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Identification
NameEthchlorvynol
Accession NumberDB00189  (APRD00958)
TypeSmall Molecule
GroupsApproved, Illicit, Withdrawn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 It has been used to treat insomnia, but has been largely superseded and is only offered where an intolerance or allergy to other drugs exists.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
Placidyl
β-chlorovinyl ethyl ethynyl carbinol
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Placidyl Cap 200mgcapsule200 mgoralAbbott Laboratories, Limited1956-12-312008-06-10Canada
Placidyl Cap 500mgcapsule500 mgoralAbbott Laboratories, Limited1952-12-312008-06-06Canada
Placidyl Cap 750mgcapsule750 mgoralAbbott Laboratories, Limited1971-12-312008-06-06Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
ArvynolPfizer
NostelDainippon
PlacidylAbbott
RoeridormPfizer-Roerig
SerenesilAbbott
Brand mixturesNot Available
SaltsNot Available
Categories
UNII6EIM3851UZ
CAS number113-18-8
WeightAverage: 144.599
Monoisotopic: 144.034192617
Chemical FormulaC7H9ClO
InChI KeyInChIKey=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
Taxonomy
DescriptionThis 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).
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbonyl compounds
Sub ClassAlpha,beta-unsaturated carbonyl compounds
Direct ParentYnones
Alternative Parents
Substituents
  • Ynone
  • Tertiary alcohol
  • Chloroalkene
  • Haloalkene
  • Vinyl halide
  • Vinyl chloride
  • Hydrocarbon derivative
  • Organochloride
  • Organohalogen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationUsed 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.
PharmacodynamicsEthchlorvynol 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 actionAlthough 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.
Related Articles
AbsorptionRapidly absorbed from gastrointestinal tract.
Volume of distributionNot Available
Protein binding35-50%
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 eliminationNot Available
Half lifePlasma half-life is approximately 10 to 20 hours, terminal half-life is 21-100 hours.
ClearanceNot Available
ToxicitySymptoms of overdose include thrombocytopenia.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
Manufacturers
  • Banner pharmacaps inc
  • Abbott laboratories pharmaceutical products div
PackagersNot Available
Dosage forms
FormRouteStrength
Capsuleoral200 mg
Capsuleoral500 mg
Capsuleoral750 mg
PricesNot Available
PatentsNot Available
Properties
StateLiquid
Experimental Properties
PropertyValueSource
boiling point28.5-30Bayley, 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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
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 ReferencesNot Available
External Links
ATC CodesN05CM08
AHFS Codes
  • 28:24.92
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

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. Functions as receptor for diazepines and various anesthetics, such as pentobarbital; these are bound at a separate allosteric effector binding site. Functions as ligand-gated chloride channel (By similarity).
Components:
NameUniProt IDDetails
Gamma-aminobutyric acid receptor subunit alpha-1P14867 Details
Gamma-aminobutyric acid receptor subunit alpha-2P47869 Details
Gamma-aminobutyric acid receptor subunit alpha-3P34903 Details
Gamma-aminobutyric acid receptor subunit alpha-4P48169 Details
Gamma-aminobutyric acid receptor subunit alpha-5P31644 Details
Gamma-aminobutyric acid receptor subunit alpha-6Q16445 Details
Gamma-aminobutyric acid receptor subunit beta-1P18505 Details
Gamma-aminobutyric acid receptor subunit beta-2P47870 Details
Gamma-aminobutyric acid receptor subunit beta-3P28472 Details
Gamma-aminobutyric acid receptor subunit deltaO14764 Details
Gamma-aminobutyric acid receptor subunit epsilonP78334 Details
Gamma-aminobutyric acid receptor subunit gamma-1Q8N1C3 Details
Gamma-aminobutyric acid receptor subunit gamma-2P18507 Details
Gamma-aminobutyric acid receptor subunit gamma-3Q99928 Details
Gamma-aminobutyric acid receptor subunit piO00591 Details
Gamma-aminobutyric acid receptor subunit thetaQ9UN88 Details
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]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23