Page last updated: 2024-12-05

ethchlorvynol

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

Description

Ethchlorvynol: A sedative and hypnotic that has been used in the short-term management of INSOMNIA. Its use has been superseded by other drugs. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ethchlorvynol : Propargyl alcohol in which the methylene hydrogens are substituted by ethyl and 2-chlorovinyl groups. A hypnotic and sedative, it is used for treatment of insomnia in some cases where an intolerance or allergy to more commonly used drugs exists. [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 CID5281077
CHEMBL ID591
CHEBI ID4882
SCHEMBL ID113591
SCHEMBL ID113589
MeSH IDM0007824

Synonyms (96)

Synonym
ethchlorvinol
ethchlorovynol
serensil
ethyl .beta.-chlorovinyl ethynyl carbinol
etchlorvinolo
normoson
ethchlorvinyl
ethychlorvynol
nostel
serenil
placidyl
ethochlorvynol
aethyl-chlorvynol
arvynol
a 71
placidil
normonson
.beta.-chlorovinyl ethyl ethynyl carbinol
alvinol
nsc-30372
1-chloro-3-ethyl-1-penten-4-yn-3-ol
normosan
1-penten-4-yn-3-ol, 1-chloro-3-ethyl-
roeridorm
3-(.beta.-chlorovinyl)-1-pentyn-3-ol
5-chloro-3-ethylpent-1-yn-4-en-3-ol
ethclorvynol
etclorvinol [inn-spanish]
ethchlorvynolum [inn-latin]
1-chloro-3-ethylpent-1-4-yn-3-ol
ai3-23721
dea no. 2540
nsc 30372
hsdb 3079
brn 1702245
beta-chlorvinyl ethyl ethynyl carbinol
C07833
113-18-8
ethchlorvynol
beta-chlorovinyl ethyl ethynyl carbinol
1-chloro-3-ethyl-pent-1-en-4-yn-3-ol
DB00189
3-(beta-chlorovinyl)-1-pentyn-3-ol
ethyl beta-chlorovinyl ethynyl carbinol
D00704
placidyl (tn)
ethchlorvynol (jan/usp/inn)
CHEBI:4882 ,
ethchlorvynolum
etclorvinol
1-chloro-3-ethylpent-1-en-4-yn-3-ol
serenesil
CHEMBL591
ethchlorvynol civ
(e)-1-chloro-3-ethylpent-1-en-4-yn-3-ol
ethchlorvynol [usp:inn:ban]
6eim3851uz ,
unii-6eim3851uz
serensiloline
nromoson
AKOS015903758
1-penten-4-yn-3-ol, 1-chloro-3-ethyl-, (1e)-
ethchlorvynol [who-dd]
ethchlorvynol [usp monograph]
ethchlorvynol civ [usp-rs]
ethchlorvynol [hsdb]
ethchlorvynol [mi]
1135334-09-6
ethchlorvynol [vandf]
ethchlorvynol [inn]
ethchlorvynol [jan]
3-(.beta.-chlorvinyl)-1-pentyn-3-ol
ethchlorvynol [mart.]
ethchlorvynol [orange book]
gtpl7180
(1e)-1-chloro-3-ethylpent-1-en-4-yn-3-ol
SCHEMBL113591
SCHEMBL113589
dtxsid2023010 ,
tox21_113732
dtxcid30809588
cas-113-18-8
NCGC00253596-01
1-chloro-3-ethyl-1-penten-4-yn-3-ol #
ZEHYJZXQEQOSON-AATRIKPKSA-N
3-(beta-chlorvinyl)-1-pentyn-3-ol
Q3085140
ethchlorvynol (usp:inn:ban)
1-chloro-3-ethyl-1-penten-4-yl-3-ol
ethchlorvynol (mart.)
ethchlorvynolum (inn-latin)
etclorvinol (inn-spanish)
ethchlorvynol (usp monograph)
ethchlorvynol civ (usp-rs)
n05cm08
etclorvinolo

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
"0 liters, and half-life 78 hours."( Ethchlorvynol pharmacokinetics during long-term administration in a patient with hyperlipidemia and hypothyroidism.
Flueck, JA; Kolpek, JH; Marshall, ML; Parr, MD,
)
0.13

Compound-Compound Interactions

ExcerptReferenceRelevance
" This procedure discusses the details of detecting ethchlorvynol in combination with the entire array of drugs of abuse depending on the needs of a clinical program."( Qualitative detection of placidyl (ethchlorvynol) alone or in combination with poly-drugs in drug abuse urine screening programs using ion-exchange paper and/or liquid-liquid extraction.
Kaistha, KK; Tadrus, R, 1978
)
0.26

Dosage Studied

A titrimetric method is described for the determination of three acetylenic hypnotics. Bone marrow/blood ratios of ethchlorvynol as a function of time and dosage level were determined in 40 rabbits.

ExcerptRelevanceReference
" The dose-response seen with most of the parameters suggests that the changes are drug related."( Preliminary report on the effects of totigestational exposure to ethchlorvynol.
Hudson, PM; Peters, MA, 1977
)
0.26
" Due to many different pharmacokinetic properties, no perfect rules for dosage in acute or chronic hemodialysis exist."( Tranquilizers, analgetics and antidepressants in patients treated with hemodialysis.
Forycki, Z; Ibe, K; Martens, F; Thalhofer, S, 1985
)
0.27
"A titrimetric method is described for the determination of three acetylenic hypnotics, namely ethchlorvynol, ethinamate, and methylpentynol carbamate, in bulk and in dosage forms."( Titrimetric determination of acetylenic hyponotics using organic brominating agents.
Belal, F; el-Brashy, A; Rizk, M; Walash, MI, 1988
)
0.27
"Titrimetric and spectrophotometric titration methods are described for the quantitative determination of acetylenic hypnotics ethchlorvynol, ethinamate, and meparfynol carbamate as pure substances and in dosage forms."( Titrimetric and spectrophotometric determination of acetylenic hypnotics, using brominating agents.
el-Brashy, A; Rizk, MS; Walash, MI,
)
0.13
" Bone marrow/blood ratios of ethchlorvynol as a function of time and dosage level were determined in 40 rabbits."( A comparative study of ethchlorvynol levels in blood versus bone marrow.
Cibulas, W; Wahba, WW; Winek, CL,
)
0.13
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (63)

Assay IDTitleYearJournalArticle
AID1347407qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: primary screen against the NCATS Pharmaceutical Collection2020ACS chemical biology, 07-17, Volume: 15, Issue:7
High-Throughput Screening to Identify Inhibitors of the Type I Interferon-Major Histocompatibility Complex Class I Pathway in Skeletal Muscle.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1347107qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh30 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347103qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for OHS-50 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347098qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SK-N-SH cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1347102qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh18 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347105qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for MG 63 (6-TG R) cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347089qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for TC32 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347425Rhodamine-PBP qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1)2019The Journal of biological chemistry, 11-15, Volume: 294, Issue:46
Physiologically relevant orthogonal assays for the discovery of small-molecule modulators of WIP1 phosphatase in high-throughput screens.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1347091qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SJ-GBM2 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347095qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for NB-EBc1 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347108qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh41 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347100qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for LAN-5 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347104qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for RD cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347097qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Saos-2 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347099qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for NB1643 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347092qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for A673 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347106qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for control Hh wild type fibroblast cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347090qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for DAOY cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347093qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SK-N-MC cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347101qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for BT-12 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347424RapidFire Mass Spectrometry qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1)2019The Journal of biological chemistry, 11-15, Volume: 294, Issue:46
Physiologically relevant orthogonal assays for the discovery of small-molecule modulators of WIP1 phosphatase in high-throughput screens.
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347094qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for BT-37 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347096qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for U-2 OS cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID174696Percentage cytochrome P-450 loss from phenobarbital pretreated rats was measured in the presence of oxygen and NADPH after 10 min1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Alkylation of the prosthetic heme in cytochrome P-450 during oxidative metabolism of the sedative-hypnotic ethchlorvynol.
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID174697Percentage cytochrome P-450 loss from phenobarbital pretreated rats was measured in the presence of oxygen and NADPH after 20 min1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Alkylation of the prosthetic heme in cytochrome P-450 during oxidative metabolism of the sedative-hypnotic ethchlorvynol.
AID174699Percentage cytochrome P-450 loss from phenobarbital pretreated rats was measured in the presence of the Ethchlorvynol after 10 min; Not detectable1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Alkylation of the prosthetic heme in cytochrome P-450 during oxidative metabolism of the sedative-hypnotic ethchlorvynol.
AID174700Percentage cytochrome P-450 loss from phenobarbital pretreated rats was measured in the presence of the Ethchlorvynol after 20 min; Not detectable1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Alkylation of the prosthetic heme in cytochrome P-450 during oxidative metabolism of the sedative-hypnotic ethchlorvynol.
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID174704Percentage cytochrome P-450 loss from phenobarbital pretreated rats was measured in the presence of the NADPH after 30 min; Not detectable1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Alkylation of the prosthetic heme in cytochrome P-450 during oxidative metabolism of the sedative-hypnotic ethchlorvynol.
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID174702Percentage cytochrome P-450 loss from phenobarbital pretreated rats was measured in the presence of the NADPH after 10 min; Not detectable1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Alkylation of the prosthetic heme in cytochrome P-450 during oxidative metabolism of the sedative-hypnotic ethchlorvynol.
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID174698Percentage cytochrome P-450 loss from phenobarbital pretreated rats was measured in the presence of oxygen and NADPH after 30 min1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Alkylation of the prosthetic heme in cytochrome P-450 during oxidative metabolism of the sedative-hypnotic ethchlorvynol.
AID174703Percentage cytochrome P-450 loss from phenobarbital pretreated rats was measured in the presence of the NADPH after 20 min; Not detectable1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Alkylation of the prosthetic heme in cytochrome P-450 during oxidative metabolism of the sedative-hypnotic ethchlorvynol.
AID181016Heme loss from phenobarbital pretreated rats was measured in the presence of oxygen and NADPH after 20 min1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Alkylation of the prosthetic heme in cytochrome P-450 during oxidative metabolism of the sedative-hypnotic ethchlorvynol.
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID174701Percentage cytochrome P-450 loss from phenobarbital pretreated rats was measured in the presence of the Ethchlorvynol after 30 min; Not detectable1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Alkylation of the prosthetic heme in cytochrome P-450 during oxidative metabolism of the sedative-hypnotic ethchlorvynol.
AID588220Literature-mined public compounds from Kruhlak et al phospholipidosis modelling dataset2008Toxicology mechanisms and methods, , Volume: 18, Issue:2-3
Development of a phospholipidosis database and predictive quantitative structure-activity relationship (QSAR) models.
AID174705Percentage cytochrome P-450 loss from phenobarbital pretreated rats was measured in the presence of the oxygen after 20 min1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Alkylation of the prosthetic heme in cytochrome P-450 during oxidative metabolism of the sedative-hypnotic ethchlorvynol.
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID188456Cytochrome P-450 loss from phenobarbital pretreated rats was measured in the presence of oxygen and NADPH after 20 min1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Alkylation of the prosthetic heme in cytochrome P-450 during oxidative metabolism of the sedative-hypnotic ethchlorvynol.
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (229)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990207 (90.39)18.7374
1990's11 (4.80)18.2507
2000's3 (1.31)29.6817
2010's2 (0.87)24.3611
2020's6 (2.62)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 (%)
Trials6 (2.45%)5.53%
Reviews12 (4.90%)6.00%
Case Studies39 (15.92%)4.05%
Observational0 (0.00%)0.25%
Other188 (76.73%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]