Page last updated: 2024-11-06

homocarnosine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth

Description

homocarnosine: RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

homocarnosine : A histidine derivative that is histidine in which one of the hydrogens attached to the alpha-amino group has been replaced by a 4-aminobutanoyl group. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID10243361
CHEMBL ID243618
CHEBI ID85981
SCHEMBL ID541261
MeSH IDM0046319

Synonyms (39)

Synonym
.gamma.-aminobutyryl-l-histidine
.gamma.-aminobutyrylhistidine
nsc-92522
C00884
gamma-aminobutyryl histidine
3650-73-5
homocarnosine
n-(4-amino-1-oxobutyryl)histidine
CHEMBL243618
gamma-aminobutyrilhistidine
chebi:85981 ,
n-(4-aminobutyryl)-l-histidine
histidine, n-(4-aminobutyryl)-, l-
gamma-aminobutyryl-l-histidine
m8l4bh36sc ,
AKOS010421285
SCHEMBL541261
(s)-2-(4-aminobutanamido)-3-(1h-imidazol-4-yl)propanoic acid
n(alpha)-(4-aminobutyryl)-l-histidine
n-(4-aminobutanoyl)-l-histidine
(s)-homocarnosine
(2s)-homocarnosine
n-(4-aminobutanoyl)-(s)-histidine
gamma-aminobutyryl-l-his
CCLQKVKJOGVQLU-QMMMGPOBSA-N
n-(4-aminobutanoyl)histidine #
(2s)-2-(4-aminobutanamido)-3-(1h-imidazol-4-yl)propanoic acid
g-aminobutyryl-l-histidine
n-(4-aminobutyryl)-histidine
Q27158831
l-homocarnosine free base
n-(4-amino-1-hydroxybutylidene)histidine
DTXSID50942461
(4-aminobutanoyl)-l-histidine
n-(4-amino-1-oxobutyl)-l-histidine
HY-114883
CS-0064557
EN300-172451
AKOS040752034

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Toxic effects of the peptide were seen at 200 microg/ml A beta using a mitochondrial dehydrogenase activity (MTT) reduction assay, lactate dehydrogenase release and glucose consumption."( Toxic effects of beta-amyloid(25-35) on immortalised rat brain endothelial cell: protection by carnosine, homocarnosine and beta-alanine.
Abbott, JN; Himsworth, DT; Hipkiss, AR; Preston, JE; Romero, IA, 1998
)
0.3

Dosage Studied

ExcerptRelevanceReference
" Lumbar punctures were carried out prior to treatment and at the end of each dosage regimen and cerebrospinal fluid (CSF) evaluated for concentrations of free and total GABA, homocarnosine (GABA-histidine dipeptide), homovanillic acid (HVA), 5-hydroxyindole acetic acid (5-HIAA) and vigabatrin."( The effect of different vigabatrin treatment regimens on CSF biochemistry and seizure control in epileptic patients.
Ben-Menachem, E; Dahlgren, L; Haegele, KD; Hardenberg, J; Huebert, N; Mumford, JP; Persson, LI; Schechter, PJ, 1989
)
0.28
"645), a potent irreversible inhibitor of gamma-aminobutyric acid transaminase, was given orally in various dosage schedules to 14 patients with Huntington disease."( Treatment of Huntington disease with gamma-acetylenic GABA an irreversible inhibitor of GABA-transaminase: increased CSF GABA and homocarnosine without clinical amelioration.
Agid, Y; Böhlen, P; Bonnet, AM; Chazot, G; Coquillat, G; Fischer, C; Koch-Weser, J; Schechter, PJ; Tell, G, 1981
)
0.26
" Once-a-day dosing is sufficient to increase GABA."( Acute effects of vigabatrin on brain GABA and homocarnosine in patients with complex partial seizures.
Collins, T; Hyder, F; Mattson, RH; Petroff, OA; Rothman, DL, 1999
)
0.3
" We reported that daily dosing increased brain gamma-aminobutyric acid (GABA) in patients with epilepsy."( Effects of gabapentin on brain GABA, homocarnosine, and pyrrolidinone in epilepsy patients.
Hyder, F; Mattson, RH; Petroff, OA; Rothman, DL, 2000
)
0.31
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
human metaboliteAny mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (6)

ClassDescription
N-acyl-L-alpha-amino acid anionA carboxylic acid anion that is the conjugate base of an N-acyl-L-alpha-amino acid arising from deprotonation of the C-1 carboxy group.
dipeptide zwitterionAny peptide zwitterion comprising two amino acid residues. Major structure at pH 7.3.
homocarnosineA histidine derivative that is histidine in which one of the hydrogens attached to the alpha-amino group has been replaced by a 4-aminobutanoyl group.
N-acyl-L-alpha-amino acidAny L-alpha-amino acid carrying an N-acyl substituent.
L-histidine derivativeA proteinogenic amino acid derivative resulting from the formal reaction of L-histidine at the amino group, carboxy group, or the imidazolyl moiety, or from the replacement of any hydrogen of L-histidine by a heteroatom.
dipeptideAny molecule that contains two amino-acid residues connected by peptide linkages.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (2)

PathwayProteinsCompounds
Inner Membrane Transport7862
GABA metabolism (aka GHB)1128

Bioassays (15)

Assay IDTitleYearJournalArticle
AID294864Effect on copper-induced human LDL peroxidation assessed as inhibition of malonaldehyde production at 100 uM after 4 hrs2007European journal of medicinal chemistry, Jul, Volume: 42, Issue:7
Synthesis and antioxidant activity of new homocarnosine beta-cyclodextrin conjugates.
AID294885Protective effect on copper-induced LDL oxidation at 1:2.5 copper to drug ratio relative to 40 uM copper2007European journal of medicinal chemistry, Jul, Volume: 42, Issue:7
Synthesis and antioxidant activity of new homocarnosine beta-cyclodextrin conjugates.
AID294883Protective effect on copper-induced LDL oxidation at 2:1 copper to drug ratio relative to 40 uM copper2007European journal of medicinal chemistry, Jul, Volume: 42, Issue:7
Synthesis and antioxidant activity of new homocarnosine beta-cyclodextrin conjugates.
AID294859Effect on copper-induced human LDL peroxidation assessed as inhibition of malonaldehyde production at 2 uM after 4 hrs2007European journal of medicinal chemistry, Jul, Volume: 42, Issue:7
Synthesis and antioxidant activity of new homocarnosine beta-cyclodextrin conjugates.
AID294886Protective effect on copper-induced LDL oxidation at 1:5 copper to drug ratio relative to 40 uM copper2007European journal of medicinal chemistry, Jul, Volume: 42, Issue:7
Synthesis and antioxidant activity of new homocarnosine beta-cyclodextrin conjugates.
AID294880Protective effect on copper-induced LDL oxidation at 20:1 copper to drug ratio relative to 40 uM copper2007European journal of medicinal chemistry, Jul, Volume: 42, Issue:7
Synthesis and antioxidant activity of new homocarnosine beta-cyclodextrin conjugates.
AID294862Effect on copper-induced human LDL peroxidation assessed as inhibition of malonaldehyde production at 20 uM after 4 hrs2007European journal of medicinal chemistry, Jul, Volume: 42, Issue:7
Synthesis and antioxidant activity of new homocarnosine beta-cyclodextrin conjugates.
AID294865Effect on copper-induced human LDL peroxidation assessed as inhibition of malonaldehyde production at 200 uM after 4 hrs2007European journal of medicinal chemistry, Jul, Volume: 42, Issue:7
Synthesis and antioxidant activity of new homocarnosine beta-cyclodextrin conjugates.
AID294860Effect on copper-induced human LDL peroxidation assessed as inhibition of malonaldehyde production at 5 uM after 4 hrs2007European journal of medicinal chemistry, Jul, Volume: 42, Issue:7
Synthesis and antioxidant activity of new homocarnosine beta-cyclodextrin conjugates.
AID294863Effect on copper-induced human LDL peroxidation assessed as inhibition of malonaldehyde production at 50 uM after 4 hrs2007European journal of medicinal chemistry, Jul, Volume: 42, Issue:7
Synthesis and antioxidant activity of new homocarnosine beta-cyclodextrin conjugates.
AID294884Protective effect on copper-induced LDL oxidation at 1:1.25 copper to drug ratio relative to 40 uM copper2007European journal of medicinal chemistry, Jul, Volume: 42, Issue:7
Synthesis and antioxidant activity of new homocarnosine beta-cyclodextrin conjugates.
AID294881Protective effect on copper-induced LDL oxidation at 8:1 copper to drug ratio relative to 40 uM copper2007European journal of medicinal chemistry, Jul, Volume: 42, Issue:7
Synthesis and antioxidant activity of new homocarnosine beta-cyclodextrin conjugates.
AID294861Effect on copper-induced human LDL peroxidation assessed as inhibition of malonaldehyde production at 10 uM after 4 hrs2007European journal of medicinal chemistry, Jul, Volume: 42, Issue:7
Synthesis and antioxidant activity of new homocarnosine beta-cyclodextrin conjugates.
AID500816Inhibition of nitrogen-starved wild type sigma1278b yeast Gap1-mediated amino acid uptake at 5 mM after 60 secs relative to L-citrulline2009Nature chemical biology, Jan, Volume: 5, Issue:1
Transport and signaling via the amino acid binding site of the yeast Gap1 amino acid transceptor.
AID294882Protective effect on copper-induced LDL oxidation at 4:1 copper to drug ratio relative to 40 uM copper2007European journal of medicinal chemistry, Jul, Volume: 42, Issue:7
Synthesis and antioxidant activity of new homocarnosine beta-cyclodextrin conjugates.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (138)

TimeframeStudies, This Drug (%)All Drugs %
pre-199052 (37.68)18.7374
1990's32 (23.19)18.2507
2000's33 (23.91)29.6817
2010's16 (11.59)24.3611
2020's5 (3.62)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials5 (3.18%)5.53%
Reviews8 (5.10%)6.00%
Case Studies5 (3.18%)4.05%
Observational0 (0.00%)0.25%
Other139 (88.54%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]