HISTIDINE

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

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	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

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	Substrate 661

Conditions

Condition	Modality	Highest Phase	Product
Burn 40	Primary	Approved 8,429	FreAmine III
Cholera 7	Primary	Not Provided 504	Unknown
Menkes disease 5	Primary	Phase III 656	Unknown
Histidyl-tRNA synthetase deficiency 5	Primary	Phase I 428	Unknown
Rheumatoid arthritis 316	Primary	Not Provided 504	Unknown

PubMed

Show entries

Title	Date	PubMed
L-amino acid sensing by the extracellular Ca2+-sensing receptor.	2000 Apr 25	10781086
Disruption of an active site hydrogen bond converts human heme oxygenase-1 into a peroxidase.	2001 Apr 6	11121422
Genetic and transcriptional analysis of absA, an antibiotic gene cluster-linked two-component system that regulates multiple antibiotics in Streptomyces coelicolor.	2001 Feb	11169098
Active site characterization of the single endo-polygalacturonase produced by Fusarium moniliforme NCIM 1276.	2001 Feb	11168425
Purification and kinetic characterization of CTP:phosphocholine cytidylyltransferase from Saccharomyces cerevisiae.	2001 Feb	11162399

Showing 1 to 5 of 26 entries

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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.