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Identification
NameEthinamate
Accession NumberDB01031  (APRD00959)
TypeSmall Molecule
GroupsApproved, Illicit, Withdrawn
DescriptionEthinamate is a short-acting sedative-hypnotic medication used to treat insomnia. Regular use leads to tolerance, and it is usually not effective for more 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.
Structure
Thumb
Synonyms
1-Ethynylcyclohexanol carbamate
Aethinyl-cyclohexyl-carbamat
Ethinamate
Ethinamatum
Etinamato
External Identifiers
  • USAF EL-42
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
ValaminSchering
ValmidDista
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIIAN371PP48
CAS number126-52-3
WeightAverage: 167.205
Monoisotopic: 167.094628665
Chemical FormulaC9H13NO2
InChI KeyGXRZIMHKGDIBEW-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
Pharmacology
IndicationUsed for the short-term treatment of insomnia, however, it generally has been replaced by other sedative-hypnotic agents.
Structured Indications Not Available
PharmacodynamicsEthinamate 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 However, it has generally been replaced by other medicines for the treatment of insomnia.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 actionThe 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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Carbonic anhydrase 2Proteinyes
inhibitor
HumanP00918 details
Carbonic anhydrase 1Proteinyes
inhibitor
HumanP00915 details
Related Articles
AbsorptionRapidly absorbed following oral administration.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic.

Route of eliminationNot Available
Half life2.5 hours
ClearanceNot Available
ToxicitySymptoms of overdose include shortness of breath or slow or troubled breathing, slow heartbeat, severe weakness, chronic confusion, slurred speech, and staggering.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
References
Synthesis Reference

Junkmann, K. and Pfeiffer, H.; US. Patent 2,816,910; December 17, 1957; assigned to
Schering AG, Germany.

General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9809
Blood Brain Barrier+0.9923
Caco-2 permeable+0.5
P-glycoprotein substrateNon-substrate0.8609
P-glycoprotein inhibitor INon-inhibitor0.9198
P-glycoprotein inhibitor IINon-inhibitor0.972
Renal organic cation transporterNon-inhibitor0.8683
CYP450 2C9 substrateNon-substrate0.8427
CYP450 2D6 substrateNon-substrate0.7642
CYP450 3A4 substrateNon-substrate0.5213
CYP450 1A2 substrateNon-inhibitor0.7904
CYP450 2C9 inhibitorNon-inhibitor0.8493
CYP450 2D6 inhibitorNon-inhibitor0.9299
CYP450 2C19 inhibitorNon-inhibitor0.8006
CYP450 3A4 inhibitorNon-inhibitor0.852
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8627
Ames testNon AMES toxic0.669
CarcinogenicityNon-carcinogens0.8886
BiodegradationNot ready biodegradable0.9584
Rat acute toxicity2.6719 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9551
hERG inhibition (predictor II)Non-inhibitor0.9467
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point94-96Junkmann, K. and Pfeiffer, H.; US. Patent 2,816,910; December 17, 1957; assigned to Schering AG, Germany.
boiling point120 °C at 3.00E+00 mm HgPhysProp
water solubility2500 mg/L (at 25 °C)MERCK INDEX (1996)
logP1.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.106 mg/mLALOGPS
logP1.09ALOGPS
logP1.54ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)15.37ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area52.32 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.57 m3·mol-1ChemAxon
Polarizability17.73 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-0arv-9100000000-713c62aa52e71fc3560aView in MoNA
Taxonomy
DescriptionThis 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).
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbonyl compounds
Sub ClassAlpha,beta-unsaturated carbonyl compounds
Direct ParentYnones
Alternative Parents
Substituents
  • Ynone
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
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 into the anterior chamber of the eye. Contributes to intracellular pH regulation in the duodenal upper villous epithelium during proton-coupled peptide absorption. Stimulates the chloride-bicarbonate ex...
Gene Name:
CA2
Uniprot ID:
P00918
Molecular Weight:
29245.895 Da
References
  1. 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. [PubMed:1460006 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
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
Molecular Weight:
28870.0 Da
References
  1. 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. [PubMed:1460006 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23