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Identification
- Summary
Ethchlorvynol is a sedative hypnotic agent used for the short-term management of insomnia.
- Generic Name
- Ethchlorvynol
- DrugBank Accession Number
- DB00189
- Background
Ethchlorvynol is a sedative and hypnotic drug. It has been used to treat insomnia, but has been largely superseded and is only offered where an intolerance or allergy to other drugs exists.
- Type
- Small Molecule
- Groups
- Approved, Illicit, Withdrawn
- Structure
Structure for Ethchlorvynol (DB00189)
- Weight
- Average: 144.6
Monoisotopic: 144.0341926 - Chemical Formula
- C7H9ClO
- Synonyms
- 1-chloro-3-ethyl-1-penten-4-yn-3-ol
- 1-Chloro-3-ethyl-pent-1-en-4-yn-3-ol
- 3-(beta-chlorovinyl)-1-pentyn-3-ol
- 3-(β-chlorovinyl)-1-pentyn-3-ol
- etclorvinol
- Ethchlorvynol
- ethyl β-chlorovinyl ethynyl carbinol
- β-chlorovinyl ethyl ethynyl carbinol
Pharmacology
- Indication
Used for short-term hypnotic therapy in the management of insomnia for periods of up to one week in duration; however, this medication generally has been replaced by other sedative-hypnotic agents.
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Ethchlorvynol is a sedative drug and schedule IV (USA) controlled substance. It produces cerebral depression, however the exact mechanism of action is not known.
- Mechanism of action
Although the exact mechanism of action is unknown, ethchlorvynol appears to depress the central nervous system in a manner similar to that of barbiturates. Barbiturates bind at a distinct binding sites associated with a Cl- ionopore at the GABAA receptor, increasing the duration of time for which the Cl- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged.
Target Actions Organism AGamma-aminobutyric acid receptor subunit beta-2 antagonistHumans AGamma-aminobutyric acid receptor subunit alpha-1 antagonistHumans AGABA(A) Receptor positive allosteric modulatorHumans - Absorption
Rapidly absorbed from gastrointestinal tract.
- Volume of distribution
Not Available
- Protein binding
35-50%
- Metabolism
About 90% of a dose is metabolized in the liver. Some ethchlorvynol may also be metabolized in the kidneys. Ethchlorvynol and metabolites undergo extensive enterohepatic recirculation.
- Route of elimination
Not Available
- Half-life
Plasma half-life is approximately 10 to 20 hours, terminal half-life is 21-100 hours.
- Clearance
Not Available
- Adverse Effects
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Symptoms of overdose include thrombocytopenia.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Ethchlorvynol is combined with 1,2-Benzodiazepine. Acetazolamide The risk or severity of CNS depression can be increased when Ethchlorvynol is combined with Acetazolamide. Acetophenazine The risk or severity of CNS depression can be increased when Ethchlorvynol is combined with Acetophenazine. Agomelatine The risk or severity of CNS depression can be increased when Ethchlorvynol is combined with Agomelatine. Alfentanil The risk or severity of CNS depression can be increased when Ethchlorvynol is combined with Alfentanil. - Food Interactions
- Avoid alcohol.
- Take with food. Food reduces irritation.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Arvynol (Pfizer) / Nostel (Dainippon) / Placidyl (Abbott) / Roeridorm (Pfizer-Roerig) / Serenesil (Abbott)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Placidyl Cap 200mg Capsule 200 mg Oral Abbott 1956-12-31 2008-06-10 Canada 
Placidyl Cap 500mg Capsule 500 mg Oral Abbott 1952-12-31 2008-06-06 Canada Placidyl Cap 750mg Capsule 750 mg Oral Abbott 1971-12-31 2008-06-06 Canada
Categories
- ATC Codes
- N05CM08 — Ethchlorvynol
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as ynones. These are organic compounds containing the ynone functional group, an alpha,beta unsaturated ketone group with the general structure RC#C-C(=O)R' (R' not H).
- Kingdom
- Organic compounds
- Super Class
- Organic oxygen compounds
- Class
- Organooxygen compounds
- Sub Class
- Carbonyl compounds
- Direct Parent
- Ynones
- Alternative Parents
- Tertiary alcohols / Vinyl chlorides / Chloroalkenes / Acetylides / Organochlorides / Hydrocarbon derivatives
- Substituents
- Acetylide / Alcohol / Aliphatic acyclic compound / Chloroalkene / Haloalkene / Hydrocarbon derivative / Organochloride / Organohalogen compound / Tertiary alcohol / Vinyl chloride
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 6EIM3851UZ
- CAS number
- 113-18-8
- InChI Key
- ZEHYJZXQEQOSON-AATRIKPKSA-N
- InChI
- InChI=1S/C7H9ClO/c1-3-7(9,4-2)5-6-8/h1,5-6,9H,4H2,2H3/b6-5+
- IUPAC Name
- (1E)-1-chloro-3-ethylpent-1-en-4-yn-3-ol
- SMILES
- CCC(O)(\C=C\Cl)C#C
References
- Synthesis Reference
Bayley, A. and McLamore, W.M.; U.S. Patent 2,746,900; May 22,1956; assigned to Chas. Pfizer & Co., Inc.
- General References
- Not Available
- External Links
- KEGG Drug
- D00704
- KEGG Compound
- C07833
- PubChem Compound
- 5281077
- PubChem Substance
- 46505006
- ChemSpider
- 4444534
- 4118
- ChEBI
- 4882
- ChEMBL
- CHEMBL591
- Therapeutic Targets Database
- DAP000163
- PharmGKB
- PA164746383
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Ethchlorvynol
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Banner pharmacaps inc
- Abbott laboratories pharmaceutical products div
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Capsule Oral 200 mg Capsule Oral 500 mg Capsule Oral 750 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Liquid
- Experimental Properties
Property Value Source boiling point (°C) 28.5-30 Bayley, A. and McLamore, W.M.; U.S. Patent 2,746,900; May 22,1956; assigned to Chas. Pfizer & Co., Inc. logP 1.8 Not Available - Predicted Properties
Property Value Source Water Solubility 0.143 mg/mL ALOGPS logP 1.45 ALOGPS logP 1.62 Chemaxon logS -3 ALOGPS pKa (Strongest Acidic) 12.88 Chemaxon pKa (Strongest Basic) -3.7 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 20.23 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 38.64 m3·mol-1 Chemaxon Polarizability 14.77 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9965 Blood Brain Barrier + 0.9685 Caco-2 permeable + 0.646 P-glycoprotein substrate Non-substrate 0.743 P-glycoprotein inhibitor I Non-inhibitor 0.9023 P-glycoprotein inhibitor II Non-inhibitor 0.9672 Renal organic cation transporter Non-inhibitor 0.9589 CYP450 2C9 substrate Non-substrate 0.7267 CYP450 2D6 substrate Non-substrate 0.9 CYP450 3A4 substrate Non-substrate 0.6176 CYP450 1A2 substrate Non-inhibitor 0.5224 CYP450 2C9 inhibitor Non-inhibitor 0.6241 CYP450 2D6 inhibitor Non-inhibitor 0.9316 CYP450 2C19 inhibitor Inhibitor 0.5539 CYP450 3A4 inhibitor Non-inhibitor 0.7814 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7382 Ames test AMES toxic 0.867 Carcinogenicity Carcinogens 0.8102 Biodegradation Not ready biodegradable 0.9614 Rat acute toxicity 2.7881 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9406 hERG inhibition (predictor II) Non-inhibitor 0.9289
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-6900000000-90e05043de4d62438541 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-001l-9600000000-3df67fe13248cbaca037 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9100000000-bf8f826fbfbe2b4b30fd Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00kf-9000000000-037115e4b186bb1eeb35 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9000000000-39f6c5eb39b73e1c99dd Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-02be-9000000000-f051cacd6b074fc5eb26 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 134.35835 predictedDeepCCS 1.0 (2019) [M+H]+ 136.75392 predictedDeepCCS 1.0 (2019) [M+Na]+ 143.62088 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Beta subunit of the heteropentameric ligand-gated chloride channel gated by gamma-aminobutyric acid (GABA), a major inhibitory neurotransmitter in the brain (PubMed:19763268, PubMed:27789573, PubMed:29950725, PubMed:8264558). GABA-gated chloride channels, also named GABA(A) receptors (GABAAR), consist of five subunits arranged around a central pore and contain GABA active binding site(s) located at the alpha and beta subunit interface(s) (PubMed:29950725). When activated by GABA, GABAARs selectively allow the flow of chloride anions across the cell membrane down their electrochemical gradient (By similarity). Chloride influx into the postsynaptic neuron following GABAAR opening decreases the neuron ability to generate a new action potential, thereby reducing nerve transmission (By similarity). GABAARs containing alpha-1 and beta-2 or -3 subunits exhibit synaptogenic activity; the gamma-2 subunit being necessary but not sufficient to induce rapid synaptic contacts formation (PubMed:23909897, PubMed:25489750). Extrasynaptic beta-2 receptors contribute to the tonic GABAergic inhibition (By similarity). Beta-containing GABAARs can simultaneously bind GABA and histamine where histamine binds at the interface of two neighboring beta subunits, which may be involved in the regulation of sleep and wakefulness (By similarity)
- Specific Function
- Chloride channel activity
- Gene Name
- GABRB2
- Uniprot ID
- P47870
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit beta-2
- Molecular Weight
- 59149.895 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Alpha subunit of the heteropentameric ligand-gated chloride channel gated by Gamma-aminobutyric acid (GABA), a major inhibitory neurotransmitter in the brain (PubMed:23909897, PubMed:25489750, PubMed:29950725, PubMed:30602789). GABA-gated chloride channels, also named GABA(A) receptors (GABAAR), consist of five subunits arranged around a central pore and contain GABA active binding site(s) located at the alpha and beta subunit interface(s) (PubMed:29950725, PubMed:30602789). When activated by GABA, GABAARs selectively allow the flow of chloride anions across the cell membrane down their electrochemical gradient (PubMed:23909897, PubMed:29950725, PubMed:30602789). Alpha-1/GABRA1-containing GABAARs are largely synaptic (By similarity). Chloride influx into the postsynaptic neuron following GABAAR opening decreases the neuron ability to generate a new action potential, thereby reducing nerve transmission (By similarity). GABAARs containing alpha-1 and beta-2 or -3 subunits exhibit synaptogenic activity; the gamma-2 subunit being necessary but not sufficient to induce rapid synaptic contacts formation (PubMed:23909897, PubMed:25489750). GABAARs function also as histamine receptor where histamine binds at the interface of two neighboring beta subunits and potentiates GABA response (By similarity). GABAARs containing alpha, beta and epsilon subunits also permit spontaneous chloride channel activity while preserving the structural information required for GABA-gated openings (By similarity). Alpha-1-mediated plasticity in the orbitofrontal cortex regulates context-dependent action selection (By similarity). Together with rho subunits, may also control neuronal and glial GABAergic transmission in the cerebellum (By similarity)
- Specific Function
- Gaba-a receptor activity
- Gene Name
- GABRA1
- Uniprot ID
- P14867
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit alpha-1
- Molecular Weight
- 51801.395 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Positive allosteric modulator
- General Function
- Alpha subunit of the heteropentameric ligand-gated chloride channel gated by Gamma-aminobutyric acid (GABA), a major inhibitory neurotransmitter in the brain (PubMed:23909897, PubMed:25489750, PubMed:29950725, PubMed:30602789). GABA-gated chloride channels, also named GABA(A) receptors (GABAAR), consist of five subunits arranged around a central pore and contain GABA active binding site(s) located at the alpha and beta subunit interface(s) (PubMed:29950725, PubMed:30602789). When activated by GABA, GABAARs selectively allow the flow of chloride anions across the cell membrane down their electrochemical gradient (PubMed:23909897, PubMed:29950725, PubMed:30602789). Alpha-1/GABRA1-containing GABAARs are largely synaptic (By similarity). Chloride influx into the postsynaptic neuron following GABAAR opening decreases the neuron ability to generate a new action potential, thereby reducing nerve transmission (By similarity). GABAARs containing alpha-1 and beta-2 or -3 subunits exhibit synaptogenic activity; the gamma-2 subunit being necessary but not sufficient to induce rapid synaptic contacts formation (PubMed:23909897, PubMed:25489750). GABAARs function also as histamine receptor where histamine binds at the interface of two neighboring beta subunits and potentiates GABA response (By similarity). GABAARs containing alpha, beta and epsilon subunits also permit spontaneous chloride channel activity while preserving the structural information required for GABA-gated openings (By similarity). Alpha-1-mediated plasticity in the orbitofrontal cortex regulates context-dependent action selection (By similarity). Together with rho subunits, may also control neuronal and glial GABAergic transmission in the cerebellum (By similarity)
- Specific Function
- Gaba-a receptor activity
Components:
References
Drug created at June 13, 2005 13:24 / Updated at August 26, 2024 19:23