Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C3H7NO2 |
| Molecular Weight | 89.0932 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCOC(N)=O
InChI
InChIKey=JOYRKODLDBILNP-UHFFFAOYSA-N
InChI=1S/C3H7NO2/c1-2-6-3(4)5/h2H2,1H3,(H2,4,5)
| Molecular Formula | C3H7NO2 |
| Molecular Weight | 89.0932 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/28818685 | https://www.ncbi.nlm.nih.gov/pubmed/18921082 https://www.ncbi.nlm.nih.gov/pubmed/2188890
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/28818685 | https://www.ncbi.nlm.nih.gov/pubmed/18921082 https://www.ncbi.nlm.nih.gov/pubmed/2188890
Urethane (Ethyl carbamate) is is an ethyl ester of carbamic acid, that has been found in many fermented food products and alcoholic beverages such as cheese, bread, yogurt, wine, whiskey, soya sauce etc. An in vitro study indicated that Urethane has a potential to inhibit the growth of bacteria, plant tissue, and rat carcinoma. Urethane has been used for many years as an antineoplastic agent for medical purposes but this application ended after it was discovered to be carcinogenic in 1943. Urethane can produce long-lasting anesthesia without affecting blood gases or blood pressure, it has been used in acute studies. In earlier studies, Urethane was also used as a co-solvent for water-insoluble analgesic and sedative drugs in Japan. By US FDA regulations, ethyl carbamate has been withdrawn from pharmaceutical use. However, small quantities of ethyl carbamate are also used in laboratories as an anesthetic for animals.
Approval Year
Doses
| Dose | Population | Adverse events |
|---|---|---|
0.5 g 3 times / day multiple, oral Studied dose Dose: 0.5 g, 3 times / day Route: oral Route: multiple Dose: 0.5 g, 3 times / day Sources: |
unhealthy, 2 year n = 1 Health Status: unhealthy Age Group: 2 year Sex: F Population Size: 1 Sources: |
Other AEs: Vomiting, White blood cell increased... Other AEs: Vomiting (1 patient) Sources: White blood cell increased (grade 5, 1 patient) Hemorrhage (grade 5, 1 patient) |
10 % multiple, topical Dose: 10 % Route: topical Route: multiple Dose: 10 % Co-administed with:: acetic acid(0.005) Sources: penicillin |
unhealthy, 21 years n = 1 Health Status: unhealthy Condition: burns Age Group: 21 years Sex: M Population Size: 1 Sources: |
Other AEs: Nausea, Vomiting... Other AEs: Nausea (1 patient) Sources: Vomiting (1 patient) Leukopenia (grade 5, 1 patient) Hemorrhage (grade 5, 1 patient) Renal disorder NOS (grade 5, 1 patient) Liver injury (grade 5, 1 patient) |
6 g 1 times / day multiple, oral Studied dose Dose: 6 g, 1 times / day Route: oral Route: multiple Dose: 6 g, 1 times / day Sources: |
unhealthy, 51-76 years n = 8 Health Status: unhealthy Age Group: 51-76 years Sex: M+F Population Size: 8 Sources: |
Other AEs: Anorexia, Leukopenia... Other AEs: Anorexia (4 patients) Sources: Leukopenia (1 patient) Weight loss (severe, 1 patient) Neutrophilia (1 patient) Nausea (1 patient) Vomiting (1 patient) |
10 g multiple, intravenous (total) Dose: 10 g Route: intravenous Route: multiple Dose: 10 g Sources: |
unhealthy |
Other AEs: Drowsiness... |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Vomiting | 1 patient | 0.5 g 3 times / day multiple, oral Studied dose Dose: 0.5 g, 3 times / day Route: oral Route: multiple Dose: 0.5 g, 3 times / day Sources: |
unhealthy, 2 year n = 1 Health Status: unhealthy Age Group: 2 year Sex: F Population Size: 1 Sources: |
| Hemorrhage | grade 5, 1 patient | 0.5 g 3 times / day multiple, oral Studied dose Dose: 0.5 g, 3 times / day Route: oral Route: multiple Dose: 0.5 g, 3 times / day Sources: |
unhealthy, 2 year n = 1 Health Status: unhealthy Age Group: 2 year Sex: F Population Size: 1 Sources: |
| White blood cell increased | grade 5, 1 patient | 0.5 g 3 times / day multiple, oral Studied dose Dose: 0.5 g, 3 times / day Route: oral Route: multiple Dose: 0.5 g, 3 times / day Sources: |
unhealthy, 2 year n = 1 Health Status: unhealthy Age Group: 2 year Sex: F Population Size: 1 Sources: |
| Nausea | 1 patient | 10 % multiple, topical Dose: 10 % Route: topical Route: multiple Dose: 10 % Co-administed with:: acetic acid(0.005) Sources: penicillin |
unhealthy, 21 years n = 1 Health Status: unhealthy Condition: burns Age Group: 21 years Sex: M Population Size: 1 Sources: |
| Vomiting | 1 patient | 10 % multiple, topical Dose: 10 % Route: topical Route: multiple Dose: 10 % Co-administed with:: acetic acid(0.005) Sources: penicillin |
unhealthy, 21 years n = 1 Health Status: unhealthy Condition: burns Age Group: 21 years Sex: M Population Size: 1 Sources: |
| Hemorrhage | grade 5, 1 patient | 10 % multiple, topical Dose: 10 % Route: topical Route: multiple Dose: 10 % Co-administed with:: acetic acid(0.005) Sources: penicillin |
unhealthy, 21 years n = 1 Health Status: unhealthy Condition: burns Age Group: 21 years Sex: M Population Size: 1 Sources: |
| Leukopenia | grade 5, 1 patient | 10 % multiple, topical Dose: 10 % Route: topical Route: multiple Dose: 10 % Co-administed with:: acetic acid(0.005) Sources: penicillin |
unhealthy, 21 years n = 1 Health Status: unhealthy Condition: burns Age Group: 21 years Sex: M Population Size: 1 Sources: |
| Liver injury | grade 5, 1 patient | 10 % multiple, topical Dose: 10 % Route: topical Route: multiple Dose: 10 % Co-administed with:: acetic acid(0.005) Sources: penicillin |
unhealthy, 21 years n = 1 Health Status: unhealthy Condition: burns Age Group: 21 years Sex: M Population Size: 1 Sources: |
| Renal disorder NOS | grade 5, 1 patient | 10 % multiple, topical Dose: 10 % Route: topical Route: multiple Dose: 10 % Co-administed with:: acetic acid(0.005) Sources: penicillin |
unhealthy, 21 years n = 1 Health Status: unhealthy Condition: burns Age Group: 21 years Sex: M Population Size: 1 Sources: |
| Leukopenia | 1 patient | 6 g 1 times / day multiple, oral Studied dose Dose: 6 g, 1 times / day Route: oral Route: multiple Dose: 6 g, 1 times / day Sources: |
unhealthy, 51-76 years n = 8 Health Status: unhealthy Age Group: 51-76 years Sex: M+F Population Size: 8 Sources: |
| Nausea | 1 patient | 6 g 1 times / day multiple, oral Studied dose Dose: 6 g, 1 times / day Route: oral Route: multiple Dose: 6 g, 1 times / day Sources: |
unhealthy, 51-76 years n = 8 Health Status: unhealthy Age Group: 51-76 years Sex: M+F Population Size: 8 Sources: |
| Neutrophilia | 1 patient | 6 g 1 times / day multiple, oral Studied dose Dose: 6 g, 1 times / day Route: oral Route: multiple Dose: 6 g, 1 times / day Sources: |
unhealthy, 51-76 years n = 8 Health Status: unhealthy Age Group: 51-76 years Sex: M+F Population Size: 8 Sources: |
| Vomiting | 1 patient | 6 g 1 times / day multiple, oral Studied dose Dose: 6 g, 1 times / day Route: oral Route: multiple Dose: 6 g, 1 times / day Sources: |
unhealthy, 51-76 years n = 8 Health Status: unhealthy Age Group: 51-76 years Sex: M+F Population Size: 8 Sources: |
| Anorexia | 4 patients | 6 g 1 times / day multiple, oral Studied dose Dose: 6 g, 1 times / day Route: oral Route: multiple Dose: 6 g, 1 times / day Sources: |
unhealthy, 51-76 years n = 8 Health Status: unhealthy Age Group: 51-76 years Sex: M+F Population Size: 8 Sources: |
| Weight loss | severe, 1 patient | 6 g 1 times / day multiple, oral Studied dose Dose: 6 g, 1 times / day Route: oral Route: multiple Dose: 6 g, 1 times / day Sources: |
unhealthy, 51-76 years n = 8 Health Status: unhealthy Age Group: 51-76 years Sex: M+F Population Size: 8 Sources: |
| Drowsiness | slight | 10 g multiple, intravenous (total) Dose: 10 g Route: intravenous Route: multiple Dose: 10 g Sources: |
unhealthy |
PubMed
| Title | Date | PubMed |
|---|---|---|
| A role of proton transfer in peroxidase-catalyzed process elucidated by substrates docking calculations. | 2001 |
|
| [A plastic property in the change of rat muscle potentials clarified in the presence of neostigmine: a conjecture on the recycling process of ACh]. | 2001 |
|
| Monoclonal antibody to rat galanin: production, characterization, and in vivo immunoneutralization activity. | 2001 Apr |
|
| The effects of moisture on the dielectric relaxation of urethane dimethacrylate polymer and composites. | 2001 Apr |
|
| A novel traceless resin-bound guanidinylating reagent for secondary amines to prepare N,N-disubstituted guanidines. | 2001 Apr 19 |
|
| Stimulatory effects of centrally injected kappa-opioid receptor agonists on gastric acid secretion in urethane-anesthetized rats. | 2001 Apr 27 |
|
| Two unusual glycerophospholipids from a filamentous fungus, Absidia corymbifera. | 2001 Apr 30 |
|
| Clinical wear performance of eight experimental dental composites over three years determined by two measuring methods. | 2001 Aug |
|
| Capillary zone electrophoresis for the characterization of latex particles. | 2001 Aug |
|
| Anesthetic induction agents, sympathetic nerve activity and baroreflex sensitivity: a study in rabbits comparing thiopental, propofol and etomidate. | 2001 Aug |
|
| Cardiovascular effects of the methanol and dichloromethanol extracts from Mentha suaveolens Ehrh. | 2001 Aug |
|
| Involvement of a urethane-sensitive system in timing the onset of gastrulation in Xenopus laevis embryos. | 2001 Aug |
|
| Extracellular signal-regulated kinases 1 and 2 phosphorylated neurons in the tele- and diencephalon of rat after visceral pain stimulation: an immunocytochemical study. | 2001 Aug 10 |
|
| Differences in parasympathetic vasodilator and salivary responses in the cat submandibular gland between lingual and chorda-lingual nerve stimulation. | 2001 Feb |
|
| Modulation of diaspirin crosslinked hemoglobin induced systemic and regional hemodynamic response by ethanol in normal rats. | 2001 Feb 9 |
|
| [Liver angiosarcoma in humans: epidemiologic considerations]. | 2001 Jan-Feb |
|
| Preferential acetazolamide-induced vasodilation based on vessel size and organ: confirmation of peripheral vasodilation with use of colored microspheres. | 2001 Jul |
|
| Occupational hypersensitivity pneumonitis due to isocyanates: mechanisms of action and case reports in Japan. | 2001 Jul |
|
| Effect of nitric oxide synthase inhibition on fos expression in the hypothalamus of female rats following central oxytocin and systemic urethane administration. | 2001 Jul |
|
| Flexural behaviour of post-cured composites at oral-simulating temperatures. | 2001 Jul |
|
| Denture base polymer Alldent Sinomer: mechanical properties, water sorption and release of residual compounds. | 2001 Jul |
|
| Macroporous copolymer matrix. IV. Expanded bed adsorption application. | 2001 Jul 13 |
|
| Anesthesia alters NO-mediated functional hyperemia. | 2001 Jul 13 |
|
| Effects of anesthesia on cystometry and leak point pressure of the female rat. | 2001 Jul 27 |
|
| Fine chromosomal localization of the mouse Par2 gene that confers resistance against urethane-induction of pulmonary adenomas. | 2001 Jul 5 |
|
| Utilization of an intramolecular hydrogen bond to increase the CNS penetration of an NK(1) receptor antagonist. | 2001 Jul 5 |
|
| In vitro comparison of cuspal fracture resistances of posterior teeth restored with various adhesive restorations. | 2001 Jul-Aug |
|
| Delayed-type hypersensitivity and humoral immunity modulation by dietary lipids in a murine model of pulmonary tumorigenesis induced by urethan. | 2001 Jun |
|
| Azo-containing urethane analogues for colonic drug delivery: synthesis, characterization and in-vitro evaluation. | 2001 Jun |
|
| Copper(II) catalysis in cyanide conversion into ethyl carbamate in spirits and relevant reactions. | 2001 Jun |
|
| Topical bicuculline to the rat spinal cord induces highly localized allodynia that is mediated by spinal prostaglandins. | 2001 Jun |
|
| Sympathetic nerve and cardiovascular responses to chemical activation of the midbrain defense region. | 2001 Jun |
|
| Use of a simplified method of optical recording to identify foci of maximal neuron activity in the somatosensory cortex of white rats. | 2001 Mar-Apr |
|
| 2-Chloroacetaldehyde induces epsilondA DNA adducts in DNA of Raji cells as demonstrated by an improved HPLC-fluorimetry method. | 2001 May |
|
| An in vitro wear study of posterior denture tooth materials on human enamel. | 2001 May |
|
| Optimization of an exogenous metabolic activation system for FETAX. II. Preliminary evaluation. | 2001 May |
|
| Adrenomedullin acts in the rat paraventricular nucleus to decrease blood pressure. | 2001 May |
|
| The role of alpha(1)-adrenoceptors and 5-HT(1A) receptors in the control of the micturition reflex in male anaesthetized rats. | 2001 May |
|
| Telomerase activation and p53 mutations in urethane-induced A/J mouse lung tumor development. | 2001 May |
|
| Muscarinic dependence of nucleus basalis induced conditioned receptive field plasticity. | 2001 May 25 |
|
| Indomethacin reduces lung adenoma number in A/J mice. | 2001 May-Jun |
|
| Shear bond strength of denture reline polymers to denture base polymers. | 2001 May-Jun |
|
| The release of spinal prostaglandin E2 and the effect of nitric oxide synthetase inhibition during strychnine-induced allodynia. | 2001 Sep |
|
| Abrogation of alpha-adrenergic vasoactivity in chronically inflamed rat knee joints. | 2001 Sep |
|
| The application of magnetic resonance microimaging to the visible light curing of dental resins. 3. Stray-field nuclear magnetic resonance imaging (STRAFI). | 2001 Sep |
|
| GDNF improves cerebellar Purkinje neuron function in aged F344 rats. | 2001 Sep 1 |
|
| Excitatory stimulation of neurons in the arcuate nucleus inhibits gastric acid secretion via vagal pathways in anesthetized rats. | 2001 Sep 14 |
|
| Enzyme-induced biodegradation of polycarbonate polyurethanes: dependence on hard-segment concentration. | 2001 Sep 15 |
|
| Loss of p16Ink4a with retention of p19Arf predisposes mice to tumorigenesis. | 2001 Sep 6 |
|
| Discrete regions in the laterodorsal tegmental area of the rat regulating the urinary bladder and external urethral sphincter. | 2001 Sep 7 |
Sample Use Guides
In the 1940s, ethyl carbamate was used in man at doses of 1 g/person/day
Route of Administration:
Oral
HepG2 cells were cultured in DMEM medium containing 10% fetal bovine serum and 1% mixture of penicillin
(100 IU/ml) and streptomycin (100g/ml) at 37 °C in the presence of 5% CO2. Cells at 80% confluent were treated with 100 mM (dissolved in DMEM medium) for different times and cell viability and mortality were timely examined. Cells without EC (Urethane) treatment were grown at the same time as control. For metabolomics and transcriptomic analyses, cells were collected at 4 h and 12 h after treatment, respectively, digested with trypsin and centrifuged in 2 mL Eppendorf tubes at 1000 rpm for 5 min in 4 °C. The cell pellets were washed with ice-cold PBS solution twice, frozen immediately in liquid nitrogen and stored at −80 °C until analysis.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 17:32:11 GMT 2023
by
admin
on
Sat Dec 16 17:32:11 GMT 2023
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| Record UNII |
3IN71E75Z5
|
| Record Status |
Validated (UNII)
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| Record Version |
|
-
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NCI_THESAURUS |
C45176
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3IN71E75Z5
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100000076664
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m11329
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Ethyl carbamate
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5641
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SUB11388MIG
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200-123-1
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51-79-6
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D014520
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CHEMBL462547
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DTXSID9021427
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2555
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17967
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C920
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DB04827
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3IN71E75Z5
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1329
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746
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1420982
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METABOLITE -> PARENT |
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ACTIVE MOIETY |
