Identification
- Generic Name
- Ethinamate
- DrugBank Accession Number
- DB01031
- Background
Ethinamate is a short-acting sedative-hypnotic medication used to treat insomnia. Like many such similar medications, the regular use of ethinamate can result in the development of drug tolerance in a patient. Nevertheless, the medication itself is generally no longer effective after using it for greater than 7 days. Structurally, it does not resemble the barbituates, but it shares many effects with this class of drugs; the depressant effects of ethinamate are, however, generally milder than those of most barbiturates.
- Type
- Small Molecule
- Groups
- Approved, Illicit, Withdrawn
- Structure
Structure for Ethinamate (DB01031)
- Weight
- Average: 167.205
Monoisotopic: 167.094628665 - Chemical Formula
- C9H13NO2
- Synonyms
- 1-ethynylcyclohexanol carbamate
- Aethinyl-cyclohexyl-carbamat
- Ethinamate
- Ethinamatum
- Etinamato
- External IDs
- USAF EL-42
Pharmacology
- Indication
Used for the short-term treatment of insomnia, however, it generally has been replaced by other sedative-hypnotic agents.
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Ethinamate is used to treat insomnia (trouble in sleeping). However, it has generally been replaced by other medicines for the treatment of insomnia. If ethinamate is used regularly (for example, every day) to help produce sleep, it is usually not effective for more than 7 days. Structurally, it does not resemble the barbiturates, but it shares many effects with this class of drugs; the depressant effects of ethinamate are, however, generally milder than those of most barbiturates. Continued and inappropriate use of ethinamate can lead to tolerance and physical dependence, with withdrawal symptoms very similar to those of the barbiturates.
- Mechanism of action
The mechanism of action is not known. However, studies have shown that ethinamate inhibits carbonic anhydrases I and II (J Biol Chem. 1992 Dec 15;267(35):25044-50). This inhibition by ethinamate is not sufficiently strong, however, to implicate carbonic anhydrases I and II in the mechanism of action.
Target Actions Organism ACarbonic anhydrase 2 inhibitorHumans ACarbonic anhydrase 1 inhibitorHumans - Absorption
Rapidly absorbed following oral administration.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Hepatic.
- Route of elimination
Not Available
- Half-life
2.5 hours
- Clearance
Not Available
- Adverse Effects
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Symptoms of overdose include shortness of breath or slow or troubled breathing, slow heartbeat, severe weakness, chronic confusion, slurred speech, and staggering.
- 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.Not Available
- Food Interactions
- Not Available
Products
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- Valamin (Schering) / Valmid (Dista)
Categories
- Drug Categories
- 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
- Carbamate esters / Organic carbonic acids and derivatives / Acetylides / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
- Substituents
- Acetylide / Aliphatic homomonocyclic compound / Carbamic acid ester / Carbonic acid derivative / Hydrocarbon derivative / Organic nitrogen compound / Organic oxide / Organonitrogen compound / Organopnictogen compound / Ynone
- Molecular Framework
- Aliphatic homomonocyclic compounds
- External Descriptors
- terminal acetylenic compound, carbamate ester (CHEBI:4884)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- IAN371PP48
- CAS number
- 126-52-3
- InChI Key
- GXRZIMHKGDIBEW-UHFFFAOYSA-N
- InChI
- InChI=1S/C9H13NO2/c1-2-9(12-8(10)11)6-4-3-5-7-9/h1H,3-7H2,(H2,10,11)
- IUPAC Name
- 1-ethynylcyclohexyl carbamate
- SMILES
- NC(=O)OC1(CCCCC1)C#C
References
- Synthesis Reference
Junkmann, K. and Pfeiffer, H.; US. Patent 2,816,910; December 17, 1957; assigned to Schering AG, Germany.
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015165
- KEGG Drug
- D00703
- KEGG Compound
- C07832
- PubChem Compound
- 3284
- PubChem Substance
- 46507468
- ChemSpider
- 3169
- 24474
- ChEBI
- 4884
- ChEMBL
- CHEMBL1576
- ZINC
- ZINC000000001385
- Therapeutic Targets Database
- DAP000606
- PharmGKB
- PA164745394
- Wikipedia
- Ethinamate
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 94-96 Junkmann, K. and Pfeiffer, H.; US. Patent 2,816,910; December 17, 1957; assigned to Schering AG, Germany. boiling point (°C) 120 °C at 3.00E+00 mm Hg PhysProp water solubility 2500 mg/L (at 25 °C) MERCK INDEX (1996) logP 1.2 Not Available - Predicted Properties
Property Value Source Water Solubility 0.106 mg/mL ALOGPS logP 1.09 ALOGPS logP 1.54 Chemaxon logS -3.2 ALOGPS pKa (Strongest Acidic) 15.37 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 52.32 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 44.57 m3·mol-1 Chemaxon Polarizability 17.65 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9809 Blood Brain Barrier + 0.9923 Caco-2 permeable + 0.5 P-glycoprotein substrate Non-substrate 0.8609 P-glycoprotein inhibitor I Non-inhibitor 0.9198 P-glycoprotein inhibitor II Non-inhibitor 0.972 Renal organic cation transporter Non-inhibitor 0.8683 CYP450 2C9 substrate Non-substrate 0.8427 CYP450 2D6 substrate Non-substrate 0.7642 CYP450 3A4 substrate Non-substrate 0.5213 CYP450 1A2 substrate Non-inhibitor 0.7904 CYP450 2C9 inhibitor Non-inhibitor 0.8493 CYP450 2D6 inhibitor Non-inhibitor 0.9299 CYP450 2C19 inhibitor Non-inhibitor 0.8006 CYP450 3A4 inhibitor Non-inhibitor 0.852 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8627 Ames test Non AMES toxic 0.669 Carcinogenicity Non-carcinogens 0.8886 Biodegradation Not ready biodegradable 0.9584 Rat acute toxicity 2.6719 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9551 hERG inhibition (predictor II) Non-inhibitor 0.9467
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 140.8877449 predictedDarkChem Lite v0.1.0 [M-H]- 140.9714449 predictedDarkChem Lite v0.1.0 [M-H]- 131.30766 predictedDeepCCS 1.0 (2019) [M+H]+ 139.6588449 predictedDarkChem Lite v0.1.0 [M+H]+ 140.2587449 predictedDarkChem Lite v0.1.0 [M+H]+ 135.07942 predictedDeepCCS 1.0 (2019) [M+Na]+ 140.9226449 predictedDarkChem Lite v0.1.0 [M+Na]+ 144.11287 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Zinc ion binding
- Specific Function
- Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion in...
- Gene Name
- CA2
- Uniprot ID
- P00918
- Uniprot Name
- Carbonic anhydrase 2
- Molecular Weight
- 29245.895 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Zinc ion binding
- Specific Function
- Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
- Gene Name
- CA1
- Uniprot ID
- P00915
- Uniprot Name
- Carbonic anhydrase 1
- Molecular Weight
- 28870.0 Da
References
- Parr JS, Khalifah RG: Inhibition of carbonic anhydrases I and II by N-unsubstituted carbamate esters. J Biol Chem. 1992 Dec 15;267(35):25044-50. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 02, 2024 22:47