DrugBank: Ethchlorvynol (DB00189)

targets (9)

Identification

Name

Ethchlorvynol

Accession Number

DB00189 (APRD00958)

Type

small molecule

Groups

illicit, approved

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 It has been used to treat insomnia, but has been largely superseded and is only offered where an intolerance or allergy to other drugs exists.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

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Aethyl-chlorvynol
Etchlorvinolo
Ethchlorovynol
Ethchlorvinol
Ethchlorvinyl
Ethclorvynol
Ethochlorvynol
Ethychlorvynol

Brand names

Alvinol
Arvynol
Normonson
Normosan
Normoson
Nostel
Nromoson
Placidil
Placidyl
Roeridorm
Serenesil
Serenil
Serensil
Serensiloline

Brand name mixtures

Not Available

Categories

Hypnotics and Sedatives

CAS number

113-18-8

Weight

Average: 144.599
Monoisotopic: 144.034192617

Chemical Formula

C₇H₉ClO

InChI Key

InChIKey=ZEHYJZXQEQOSON-AATRIKPKSA-N

InChI

InChI=1S/C7H9ClO/c1-3-7(9,4-2)5-6-8/h1,5-6,9H,4H2,2H3/b6-5+

Plain Text

IUPAC Name

(1E)-1-chloro-3-ethylpent-1-en-4-yn-3-ol

SMILES

CCC(O)(\C=C\Cl)C#C

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Not Available

Classes

Not Available

Substructures

Not Available

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in the management of insomnia for periods of up to one week in duration; however, this medication generally has been replaced by other sedative-hypnotic agents.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

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

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

Melting point

< 25 oC

Experimental Properties

Property	Value	Source
logP	1.8	PhysProp

Predicted Properties

Property	Value	Source
water solubility	1.43e-01 g/l	ALOGPS
logP	1.45	ALOGPS
logP	1.54	ChemAxon Molconvert
logS	-3.00	ALOGPS
pKa		ChemAxon Molconvert
hydrogen acceptor count	1	ChemAxon Molconvert
hydrogen donor count	1	ChemAxon Molconvert
polar surface area	20.23	ChemAxon Molconvert
rotatable bond count	2	ChemAxon Molconvert
refractivity	38.64	ChemAxon Molconvert
polarizability	14.78	ChemAxon Molconvert

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
KEGG Drug	D00704
KEGG Compound	C07833
ChEBI	4882
ChEMBL	4882
Therapeutic Targets Database	DAP000163
PharmGKB	PA449524
Drug Product Database	27
Drugs.com	http://www.drugs.com/cons/ethchlorvynol.html
Wikipedia	http://en.wikipedia.org/wiki/Ethchlorvynol

ATC Codes

N05CM08

AHFS Codes

28:24.92

PDB Entries

Not Available

FDA label

Not Available

MSDS

Not Available

Interactions

Drug Interactions

Not Available

Food Interactions

Avoid alcohol
Take with food to reduce irritation.

Targets
1. Gamma-aminobutyric-acid receptor subunit alpha-1 Pharmacological action: yes Actions: agonist GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel Organism class: human UniProt ID: P14867 Gene: GABRA1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed 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 Feller DJ, Crabbe JC: Effect of alcohols and other hypnotics in mice selected for differential sensitivity to hypothermic actions of ethanol. J Pharmacol Exp Ther. 1991 Mar;256(3):947-53. Pubmed Hypnotic drugs. Med Lett Drugs Ther. 2000 Aug 7;42(1084):71-2. Pubmed Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed 2. Gamma-aminobutyric-acid receptor subunit beta-1 Pharmacological action: yes Actions: agonist GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel Organism class: human UniProt ID: P18505 Gene: GABRB1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed 3. Gamma-aminobutyric-acid receptor subunit alpha-2 Pharmacological action: yes Actions: agonist GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel Organism class: human UniProt ID: P47869 Gene: GABRA2 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed 4. Gamma-aminobutyric-acid receptor subunit beta-2 Pharmacological action: yes Actions: agonist GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel Organism class: human UniProt ID: P47870 Gene: GABRB2 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed 5. Gamma-aminobutyric-acid receptor subunit alpha-3 Pharmacological action: yes Actions: agonist GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel Organism class: human UniProt ID: P34903 Gene: GABRA3 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed 6. Gamma-aminobutyric-acid receptor subunit beta-3 Pharmacological action: yes Actions: agonist GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel Organism class: human UniProt ID: P28472 Gene: GABRB3 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed 7. Gamma-aminobutyric-acid receptor subunit alpha-4 Pharmacological action: unknown Actions: agonist GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel Organism class: human UniProt ID: P48169 Gene: GABRA4 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed 8. Gamma-aminobutyric-acid receptor subunit alpha-5 Pharmacological action: unknown Actions: agonist GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel Organism class: human UniProt ID: P31644 Gene: GABRA5 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed 9. Gamma-aminobutyric-acid receptor subunit alpha-6 Pharmacological action: unknown Actions: agonist GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel Organism class: human UniProt ID: Q16445 Gene: GABRA6 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

Targets

1. Gamma-aminobutyric-acid receptor subunit alpha-1

Pharmacological action: yes
Actions: agonist

GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel

Organism class: human
UniProt ID: P14867 Link_out

Gene: GABRA1 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
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
Feller DJ, Crabbe JC: Effect of alcohols and other hypnotics in mice selected for differential sensitivity to hypothermic actions of ethanol. J Pharmacol Exp Ther. 1991 Mar;256(3):947-53. Pubmed
Hypnotic drugs. Med Lett Drugs Ther. 2000 Aug 7;42(1084):71-2. Pubmed
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Gamma-aminobutyric-acid receptor subunit beta-1

Pharmacological action: yes
Actions: agonist

GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel

Organism class: human
UniProt ID: P18505 Link_out

Gene: GABRB1 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

3. Gamma-aminobutyric-acid receptor subunit alpha-2

Pharmacological action: yes
Actions: agonist

GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel

Organism class: human
UniProt ID: P47869 Link_out

Gene: GABRA2 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

4. Gamma-aminobutyric-acid receptor subunit beta-2

Pharmacological action: yes
Actions: agonist

GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel

Organism class: human
UniProt ID: P47870 Link_out

Gene: GABRB2 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

5. Gamma-aminobutyric-acid receptor subunit alpha-3

Pharmacological action: yes
Actions: agonist

GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel

Organism class: human
UniProt ID: P34903 Link_out

Gene: GABRA3 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

6. Gamma-aminobutyric-acid receptor subunit beta-3

Pharmacological action: yes
Actions: agonist

GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel

Organism class: human
UniProt ID: P28472 Link_out

Gene: GABRB3 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

7. Gamma-aminobutyric-acid receptor subunit alpha-4

Pharmacological action: unknown
Actions: agonist

GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel

Organism class: human
UniProt ID: P48169 Link_out

Gene: GABRA4 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

8. Gamma-aminobutyric-acid receptor subunit alpha-5

Pharmacological action: unknown
Actions: agonist

GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel

Organism class: human
UniProt ID: P31644 Link_out

Gene: GABRA5 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

9. Gamma-aminobutyric-acid receptor subunit alpha-6

Pharmacological action: unknown
Actions: agonist

GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel

Organism class: human
UniProt ID: Q16445 Link_out

Gene: GABRA6 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

Comments

Drug created on June 13, 2005 07:24 / Updated on April 19, 2011 15:01

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.