Ethchlorvynol
Identification
- Name
- Ethchlorvynol
- Accession Number
- DB00189
- Description
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 It has been used to treat insomnia, but has been largely superseded and is only offered where an intolerance or allergy to other drugs exists.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- Approved, Illicit, Withdrawn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therapy in the management of insomnia for periods of up to one week in duration; however, this medication generally has been replaced by other sedative-hypnotic agents.
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- 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 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
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
Symptoms of overdose include thrombocytopenia.
- Affected organisms
- Humans and other mammals
- 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 Unlock Additional DataAcetazolamide The risk or severity of adverse effects can be increased when Ethchlorvynol is combined with Acetazolamide. Acetophenazine The risk or severity of adverse effects can be increased when Ethchlorvynol is combined with Acetophenazine. Aclidinium Ethchlorvynol may increase the central nervous system depressant (CNS depressant) activities of Aclidinium. Agomelatine The risk or severity of adverse effects can be increased when Ethchlorvynol is combined with Agomelatine. Alfentanil The risk or severity of adverse effects can be increased when Ethchlorvynol is combined with Alfentanil. Alimemazine The risk or severity of adverse effects can be increased when Ethchlorvynol is combined with Alimemazine. Almotriptan The risk or severity of adverse effects can be increased when Ethchlorvynol is combined with Almotriptan. Alosetron The risk or severity of adverse effects can be increased when Ethchlorvynol is combined with Alosetron. Alprazolam The risk or severity of adverse effects can be increased when Ethchlorvynol is combined with Alprazolam. Alverine The risk or severity of adverse effects can be increased when Ethchlorvynol is combined with Alverine. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Avoid alcohol.
- Take with food. Food reduces irritation.
Products
- 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 Unlock Additional DataPlacidyl Cap 200mg Capsule Oral Abbott 1956-12-31 2008-06-10 Canada 
Placidyl Cap 500mg Capsule Oral Abbott 1952-12-31 2008-06-06 Canada Placidyl Cap 750mg Capsule Oral Abbott 1971-12-31 2008-06-06 Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
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
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
Pharmacoeconomics
- Manufacturers
- Banner pharmacaps inc
- Abbott laboratories pharmaceutical products div
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Capsule Oral - 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 Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Positive allosteric modulator
- General Function
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function
- Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
Components:
References
- Smeyatsky N, Baldwin D, Botros W, Gura R, Kurian T, Lambert MT, Patel AG, Steinert J, Priest RG: The treatment of sleep disorders. S Afr Med J. 1992 May 2;Suppl:1-8. [PubMed:1585214]
- ChEMBL Compound Report Card [Link]
Drug created on June 13, 2005 07:24 / Updated on September 03, 2020 19:01
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