Ethyl carbamate

Enzymes (3)Biointeractions (3)

Identification

Name
Ethyl carbamate
Accession Number
DB04827
Type
Small Molecule
Groups
Withdrawn
Description

Ethyl carbamate (also known as urethan and urethane), formerly marketed as an inactive ingredient in Profenil injection, was determined to be carcinogenic and was removed from the Canadian, US, and UK markets in 1963.

Structure
Thumb
3D
Similar Structures
Synonyms
  • Aethylcarbamat
  • Aethylurethan
  • Carbamic acid ethyl ester
  • Carbamidsaeure-aethylester
  • Estane 5703
  • Ethyl ester of carbamic acid
  • Ethyl urethan
  • Ethyl urethane
  • Ethylcarbamate
  • Ethylester kyseliny karbaminove
  • Ethylurethan
  • Ethylurethane
  • O-ethyl urethane
  • O-ethylurethane
  • Uretan
  • Uretan etylowy
  • Uretano
  • Urethan
  • Urethane
  • Urethanum
External IDs
NSC-746
International/Other Brands
Leucethane / Leucothane / Pracarbamin / Pracarbamine
Categories
UNII
3IN71E75Z5
CAS number
51-79-6
Weight
Average: 89.0932
Monoisotopic: 89.047678473
Chemical Formula
C3H7NO2
InChI Key
JOYRKODLDBILNP-UHFFFAOYSA-N
InChI
InChI=1S/C3H7NO2/c1-2-6-3(4)5/h2H2,1H3,(H2,4,5)
IUPAC Name
ethyl carbamate
SMILES
CCOC(N)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Ethyl carbamate is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when 3,4-Methylenedioxyamphetamine is combined with Ethyl carbamate.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Ethyl carbamate.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Ethyl carbamate.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Ethyl carbamate is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when 7-Nitroindazole is combined with Ethyl carbamate.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when Ethyl carbamate is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.
AcepromazineThe risk or severity of adverse effects can be increased when Acepromazine is combined with Ethyl carbamate.
AceprometazineThe risk or severity of adverse effects can be increased when Aceprometazine is combined with Ethyl carbamate.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Ethyl carbamate.
Food Interactions
Not Available

References

Synthesis Reference

Norton A. Cashen, "Method of producing anhydrous crystalline reaction products of formaldehyde and methyl-, ethyl carbamate." U.S. Patent US4002668, issued July, 1973.

US4002668
General References
Not Available
External Links
Human Metabolome Database
HMDB0031219
KEGG Compound
C01537
PubChem Compound
5641
PubChem Substance
46505215
ChemSpider
5439
ChEBI
17967
ChEMBL
CHEMBL462547
Wikipedia
Urethane

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)49 °CPhysProp
boiling point (°C)185 °CPhysProp
water solubility4.8E+005 mg/L (at 15 °C)SEIDELL,A (1941)
logP-0.15HANSCH,C ET AL. (1995)
logS0.85ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility371.0 mg/mLALOGPS
logP-0.14ALOGPS
logP-0.054ChemAxon
logS0.62ALOGPS
pKa (Strongest Acidic)15.47ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area52.32 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity20.84 m3·mol-1ChemAxon
Polarizability8.64 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9922
Caco-2 permeable+0.516
P-glycoprotein substrateNon-substrate0.892
P-glycoprotein inhibitor INon-inhibitor0.9593
P-glycoprotein inhibitor IINon-inhibitor0.9677
Renal organic cation transporterNon-inhibitor0.9397
CYP450 2C9 substrateNon-substrate0.8579
CYP450 2D6 substrateNon-substrate0.7888
CYP450 3A4 substrateNon-substrate0.7321
CYP450 1A2 substrateNon-inhibitor0.5553
CYP450 2C9 inhibitorNon-inhibitor0.9306
CYP450 2D6 inhibitorNon-inhibitor0.9168
CYP450 2C19 inhibitorNon-inhibitor0.9537
CYP450 3A4 inhibitorNon-inhibitor0.9765
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9452
Ames testAMES toxic0.7773
CarcinogenicityNon-carcinogens0.6285
BiodegradationReady biodegradable0.6313
Rat acute toxicity1.6607 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9864
hERG inhibition (predictor II)Non-inhibitor0.9783
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (8.45 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-01r7-9000000000-ba57e1f4b939a6bb2c1c
GC-MS Spectrum - EI-BGC-MSsplash10-01r7-9000000000-4905daa85aa870eff5d7
Mass Spectrum (Electron Ionization)MSsplash10-01r7-9000000000-dbaaf921e6f73cb42292
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as carboximidic acids and derivatives. These are compounds containing a carboximidic group, with the general formula R-C(=NR1)OR2.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboximidic acids and derivatives
Sub Class
Not Available
Direct Parent
Carboximidic acids and derivatives
Alternative Parents
Organopnictogen compounds / Organooxygen compounds / Imines / Hydrocarbon derivatives
Substituents
Carboximidic acid derivative / Organic nitrogen compound / Organic oxygen compound / Organopnictogen compound / Hydrocarbon derivative / Organooxygen compound / Organonitrogen compound / Imine / Aliphatic acyclic compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
carbamate ester (CHEBI:17967) / a small molecule (URETHAN)

Enzymes

Details1. Cytosolic phospholipase A2
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Phospholipase a2 activity
Specific Function
Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory...
Gene Name
PLA2G4A
Uniprot ID
P47712
Uniprot Name
Cytosolic phospholipase A2
Molecular Weight
85238.2 Da
References
  1. Dinnes DL, Santerre JP, Labow RS: Phospholipase A2 pathway association with macrophage-mediated polycarbonate-urethane biodegradation. Biomaterials. 2005 Jun;26(18):3881-9. [PubMed:15626436]
  2. Labow RS, Santerre JP, Waghray G: The effect of phospholipids on the biodegradation of polyurethanes by lysosomal enzymes. J Biomater Sci Polym Ed. 1997;8(10):779-95. [PubMed:9297603]
Details2. Myeloperoxidase
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Peroxidase activity
Specific Function
Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production o...
Gene Name
MPO
Uniprot ID
P05164
Uniprot Name
Myeloperoxidase
Molecular Weight
83867.71 Da
References
  1. Kotanidou A, Choi AM, Winchurch RA, Otterbein L, Fessler HE: Urethan anesthesia protects rats against lethal endotoxemia and reduces TNF-alpha release. J Appl Physiol (1985). 1996 Nov;81(5):2305-11. [PubMed:8941558]
Details3. Aldehyde oxidase
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Xanthine dehydrogenase activity
Specific Function
Oxidase with broad substrate specificity, oxidizing aromatic azaheterocycles, such as N1-methylnicotinamide and N-methylphthalazinium, as well as aldehydes, such as benzaldehyde, retinal, pyridoxal...
Gene Name
AOX1
Uniprot ID
Q06278
Uniprot Name
Aldehyde oxidase
Molecular Weight
147916.735 Da
References
  1. Sugihara K, Kitamura S, Tatsumi K: Involvement of liver aldehyde oxidase in conversion of N-hydroxyurethane to urethane. J Pharmacobiodyn. 1983 Sep;6(9):677-83. [PubMed:6689178]

Drug created on September 11, 2007 14:32 / Updated on November 02, 2018 06:06