PRIMARY
EVMPD
SUB12023MIG
Created by admin on Fri Dec 15 15:26:39 GMT 2023 , Edited by admin on Fri Dec 15 15:26:39 GMT 2023
PRIMARY
CAS
7048-02-4
Created by admin on Fri Dec 15 15:26:39 GMT 2023 , Edited by admin on Fri Dec 15 15:26:39 GMT 2023
NON-SPECIFIC STOICHIOMETRY
SMS_ID
100000091553
Created by admin on Fri Dec 15 15:26:39 GMT 2023 , Edited by admin on Fri Dec 15 15:26:39 GMT 2023
PRIMARY
NCI_THESAURUS
C87334
Created by admin on Fri Dec 15 15:26:39 GMT 2023 , Edited by admin on Fri Dec 15 15:26:39 GMT 2023
PRIMARY
FDA UNII
X573657P6P
Created by admin on Fri Dec 15 15:26:39 GMT 2023 , Edited by admin on Fri Dec 15 15:26:39 GMT 2023
PRIMARY
RXCUI
1305609
Created by admin on Fri Dec 15 15:26:39 GMT 2023 , Edited by admin on Fri Dec 15 15:26:39 GMT 2023
PRIMARY RxNorm
NCI_THESAURUS
C1505
Created by admin on Fri Dec 15 15:26:39 GMT 2023 , Edited by admin on Fri Dec 15 15:26:39 GMT 2023
CONCEPT Dietary Supplement
DRUG BANK
DBSALT002949
Created by admin on Fri Dec 15 15:26:39 GMT 2023 , Edited by admin on Fri Dec 15 15:26:39 GMT 2023
PRIMARY
DAILYMED
X573657P6P
Created by admin on Fri Dec 15 15:26:39 GMT 2023 , Edited by admin on Fri Dec 15 15:26:39 GMT 2023
PRIMARY
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