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Identification
NameEthyl carbamate
Accession NumberDB04827
TypeSmall Molecule
GroupsWithdrawn
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
Synonyms
SynonymLanguageCode
AethylcarbamatGermanNot Available
AethylurethanGermanNot Available
Carbamic acid ethyl esterNot AvailableNot Available
Carbamidsaeure-aethylesterGermanNot Available
Estane 5703Not AvailableNot Available
Ethyl ester of carbamic acidNot AvailableNot Available
Ethyl urethanNot AvailableNot Available
Ethyl urethaneNot AvailableNot Available
EthylcarbamateNot AvailableNot Available
Ethylester kyseliny karbaminoveCzechNot Available
EthylurethanNot AvailableNot Available
EthylurethaneNot AvailableNot Available
O-ethyl urethaneNot AvailableNot Available
O-ethylurethaneNot AvailableNot Available
UretanNot AvailableNot Available
Uretan etylowyPolishNot Available
UretanoNot AvailableDCIT
UrethanNot AvailableNot Available
UrethaneNot AvailableNot Available
UrethanumLatinINN
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
LeucethaneNot Available
LeucothaneNot Available
PracarbaminNot Available
PracarbamineNot Available
Brand mixtures
Brand NameIngredients
Profenil
SaltsNot Available
Categories
CAS number51-79-6
WeightAverage: 89.0932
Monoisotopic: 89.047678473
Chemical FormulaC3H7NO2
InChI KeyJOYRKODLDBILNP-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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as organooxygen compounds. These are organic compounds containing a bond between a carbon atom and an oxygen atom.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassNot Available
Sub ClassNot Available
Direct ParentOrganooxygen compounds
Alternative Parents
Substituents
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrateNon-inhibitor0.9306
CYP450 2D6 substrateNon-inhibitor0.9168
CYP450 2C19 substrateNon-inhibitor0.9537
CYP450 3A4 substrateNon-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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point49 °CPhysProp
boiling point185 °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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (8.45 KB)
SpectraMS1D NMR
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 ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Enzymes

1. Cytosolic phospholipase A2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytosolic phospholipase A2 P47712 Details

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
  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

2. Myeloperoxidase

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Myeloperoxidase P05164 Details

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. 1996 Nov;81(5):2305-11. Pubmed

3. Aldehyde oxidase

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Aldehyde oxidase Q06278 Details

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
  2. 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

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Drug created on September 11, 2007 14:32 / Updated on September 16, 2013 17:25