General Information of Drug (ID: DM53IP1)

Drug Name
Ethchlorvynol
Synonyms
Alvinol; Arvynol; Etchlorvinolo; Etclorvinol; Ethchlorovynol; Ethchlorvinol; Ethchlorvinyl; Ethchlorvynolum;Ethclorvynol; Ethochlorvynol; Ethychlorvynol; Normonson; Normosan; Normoson; Nostel; Nromoson; Placidil; Placidyl; Roeridorm; Serenesil; Serenil; Serensil; Serensiloline; A 71; Aethyl-chlorvynol; Beta-Chlorovinyl ethyl ethynyl carbinol; Beta-Chlorvinyl ethyl ethynyl carbinol; Etclorvinol [INN-Spanish]; Ethchlorvynolum [INN-Latin]; Ethyl beta-chlorovinyl ethynyl carbinol; Placidyl (TN); Ethchlorvynol [USAN:INN:BAN]; Ethchlorvynol (JAN/USP/INN); (E)-1-chloro-3-ethylpent-1-en-4-yn-3-ol; 1-Chloro-3-ethyl-1-penten-4-yn-3-ol; 1-Chloro-3-ethylpent-1-4-yn-3-ol; 1-chloro-3-ethylpent-1-en-4-yn-3-ol; 3-(beta-Chlorovinyl)-1-pentyn-3-ol; 5-Chloro-3-ethylpent-1-yn-4-en-3-ol
Indication
Disease Entry ICD 11 Status REF
Insomnia 7A00-7A0Z Approved [1]
Therapeutic Class
Hypnotics and Sedatives
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 144.6
Logarithm of the Partition Coefficient (xlogp) 1.5
Rotatable Bond Count (rotbonds) 3
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 1
ADMET Property
Absorption
The drug is rapidly absorbed from gastrointestinal tract []
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [2]
Elimination
0.05% of drug is excreted from urine in the unchanged form [2]
Half-life
The concentration or amount of drug in body reduced by one-half in 10 - 20 hours [3]
Metabolism
The drug is metabolized via the liver []
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 115.48927 micromolar/kg/day [4]
Chemical Identifiers
Formula
C7H9ClO
IUPAC Name
(E)-1-chloro-3-ethylpent-1-en-4-yn-3-ol
Canonical SMILES
CCC(/C=C/Cl)(C#C)O
InChI
InChI=1S/C7H9ClO/c1-3-7(9,4-2)5-6-8/h1,5-6,9H,4H2,2H3/b6-5+
InChIKey
ZEHYJZXQEQOSON-AATRIKPKSA-N
Cross-matching ID
PubChem CID
5281077
ChEBI ID
CHEBI:4882
CAS Number
113-18-8
DrugBank ID
DB00189
TTD ID
D03VZH
INTEDE ID
DR1753

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
GABA(A) receptor alpha-1 (GABRA1) TT1MPAY GBRA1_HUMAN Antagonist [5]
GABA(A) receptor beta-2 (GABRB2) TTZA1NY GBRB2_HUMAN Antagonist [5]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME
DE4LYSA CP3A4_HUMAN Substrate [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Ethchlorvynol (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Oliceridine DM6MDCF Major Additive CNS depression effects by the combination of Ethchlorvynol and Oliceridine. Acute pain [MG31] [7]
Dihydrocodeine DMB0FWL Major Additive CNS depression effects by the combination of Ethchlorvynol and Dihydrocodeine. Chronic pain [MG30] [7]
Morphine DMRMS0L Major Additive CNS depression effects by the combination of Ethchlorvynol and Morphine. Chronic pain [MG30] [8]
Olopatadine DMKMWQG Moderate Additive CNS depression effects by the combination of Ethchlorvynol and Olopatadine. Conjunctiva disorder [9A60] [9]
Propofol DMB4OLE Moderate Additive CNS depression effects by the combination of Ethchlorvynol and Propofol. Corneal disease [9A76-9A78] [10]
Alfentanil DMVO0UB Major Additive CNS depression effects by the combination of Ethchlorvynol and Alfentanil. Corneal disease [9A76-9A78] [8]
Remifentanil DMZTXCH Major Additive CNS depression effects by the combination of Ethchlorvynol and Remifentanil. Corneal disease [9A76-9A78] [8]
Methadone DMTW6IU Major Additive CNS depression effects by the combination of Ethchlorvynol and Methadone. Cough [MD12] [8]
Ethanol DMDRQZU Moderate Additive CNS depression effects by the combination of Ethchlorvynol and Ethanol. Cystitis [GC00] [9]
Esketamine DMVU687 Moderate Additive CNS depression effects by the combination of Ethchlorvynol and Esketamine. Depression [6A70-6A7Z] [11]
Brimonidine DMQLT4N Moderate Additive CNS depression effects by the combination of Ethchlorvynol and Brimonidine. Glaucoma [9C61] [12]
Allopregnanolone DMNLHAC Moderate Additive CNS depression effects by the combination of Ethchlorvynol and Allopregnanolone. Mental/behavioural/neurodevelopmental disorder [6E20-6E8Z] [13]
Lasmiditan DMXLVDT Moderate Additive CNS depression effects by the combination of Ethchlorvynol and Lasmiditan. Migraine [8A80] [14]
Flibanserin DM70DTN Moderate Additive CNS depression effects by the combination of Ethchlorvynol and Flibanserin. Mood disorder [6A60-6E23] [15]
Thalidomide DM70BU5 Moderate Additive CNS depression effects by the combination of Ethchlorvynol and Thalidomide. Multiple myeloma [2A83] [9]
Apraclonidine DMO4PVE Moderate Additive CNS depression effects by the combination of Ethchlorvynol and Apraclonidine. Optic nerve disorder [9C40] [12]
Pentazocine DM1XBHS Major Additive CNS depression effects by the combination of Ethchlorvynol and Pentazocine. Pain [MG30-MG3Z] [8]
Dextropropoxyphene DM23HCX Major Additive CNS depression effects by the combination of Ethchlorvynol and Dextropropoxyphene. Pain [MG30-MG3Z] [16]
Butorphanol DM5KYPJ Major Additive CNS depression effects by the combination of Ethchlorvynol and Butorphanol. Pain [MG30-MG3Z] [8]
Oxymorphone DM65AGJ Major Additive CNS depression effects by the combination of Ethchlorvynol and Oxymorphone. Pain [MG30-MG3Z] [8]
Levorphanol DMGS80V Major Additive CNS depression effects by the combination of Ethchlorvynol and Levorphanol. Pain [MG30-MG3Z] [8]
Hydromorphone DMHP21E Major Additive CNS depression effects by the combination of Ethchlorvynol and Hydromorphone. Pain [MG30-MG3Z] [8]
Codeine DMJX6ZG Major Additive CNS depression effects by the combination of Ethchlorvynol and Codeine. Pain [MG30-MG3Z] [8]
Nalbuphine DMOSQGU Major Additive CNS depression effects by the combination of Ethchlorvynol and Nalbuphine. Pain [MG30-MG3Z] [8]
Buprenorphine DMPRI8G Major Additive CNS depression effects by the combination of Ethchlorvynol and Buprenorphine. Pain [MG30-MG3Z] [17]
Hydrocodone DMQ2JO5 Major Additive CNS depression effects by the combination of Ethchlorvynol and Hydrocodone. Pain [MG30-MG3Z] [8]
Tramadol DMRQD04 Major Additive CNS depression effects by the combination of Ethchlorvynol and Tramadol. Pain [MG30-MG3Z] [8]
Meperidine DMX4GND Major Additive CNS depression effects by the combination of Ethchlorvynol and Meperidine. Pain [MG30-MG3Z] [8]
Oxycodone DMXLKHV Major Additive CNS depression effects by the combination of Ethchlorvynol and Oxycodone. Pain [MG30-MG3Z] [8]
Fentanyl DM8WAHT Major Additive CNS depression effects by the combination of Ethchlorvynol and Fentanyl. Sensation disturbance [MB40] [8]
Sufentanil DMU7YEL Major Additive CNS depression effects by the combination of Ethchlorvynol and Sufentanil. Sensation disturbance [MB40] [8]
Warfarin DMJYCVW Minor Increased metabolism of Ethchlorvynol caused by Warfarin mediated induction of CYP450 enzyme. Supraventricular tachyarrhythmia [BC81] [18]
Tizanidine DMR2IQ4 Moderate Additive CNS depression effects by the combination of Ethchlorvynol and Tizanidine. Tonus and reflex abnormality [MB47] [19]
Cetirizine DMOMP9U Moderate Additive CNS depression effects by the combination of Ethchlorvynol and Cetirizine. Vasomotor/allergic rhinitis [CA08] [20]
⏷ Show the Full List of 34 DDI Information of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7180).
2 BDDCS applied to over 900 drugs
3 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
5 DrugBank: a knowledgebase for drugs, drug actions and drug targets. Nucleic Acids Res. 2008 Jan;36(Database issue):D901-6.
6 Alkylation of the prosthetic heme in cytochrome P-450 during oxidative metabolism of the sedative-hypnotic ethchlorvynol. J Med Chem. 1982 Oct;25(10):1174-9.
7 US Food and Drug Administration "FDA warns about serious risks and death when combining opioid pain or cough medicines with benzodiazepines requires its strongest warning.".
8 US Food and Drug Administration "FDA warns about serious risks and death when combining opioid pain or cough medicines with benzodiazepines requires its strongest warning.".
9 Warrington SJ, Ankier SI, Turner P "Evaluation of possible interactions between ethanol and trazodone or amitriptyline." Neuropsychobiology 15 (1986): 31-7. [PMID: 3725002]
10 Gill SS, Wright EM, Reilly CS "Pharmacokinetic interaction of propofol and fentanyl: single bolus injection study." Br J Anaesth 65 (1990): 760-5. [PMID: 2265045]
11 Cerner Multum, Inc. "Australian Product Information.".
12 Product Information. Alphagan (brimonidine ophthalmic). Allergan Inc, Irvine, CA.
13 Product Information. Zulresso (brexanolone). Sage Therapeutics, Inc., Cambridge, MA.
14 Product Information. Reyvow (lasmiditan). Lilly, Eli and Company, Indianapolis, IN.
15 Product Information. Addyi (flibanserin). Sprout Pharmaceuticals, Raleigh, NC.
16 Hansen BS, Dam M, Brandt J, et al "Influence of dextropropoxyphene on steady state serum levels and protein binding of three anti-epileptic drugs in man." Acta Neurol Scand 61 (1980): 357-67. [PMID: 6998251]
17 Sekar M, Mimpriss TJ "Buprenorphine, benzodiazepines and prolonged respiratory depression." Anaesthesia 42 (1987): 567-8. [PMID: 3592200]
18 Product Information. Coumadin (warfarin). DuPont Pharmaceuticals, Wilmington, DE.
19 Product Information. Zanaflex (tizanidine). Acorda Therapeutics, Hawthorne, NY.
20 Product Information. Zyrtec (cetirizine). Pfizer US Pharmaceuticals, New York, NY.