DT-Web

DB00189 - Ethchlorvynol


Identification
Name Ethchlorvynol
Accession Number DB00189 (APRD00958)
Type small molecule
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 It has been used to treat insomnia, but has been largely superseded and is only offered where an intolerance or allergy to other drugs exists.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
MOL SDF PDB SMILES InChI
Categories (*)
Molecular Weight 144.599
Groups illicit
Monoisotopic Weight 144.034192617
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therapy in the management of insomnia for periods of up to one week in duration; however, this medication generally has been replaced by other sedative-hypnotic agents.
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.
Absorption Rapidly absorbed from gastrointestinal tract.
Protein binding 35-50%
Biotransformation 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
Toxicity Symptoms of overdose include thrombocytopenia.
Affected organisms
  • Humans and other mammals
Interactions
Drug Interactions
Drug Mechanism of interaction
Acenocoumarol Ethchlorvynol may decrease the anticoagulant effect of acenocoumarol.
Anisindione Ethchlorvynol may decrease the anticoagulant effect of anisindione.
Dicumarol Ethchlorvynol may decrease the anticoagulant effect of dicumarol.
Warfarin Ethchlorvynol may decrease the anticoagulant effect of warfarin.
Food Interactions
  • Avoid alcohol
  • Take with food to reduce irritation.

Targets


Gamma-aminobutyric-acid receptor subunit alpha-1
Name Gamma-aminobutyric-acid receptor subunit alpha-1
Gene Name GABRA1
Pharmacological action yes
Actions agonist
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
DTHybrid score 0.7385
Gamma-aminobutyric-acid receptor subunit beta-1
Name Gamma-aminobutyric-acid receptor subunit beta-1
Gene Name GABRB1
Pharmacological action yes
Actions agonist
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
DTHybrid score 0.4187
Gamma-aminobutyric-acid receptor subunit alpha-2
Name Gamma-aminobutyric-acid receptor subunit alpha-2
Gene Name GABRA2
Pharmacological action yes
Actions agonist
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
DTHybrid score 0.6691
Gamma-aminobutyric-acid receptor subunit beta-2
Name Gamma-aminobutyric-acid receptor subunit beta-2
Gene Name GABRB2
Pharmacological action yes
Actions agonist
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
DTHybrid score 0.4302
Gamma-aminobutyric-acid receptor subunit alpha-3
Name Gamma-aminobutyric-acid receptor subunit alpha-3
Gene Name GABRA3
Pharmacological action yes
Actions agonist
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
DTHybrid score 0.6625
Gamma-aminobutyric-acid receptor subunit beta-3
Name Gamma-aminobutyric-acid receptor subunit beta-3
Gene Name GABRB3
Pharmacological action yes
Actions agonist
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
DTHybrid score 0.4507
Gamma-aminobutyric-acid receptor subunit alpha-4
Name Gamma-aminobutyric-acid receptor subunit alpha-4
Gene Name GABRA4
Pharmacological action unknown
Actions agonist
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
DTHybrid score 0.5422
Gamma-aminobutyric-acid receptor subunit alpha-5
Name Gamma-aminobutyric-acid receptor subunit alpha-5
Gene Name GABRA5
Pharmacological action unknown
Actions agonist
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
DTHybrid score 0.6726
Gamma-aminobutyric-acid receptor subunit alpha-6
Name Gamma-aminobutyric-acid receptor subunit alpha-6
Gene Name GABRA6
Pharmacological action unknown
Actions agonist
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
DTHybrid score 0.5341

Predictions


Id Partner name Gene Name Score
6086 Gamma-aminobutyric acid receptor subunit gamma-2 GABRG2 0.3658
6087 Gamma-aminobutyric acid receptor subunit gamma-1 GABRG1 0.3436
6093 Gamma-aminobutyric acid receptor subunit delta GABRD 0.3421
6089 Gamma-aminobutyric acid receptor subunit epsilon GABRE 0.3414
6088 Gamma-aminobutyric acid receptor subunit gamma-3 GABRG3 0.3393
6090 Gamma-aminobutyric acid receptor subunit pi GABRP 0.3387
6092 Gamma-aminobutyric acid receptor subunit rho-2 GABRR2 0.3383
6115 Gamma-aminobutyric acid receptor subunit rho-3 GABRR3 0.338
142 Gamma-aminobutyric-acid receptor subunit rho-1 GABRR1 0.3355
4095 Neuronal acetylcholine receptor subunit alpha-7 CHRNA7 0.2858
947 Neuronal acetylcholine receptor subunit alpha-4 CHRNA4 0.2856
918 Glutamate receptor, ionotropic kainate 2 GRIK2 0.2792
921 Glutamate receptor 2 GRIA2 0.2463
6091 Gamma-aminobutyric acid receptor subunit theta GABRQ 0.2291
4512 Cytochrome P450 3A4 CYP3A4 0.1839
811 Translocator protein TSPO 0.1604
6016 Cytochrome P450 2C19 CYP2C19 0.1169
6013 Cytochrome P450 2E1 CYP2E1 0.1095
4757 Cytochrome P450 2C9 CYP2C9 0.0954
6030 Cytochrome P450 2B6 CYP2B6 0.0766
4924 Cytochrome P450 2C8 CYP2C8 0.058
1588 Multidrug resistance protein 1 ABCB1 0.0568
4200 Cytochrome P450 1A2 CYP1A2 0.0537
6107 Cytochrome P450 3A7 CYP3A7 0.0514
4118 Cytochrome P450 3A5 CYP3A5 0.0484
587 Serum albumin ALB 0.0432
5718 Cytochrome P450 2A6 CYP2A6 0.0413
6106 Cytochrome P450 2C18 CYP2C18 0.0406
4119 Cytochrome P450 2D6 CYP2D6 0.0402
20 Prostaglandin G/H synthase 1 PTGS1 0.0353
6027 Alkaline phosphatase, tissue-nonspecific isozyme ALPL 0.035
482 Glycine receptor subunit alpha-1 GLRA1 0.0346
461 Glycine receptor subunit alpha-3 GLRA3 0.024
3937 Fatty-acid amide hydrolase FAAH 0.0228
6178 UDP-glucuronosyltransferase 2B7 UGT2B7 0.0206
158 Sodium channel protein type 1 subunit alpha SCN1A 0.0202
276 Sodium- and chloride-dependent GABA transporter 1 SLC6A1 0.0184
820 Glycine receptor subunit alpha-2 GLRA2 0.0179
6102 Arylamine N-acetyltransferase 2 NAT2 0.0159
6018 UDP-glucuronosyltransferase 1-9 UGT1A9 0.0159
240 Gamma-aminobutyric acid type B receptor, subunit 1 GABBR1 0.0151
172 Potassium channel subfamily K member 1 KCNK1 0.0144
6031 Cytochrome P450 3A43 CYP3A43 0.0143
241 Calcium-transporting ATPase type 2C member 1 ATP2C1 0.0138
6025 UDP-glucuronosyltransferase 1-4 UGT1A4 0.0134
62 Glycine receptor subunit beta GLRB 0.0132
537 ATP synthase delta chain, mitochondrial ATP5D 0.0132
6022 UDP-glucuronosyltransferase 1-1 UGT1A1 0.0127
705 Glutamate receptor 1 GRIA1 0.0127
559 NADH-ubiquinone oxidoreductase chain 1 MT-ND1 0.0124
489 Monocarboxylate transporter 2 SLC16A7 0.0121
500 Monocarboxylate transporter 4 SLC16A3 0.0118
858 Potassium voltage-gated channel subfamily A member 1 KCNA1 0.0116
6024 Cytochrome P450 1A1 CYP1A1 0.0111
2981 Phospholipase A2, membrane associated PLA2G2A 0.0107
6144 Solute carrier family 22 member 2 SLC22A2 0.0104
738 Monocarboxylate transporter 1 SLC16A1 0.0104
540 Sodium-dependent noradrenaline transporter SLC6A2 0.01
6176 UDP-glucuronosyltransferase 1-3 UGT1A3 0.0098
862 Multidrug resistance-associated protein 1 ABCC1 0.0097
1898 Cytochrome P450 1B1 CYP1B1 0.0093
1735 Canalicular multispecific organic anion transporter 1 ABCC2 0.0091
220 Sodium channel protein type 5 subunit alpha SCN5A 0.0091
6145 Solute carrier family 22 member 1 SLC22A1 0.0088
3426 Glutamine synthetase glnA 0.0084
3987 Glutamine synthetase GLUL 0.0084
468 Cytochrome P450 4A11 CYP4A11 0.0084
6017 Cholesterol side-chain cleavage enzyme, mitochondrial CYP11A1 0.0072
4209 ATP-sensitive inward rectifier potassium channel 8 KCNJ8 0.0069
3802 Sodium channel protein type 2 subunit alpha SCN2A 0.0065
781 ATP-sensitive inward rectifier potassium channel 11 KCNJ11 0.0065
6152 Solute carrier organic anion transporter family member 2A1 SLCO2A1 0.0063
3804 Sodium channel protein type 4 subunit alpha SCN4A 0.006
1709 Canalicular multispecific organic anion transporter 2 ABCC3 0.0055
6181 UDP-glucuronosyltransferase 1-8 UGT1A8 0.0054
776 Bile salt export pump ABCB11 0.0052
1680 Solute carrier family 2, facilitated glucose transporter member 1 SLC2A1 0.0049
23 D(1A) dopamine receptor DRD1 0.0046
1732 ATP-binding cassette sub-family G member 2 ABCG2 0.0045
382 Glutamate receptor, ionotropic kainate 1 GRIK1 0.0045
318 Alpha-2A adrenergic receptor ADRA2A 0.0045
6023 Cytochrome P450 11B2, mitochondrial CYP11B2 0.0042
556 Alpha-1A adrenergic receptor ADRA1A 0.0042
805 Cytochrome P450 11B1, mitochondrial CYP11B1 0.0037
6020 Aldehyde oxidase AOX1 0.0037
610 Calcium-activated potassium channel subunit alpha 1 KCNMA1 0.0034
629 Alpha-2B adrenergic receptor ADRA2B 0.0031
3811 Cytochrome P450 19A1 CYP19A1 0.003
592 Carbonic anhydrase 4 CA4 0.003
502 5-hydroxytryptamine 2A receptor HTR2A 0.0027
706 Glutamate [NMDA] receptor subunit 3A GRIN3A 0.0023
357 Carbonic anhydrase 2 CA2 0.0021
251 Alcohol dehydrogenase 1A ADH1A 0.0019
465 Calmodulin CALM1 0.0018
1181 Alpha-1-acid glycoprotein 1 ORM1 0.0018
824 Sodium-dependent serotonin transporter SLC6A4 0.0018
444 Alcohol dehydrogenase 1B ADH1B 0.0016
831 D(2) dopamine receptor DRD2 0.0016
103 Muscarinic acetylcholine receptor M1 CHRM1 0.0016
1768 Guanine nucleotide-binding protein G(I)/G(S)/G(O) gamma-2 subunit GNG2 0.0015
1581 G protein-activated inward rectifier potassium channel 2 KCNJ6 0.0015
1268 Neuropeptide S receptor NPSR1 0.0015
1571 G protein-activated inward rectifier potassium channel 1 KCNJ3 0.0015
517 Alcohol dehydrogenase 1C ADH1C 0.0014
6073 Potassium channel subfamily K member 9 KCNK9 0.0014
6072 Potassium channel subfamily K member 3 KCNK3 0.0014
462 Intermediate conductance calcium-activated potassium channel protein 4 KCNN4 0.0012
591 Glutamate [NMDA] receptor subunit 3B GRIN3B 0.0011
837 Glutamate [NMDA] receptor subunit epsilon-1 GRIN2A 0.001
2207 Rhodopsin RHO 0.001
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