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

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 5.4431998E10
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
Disruption of an active site hydrogen bond converts human heme oxygenase-1 into a peroxidase.	2001 Apr 6	11121422
Three-dimensional structure of the histidine-containing phosphocarrier protein (HPr) from Enterococcus faecalis in solution.	2001 Feb	11168402
Refolding and purification of Bothropstoxin-I, a Lys49-phospholipase A2 homologue, expressed as inclusion bodies in Escherichia coli.	2001 Feb	11162398
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	11160624
DNA-protein crosslinks induced by nickel compounds in isolated rat lymphocytes: role of reactive oxygen species and specific amino acids.	2001 Feb 1	11162780
Involvement of acetyl phosphate in the in vivo activation of the response regulator ComA in Bacillus subtilis.	2001 Feb 20	11179649
CCME, a nuclear-encoded heme-binding protein involved in cytochrome c maturation in plant mitochondria.	2001 Feb 23	11069919
The pagetoid variant of urothelial carcinoma in situ of urinary bladder in a cow.	2001 Jan	11199158
Rapid deposition of wheat cell wall structural proteins in response to Fusarium-derived elicitors.	2001 Jan	11181716
Proximal cysteine residue is essential for the enzymatic activities of cytochrome P450cam.	2001 Jan	11168358
In vitro removal of human IgG autoantibodies by affinity filtration using immobilized L-histidine onto PEVA hollow fiber membranes.	2001 Jan	11163754
Multiple regions with allelic loss at chromosome 3 in superficial multifocal bladder tumors.	2001 Jan	11115560
Regulation of a mammalian Shaker-related potassium channel, hKv1.5, by extracellular potassium and pH.	2001 Jan 12	11163793
Structures of prolyl oligopeptidase substrate/inhibitor complexes. Use of inhibitor binding for titration of the catalytic histidine residue.	2001 Jan 12	11031266
Expression and purification of polyhistidine-tagged firefly luciferase in insect cells--a potential alternative for process scale-up.	2001 Jan 23	11164962
The role of histidine 632 in catalysis by human topoisomerase I.	2001 Jan 5	11024057
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
Quaternary structure of rice nonsymbiotic hemoglobin.	2001 Mar 2	11106662
Redox properties and coordination structure of the heme in the co-sensing transcriptional activator CooA.	2001 Mar 9	11096066
The two major plant plasma membrane H+-ATPases display different regulatory properties.	2001 Mar 9	11080498

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.

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