Page last updated: 2024-11-05

homocystine

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

Homocystine is an amino acid that is produced when the body breaks down methionine, an essential amino acid. Elevated levels of homocystine in the blood can be a sign of a genetic disorder called homocystinuria, or it can be caused by a lack of certain vitamins, such as folate, vitamin B6, and vitamin B12. Homocystine can damage blood vessels, increase the risk of blood clots, and contribute to heart disease, stroke, and other health problems. High levels of homocystine have also been linked to an increased risk of Alzheimer's disease and other neurodegenerative diseases. Homocystine is studied because it is a potential biomarker for cardiovascular disease and other health problems. Understanding the role of homocystine in these diseases could lead to new ways to prevent and treat them.'

Cross-References

ID SourceID
PubMed CID10010
CHEMBL ID212056
CHEBI ID17485
SCHEMBL ID224295
MeSH IDM0010515

Synonyms (64)

Synonym
2-amino-4-[(3-amino-3-carboxypropyl)disulfanyl]butanoic acid
4,4'-disulfanediylbis(2-aminobutanoic acid)
CHEBI:17485 ,
nsc43122
butanoic acid, 4,4'-dithiobis(2-amino-, (r*,r*)-(.+-.)-
2-amino-4-[(3-amino-4-hydroxy-4-oxo-butyl)disulfanyl]butanoic acid
butyric acid,4'-dithiobis[2-amino-, dl-
870-93-9
nsc226570
butanoic acid,4'-dithiobis[2-amino-, (r*,r*)-(.+-.)-
dl-homocystine
nsc11337
462-10-2
4,4'-dithiobis[2-aminobutyric acid]
butanoic acid,4'-dithiobis[2-amino-
butyric acid,4'-dithiobis[2-amino-
nsc206271
homocystine ,
H-3000
3C9F56DF-A143-4F06-81E2-50796E255EEB
CHEMBL212056
4,4'-disulfanediylbis(2-ammoniobutanoate)
FT-0650690
H0160
l-4,4'-dithio-bis(2-aminobutanoic acid)
3-[2-[3-[(2,4-dihydroxy-3,3-dimethyl-butanoyl)amino]propanoylamino]ethylsulfanyl]-7-oxo-6-(1-sulfooxyethyl)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid;dl-homocystine
A841949
butanoic acid, 4,4'-dithiobis(2-amino)-
butanoic acid, 4,4'-dithiobis(2-amino-
4,4'-dithiobis(2-aminobutyric) acid
4,4'-dithiobis(2-aminobutyric acid)
butyric acid, 4,4'-dithiobis(2-amino-
einecs 207-323-8
A827010
c8h16n2o4s2
FT-0627631
FT-0625472
AKOS009157442
SCHEMBL224295
butanoic acid, 4,4'-dithiobis[2-amino-, (2r,2'r)-rel-
octafluoroadipicacid
4,4'-dithiobis
C20788
ZTVZLYBCZNMWCF-UHFFFAOYSA-N
butanoic acid, 4,4'-dithiobis[2-amino-
mfcd00063095
mfcd00020391
homocystin
dl-homocystine (3,3,3',3',4,4,4',4'-d8)
DS-9173
Q58879461
HY-W009390A
FT-0770473
AMY25800
CS-0031479
(h-homocys-oh)
4,4'-disulfanediylbis(2-aminobutanoicacid)
EN300-52797
SY026490
(rs)-homocystine
DTXSID90861945
Z759968104
SY112616
4,4 inverted exclamation mark -disulfanediylbis(2-aminobutanoic acid)

Research Excerpts

Treatment

ExcerptReferenceRelevance
"Homocystine treatment did not cause significant alterations in CBS levels (P=0.992)."( Increasing levels of dietary homocystine with carotid endarterectomy produced proportionate increases in plasma homocysteine and intimal hyperplasia.
Brown, AT; Cruz, C; Drouilhet, J; Eidt, J; Moursi, MM; Mukunyadzi, P; Poirier, LA; Southern, F; Wang, YF; Williams, DK, 2001
)
1.32

Toxicity

ExcerptReferenceRelevance
"5 rat embryos L-homocysteine was not toxic at 1- and 2-mM concentrations."( Prevention of neural tube defects by and toxicity of L-homocysteine in cultured postimplantation rat embryos.
Blom, HJ; Copius Peereboom-Stegeman, JH; Deabreu, RA; Eskes, TK; Noordhoek, J; Trijbels, FJ; Vanaerts, LA, 1994
)
0.29
" Hcy is directly toxic to vascular endothelium and it and its metabolites are excitatory agonists of the N-methyl-D-aspartate (NMDA) receptor."( Dextromethorphan is effective in the treatment of subacute methotrexate neurotoxicity.
Aisner, J; Cole, PD; Drachtman, RA; Golden, CB; James, SJ; Kamen, BA; Melnyk, S,
)
0.13
" The addition of homocysteinic acid in a nontoxic concentration of 100 microM potentiated the toxic effect of NMDA and led to massive cell death."( Homocysteinic acid causes oxidative stress in lymphocytes by potentiating toxic effect of NMDA.
Boldyrev, AA, 2005
)
0.33

Bioavailability

ExcerptReferenceRelevance
"These data indicate that hyperhomocyst(e)inemia is associated with impaired endothelium-dependent vasodilation in humans and suggest that the bioavailability of nitric oxide is decreased in hyperhomocyst(e)inemic humans."( Hyperhomocyst(e)inemia is associated with impaired endothelium-dependent vasodilation in humans.
Creager, MA; Gerhard, M; Omland, T; Tawakol, A; Wu, JT, 1997
)
0.3

Dosage Studied

ExcerptRelevanceReference
" From reviews of metabolite values in blood samples either fasting (11 articles) or after a methionine load (8 articles), and of measures of enzyme activity (12 articles), it is apparent that (1) The heterozygous phenotype cannot be identified consistently by any single measure (there is overlap with normal values); and (2) the exaggerated gene dosage effect (negative allelic complementation) present in most heterozygotes does not assist their classification."( Detection of heterozygotes for recessive alleles. Homocyst(e)inemia: paradigm of pitfalls in phenotypes.
McGill, JJ; Mettler, G; Rosenblatt, DS; Scriver, CR, 1990
)
0.28
" We also tested the influence of folic acid dosage (5 mg OD) on the levels of homocysteine and the allied vitamin supplements, vitamin B12 and folate in smaller groups selected from the larger group."( Homocystine levels, polymorphisms and the risk of ischemic stroke in young Asian Indians.
Akhter, MS; Behari, M; Biswas, A; Meena, A; Munisamy, M; Ranjan, R; Saxena, R; Subbiah, V; Yadav, BK,
)
1.57
" There was an almost total response to folic acid dosage as all hyperhomocysteinemic patients showed lowering of homocysteine levels in response to the dosage."( Homocystine levels, polymorphisms and the risk of ischemic stroke in young Asian Indians.
Akhter, MS; Behari, M; Biswas, A; Meena, A; Munisamy, M; Ranjan, R; Saxena, R; Subbiah, V; Yadav, BK,
)
1.57
[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).
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 (2)

ClassDescription
homocystinesA non-proteinogenic alpha-amino acid obtained by oxidative dimerisation of homocysteine and its derivatives.
amino acid zwitterionThe zwitterionic form of an amino acid having a negatively charged carboxyl group and a positively charged amino group.
[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 (1)

PathwayProteinsCompounds
One-carbon metabolism013

Bioassays (4)

Assay IDTitleYearJournalArticle
AID266697Inhibition of human BHMT at 20 uM2006Journal of medicinal chemistry, Jun-29, Volume: 49, Issue:13
S-alkylated homocysteine derivatives: new inhibitors of human betaine-homocysteine S-methyltransferase.
AID266698Inhibition of human BHMT at 1 uM2006Journal of medicinal chemistry, Jun-29, Volume: 49, Issue:13
S-alkylated homocysteine derivatives: new inhibitors of human betaine-homocysteine S-methyltransferase.
AID1147029Detoxification of acetaldehyde in aldehyde dehydrogenase inhibitor disuifiram/ethanol-treated rat assessed as reduction of blood acetaldehyde level at 8 mmol/kg, po administered 24 hrs prior to ethanol treatment measured after 1 hr by head space gas chrom1978Journal of medicinal chemistry, Dec, Volume: 21, Issue:12
2,5,5-Trimethylthiazolidine-4-carboxylic acid, a D(-)-penicillamine-directed pseudometabolite of ethanol. Detoxication mechanism for acetaldehyde.
AID266699Inhibition of human BHMT2006Journal of medicinal chemistry, Jun-29, Volume: 49, Issue:13
S-alkylated homocysteine derivatives: new inhibitors of human betaine-homocysteine S-methyltransferase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (501)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990232 (46.31)18.7374
1990's81 (16.17)18.2507
2000's153 (30.54)29.6817
2010's30 (5.99)24.3611
2020's5 (1.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 102.39

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index102.39 (24.57)
Research Supply Index6.30 (2.92)
Research Growth Index4.34 (4.65)
Search Engine Demand Index186.56 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (102.39)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials22 (4.21%)5.53%
Reviews46 (8.81%)6.00%
Case Studies32 (6.13%)4.05%
Observational0 (0.00%)0.25%
Other422 (80.84%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]