Page last updated: 2024-11-11

s-allylcysteine

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

Description

S-allylcysteine: structure in first source; RN given refers to (L)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

S-allylcysteine : An S-hydrocarbyl-L-cysteine that is L-cysteine in which the hydrogen attached to the sulphur is replaced by a prop-2-enyl group. It commonly occurs in garlic and has been found to exhibit antineoplastic activity. [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 CID9793905
CHEMBL ID2048654
CHEBI ID74077
SCHEMBL ID119989
MeSH IDM0179599

Synonyms (56)

Synonym
AKOS002683883
AKOS015839120
s-allyl cysteine
nsc-96449
21593-77-1
ccris 7667
l-cysteine, s-2-propenyl-
s-allylcysteine
s-allyl-l-cysteine
(r)-allylthio-2-aminopropionic acid
s-prop-2-en-1-yl-l-cysteine
unii-81r3x99m15
81r3x99m15 ,
nsc 96449
s-allyl-laevo-cysteine
l-cysteine, s-2-propen-1-yl
AM20090195
(r)-3-(allylthio)-2-aminopropanoic acid
CHEMBL2048654
chebi:74077 ,
S4791
SCHEMBL119989
(r)-allylthio-2-aminopropanoic acid
(2r)-3-(allylthio)-2-aminopropanoic acid
(2r)-2-amino-3-(prop-2-en-1-ylsulfanyl) propanoic acid
s-allyl-l-cysteine [fhfi]
s-allyl-l-cysteine [usp-rs]
s-allylcysteine [inci]
l-cysteine, s-2-propen-1-yl-
alanine, 3-(allylthio)-, l-
deoxyalliin
s-allyl-l-cysteine (constituent of garlic) [dsc]
fema no. 4322
3-(allylthio)-l-alanine
s-(2-propenyl)-l-cysteine
(+)-s-allylcysteine
alanine, 3-(allylthio)-
ZFAHNWWNDFHPOH-YFKPBYRVSA-N
AC-31029
mfcd00151975
s-allyl-l-cysteine, united states pharmacopeia (usp) reference standard
s-allyl-l-cysteine, >=98% (hplc)
CS-W014289
HY-W013573
DS-3406
DTXSID20894862 ,
F10957
allyl-cysteine
I3L ,
(2r)-2-amino-3-prop-2-enylsulfanylpropanoic acid
Q7387047
CCG-266290
(r)-3-(allylthio)-2-aminopropanoicacid
s-allyl-l-cysteine (usp-rs)
s-allyl-l-cysteine (constituent of garlic)
dtxcid901324424

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" These results suggest that SAC research may ultimately lead to a resolution of the adverse effects of doxorubicin treatment in cancer chemotherapy."( S-allylcysteine ameliorates doxorubicin toxicity in the heart and liver in mice.
Mima, T; Mori, K; Mostafa, MG; Ohnishi, ST, 2000
)
1.75
" In the rat striatum, the SAC-induced activation of Nrf2 is likely to contribute to inhibit the toxic effects of 6-OHDA evidenced by phase 2 antioxidant enzymes up-regulation, glutathione recovery, and attenuation of reactive oxygen species (ROS), nitric oxide (NO), and lipid peroxides formation."( RETRACTED: S-allyl cysteine protects against 6-hydroxydopamine-induced neurotoxicity in the rat striatum: involvement of Nrf2 transcription factor activation and modulation of signaling kinase cascades.
Ali, SF; Cuadrado, A; Cuevas, E; González-Trujano, ME; Macías-Silva, M; Maldonado, PD; Pedraza-Chaverrí, J; Santamaría, A; Tobón-Velasco, JC; Vázquez-Victorio, G, 2012
)
0.38
" Recently, SAC has also been shown to induce neuroprotection in the rat striatum in a toxic model induced by 6-hydroxydopamine in rats through a concerted antioxidant response involving Nrf2 transcription factor nuclear transactivation and Phase 2 enzymes' upregulation."( S-allyl cysteine protects against MPTP-induced striatal and nigral oxidative neurotoxicity in mice: participation of Nrf2.
Colín-González, AL; Galván-Arzate, S; García, E; Heras, Y; Maldonado, PD; Santamaría, A; Santana-Martínez, R; Silva-Islas, CA; Sotelo, J, 2014
)
0.4

Pharmacokinetics

ExcerptReferenceRelevance
"The pharmacokinetic behavior of S-allylcysteine (SAC), one of the biologically active transformation products from garlic, was investigated after oral administration to rats, mice, and dogs."( Pharmacokinetics of the garlic compound S-allylcysteine.
Hatono, S; Higashi, Y; Imai, J; Itakura, Y; Kasuga, S; Matsuura, H; Nagae, S; Ushijima, M, 1994
)
0.84
" After being fully validated, the method was successfully applied to the pharmacokinetic monitoring of SAC in rat plasma."( Development and validation of S-allyl-L-cysteine in rat plasma using a mixed-mode reversed-phase and cation-exchange LC-ESI-MS/MS method: application to pharmacokinetic studies.
Chang, NI; Choi, JH; Lee, S; Shin, D; Yoo, M, 2015
)
0.42
"01 l/h/kg) of SAC indicated its extensive renal reabsorption, which contributed to the long elimination half-life of SAC, especially in dogs (12 hours)."( Metabolism, excretion, and pharmacokinetics of S-allyl-L-cysteine in rats and dogs.
Amano, H; Itoh, K; Kazamori, D; Kodera, Y, 2015
)
0.42

Compound-Compound Interactions

ExcerptReferenceRelevance
" These findings suggest that SAMC may be useful in colon cancer prevention when used alone or in combination with SS or other chemopreventive agents."( Antiproliferative effects of S-allylmercaptocysteine on colon cancer cells when tested alone or in combination with sulindac sulfide.
Delohery, T; Holt, PR; Kawabata, Y; Moss, SF; Murty, V; Pinto, JT; Rivlin, RS; Shirin, H; Soh, JW; Weinstein, IB, 2001
)
0.31

Bioavailability

ExcerptReferenceRelevance
" The bioavailability was 98."( Pharmacokinetics of the garlic compound S-allylcysteine.
Hatono, S; Higashi, Y; Imai, J; Itakura, Y; Kasuga, S; Matsuura, H; Nagae, S; Ushijima, M, 1994
)
0.56
" SAC was well absorbed (bioavailability >90%) and its four metabolites-N-acetyl-S-allyl-l-cysteine (NAc-SAC), N-acetyl-S-allyl-l-cysteine sulfoxide (NAc-SACS), S-allyl-l-cysteine sulfoxide (SACS), and l-γ-glutamyl-S-allyl-l-cysteine-were identified in the plasma and/or urine."( Metabolism, excretion, and pharmacokinetics of S-allyl-L-cysteine in rats and dogs.
Amano, H; Itoh, K; Kazamori, D; Kodera, Y, 2015
)
0.42
"After oral administration, SAC was well absorbed with a bioavailability of 98%."( Pharmacokinetics of S-Allyl-l-cysteine in Rats Is Characterized by High Oral Absorption and Extensive Renal Reabsorption.
Amano, H; Itoh, K; Kazamori, D, 2016
)
0.43

Dosage Studied

ExcerptRelevanceReference
"A total of 79 general practice patients with uncontrolled systolic hypertension participated in a double-blind randomised placebo-controlled dose-response trial of 12 weeks."( Aged garlic extract reduces blood pressure in hypertensives: a dose-response trial.
Frank, OR; Ried, K; Stocks, NP, 2013
)
0.39
" However, these preventive effects of SAC were dependent on dosage of SAC; higher dose above 10 μM paradoxically aggravated NSAID-induced inflammation."( S-allyl cysteine alleviates nonsteroidal anti-inflammatory drug-induced gastric mucosal damages by increasing cyclooxygenase-2 inhibition, heme oxygenase-1 induction, and histone deacetylation inhibition.
Hahm, KB; Han, YM; Jung, MK; Kangwan, N; Kim, EH; Lee, SY; Park, JM, 2014
)
0.4
" The Cr (VI)-induced rats were treated with 100 mg/kg body weight of SAC as an optimum dosage to treat hepatotoxicity."( S-Allyl cysteine alleviates inflammation by modulating the expression of NF-κB during chromium (VI)-induced hepatotoxicity in rats.
Anandasadagopan, SK; Ganapasam, S; Nagarajan, V; Pandurangan, AK; Srinivasan, K; Sundaramoorthy, C, 2017
)
0.46
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
[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
L-alpha-amino acid zwitterionZwitterionic form of an L-alpha-amino acid having an anionic carboxy group and a protonated amino group.
S-hydrocarbyl-L-cysteine
[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]

Bioassays (3)

Assay IDTitleYearJournalArticle
AID1599998Antagonist activity at TLR2 in mouse RAW264.7 cells assessed as PAM3CSK4-induced NO production at 150 uM measured after 24 hrs by Griess assay2019European journal of medicinal chemistry, Oct-01, Volume: 179Structure-activity relationship study and biological evaluation of SAC-Garlic acid conjugates as novel anti-inflammatory agents.
AID1599996Inhibition of TLR2 in human HEK-Blue hTLR2 cells assessed as suppression of PAM3CSK4-induced SEAP signaling after 24 hrs by quanti-blue assay2019European journal of medicinal chemistry, Oct-01, Volume: 179Structure-activity relationship study and biological evaluation of SAC-Garlic acid conjugates as novel anti-inflammatory agents.
AID670330Inhibition of human ENaC alpha-beta-gamma expressed in Xenopus laevis oocytes assessed as effect on transmembrane currents at 1 mM by two-electrode voltage-clamp technique2012Bioorganic & medicinal chemistry, Jul-01, Volume: 20, Issue:13
Thiol-reactive compounds from garlic inhibit the epithelial sodium channel (ENaC).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (234)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (0.43)18.7374
1990's22 (9.40)18.2507
2000's81 (34.62)29.6817
2010's98 (41.88)24.3611
2020's32 (13.68)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 32.74

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index32.74 (24.57)
Research Supply Index5.49 (2.92)
Research Growth Index6.23 (4.65)
Search Engine Demand Index64.21 (26.88)
Search Engine Supply Index3.12 (0.95)

This Compound (32.74)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (0.41%)5.53%
Reviews10 (4.15%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other230 (95.44%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]