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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyEthchlorvynol
Identification
- Name
- Ethchlorvynol
- Accession Number
- DB00189 (APRD00958)
- Type
- Small Molecule
- Groups
- Approved, Illicit, Withdrawn
- 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 It has been used to treat insomnia, but has been largely superseded and is only offered where an intolerance or allergy to other drugs exists.
- Structure
Structure for Ethchlorvynol (DB00189)
- 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
- Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End 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 - International/Other Brands
- Arvynol (Pfizer) / Nostel (Dainippon) / Placidyl (Abbott) / Roeridorm (Pfizer-Roerig) / Serenesil (Abbott)
- Categories
- UNII
- 6EIM3851UZ
- CAS number
- 113-18-8
- Weight
- Average: 144.599
Monoisotopic: 144.034192617 - Chemical Formula
- C7H9ClO
- 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
- 1-chloro-3-ethylpent-1-en-4-yn-3-ol
- SMILES
- [H]C(Cl)=CC(O)(CC)C#C
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therapy in the management of insomnia for periods of up to one week in duration; however, this medication generally has been replaced by other sedative-hypnotic agents.
- 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 (anion channel) 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
- Toxicity
Symptoms of overdose include thrombocytopenia.
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
Drug Interaction 4-Methoxyamphetamine The risk or severity of adverse effects can be increased when Ethchlorvynol is combined with 4-Methoxyamphetamine. 7-Nitroindazole The risk or severity of adverse effects can be increased when Ethchlorvynol is combined with 7-Nitroindazole. Acepromazine The risk or severity of adverse effects can be increased when Ethchlorvynol is combined with Acepromazine. Aceprometazine The risk or severity of adverse effects can be increased when Ethchlorvynol is combined with Aceprometazine. Acetazolamide 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. Acetylglycinamide chloral hydrate The risk or severity of adverse effects can be increased when Ethchlorvynol is combined with Acetylglycinamide chloral hydrate. Aclidinium Ethchlorvynol may increase the central nervous system depressant (CNS depressant) activities of Aclidinium. Adinazolam The risk or severity of adverse effects can be increased when Ethchlorvynol is combined with Adinazolam. Adipiplon The risk or severity of adverse effects can be increased when Ethchlorvynol is combined with Adipiplon. - Food Interactions
- Avoid alcohol
- Take with food to reduce irritation.
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
- ChEBI
- 4882
- ChEMBL
- CHEMBL591
- Therapeutic Targets Database
- DAP000163
- PharmGKB
- PA164746383
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Ethchlorvynol
- ATC Codes
- N05CM08 — Ethchlorvynol
Clinical Trials
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 GC-MS Spectrum - GC-MS Predicted GC-MS Not Available 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
Taxonomy
- 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
- Ynone / Tertiary alcohol / Acetylide / Chloroalkene / Haloalkene / Vinyl halide / Vinyl chloride / Hydrocarbon derivative / Organochloride / Organohalogen compound
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- terminal acetylenic compound, tertiary alcohol, organochlorine compound, enyne (CHEBI:4882)
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 January 02, 2019 21:24