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enzymes (3)
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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Groups withdrawn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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Aethylcarbamat [german]
Aethylurethan [german]
Carbamic acid ethyl ester
Carbamidsaeure-aethylester [german]
Estane 5703
Ethyl ester of carbamic acid
Ethyl urethan
Ethyl urethane
Ethylcarbamate
Ethylester kyseliny karbaminove [czech]
Ethylurethan
Ethylurethane
O-ethyl urethane
O-ethylurethane
Uretan
Uretan etylowy [polish]
Uretano [dcit]
Urethan
Urethane
Urethanum [inn-latin]
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Salts Not Available
Brand names
Name Company
Leucethane
Leucothane
Pracarbamin
Pracarbamine
Brand mixtures
Brand Name Ingredients
Profenil
Categories
  • Antineoplastic Agents
  • Carcinogens
  • Anesthetics, Intravenous
CAS number 51-79-6
Weight Average: 89.0932
Monoisotopic: 89.047678473
Chemical Formula C3H7NO2
InChI Key InChIKey=JOYRKODLDBILNP-UHFFFAOYSA-N
InChI
InChI=1S/C3H7NO2/c1-2-6-3(4)5/h2H2,1H3,(H2,4,5)
Plain Text
IUPAC Name
ethyl carbamate
SMILES
CCOC(N)=O
Plain Text
Mass Spec show (8.45 KB)
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
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
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 49 °C PhysProp
boiling point 185 °C PhysProp
water solubility 4.8E+005 mg/L (at 15 °C) SEIDELL,A (1941)
logP -0.15 HANSCH,C ET AL. (1995)
logS 0.85 ADME Research, USCD
Predicted Properties
Property Value Source
water solubility 3.71e+02 g/l ALOGPS
logP -0.14 ALOGPS
logP -0.054 ChemAxon
logS 0.62 ALOGPS
pKa (strongest acidic) 15.47 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 1 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 52.32 ChemAxon
rotatable bond count 2 ChemAxon
refractivity 20.84 ChemAxon
polarizability 8.64 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Compound C01537 Link_out
PubChem Compound 5641 Link_out
PubChem Substance 46505215 Link_out
ChemSpider 5439 Link_out
ChEBI 17967 Link_out
ChEMBL 17967 Link_out
Wikipedia http://en.wikipedia.org/wiki/Urethane Link_out
ATC Codes Not Available
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Enzymes

1. Cytosolic phospholipase A2

Actions: substrate

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 response

UniProt ID: P47712 Link_out
Gene: PLA2G4A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: inducer

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 of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity

UniProt ID: P05164 Link_out
Gene: MPO Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: substrate

An aldehyde + H(2)O + O(2) = a carboxylic acid + H(2)O(2)

UniProt ID: Q06278 Link_out
Gene: AOX1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Comments
Drug created on September 11, 2007 14:32 / Updated on February 08, 2013 16:23