Details of the Drug

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]
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Therapeutic Class

Hypnotics and Sedatives

Affected Organisms

Humans and other mammals

ATC Code

N05CM08: Ethchlorvynol

N05CM: Other hypnotics and sedatives

N05C: HYPNOTICS AND SEDATIVES

N05: PSYCHOLEPTICS

N: NERVOUS SYSTEM

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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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
UNII: 6EIM3851UZ
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]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)_{Main DME}	DE4LYSA	CP3A4_HUMAN	Substrate	[6]

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Molecular Interaction Atlas (MIA)

MIA Detail

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]
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⏷ 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.