Urethane
Identification
- Name
- Urethane
- Accession Number
- DB04827
- Description
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.
- Type
- Small Molecule
- Groups
- Approved, Withdrawn
- Structure
Structure for Urethane (DB04827)
- Weight
- Average: 89.0932
Monoisotopic: 89.047678473 - Chemical Formula
- C3H7NO2
- Synonyms
- Aethylcarbamat
- Aethylurethan
- Carbamic acid ethyl ester
- Carbamidsaeure-aethylester
- Ethyl carbamate
- Ethylester kyseliny karbaminove
- Uretan etylowy
- Uretano
- Urethan
- Urethane
- Urethanum
- External IDs
- NSC-746
Pharmacology
Accelerate your drug discovery research with the industry’s only fully connected ADMET dataset, ideal for:Accelerate your drug discovery research with our fully connected ADMET dataset- Indication
- Not Available
- Contraindications & Blackbox Warnings
Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects- 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
- Adverse Effects
Reduce medical errorsand improve treatment outcomes with our comprehensive & structured data on drug adverse effects.Reduce medical errors & improve treatment outcomes with our adverse effects data- Toxicity
- Not Available
- Affected organisms
- Humans and other mammals
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcetazolamide The risk or severity of adverse effects can be increased when Acetazolamide is combined with Urethane. Acetophenazine The risk or severity of adverse effects can be increased when Acetophenazine is combined with Urethane. Aclidinium Urethane may increase the central nervous system depressant (CNS depressant) activities of Aclidinium. Agomelatine The risk or severity of adverse effects can be increased when Urethane is combined with Agomelatine. Alfentanil The risk or severity of adverse effects can be increased when Alfentanil is combined with Urethane. Alimemazine The risk or severity of adverse effects can be increased when Alimemazine is combined with Urethane. Almotriptan The risk or severity of adverse effects can be increased when Almotriptan is combined with Urethane. Alosetron The risk or severity of adverse effects can be increased when Alosetron is combined with Urethane. Alprazolam The risk or severity of adverse effects can be increased when Alprazolam is combined with Urethane. Alverine The risk or severity of adverse effects can be increased when Alverine is combined with Urethane. 
Improve patient outcomesBuild effective decision support tools with the industry’s most comprehensive drug-drug interaction checker.Learn more - Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- Aliphatic acyclic compound / Carboximidic acid derivative / Hydrocarbon derivative / Imine / Organic nitrogen compound / Organic oxygen compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- carbamate ester (CHEBI:17967) / a small molecule (URETHAN)
Chemical Identifiers
- UNII
- 3IN71E75Z5
- CAS number
- 51-79-6
- 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
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
- BindingDB
- 50239974
- 1420982
- ChEBI
- 17967
- ChEMBL
- CHEMBL462547
- ZINC
- ZINC000000901020
- Wikipedia
- Urethane
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) 49 °C PhysProp boiling point (°C) 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 371.0 mg/mL 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 Å2 ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 20.84 m3·mol-1 ChemAxon Polarizability 8.64 Å3 ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9922 Caco-2 permeable + 0.516 P-glycoprotein substrate Non-substrate 0.892 P-glycoprotein inhibitor I Non-inhibitor 0.9593 P-glycoprotein inhibitor II Non-inhibitor 0.9677 Renal organic cation transporter Non-inhibitor 0.9397 CYP450 2C9 substrate Non-substrate 0.8579 CYP450 2D6 substrate Non-substrate 0.7888 CYP450 3A4 substrate Non-substrate 0.7321 CYP450 1A2 substrate Non-inhibitor 0.5553 CYP450 2C9 inhibitor Non-inhibitor 0.9306 CYP450 2D6 inhibitor Non-inhibitor 0.9168 CYP450 2C19 inhibitor Non-inhibitor 0.9537 CYP450 3A4 inhibitor Non-inhibitor 0.9765 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9452 Ames test AMES toxic 0.7773 Carcinogenicity Non-carcinogens 0.6285 Biodegradation Ready biodegradable 0.6313 Rat acute toxicity 1.6607 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9864 hERG inhibition (predictor II) Non-inhibitor 0.9783
Spectra
- Mass Spec (NIST)
- Download (8.45 KB)
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available GC-MS Spectrum - EI-B GC-MS splash10-01r7-9000000000-ba57e1f4b939a6bb2c1c GC-MS Spectrum - EI-B GC-MS splash10-01r7-9000000000-4905daa85aa870eff5d7 Mass Spectrum (Electron Ionization) MS splash10-01r7-9000000000-dbaaf921e6f73cb42292 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available 1H NMR Spectrum 1D NMR Not Applicable 13C NMR Spectrum 1D NMR Not Applicable
Enzymes
- Kind
- Protein
- Organism
- Humans
- 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
- 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]
- 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]
- Kind
- Protein
- Organism
- Humans
- 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
- 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]
- Kind
- Protein
- Organism
- Humans
- 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
- 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 20:32 / Updated on June 12, 2020 16:52