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Approved, Illicit, Withdrawn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 It has been used to treat insomnia, but has been largely superseded and is only offered where an intolerance or allergy to other drugs exists. [Wikipedia]

Structure
Thumb
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
  • ethyl β-chlorovinyl ethynyl carbinol
  • β-chlorovinyl ethyl ethynyl carbinol
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Placidyl Cap 200mgCapsule200 mgOralAbbott1956-12-312008-06-10Canada
Placidyl Cap 500mgCapsule500 mgOralAbbott1952-12-312008-06-06Canada
Placidyl Cap 750mgCapsule750 mgOralAbbott1971-12-312008-06-06Canada
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therapy in the management of insomnia for periods of up to one week in duration; however, this medication generally has been replaced by other sedative-hypnotic agents.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.

TargetActionsOrganism
AGABA-A receptor (anion channel)
positive allosteric modulator
Human
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
DrugInteraction
7-NitroindazoleThe risk or severity of adverse effects can be increased when Ethchlorvynol is combined with 7-Nitroindazole.
AcepromazineThe risk or severity of adverse effects can be increased when Ethchlorvynol is combined with Acepromazine.
AceprometazineThe risk or severity of adverse effects can be increased when Ethchlorvynol is combined with Aceprometazine.
AcetazolamideThe risk or severity of adverse effects can be increased when Ethchlorvynol is combined with Acetazolamide.
AdipiplonThe risk or severity of adverse effects can be increased when Ethchlorvynol is combined with Adipiplon.
AgomelatineThe risk or severity of adverse effects can be increased when Ethchlorvynol is combined with Agomelatine.
AlaproclateThe risk or severity of adverse effects can be increased when Ethchlorvynol is combined with Alaproclate.
AlfaxaloneThe risk or severity of adverse effects can be increased when Ethchlorvynol is combined with Alfaxalone.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Ethchlorvynol.
AlimemazineThe risk or severity of adverse effects can be increased when Ethchlorvynol is combined with Alimemazine.
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

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
  • Banner pharmacaps inc
  • Abbott laboratories pharmaceutical products div
Packagers
Not Available
Dosage forms
FormRouteStrength
CapsuleOral200 mg
CapsuleOral500 mg
CapsuleOral750 mg
Prices
Not Available
Patents
Not Available

Properties

State
Liquid
Experimental Properties
PropertyValueSource
boiling point (°C)28.5-30Bayley, A. and McLamore, W.M.; U.S. Patent 2,746,900; May 22,1956; assigned to Chas. Pfizer & Co., Inc.
logP1.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.143 mg/mLALOGPS
logP1.45ALOGPS
logP1.62ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)12.88ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity38.64 m3·mol-1ChemAxon
Polarizability14.77 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9965
Blood Brain Barrier+0.9685
Caco-2 permeable+0.646
P-glycoprotein substrateNon-substrate0.743
P-glycoprotein inhibitor INon-inhibitor0.9023
P-glycoprotein inhibitor IINon-inhibitor0.9672
Renal organic cation transporterNon-inhibitor0.9589
CYP450 2C9 substrateNon-substrate0.7267
CYP450 2D6 substrateNon-substrate0.9
CYP450 3A4 substrateNon-substrate0.6176
CYP450 1A2 substrateNon-inhibitor0.5224
CYP450 2C9 inhibitorNon-inhibitor0.6241
CYP450 2D6 inhibitorNon-inhibitor0.9316
CYP450 2C19 inhibitorInhibitor0.5539
CYP450 3A4 inhibitorNon-inhibitor0.7814
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7382
Ames testAMES toxic0.867
CarcinogenicityCarcinogens 0.8102
BiodegradationNot ready biodegradable0.9614
Rat acute toxicity2.7881 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9406
hERG inhibition (predictor II)Non-inhibitor0.9289
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot 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
Human
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
  1. 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]
  2. ChEMBL Compound Report Card [Link]

Drug created on June 13, 2005 07:24 / Updated on October 01, 2018 12:44