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 It has been used to treat insomnia, but has been largely superseded and is only offered where an intolerance or allergy to other drugs exists.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Approved, Illicit, Withdrawn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

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Ethchlorvynol (DB00189)

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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therapy in the management of insomnia for periods of up to one week in duration; however, this medication generally has been replaced by other sedative-hypnotic agents.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.

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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 GABA_A 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 modulator	Humans

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.

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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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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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.
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 Description
Extended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
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Severity
Severity
A severity rating for each drug interaction, from minor to major.
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Evidence Level
Evidence Level
A rating for the strength of the evidence supporting each drug interaction.
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Action
Action
An effect category for each drug interaction. Know how this interaction affects the subject drug.
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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 Data
Placidyl Cap 200mg	Capsule		Oral	Abbott	1956-12-31	2008-06-10
Placidyl Cap 500mg	Capsule		Oral	Abbott	1952-12-31	2008-06-06
Placidyl Cap 750mg	Capsule		Oral	Abbott	1971-12-31	2008-06-06

Additional Data Available

Application Number
Application Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
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Product Code
Product Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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Categories

ATC Codes

N05CM08 — Ethchlorvynol

• N05CM — Other hypnotics and sedatives
• N05C — HYPNOTICS AND SEDATIVES
• N05 — PSYCHOLEPTICS
• N — NERVOUS SYSTEM

Drug Categories

• Alcohols
• Central Nervous System Agents
• Central Nervous System Depressants
• Chlorohydrins
• Hypnotics and Sedatives
• Nervous System
• Psycholeptics

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

RxNav

4118

ChEBI

4882

ChEMBL

CHEMBL591

Therapeutic Targets Database

DAP000163

PharmGKB

PA164746383

Drugs.com

Drugs.com Drug Page

Wikipedia

Ethchlorvynol

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count

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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

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

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Drug created on June 13, 2005 07:24 / Updated on June 12, 2020 10:51